July 21, 2025 • 50 mins
Wade Callison, CRO of Files.com, shares his journey from product leadership to sales and reveals how technical domain expertise creates credibility that transforms selling relationships from transactional to consultative.
Curiosity, coachability, growth mindset, and self-awareness form Wade's core framework for identifying and developing sales talent.
Wade details creating a culture of continuous learning helps sales teams adapt and improve. In one example, Wade outlines the pre-call brief that models it's thinking on the pre-flight plan that pilots benefit from.
Currently focused on improving win rates at Files.com, Wade shares his strategic approach: rather than trying to fix everything at once, he's identified specific leverage points like establishing value before discussing price and strengthening champion enablement. This targeted methodology exemplifies the thoughtful, measured leadership style that has defined his career.
Whether you're an aspiring sales leader or looking to refine your coaching approach, Wade's insights offer practical guidance for transforming individual contributors into cohesive, high-performing teams. Connect with him on LinkedIn to continue the conversation and exchange ideas about sales leadership excellence.
Music by Ben Cina & Ayler Young
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Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:16):
Hello everyone and welcome to another episode of
Pillar Talk, where we build thefoundations of sales leadership
and create clarity in terms ofwhat good looks like for current
and aspiring sales leaders.
Before we jump in, I alwayslike to review what the six
pillars of successful salesleadership are, or what I came
up with to try to define whatthe behaviors of good leadership
(00:40):
is in a sales leadershipcapacity.
It starts with talent,identification and attraction.
Obviously, building andmaintaining the team of winners
is critical to success.
Building your overall operatingrhythm of how you run the
business.
Business planning, which isyour cross-functional
collaboration to make decisionsfor the future rather than
(01:01):
continuously reacting to theevents that are happening to you
.
We have communication, which, inthe world we live in today,
takes many mediums and manyforms.
Ownership, which is about howmuch do you, as a leader, do on
your own versus looking fordirection, and it's also about
how much are you about your teamversus being about the business
(01:22):
, and how do you find balancebetween the two.
The last one and obviously like, at the end of the day, when
you're in sales trying to grow abusiness, mastering the craft,
how do you help your team win?
So we've got lots of elementsthat we explore in this podcast
to try to provide tacticalinsights and actions to help
aspiring leaders be better atthe actual task of sales
(01:43):
leadership.
So today joining us on PillarTalk, we have Wade Callison.
Wade is a sales leadercurrently serving as the CRO of
Filescom, a file transferautomation company.
Along with many other thingsthat Files can do, wade
previously served in salesleadership positions at ActiveVM
(02:05):
, squid and Intralinks, just toname a few.
Wade, welcome to Pillar Talk.
Speaker 2 (02:11):
Thanks, rick, good to be here.
Speaker 1 (02:13):
Yeah, it's good to be with you.
So, Wade, you recentlyrelocated from the Northeast
down to Texas.
What's one story of surprisethat you didn't anticipate in
terms of doing that of surprisethat you didn't anticipate in
terms of doing that.
Speaker 2 (02:26):
You know it's just been the all the logistics of
relocating.
We've been in the Northeast for16 years and you end up
accumulating a lot of life withfour kids over 16 years and for
us it's just been all thelogistics.
It's been exciting, but it'sdefinitely been been something
that has taxed us over the lastfew months, especially with
(02:47):
starting a new job.
Starting a new job and movingit's like all the major
stressors of your life all inthe same way.
But we're loving being down inAustin.
It's a great city.
It's been really welcoming tous, so it's been a lot of fun.
Speaker 1 (03:00):
Well, congratulations .
Thank you, wade.
When our paths have crossed inthe past, one of the roles that
I observed you perform in is asprobably the most strategic
account executive in theorganization.
You did not work in a contextwhere you had a repeatable
solution and you simply went andtried to maximize the volume of
purchases that got made, butyou had to create solutions on a
(03:22):
curated basis based onstrategic customers, and so I
thought what we would covertoday is focus on mastering the
craft I saved.
You know the best for last yearand how you evolved in the days
of being a strategic accountexecutive into a leader that is
helping to coach and help theteam ultimately win.
As you have grown in aleadership capacity, were there
(03:45):
any formative moments?
Were there any lessons learnedalong the way that helped set
the stage for how youpragmatically or practically
coach and help your team wintoday?
Speaker 2 (03:57):
Yeah, look for me.
I didn't come to sales in thetypical journey.
I didn't come out of collegeand go to be a BDR or a
salesperson.
I really spent a bulk of mycareer in consulting in product
companies.
In fact, when you and I firstmet, I was running a product
organization and was enjoyingand loving that and I felt like
(04:17):
my whole career that I was a bitof a closeted salesperson.
I was always a salesperson butnever actually had the guts to
go be one.
And I went to our former chiefrevenue officer, who ended up
becoming the CEO, and I said tohim after a sales kickoff I
stood on stage and rolled outthis brand new product and then
afterwards I said to him I saidI think I want to be a
(04:37):
salesperson and he's like do youthink you can be a salesperson?
I said I think I can.
He said if you can't, I'll fireyou.
I said if I can't do it, youshould fire me, right?
And so I went into being asalesperson, thinking that it
was just those intrinsic skills,like, oh, I'm a good
salesperson, I think I can be agood salesperson because I have,
I think, the intrinsic skills.
(04:58):
And what I quickly realized isI knew nothing about selling,
like mean again, we have theseintrinsic skills, but like I had
to become a student of the gameand I had to learn and I had no
idea what I was doing and andit really comes back to some of
the core points which is, Ithink intrinsically someone has
to want to learn and grow andfrom that there's so much you
(05:19):
can pour into them and for me itwas that right.
It was that moment of having alot of experience and thinking
you know what you're doing andfiguring it out and having those
people teach me.
Speaker 1 (05:30):
Yeah, that's really funny.
It reminds me just.
A lot of people think you knowthe sales team is, like you know
, higher compensation.
It's easy.
They just complain aboutproduct like different things,
like I could do that, and whenyou're thrust in it it's a very
different experience it's sohard.
Speaker 2 (05:45):
It's so hard like when I, when I first met with
our cro, he showed me one of theorganizations I was selling to
and we put an order.
He goes who do you know?
And I had one name for thisglobal bank and he's like okay,
next time we meet you shouldknow more of the people there.
And we built out the org.
But, like again, these are theskills that you just have to
pour into people.
Speaker 1 (06:05):
So, as you entered a sort of sales career and again
this is going to lead to how youcoach today you got thrust in
and saw from the deep end, so tospeak, the challenges
associated with success in youknow, winning deals, hitting
numbers, doing that type ofthing, and your realization
about how important you knowcoaching is going to be to the
(06:26):
success here was in once youwere thrust in.
Was there a time, as youstarted to evolve and succeed,
where you were able to get thetype of coaching that impacted
you or you know able to get thetype of coaching that impacted
you or, you know, enabled you tobe?
Speaker 2 (06:41):
better equipped to succeed.
Absolutely like everywhere I'vebeen, I've looked for that
ability for my leadership to beable to impart wisdom upon me,
like when I went to squid.
Squid was an interesting placefor me because I had been again
advanced in my career I'd been aseller but I hadn't gotten all
the skills of being a salesleader and I found a CRO who was
(07:05):
just a servant leader who wouldpour himself into me and into
his team and would allow you tofail, would help you, coach you
and help you coach other people,and I think it's finding those
mentors in each of our lives,like for me it was those people,
but also it's the peers that Ihave that I go to.
Like I've called you at timesfor help.
(07:26):
I've called other sales leadersthat are my peers for help.
I think it's all about findingthose people around you that can
help you understand and helpyou learn those skills that you
need.
Speaker 1 (07:37):
So when you had great mentorship, as an example CRO
at Squid, are there any storiesof how that came to build up
your ability to impact others?
Speaker 2 (07:48):
Yeah.
So what he was really good atwas this cadence of look always
be open and communicate, butthen also build in the technical
skills with the team.
So we would obviously all of usgoing to be working on
discovery skills and negotiationeverything else but one of the
things he believed which is Ibelieve deeply is that sellers
(08:08):
need to be a have full commandover their domain and in having
command over your domain, thebest sellers like in the jolt
effect when you read MattDixon's book and Ted McKenna the
seller that can carry the dealthe furthest without relying on
their team around them is theone that is viewed with
credibility and the one that cansit shoulder to shoulder with
(08:29):
the customer and help them solvea problem, as opposed to being
across the table trying to do acommercial agreement.
That's very clearly not ineveryone's best interest, right?
So I think that making sure andone of the things that Rob did
well, the CRO was we had amonthly talking tech where we
went deep into topics that thesales team needed to know, and
(08:53):
because of my product background, my computer science background
, that's how I always sold.
I always sold from a place ofcredibility and it always helped
me and in fact I've had a CTOof one of the large law firms.
Stop me, he goes.
You don't feel like any othersalesperson.
I'll say what do you mean?
He goes you feel like you knowa lot about the topic you're
selling and I think that's whatI value in my team, the team
(09:15):
I've got here at Files.
That's the skill that I valuethe most, and why it was a good
fit for me is that my CEO and Iboth believe that you should be
as close to an expert in yourdomain on the topic that you're
selling, not just an expert inselling, and it makes a huge
difference.
Speaker 1 (09:34):
Now, when you say domain, you're referring to the
context.
It's not just the product, it'snot just the market, it's where
those two elements meet.
One of the things that isinteresting to me, wade, is that
the path for a successfulseller isn't a one-size-fits-all
, and so some can lean intotheir expertise.
(09:55):
So, for example, in my currentcompany we basically hire sales
team members that come fromindustry the taxonomy, the my
current company we basicallyhire sales team members that
come from industry the taxonomy,the pain points.
It's a vertical SaaS businessthat's so far in our growth, you
know, provides higherconfidence of their success.
So they do tend to have muchmore subject matter expertise.
But that's not the only optionhere.
(10:16):
It sounds like in your career,what's given you the most
comfort around your path tosuccess is around building that
level of like.
I understand the customer, Iunderstand the problem, I
understand how we meet thatproblem along the way and I can
engage successfully because I'mbringing real expertise to.
You know any given salessituation.
Did you find that?
That you know like there wereother paths where you had to
(10:39):
coach a little bit differentlyon somebody that maybe their
skill set isn't as strong in thetechnical sides, but they bring
much more process.
They bring much more structureand other elements of the deal,
and how have you handled it?
Speaker 2 (10:51):
Yeah, and I should say, like with yours, yours is
verticalized.
I've tended in my career to gowith horizontal platforms, ones
that one of my sales reps saidwere more liquid than solids.
We're not selling a solid thing, we're really being more
consultative in the selling.
So those are the sorts ofenvironments I lean into and the
sorts of environments that Ilike.
Which then changes the sellingskills, and I think to your
(11:12):
point is that we do get peoplewho have industry experience,
but it's more around thehorizontal.
So for us here it's aroundnetwork infrastructure, it's
around the protocols onbusiness-to-business integration
, sftp, managed file transfer,these sorts of things, and so
you need to understand thatdomain, you need to understand
(11:32):
the architectures, because whenyou're talking with our
customers and I've said this toone of my reps yesterday we see
more of those than any of ourcustomers who are buying.
We know what it takes tomigrate from one legacy
environment to the cloud, andour customers are doing it for
the first, maybe second time intheir career, and so we need to
(11:53):
be able to provide that sort ofguidance.
And so if you are deep intothis domain, if you care and
you're curious about what ittakes to do that, then we can be
that Sherpa that helps them ontheir journey to get to more
success.
Speaker 1 (12:06):
So sure.
So you, as an individualcontributor, leaned into your
technical skills andunderstanding the customer and
the problem as a way to helpsolve issues for them, which is
fantastic.
You then become a leader andnow you've got a whole team of
people, and one of the things anew leader tends to run into is
that the path that works forthem isn't necessarily the same
(12:28):
for all the individuals.
How did you address thatdynamic where everybody on your
team wasn't just like you?
Speaker 2 (12:35):
Yeah, no, and thank goodness they're not.
It would be a horrible team ifit was.
Yeah, no, and thank goodnessthey're not.
(12:55):
It would be a horrible team ifit was.
Look, it's about a as me, but Ido think there's some things
that really matter in being ableto sell and sell effectively,
and those skills are things thatwe sit and diagnose.
I work with my managers to sitand diagnose and then to invest
in the individual.
But again, I think for me it'sone thing for us to diagnose
that, but the individual sellerhas to know and recognize that
(13:20):
and want that feedback and wantto grow.
I just had a one-on-one with oneof my reps yesterday.
He said can we make ourone-on-ones longer?
There's so many things I wantto learn and so many ways I want
to develop and I need more timewith you to be able to do that.
And that's the sort of personthat I'm willing to pour all of
my time into, because they'rethe ones that are listening to a
thousand gong calls, likeanyone who listens to more gong
(13:41):
calls than I do is probablysomeone who's trying to get to
the next level.
Those are some of theindicators I look for and so,
yeah, it is difficult, but again, it's about a plan, for what
are the skills that you arelacking?
Whether they're technical,whether they're selling, whether
they're just interpersonalskills Like empathy for me, is
one of the biggest skills that Ithink, as a seller, we need to
(14:01):
have, and we need to understandwhat it means to buy and the
risks that it takes to buy inthis sort of environment.
Speaker 1 (14:09):
Do you have a list of skills that you've sort of
developed that define how youcoach?
Speaker 2 (14:17):
Yeah, so I mean, there's a set of skills that, as
an individual, that I expectyou to have.
Number one is curiosity.
I want you to be absolutelycurious about your customer,
their environment, and genuinelycurious.
Like we all know the differencebetween an interrogation and
genuine curiosity.
One of the best reps that everdid this was a rep you and I
worked with in the past and hewas childlike in his questioning
(14:41):
.
He was fearless, he would askquestions and it was so
disarming that the customerwould answer them, and there
were questions that I'd be like,ooh, we shouldn't ask that.
But he was just genuinelycurious and he wanted to ask
that question.
He wanted to earnestly know,and that's so disarming and it's
great.
And so curiosity is number one.
The second is coachability.
(15:02):
I want someone some of the bestindividuals that I've ever
worked with had played athleticson an athletic team at some
level and they know whatcoaching feels like.
They don't take it badly, theywant it, they seek it and you
can give it to them verydirectly and they, they take
that on and they, they, theychange right and they try it.
(15:25):
The next call and I just had arep come into me five minutes
before we spoke hey, the thingyou were telling me.
I tried on this call and it didhelp and it worked.
Thank you, um.
The third one for me is a growthmindset.
I want someone who again wantsto grow, wants to intrinsically
get better.
I've worked with people intheir career that are late in
their career, and I've workedwith people early in their
(15:47):
career Like some of the folks onmy team at one of my stops were
in their 60s and that workedfor this environment and this
organization.
Some of them had a growthmindset, others didn't right,
and those again, when you'relater in your career, it's
easier to think you've got itall figured out, but I don't
know about you, but I haven'tgot it figured out.
I'm learning it every day.
I'm a first-time CRO.
(16:07):
There's things I learn everysingle day about how to do this
job better, and for me it'sabout that growth mindset.
And then the last one really isaround self-awareness is that
Are we self-aware of where weare good and where we're not?
One of the things that struckme about you on your last
podcast with the CRO from Gongwas you said look, there are
(16:30):
some things I need to get betterat, your self-awareness about
the things you need to getbetter at.
Personally, stuck with me, it'seasy for us to think that we've
all got it figured out.
We don't, and so I think thatthis self-awareness and ability
to reflect and and own them sothose are the more soft skills.
Speaker 1 (16:49):
What about the types of technical skills or other
sales skills associated withyour you know, coaching strategy
or how you'll develop folks?
Speaker 2 (16:57):
yeah, look, I mean, like I said, the number one is
that sort of domain skill.
So the domain skill in whatyou're selling, you need to be
as close to an expert as you canbe in that area.
Now it's going to be difficultbecause if you're selling into
an expert field you're nevergoing to be as expert as the
expert.
But you still need to have thatability and depth and knowledge
(17:20):
and curiosity to learn and togrow in these, like when I know,
when I was a new rep sellinginto banking, there's so much
about these large internationalbanks I know nothing about and
you learn and you guide and youdo that.
And then there's all those theselling skills and again, I'm
not going to go through all theselling skills, but there's
there's a ton of selling skillsaround better discovery.
One of the things we'restruggling with here right now,
(17:42):
frankly and again I'm not goingto go through all the selling
skills, but there's a ton ofselling skills around better
discovery.
One of the things we'restruggling with here right now,
frankly, is we do a lot oftechnical discovery and in my
diagnostics in the first 90 dayshere, I've realized we don't do
a lot of business discovery Ourpeople were so trained to do
technical discovery that theyknow everything about the
environment and they don'treally know the why behind the
problem.
And so here we're focusing ondigging into okay, be curious
(18:03):
about the business domain,understand what matters,
understand the impact of why afailure or something is
impactful for the business, andso there's a lot of skills like
that around negotiation.
I know for me, I'm alwaysreading because, like these
things like negotiation, that weall only do infrequently in
deals and we need got to getbetter at it.
(18:24):
Like we do a lot of discovery,we don't do as many negotiations
, and so we need to get betterat those.
Speaker 1 (18:31):
Wade, in your career you've been at varied businesses
at different sizes and indifferent levels of maturity
different levels of maturity.
Do you have you formulated acoaching framework Like is there
a process that Wade uses that'sindependent of the business
that you're in?
That helps give you confidencethat you can make the team
better, because you know whatI'm thinking of?
(18:51):
It's really funny.
It's like as somebody movesinto leadership, and especially
if they've been successful atsales, the sales team then goes
to them from help and the easierthing for the leader to do is
what?
Do it for them right?
It's the easiest thing, right.
And so now they start to builda dependency.
Now the leader is doing some ofthe things that the salesperson
finds more difficult and theindividual contributor isn't
(19:13):
learning.
In fact, they're learning adependency.
And so now the sales leader isdoing so much.
It didn't happen right away, ithappened slowly.
They started doing this for oneperson, then something else for
another, and this dependencystarts to build and all of a
sudden the salesperson has got apretty good life and the sales
manager is like burning outcompletely.
(19:33):
And so one of the challengesaround coaching is this whole
idea of like how do I getindividuals on my team to
perform at a high level but nottake the easy road, which is
that do it for them.
That's all right there,especially if you're actually
good at sales.
Speaker 2 (19:47):
Yeah, look, I've actually made that mistake.
I, in one of my stops, becamethe person who could deliver the
message the best and I wouldfind myself taking over these
sales calls and I realized thatat one point I was like this is
not helping anyone.
I felt pretty good about myselfbecause look at me, I'm really
good at delivering this andcustomers are being attracted.
(20:08):
But that's that supersalesperson and that just does
not work, and I think for meit's become a bias, for coaching
is while I had thisconversation in this last week
with one of my reps is that hewas talking about his
progression in his career,whether he wanted to be a sales
leader or not, and I said look.
I said all of us like the dealsyou're working on I view as my
(20:29):
deals.
I just delegated them to you toexecute on them and execute on
a well, your deals.
You should feel like you'rebringing people around you to
help you deliver them, but notbe dependent upon them and no
one's stepping in.
And so when I'm looking forleaders and we're hiring a bunch
of leaders right now, numberone is a bias for coaching, not
a bias for taking over, and Ithink for me that's one of the
(20:50):
skills that it's.
It's a hard one.
You have to have learned it,you have to have those battle
scars.
We're saying, yeah, I've triedthat it didn't work, and so
that's one of them.
But your question originally wasdo I have a framework that I
bring in?
And frankly, I don't have oneyet.
And it's one of those thingsthat I know what I value and I
(21:10):
know what I do and I'msituationally applying that.
But it's not been one of thosethings that I have really looked
at codifying a framework,because for me it's been each
environment is environmentslightly different.
I've got a set of things Ibelieve in and a set of things
that I I look for and I reallyapply those in differently and
independently.
So, like the business of activeVM was two-year sales cycles,
(21:33):
large financial servicesorganizations in the world, a
category that didn't exist.
So we're creating need in acategory, very different things
and we had to coach verydifferently than here, which is
known categories, technology,modernization, technology
replacement, different people intheir sales journeys, and so
for me I found that it's beenvery different.
So I haven't been able to applynecessarily a framework yet,
(21:55):
but I do have a set of thingsthat I believe in and believe in
deeply, and the things that Ialso know that I look out for
and make sure that I don't do.
Speaker 1 (22:02):
What are the things that are consistent?
Is it the frequency ofone-on-ones?
Is it the way you do callreviews?
Is it the way pipelinemanagement turns into
forecasting?
What are the tactics thatyou've learned that are helping
you?
Sometimes it's solving morethan one thing.
Coaching in and of itself isnice.
Speaker 2 (22:24):
Coaching within one thing, like coaching in and of
itself is nice.
Coaching within the context ofyour operating rhythm, as an
example, is like even better.
So one of the things that'sbeen new for me, so call
coaching has been awesome.
I've done that for a while.
We were talking about gomearlier, and call coaching
transformed everything.
What I find with with callreviews that way is it gives you
some independent insights.
But one of the things I justembarked on a project and just
got the results back was usingAI to do a longitudinal view
across all my projects and allmy sales calls, rather, and so
(22:46):
we took 141 sales calls, ranthrough an engine and looked for
those things that, across theboard, were not doing well, and
so for me, that gave me a lot ofpoints of coaching where I
didn't have to listen to 141calls.
Some of the things were thingsthat I had experienced, but some
of them I hadn't picked up onyet because it's difficult to do
that.
So I think that leveragingtechnology to do it has helped.
(23:09):
Definitely, call reviews,definitely one-on-ones.
I mean, I'm a big forone-on-ones.
I was in an organization thatsaid that maybe we shouldn't be
doing one-on-ones, we shouldonly be doing it in a team
setting?
I don't know for me I love aone-on-one because it's a chance
for us to have a very specificconversation.
I do like coaching individually, but I also like coaching in a
team setting because everyonelearns from it.
(23:30):
But I'm a big one for thatconversation, that structure.
Speaker 1 (23:34):
How's a one-on-one happen with Wade Like?
Is it structured?
Is it informal?
I'm literally trying to figureout because I also agree that
one on ones are important andyou know, but I am also a bit of
an extrovert.
So, like I like to interactwith people, I know other people
want a one on one only ifthere's like a detailed agenda,
(23:55):
because they like to be focusedon work and don't want to be
distracted.
How do you approach it?
Speaker 2 (24:01):
So what I've done is what I found is each individual
likes their one-on-ones to go adifferent way, and I've done it
where I've done them structuredand it didn't seem to fit all
the cases.
And so what I now do is I havea set of topics that I'd like to
go through right.
We typically talk about a deal,we typically talk about some of
the issues that they'reexperiencing in their pipeline
or whatever else, but it'sreally very specific in their
(24:22):
development.
But what I do is I put a listout and they can add topics to
the list.
Some of them come with a fulllist of topics that they've
thought out ahead of time.
Some of them show up and arewinging it, and it tells me
something whether they are sortof thinking about this and
investing in that time assomething in their development
or not.
If they sort of come in and wingit, that tells me one thing
(24:43):
it's not necessarily bad, itjust tells me something For
those that have.
All right, I've got 12 thingson my list I need to talk to you
today about, and they gothrough that right.
So for me I'd leave it a littlebit more open.
Definitely try to focus on thesimilar sort of topics in there,
but I let the rep also dictatewhat they need from me, because
in a lot of cases I'm servingthem in their ability to close
(25:06):
business on my behalf, and so Iwant them to also pull from me,
as opposed to me just alwayspushing into them.
Speaker 1 (25:13):
What does it say about some?
Like you do see highvariability in preparation for a
one-on-one with somebody seniorin the org, and I agree with
you, it doesn't like the levelof preparation doesn't
necessarily matter.
Like some people are just notfocused on that.
(25:34):
They have a list for the thingsthey're focused on, like maybe
their pipeline, but I don't knowwhat to extrapolate from that
huge variance in repetition.
I think perhaps as a leader,one of the things I think about
is am I setting a clear enoughstage around, like what a good
one-on-one should look like orwhat I consider to be, and
(25:54):
creating a bit of a roadmap tohow I think we make best use of
the time?
At the same time, it's not allabout me, so it's a tough
balance to kind of strike itmight be.
Speaker 2 (26:05):
It might be all about you.
Here's my thing is that whetheryou come in with a list or not
is a data point.
Whether you're prepared or notcan be something separate.
If you come in and you'reunprepared, we're going to talk
about you coming in unprepared.
That's going to be theconversation.
But if you come in prepared andyou don't have a list, that's
(26:25):
okay.
Some people use lists For us.
I tell you one of the thingsthat we do on calls which is, I
think, really valuable and it'sdifferent than what we're
talking about.
But we started this pre-callbrief and it's like a pilot does
before they take off, and ourreps jump on a call five to 10
minutes before the prospect andthey talk about that call, what
(26:46):
they're preparing to do, whatthey're preparing to learn, and
they do that.
They do that out loud to therecording so that they've really
prepared themselves for that.
So I do think that prep isimportant.
Speaker 1 (26:57):
This sounds interesting.
Let's talk about this pre-callbrief.
Speaker 2 (27:01):
Yeah, I have not heard this before I know like it
is something new here.
So our ceo is a pilot, um, andone of the things he believes is
that, as a pilot, the importantpart of flying the plane is
doing that pre-flight brief,making sure that everything like
the checklist manifesto.
If you haven't read a toolgawande's checklist manifesto,
love the book very simple, butit's really about we do the
(27:23):
things that we have a checklistfor and we get better at that
repetition.
And so his point of view on thiswas if you go into a call and
haven't really thought about andarticulated what your goals are
for the call, then you likelyare going to miss something.
And so the fact of preparingfor that pre-call brief, saying
it out loud okay, this is thecall I'm going into with this
(27:43):
person in this title, this iswhat I need to learn, this is
what I need to understand, thisis my goals for the meeting.
Then that allows me, as aleader as well, when I do a call
review, to see what they saidthey were going to accomplish
and where they were going andhow they actually executed
against that and it's much, it'sreally helpful.
My team started to get out ofdoing it a couple of weeks ago
(28:04):
and I was like, guys, thismatters, get back to doing it
again.
And now they've raised the baragain and they're doing it every
call.
So it's huge.
Speaker 1 (28:11):
Just the mechanism with which this happens.
How do they?
Speaker 2 (28:15):
they do it they jump on their zoom call.
So we use zoom with ourcustomers.
It's the same.
Speaker 1 (28:19):
Okay, so they jump into the zoom link for the
meeting that's coming up.
Speaker 2 (28:23):
They just jump in five minutes before the the
scheduled time and we use awaiting room, we use the waiting
room feature in zoom, so wedon't let the customer, we don't
let the prospect in yet, and so, like sometimes, a prospect
will join three minutes earlyand you're like you don't want
to be caught in the middle ofyour preflag yeah, yeah, 100
weird, but yes, we jump in fiveminutes early, we record that
and then we let them into thecall and so, um, I think it's, I
(28:46):
think it helps us make surewe're prepared again back to a
culture of being prepared.
That's the way, one of the ways,we're being prepared for those
calls you mentioned what I needto learn, goals for the meeting,
what else so it is.
Who am I meeting with?
What do I know about thebusiness?
This is john from thisorganization.
They do this sort of thing fromthe lead.
(29:11):
I understand that they havethis type of problem.
I need to dig into that problemsome more to find out this,
that and the other, and they'lltalk about that.
And then my goal for themeeting is to learn this and to
get this type of problem.
I need to dig into that problemsome more to find out this,
that and the other, and they'lltalk about that.
And then my goal for themeeting is to learn this and to
get this sort of outcome so wecan have a next step.
And so that'll be the way welay it out when you get into
subsequent calls.
So that's for a sort of firstdiscovery For subsequent calls.
We in our CRM are using thewinning by design spiced as our
(29:35):
framework, with medic as a layerin it, and what I've asked them
to do is for each one of thosewithin situation and pain have
the discovery questions writtenthat they want to ask in the
next subsequent calls.
So in their pre-flight or theirpre-call brief, they're going
back through those to make surethey know hey, I've got these
six questions.
I'm going to try to ask thesethree today to make sure that I
(29:56):
can move the deal forward and dothat as well.
So it's sort of bringing intheir own deal analysis, their
own assessment of where they arein their deal lifecycle into
that to make sure that theythought about.
You can't ask 20 questions in acall.
It becomes an interrogation.
So what are the three or fourthat really matter to move your
deal to the next stage.
Speaker 1 (30:17):
Really interesting how long on average is this
pre-call brief?
Is it a minute?
Is it a few minutes?
It's like two to three minutes.
Speaker 2 (30:27):
When you do it, you sort of feel like there's only
so much Now.
Speaker 1 (30:32):
some of them may last a little longer, but two to
three minutes, yeah, sure, itdepends on the situation.
But as somebody then that is,reviewing a call or reviewing a
deal with someone I'm guessingthat you are finding just that
early setup helpful in howyou'll process and digest what
(30:55):
you observe in the meetingitself.
Speaker 2 (30:59):
Yeah, yeah, and it helps the rep do that, because
they've already thought aboutwhere they're going.
They've thought about the milemarkers in this call that
they're going to try to hit.
It helps me and my managersalso review it, because you know
you go into a call you don'tknow what you're going to get.
You say I'm going to listen tothis call and it's like five
minutes of them just talkingabout the weekend and then
(31:20):
you're like, okay, where do weget to the meet?
And at least if I know wherethey're going, I can then listen
for those sort of things and Ican use the AI to ask those
questions as well.
Speaker 1 (31:29):
Yeah, have you helped equip the team with like I
don't know how to mostefficiently prepare a pre-gall
brief, or is it's like let themfigure out the way that works
for them?
Speaker 2 (31:43):
we've been.
We've been working onstandardizing that, reviewing
those and standardizing, and Ithink that to this it's there's
a certain individual style to it, but again, you need to have it
laid out and we need tounderstand what your goals are
for the call.
What do you know?
What are your goals are for thecall, what do you know, what
are your goals are and how doyou know when you've
accomplished what you set out todo in that call.
Speaker 1 (32:04):
I keep asking questions because I observe the
same thing.
And, look, there's a humanelement to being in sales,
especially when you are gettinginbound inquiries, which
obviously not everybody isfortunate to receive.
But you get into a groove,you're comfortable, you know
your domain as an example, andit's fun to learn from the
(32:27):
individuals that you're about toengage with.
And a thing that can fall downby the wayside is that
preparation.
And so, on the one hand, howshould I prepare?
You're looking to standardizethat but, more importantly than
the how is just the effort.
It's just the effort, and Ithink my hypothesis here is just
by simply doing that, to allthe points you made, the sales
(32:51):
rep now has a bit of discipline,can enter the conversation,
having done some work, and youhave a verification element
around that.
And then, as it relates tocoaching, you now know what the
because.
Think about a coaching call inthe absence of this.
Now I'm kind of playing withthis concept.
Is you start?
The first half of the coachingcall is like what were you
trying to achieve?
What was the goal of themeeting?
(33:12):
What was, what were you hopingto learn?
Which is like meeting.
Speaker 2 (33:15):
What were you hoping to learn?
Which in?
Speaker 1 (33:16):
hindsight is a very different answer.
Speaker 2 (33:19):
Yeah right, exactly.
It's easy to re-engineer whereyou got to right.
Speaker 1 (33:32):
I love those fun little things that we can do to
a small change that can have abig ripple effect on how our
team goes to market.
Speaker 2 (33:35):
I think the third one is you mentioned two aspects
that it provided, but also itprovides a different mindset for
the rep going in, their mindsetis slightly different than if
they just come in cold.
They come in, yes, they'reprepared, yes, they have a plan,
but they're also then with amindset of okay, I'm settled.
I can now get into this and Iknow where I'm going Because, to
(33:56):
your point, we get all inboundleads.
We're blessed with an allinbound motion today.
I've never been anywhere withthat.
It's awesome, love it.
Now I get to build an outbound,but the inbound is such high
variability and again, gettingthat lead and trying to figure
out what is this person tryingto accomplish today and what.
Where do I want to take themand how do I take them from
where they are to where itpoints to our differentiation.
(34:19):
And that's part of thatconversation and you need to be
prepared for it.
Speaker 1 (34:24):
Wade, I imagine in a high inbound environment, that
one of the challenges associatedis with qualification and
there's probably a chance thatthere's a high volume of
opportunities that will getdisqualified after a call.
Is it your view that thatpreparation or that pre-call
brief is still just as relevantin a world where there might be
a decent size disqualificationrate, or is there some type of
(34:44):
factoring into that?
Speaker 2 (34:46):
No, in fact, part of the pre-call brief is hey look,
I don't think this is going tobe a good fit for us.
I'm going to try to figure thisout and disqualify this as soon
as possible.
Some of them that come to uswill be a 10-person company with
, like, they've just started andthey've got a small budget and
you know what?
They're a good customer for us,but they're a good customer
through our self-service channel, not through the direct channel
(35:07):
.
And what I'm trying to trainthe reps on is every deal is not
a great deal for you.
Just because they're a goodcustomer for filescom doesn't
mean they're a good one for youas a seller.
So let's try to get them to theself-service channel and do
that.
We try to catch that as theSDRs, but some of them go
through.
But yeah, it is very useful forthose that you want to
disqualify out early.
Speaker 1 (35:28):
Yeah, so what I'm hearing you say is relevancy to
all, even if just doing thatpreparation will lead to getting
clarity that this should bedisqualified or not.
Yeah, yeah exactly Superinteresting.
What other tools are you using,what other ways are you seeing
to be able to prepare the teamto win more?
Speaker 2 (35:49):
So I go back to the conversation.
One of the things that I'mworking on right now is win rate
.
So our win rate, again againstindustry metrics, is probably
about six, seven points off ofwhere it should be, and part of
that AI project was findingthose places where we are not
doing.
We're not executing the way weneed to, and, for now, what
(36:10):
we're working on right now is aset of sales plays to be able to
put the rep in the bestposition.
I've got this strong belief andI don't know if you've thought
about this.
So when an NFL team gets theirgame plan for a game, they
script the first 10 plays of thegame, no matter down and
distance.
I'm going to run these plays inthis order and then after that
(36:32):
they've learned what the defenseis giving them, how they align,
like all the things you need tolearn in those first 10 plays,
and then you run down indistance, and I think that for
us, what we're working on isgetting those first two to three
calls really well understoodand then running a set of
situational plays after that.
And so what we're working onnow is how do you sell value
(36:55):
before price?
We get a lot of people in thefirst call hey, can you give me
your price?
And our reps were like givethem price out.
And all that happens when yougive price out in the first call
is they disqualify you becausethey're like oh, you're too
expensive, you've done a bunchof discovery and you've given
them a price.
There's no reason for them tothink you're worth that.
And so we're working on somethings in those first two to
three calls that are morescripted again, not fully
(37:17):
scripted, but like we know wherewe want you to go, we know how
you want to handle each of thesescenarios, and then from that
we're putting in a set of playsthat are then more situational
so it's just like a discoveryguide.
Speaker 1 (37:30):
Is that essentially what you're trying to do?
More than that?
Speaker 2 (37:33):
it's more than that, because discovery so.
So there's a big component ofthis discovery.
So for us again, I said earlierwe do a lot of technical
discovery, not much businessdiscovery.
So then the question is how doyou do better business discovery
?
How are you not just thrashingaround in the pool and like
asking a bunch of randomquestions?
How are you really getting tothe right questions in the right
way?
But the second is is that?
(37:54):
How do you then start toarticulate value early and
differentiation early?
What is the way to do that?
We're working on our shifting,our positioning and our
messaging to help that.
But also, how do you arm therep in that moment to start to
shift the conversation from thediscovery into the value
conversation?
One of the things we've got abad habit of doing I'm sure a
lot of people do is you can hearit in sales calls is how many
(38:17):
users do you have, how many ofthis, how many of that?
And they're really askingpricing questions, right, and
they're veiling them asdiscovery.
And it's not really discovery,it's just really pricing.
Like I'm trying to figure outhow to price.
And I think that one of thethings I've observed is that
customers realize what you'redoing.
Therefore, they're like okay,now can you give me a price,
because you've conditioned them.
But wait, so you're spot on Helpme understand what you're doing
(38:42):
to change that.
So what I'm doing is actuallyso a couple things One, stop
asking price questions in thefirst call.
That's what I'm sayingscripting.
The second call will be aboutpricing questions.
So make the first call abouttechnical and business discovery
.
We are then putting in a smallvignette type demo.
Again, it's not a full demo,but it's a little bit of.
(39:03):
We compete against reallyclunky old SFTP managed file
transfer servers that are justhorrible to use.
So I want them to show a littlebit of our product, because if
we say it's easy to use, there'sno baseline or metric for you
are much easier to use and I cansee why that's valuable.
So I want them to show a littlebit of the product and then I
(39:24):
want them to be able to get intosome some value conversation to
the next step.
So differentiation a little bitof demo and get out of that in
the first call and the secondcall will set up okay, we'll do
a proper demo for you and thendo some pricing discovery and
then we can then get to a priceeither by the end of the second
call or the third call.
But at least we've been able togo through our version of the
(39:44):
story and how do you handlethose questions which is, hey,
can you give me your price?
How do you handle that in thatmoment?
Do you give them a price?
Do you dance around?
I want them to be veryconsistent in how to handle that
question and so that they don'tfeel slimy, they have empathy
and it's honest, it's like, look, we don't lose on price, but I
don't know enough yet about yourenvironment.
(40:05):
I'd like to get into a littlebit more before we, before we go
into that, is that okay withyou?
And then it's, then it'ssomething that is is in the
customers best interest, asopposed to something where
you're being being, we arewithholding information from
them.
Speaker 1 (40:20):
Level of like change that you're observing as you
work this through?
Like.
Is it a hard change or is it,like, not that complicated?
Like?
How would you rate that?
Speaker 2 (40:33):
Look for me.
My sales team are incredibleand they're taking it on and
they're learning and they'reapplying it immediately.
So, again, depending on yourenvironment, I'm blessed with a
team that is just the right typeof people who are learning it,
and they are thirsty for thissort of change because they want
their win rates Again.
This whole project is for us,win rates.
(40:53):
We're focused on win rates, andthat focuses on putting money
in their pockets, and so theyall know why we're doing it.
We're not doing it for anyother reason other than we want
them to earn more, and sothey're taking it on and they're
trying it, and they're comingback and saying, okay, this
worked, this didn't.
Can you listen to my call andtell me what I did wrong or what
I could have done differently?
And, frankly, we're adjustingour scripts and what we think
(41:19):
our hypotheses don't alwayssurvive right, we think we know
what it is, but the six footconversation that we have is
really where it plays out, andif we're good at that and we
learn from that, we can helpthem get it better and better.
So it's on me and my leadershipteam to adapt and change the
battle plan with them to be ableto do that better.
Speaker 1 (41:35):
But if I paraphrase what you've been talking about,
it's like hey, we have anobjective which is to improve
our win rates by six to sevenpoints.
One of the reasons that wethink our win rates are lower
than they could be the six toseven points is because we
aren't having the value-basedconversation early on.
We're sort of going right into,like, offering price and
(41:58):
answering their questions, andthere's a belief that if we can
just push off that aspect of theprocess until later and just
focus on, like, maybe, somebusiness discovery and some
technical discovery for fit andget permission from the customer
to do that, that that will setus up for the customer to better
(42:18):
understand the value that theywould get, which would provide a
different lens when they get tothe actual price point.
And if we just do that, wethink that will have the biggest
impact in terms of improvingwin rates.
Is that a right way to thinkabout it?
Speaker 2 (42:33):
It is.
The only thing I would add tothat is that we've also
identified champion.
Enablement is an area where wefall down as well.
So, yes, we can do all that,but when the person that you're
talking with goes and takes itback to the economic buyer, are
they prepared to have thatconversation?
And we're getting much betterat doing that.
That's something that'sdifficult for someone in an
(42:53):
organization to go sell thatinternally and we want to be
again shoulder to shoulder withthem, helping them get this
project funded and going,because it's good for their
career and it's good for thempersonally to be able to get
this going, so we want to be theone to go alongside of them.
I don't know, you and I weretalking about being a buyer.
As sales leaders, we don'toften get to be buyers.
(43:15):
I was a buyer once for anaccount-based marketing software
and I have to tell you, everysales pitch sounded the same,
every product and every one.
I wanted to say get me to theproduct demo.
And every time I got to theproduct demo I was like I don't
care about your product, I can'ttell the difference.
I wanted someone to tell meaccount-based marketing
initiatives fail for these threereasons, and we'll help you
(43:37):
make sure that it doesn't fail,because, as a as a revenue
leader, if I had gone after anaccount based marketing um
software package and program andit's gone belly up, it would
have looked bad on me and that'sreally all I cared about.
And I don't think we do enoughof that is making sure that
people understand what it feelslike to buy and what and the
(43:57):
risks that we have.
Speaker 1 (43:58):
And that part of champion enablement is making
sure that person's confidentthat this will be successful,
and I don't think we would spendenough time on that yeah, and
that plays into some of thethings you mentioned around the
jolt effect and customerindecision laid in a deal and
how you got to have bringconfidence that, like I got you,
it's no longer about it's about?
Speaker 2 (44:18):
it's about like, hey, we're gonna go do some great
things here and we're gonna makeit a win yeah, and look, I mean
, that book for me is one of thebest books that in in selling,
that I've read in many years,and I think that one of the
things that I try to model andthis goes back to coaching with
my team is I've got a stack ofbooks on my desk.
I always, always amrecommending one.
You and I work for a leader whowould always talk about the
(44:38):
book he's reading, and I askedhim about why he did it.
He said because I want everyoneto know that I am an avid
learner and I don't care whetheryou read my book or not, but I
want you to have a point of viewon.
You're an avid learner too, andwe share books that are great
for us great for us and so likethat's.
Speaker 1 (44:56):
That's the sort of culture that I want to encourage
.
Well, we've actually referredto a couple of books here
Checklist Manifesto.
We've got Jolt Effect.
What's one more that maybeyou'd recommend for aspiring
leaders that you've recentlyread that had an impact on you?
Speaker 2 (45:05):
You know the one is.
Let me get the right title ofit, it was Super Communicators,
I think.
Have you read SuperCommunicators?
Speaker 1 (45:12):
I'm not.
Speaker 2 (45:13):
You know, this was one that, as I came here, the
leadership here had read, andit's about those people who, in
the way they talk, open upinformation in people that other
people don't.
And these super communicators,you can spot them and they're
the ones who ask the insightfulquestion, the question behind
(45:35):
the question, and they're theone who don't start with, hey,
so like, what do you do for work?
Right, that's like one of thosemost the trite ones.
Speaker 1 (45:43):
They're the ones where you're based Exactly.
I'm weathering Milwaukee today.
Speaker 2 (45:48):
Yeah, there's a guy actually from our past that
would said the best open endeddiscovery questions.
Hey, tell me your life story,because in that way yeah that's
yeah.
Yeah, I mean it's.
Yeah, I mean, when Brian saysthat, you think yeah, because
what he's doing is he's gettingyou to stop and think where do I
start and how do I learn?
And I think that finding thosesort of super communicators and
(46:11):
those skills as being a supercommunicator has been huge.
So yeah, that's another one,awesome, all right.
Speaker 1 (46:17):
Well, now I have homework coming out of this Wade
.
Where can people find you ifthey have any questions?
They want to follow up onanything we discussed.
Speaker 2 (46:24):
Yeah, so obviously on LinkedIn, happy to connect with
anyone.
I love having a big communityon LinkedIn and I'm happy to be
a resource to people there, andthen obviously, we can connect
over email.
Also, I'm a member of Pavilion,so if anyone's in Pavilion you
can hit me up through Pavilionas well.
But happy to be a resource andif you've got something I can
learn from you, I'd love to dothat as well.
Speaker 1 (46:45):
Well, wade, I want to thank you for being on Pillar
Talk.
It was great catching up withyou.
I can't wait to read a new bookand to get into this pre-call
brief aspects and some of theother areas we covered.
We'll talk to you soon AwesomeThanks.
Reflecting on the conversationwith Wade Callison, you know
(47:08):
Wade's been in sales and salesleadership now for so many years
.
I think I had forgotten aboutthe fact that before sales, wade
came from a product backgroundand I loved how he described his
transition into sales and itreminded me that sales as a job
often looks so easy to those onthe outside, but it's a totally
(47:29):
different ballgame once you'reon the inside, and it makes
sense to me that what led toWade's success and what he
continues to lean on today ishis technical and domain skills
in order to succeed, and it'swhat he looks for in new team
members as well.
We got into coaching, which Ilove.
An aspect of the interview thatstood out in that area was that
(47:52):
tactic that they enabled calledthe pre-call brief.
As Wade had mentioned, the CEOof Files is a pilot, and I love
this connection between apre-flight plan that a pilot
sets up in order to succeed onthe flight and the quote-unquote
flight that a seller is goingto go through in the journey
(48:13):
with a buyer and that simpletactic of spending the time to
define what the rep is hoping tolearn and the goals for the
meeting, that simple change.
It's not a big ask it creates.
To me it creates two thingsMore consistency in the prep of
a seller, meaning sellers aremore consistently preparing for
(48:34):
the meeting, which is just animportant discipline that we
foster.
That translates to better salesconversations.
But it also accelerates theleader or the manager's ability
to coach, because now themanager knows, going in, what to
actually be coaching for.
And lastly, I enjoyed the focusWade described for looking to
(48:58):
enact change in the organizationbased on like a single metric
In this case he talked about winrate and that Wade has found
just two areas of coachingopportunities in order to
improve win rate.
The two areas that Wadedescribed are getting to value
early instead of thoseinterrogative pricing related
(49:18):
questions, and then championenablement to help towards the
end of the deal.
I kind of think about like ifyou were trying to coach
somebody on a golf swing and youtried to tell them to work on
six different things.
Of course that's not going towork.
You got to start with like oneor two things and that's sort of
what wade is doing here in hiscoaching in order to affect a
single metric.
So, you know, wade now putshimself in a position to
(49:41):
actually help his team improveand that result actually helping
the team get better.
Well, that's what this podcastis all about.
So I want to thank wadecallison for joining in this
episode of pillar talk.
Thanks to ari smolin forproducing.
I want to thank eiler young andsons of summerolin for
producing.
I want to thank Isler Young andSons of Summer for the tunes
and I want to thank you forjoining.
We will see you next time, onthe next episode of Pillar Talk
(50:13):
hurts in me like the joke Ican't shake, I can't quit.
Speaker 2 (50:17):
It's never really what you said it was.
All you're doing is break thetrust.
Hello everyone and welcome to another episode of
Pillar Talk, where we build thefoundations of sales leadership
and create clarity in terms ofwhat good looks like for current
and aspiring sales leaders.
Before we jump in, I alwayslike to review what the six
pillars of successful salesleadership are, or what I came
up with to try to define whatthe behaviors of good leadership
(00:40):
is in a sales leadershipcapacity.
It starts with talent,identification and attraction.
Obviously, building andmaintaining the team of winners
is critical to success.
Building your overall operatingrhythm of how you run the
business.
Business planning, which isyour cross-functional
collaboration to make decisionsfor the future rather than
(01:01):
continuously reacting to theevents that are happening to you
.
We have communication, which, inthe world we live in today,
takes many mediums and manyforms.
Ownership, which is about howmuch do you, as a leader, do on
your own versus looking fordirection, and it's also about
how much are you about your teamversus being about the business
(01:22):
, and how do you find balancebetween the two.
The last one and obviously like, at the end of the day, when
you're in sales trying to grow abusiness, mastering the craft,
how do you help your team win?
So we've got lots of elementsthat we explore in this podcast
to try to provide tacticalinsights and actions to help
aspiring leaders be better atthe actual task of sales
(01:43):
leadership.
So today joining us on PillarTalk, we have Wade Callison.
Wade is a sales leadercurrently serving as the CRO of
Filescom, a file transferautomation company.
Along with many other thingsthat Files can do, wade
previously served in salesleadership positions at ActiveVM
(02:05):
, squid and Intralinks, just toname a few.
Wade, welcome to Pillar Talk.
Speaker 2 (02:11):
Thanks, rick, good to be here.
Speaker 1 (02:13):
Yeah, it's good to be with you.
So, Wade, you recentlyrelocated from the Northeast
down to Texas.
What's one story of surprisethat you didn't anticipate in
terms of doing that of surprisethat you didn't anticipate in
terms of doing that.
Speaker 2 (02:26):
You know it's just been the all the logistics of
relocating.
We've been in the Northeast for16 years and you end up
accumulating a lot of life withfour kids over 16 years and for
us it's just been all thelogistics.
It's been exciting, but it'sdefinitely been been something
that has taxed us over the lastfew months, especially with
(02:47):
starting a new job.
Starting a new job and movingit's like all the major
stressors of your life all inthe same way.
But we're loving being down inAustin.
It's a great city.
It's been really welcoming tous, so it's been a lot of fun.
Speaker 1 (03:00):
Well, congratulations .
Thank you, wade.
When our paths have crossed inthe past, one of the roles that
I observed you perform in is asprobably the most strategic
account executive in theorganization.
You did not work in a contextwhere you had a repeatable
solution and you simply went andtried to maximize the volume of
purchases that got made, butyou had to create solutions on a
(03:22):
curated basis based onstrategic customers, and so I
thought what we would covertoday is focus on mastering the
craft I saved.
You know the best for last yearand how you evolved in the days
of being a strategic accountexecutive into a leader that is
helping to coach and help theteam ultimately win.
As you have grown in aleadership capacity, were there
(03:45):
any formative moments?
Were there any lessons learnedalong the way that helped set
the stage for how youpragmatically or practically
coach and help your team wintoday?
Speaker 2 (03:57):
Yeah, look for me.
I didn't come to sales in thetypical journey.
I didn't come out of collegeand go to be a BDR or a
salesperson.
I really spent a bulk of mycareer in consulting in product
companies.
In fact, when you and I firstmet, I was running a product
organization and was enjoyingand loving that and I felt like
(04:17):
my whole career that I was a bitof a closeted salesperson.
I was always a salesperson butnever actually had the guts to
go be one.
And I went to our former chiefrevenue officer, who ended up
becoming the CEO, and I said tohim after a sales kickoff I
stood on stage and rolled outthis brand new product and then
afterwards I said to him I saidI think I want to be a
(04:37):
salesperson and he's like do youthink you can be a salesperson?
I said I think I can.
He said if you can't, I'll fireyou.
I said if I can't do it, youshould fire me, right?
And so I went into being asalesperson, thinking that it
was just those intrinsic skills,like, oh, I'm a good
salesperson, I think I can be agood salesperson because I have,
I think, the intrinsic skills.
(04:58):
And what I quickly realized isI knew nothing about selling,
like mean again, we have theseintrinsic skills, but like I had
to become a student of the gameand I had to learn and I had no
idea what I was doing and andit really comes back to some of
the core points which is, Ithink intrinsically someone has
to want to learn and grow andfrom that there's so much you
(05:19):
can pour into them and for me itwas that right.
It was that moment of having alot of experience and thinking
you know what you're doing andfiguring it out and having those
people teach me.
Speaker 1 (05:30):
Yeah, that's really funny.
It reminds me just.
A lot of people think you knowthe sales team is, like you know
, higher compensation.
It's easy.
They just complain aboutproduct like different things,
like I could do that, and whenyou're thrust in it it's a very
different experience it's sohard.
Speaker 2 (05:45):
It's so hard like when I, when I first met with
our cro, he showed me one of theorganizations I was selling to
and we put an order.
He goes who do you know?
And I had one name for thisglobal bank and he's like okay,
next time we meet you shouldknow more of the people there.
And we built out the org.
But, like again, these are theskills that you just have to
pour into people.
Speaker 1 (06:05):
So, as you entered a sort of sales career and again
this is going to lead to how youcoach today you got thrust in
and saw from the deep end, so tospeak, the challenges
associated with success in youknow, winning deals, hitting
numbers, doing that type ofthing, and your realization
about how important you knowcoaching is going to be to the
(06:26):
success here was in once youwere thrust in.
Was there a time, as youstarted to evolve and succeed,
where you were able to get thetype of coaching that impacted
you or you know able to get thetype of coaching that impacted
you or, you know, enabled you tobe?
Speaker 2 (06:41):
better equipped to succeed.
Absolutely like everywhere I'vebeen, I've looked for that
ability for my leadership to beable to impart wisdom upon me,
like when I went to squid.
Squid was an interesting placefor me because I had been again
advanced in my career I'd been aseller but I hadn't gotten all
the skills of being a salesleader and I found a CRO who was
(07:05):
just a servant leader who wouldpour himself into me and into
his team and would allow you tofail, would help you, coach you
and help you coach other people,and I think it's finding those
mentors in each of our lives,like for me it was those people,
but also it's the peers that Ihave that I go to.
Like I've called you at timesfor help.
(07:26):
I've called other sales leadersthat are my peers for help.
I think it's all about findingthose people around you that can
help you understand and helpyou learn those skills that you
need.
Speaker 1 (07:37):
So when you had great mentorship, as an example CRO
at Squid, are there any storiesof how that came to build up
your ability to impact others?
Speaker 2 (07:48):
Yeah.
So what he was really good atwas this cadence of look always
be open and communicate, butthen also build in the technical
skills with the team.
So we would obviously all of usgoing to be working on
discovery skills and negotiationeverything else but one of the
things he believed which is Ibelieve deeply is that sellers
(08:08):
need to be a have full commandover their domain and in having
command over your domain, thebest sellers like in the jolt
effect when you read MattDixon's book and Ted McKenna the
seller that can carry the dealthe furthest without relying on
their team around them is theone that is viewed with
credibility and the one that cansit shoulder to shoulder with
(08:29):
the customer and help them solvea problem, as opposed to being
across the table trying to do acommercial agreement.
That's very clearly not ineveryone's best interest, right?
So I think that making sure andone of the things that Rob did
well, the CRO was we had amonthly talking tech where we
went deep into topics that thesales team needed to know, and
(08:53):
because of my product background, my computer science background
, that's how I always sold.
I always sold from a place ofcredibility and it always helped
me and in fact I've had a CTOof one of the large law firms.
Stop me, he goes.
You don't feel like any othersalesperson.
I'll say what do you mean?
He goes you feel like you knowa lot about the topic you're
selling and I think that's whatI value in my team, the team
(09:15):
I've got here at Files.
That's the skill that I valuethe most, and why it was a good
fit for me is that my CEO and Iboth believe that you should be
as close to an expert in yourdomain on the topic that you're
selling, not just an expert inselling, and it makes a huge
difference.
Speaker 1 (09:34):
Now, when you say domain, you're referring to the
context.
It's not just the product, it'snot just the market, it's where
those two elements meet.
One of the things that isinteresting to me, wade, is that
the path for a successfulseller isn't a one-size-fits-all
, and so some can lean intotheir expertise.
(09:55):
So, for example, in my currentcompany we basically hire sales
team members that come fromindustry the taxonomy, the my
current company we basicallyhire sales team members that
come from industry the taxonomy,the pain points.
It's a vertical SaaS businessthat's so far in our growth, you
know, provides higherconfidence of their success.
So they do tend to have muchmore subject matter expertise.
But that's not the only optionhere.
(10:16):
It sounds like in your career,what's given you the most
comfort around your path tosuccess is around building that
level of like.
I understand the customer, Iunderstand the problem, I
understand how we meet thatproblem along the way and I can
engage successfully because I'mbringing real expertise to.
You know any given salessituation.
Did you find that?
That you know like there wereother paths where you had to
(10:39):
coach a little bit differentlyon somebody that maybe their
skill set isn't as strong in thetechnical sides, but they bring
much more process.
They bring much more structureand other elements of the deal,
and how have you handled it?
Speaker 2 (10:51):
Yeah, and I should say, like with yours, yours is
verticalized.
I've tended in my career to gowith horizontal platforms, ones
that one of my sales reps saidwere more liquid than solids.
We're not selling a solid thing, we're really being more
consultative in the selling.
So those are the sorts ofenvironments I lean into and the
sorts of environments that Ilike.
Which then changes the sellingskills, and I think to your
(11:12):
point is that we do get peoplewho have industry experience,
but it's more around thehorizontal.
So for us here it's aroundnetwork infrastructure, it's
around the protocols onbusiness-to-business integration
, sftp, managed file transfer,these sorts of things, and so
you need to understand thatdomain, you need to understand
(11:32):
the architectures, because whenyou're talking with our
customers and I've said this toone of my reps yesterday we see
more of those than any of ourcustomers who are buying.
We know what it takes tomigrate from one legacy
environment to the cloud, andour customers are doing it for
the first, maybe second time intheir career, and so we need to
(11:53):
be able to provide that sort ofguidance.
And so if you are deep intothis domain, if you care and
you're curious about what ittakes to do that, then we can be
that Sherpa that helps them ontheir journey to get to more
success.
Speaker 1 (12:06):
So sure.
So you, as an individualcontributor, leaned into your
technical skills andunderstanding the customer and
the problem as a way to helpsolve issues for them, which is
fantastic.
You then become a leader andnow you've got a whole team of
people, and one of the things anew leader tends to run into is
that the path that works forthem isn't necessarily the same
(12:28):
for all the individuals.
How did you address thatdynamic where everybody on your
team wasn't just like you?
Speaker 2 (12:35):
Yeah, no, and thank goodness they're not.
It would be a horrible team ifit was.
Yeah, no, and thank goodnessthey're not.
(12:55):
It would be a horrible team ifit was.
Look, it's about a as me, but Ido think there's some things
that really matter in being ableto sell and sell effectively,
and those skills are things thatwe sit and diagnose.
I work with my managers to sitand diagnose and then to invest
in the individual.
But again, I think for me it'sone thing for us to diagnose
that, but the individual sellerhas to know and recognize that
(13:20):
and want that feedback and wantto grow.
I just had a one-on-one with oneof my reps yesterday.
He said can we make ourone-on-ones longer?
There's so many things I wantto learn and so many ways I want
to develop and I need more timewith you to be able to do that.
And that's the sort of personthat I'm willing to pour all of
my time into, because they'rethe ones that are listening to a
thousand gong calls, likeanyone who listens to more gong
(13:41):
calls than I do is probablysomeone who's trying to get to
the next level.
Those are some of theindicators I look for and so,
yeah, it is difficult, but again, it's about a plan, for what
are the skills that you arelacking?
Whether they're technical,whether they're selling, whether
they're just interpersonalskills Like empathy for me, is
one of the biggest skills that Ithink, as a seller, we need to
(14:01):
have, and we need to understandwhat it means to buy and the
risks that it takes to buy inthis sort of environment.
Speaker 1 (14:09):
Do you have a list of skills that you've sort of
developed that define how youcoach?
Speaker 2 (14:17):
Yeah, so I mean, there's a set of skills that, as
an individual, that I expectyou to have.
Number one is curiosity.
I want you to be absolutelycurious about your customer,
their environment, and genuinelycurious.
Like we all know the differencebetween an interrogation and
genuine curiosity.
One of the best reps that everdid this was a rep you and I
worked with in the past and hewas childlike in his questioning
(14:41):
.
He was fearless, he would askquestions and it was so
disarming that the customerwould answer them, and there
were questions that I'd be like,ooh, we shouldn't ask that.
But he was just genuinelycurious and he wanted to ask
that question.
He wanted to earnestly know,and that's so disarming and it's
great.
And so curiosity is number one.
The second is coachability.
(15:02):
I want someone some of the bestindividuals that I've ever
worked with had played athleticson an athletic team at some
level and they know whatcoaching feels like.
They don't take it badly, theywant it, they seek it and you
can give it to them verydirectly and they, they take
that on and they, they, theychange right and they try it.
(15:25):
The next call and I just had arep come into me five minutes
before we spoke hey, the thingyou were telling me.
I tried on this call and it didhelp and it worked.
Thank you, um.
The third one for me is a growthmindset.
I want someone who again wantsto grow, wants to intrinsically
get better.
I've worked with people intheir career that are late in
their career, and I've workedwith people early in their
(15:47):
career Like some of the folks onmy team at one of my stops were
in their 60s and that workedfor this environment and this
organization.
Some of them had a growthmindset, others didn't right,
and those again, when you'relater in your career, it's
easier to think you've got itall figured out, but I don't
know about you, but I haven'tgot it figured out.
I'm learning it every day.
I'm a first-time CRO.
(16:07):
There's things I learn everysingle day about how to do this
job better, and for me it'sabout that growth mindset.
And then the last one really isaround self-awareness is that
Are we self-aware of where weare good and where we're not?
One of the things that struckme about you on your last
podcast with the CRO from Gongwas you said look, there are
(16:30):
some things I need to get betterat, your self-awareness about
the things you need to getbetter at.
Personally, stuck with me, it'seasy for us to think that we've
all got it figured out.
We don't, and so I think thatthis self-awareness and ability
to reflect and and own them sothose are the more soft skills.
Speaker 1 (16:49):
What about the types of technical skills or other
sales skills associated withyour you know, coaching strategy
or how you'll develop folks?
Speaker 2 (16:57):
yeah, look, I mean, like I said, the number one is
that sort of domain skill.
So the domain skill in whatyou're selling, you need to be
as close to an expert as you canbe in that area.
Now it's going to be difficultbecause if you're selling into
an expert field you're nevergoing to be as expert as the
expert.
But you still need to have thatability and depth and knowledge
(17:20):
and curiosity to learn and togrow in these, like when I know,
when I was a new rep sellinginto banking, there's so much
about these large internationalbanks I know nothing about and
you learn and you guide and youdo that.
And then there's all those theselling skills and again, I'm
not going to go through all theselling skills, but there's
there's a ton of selling skillsaround better discovery.
One of the things we'restruggling with here right now,
(17:42):
frankly and again I'm not goingto go through all the selling
skills, but there's a ton ofselling skills around better
discovery.
One of the things we'restruggling with here right now,
frankly, is we do a lot oftechnical discovery and in my
diagnostics in the first 90 dayshere, I've realized we don't do
a lot of business discovery Ourpeople were so trained to do
technical discovery that theyknow everything about the
environment and they don'treally know the why behind the
problem.
And so here we're focusing ondigging into okay, be curious
(18:03):
about the business domain,understand what matters,
understand the impact of why afailure or something is
impactful for the business, andso there's a lot of skills like
that around negotiation.
I know for me, I'm alwaysreading because, like these
things like negotiation, that weall only do infrequently in
deals and we need got to getbetter at it.
(18:24):
Like we do a lot of discovery,we don't do as many negotiations
, and so we need to get betterat those.
Speaker 1 (18:31):
Wade, in your career you've been at varied businesses
at different sizes and indifferent levels of maturity
different levels of maturity.
Do you have you formulated acoaching framework Like is there
a process that Wade uses that'sindependent of the business
that you're in?
That helps give you confidencethat you can make the team
better, because you know whatI'm thinking of?
(18:51):
It's really funny.
It's like as somebody movesinto leadership, and especially
if they've been successful atsales, the sales team then goes
to them from help and the easierthing for the leader to do is
what?
Do it for them right?
It's the easiest thing, right.
And so now they start to builda dependency.
Now the leader is doing some ofthe things that the salesperson
finds more difficult and theindividual contributor isn't
(19:13):
learning.
In fact, they're learning adependency.
And so now the sales leader isdoing so much.
It didn't happen right away, ithappened slowly.
They started doing this for oneperson, then something else for
another, and this dependencystarts to build and all of a
sudden the salesperson has got apretty good life and the sales
manager is like burning outcompletely.
(19:33):
And so one of the challengesaround coaching is this whole
idea of like how do I getindividuals on my team to
perform at a high level but nottake the easy road, which is
that do it for them.
That's all right there,especially if you're actually
good at sales.
Speaker 2 (19:47):
Yeah, look, I've actually made that mistake.
I, in one of my stops, becamethe person who could deliver the
message the best and I wouldfind myself taking over these
sales calls and I realized thatat one point I was like this is
not helping anyone.
I felt pretty good about myselfbecause look at me, I'm really
good at delivering this andcustomers are being attracted.
(20:08):
But that's that supersalesperson and that just does
not work, and I think for meit's become a bias, for coaching
is while I had thisconversation in this last week
with one of my reps is that hewas talking about his
progression in his career,whether he wanted to be a sales
leader or not, and I said look.
I said all of us like the dealsyou're working on I view as my
(20:29):
deals.
I just delegated them to you toexecute on them and execute on
a well, your deals.
You should feel like you'rebringing people around you to
help you deliver them, but notbe dependent upon them and no
one's stepping in.
And so when I'm looking forleaders and we're hiring a bunch
of leaders right now, numberone is a bias for coaching, not
a bias for taking over, and Ithink for me that's one of the
(20:50):
skills that it's.
It's a hard one.
You have to have learned it,you have to have those battle
scars.
We're saying, yeah, I've triedthat it didn't work, and so
that's one of them.
But your question originally wasdo I have a framework that I
bring in?
And frankly, I don't have oneyet.
And it's one of those thingsthat I know what I value and I
(21:10):
know what I do and I'msituationally applying that.
But it's not been one of thosethings that I have really looked
at codifying a framework,because for me it's been each
environment is environmentslightly different.
I've got a set of things Ibelieve in and a set of things
that I I look for and I reallyapply those in differently and
independently.
So, like the business of activeVM was two-year sales cycles,
(21:33):
large financial servicesorganizations in the world, a
category that didn't exist.
So we're creating need in acategory, very different things
and we had to coach verydifferently than here, which is
known categories, technology,modernization, technology
replacement, different people intheir sales journeys, and so
for me I found that it's beenvery different.
So I haven't been able to applynecessarily a framework yet,
(21:55):
but I do have a set of thingsthat I believe in and believe in
deeply, and the things that Ialso know that I look out for
and make sure that I don't do.
Speaker 1 (22:02):
What are the things that are consistent?
Is it the frequency ofone-on-ones?
Is it the way you do callreviews?
Is it the way pipelinemanagement turns into
forecasting?
What are the tactics thatyou've learned that are helping
you?
Sometimes it's solving morethan one thing.
Coaching in and of itself isnice.
Speaker 2 (22:24):
Coaching within one thing, like coaching in and of
itself is nice.
Coaching within the context ofyour operating rhythm, as an
example, is like even better.
So one of the things that'sbeen new for me, so call
coaching has been awesome.
I've done that for a while.
We were talking about gomearlier, and call coaching
transformed everything.
What I find with with callreviews that way is it gives you
some independent insights.
But one of the things I justembarked on a project and just
got the results back was usingAI to do a longitudinal view
across all my projects and allmy sales calls, rather, and so
(22:46):
we took 141 sales calls, ranthrough an engine and looked for
those things that, across theboard, were not doing well, and
so for me, that gave me a lot ofpoints of coaching where I
didn't have to listen to 141calls.
Some of the things were thingsthat I had experienced, but some
of them I hadn't picked up onyet because it's difficult to do
that.
So I think that leveragingtechnology to do it has helped.
(23:09):
Definitely, call reviews,definitely one-on-ones.
I mean, I'm a big forone-on-ones.
I was in an organization thatsaid that maybe we shouldn't be
doing one-on-ones, we shouldonly be doing it in a team
setting?
I don't know for me I love aone-on-one because it's a chance
for us to have a very specificconversation.
I do like coaching individually, but I also like coaching in a
team setting because everyonelearns from it.
(23:30):
But I'm a big one for thatconversation, that structure.
Speaker 1 (23:34):
How's a one-on-one happen with Wade Like?
Is it structured?
Is it informal?
I'm literally trying to figureout because I also agree that
one on ones are important andyou know, but I am also a bit of
an extrovert.
So, like I like to interactwith people, I know other people
want a one on one only ifthere's like a detailed agenda,
(23:55):
because they like to be focusedon work and don't want to be
distracted.
How do you approach it?
Speaker 2 (24:01):
So what I've done is what I found is each individual
likes their one-on-ones to go adifferent way, and I've done it
where I've done them structuredand it didn't seem to fit all
the cases.
And so what I now do is I havea set of topics that I'd like to
go through right.
We typically talk about a deal,we typically talk about some of
the issues that they'reexperiencing in their pipeline
or whatever else, but it'sreally very specific in their
(24:22):
development.
But what I do is I put a listout and they can add topics to
the list.
Some of them come with a fulllist of topics that they've
thought out ahead of time.
Some of them show up and arewinging it, and it tells me
something whether they are sortof thinking about this and
investing in that time assomething in their development
or not.
If they sort of come in and wingit, that tells me one thing
(24:43):
it's not necessarily bad, itjust tells me something For
those that have.
All right, I've got 12 thingson my list I need to talk to you
today about, and they gothrough that right.
So for me I'd leave it a littlebit more open.
Definitely try to focus on thesimilar sort of topics in there,
but I let the rep also dictatewhat they need from me, because
in a lot of cases I'm servingthem in their ability to close
(25:06):
business on my behalf, and so Iwant them to also pull from me,
as opposed to me just alwayspushing into them.
Speaker 1 (25:13):
What does it say about some?
Like you do see highvariability in preparation for a
one-on-one with somebody seniorin the org, and I agree with
you, it doesn't like the levelof preparation doesn't
necessarily matter.
Like some people are just notfocused on that.
(25:34):
They have a list for the thingsthey're focused on, like maybe
their pipeline, but I don't knowwhat to extrapolate from that
huge variance in repetition.
I think perhaps as a leader,one of the things I think about
is am I setting a clear enoughstage around, like what a good
one-on-one should look like orwhat I consider to be, and
(25:54):
creating a bit of a roadmap tohow I think we make best use of
the time?
At the same time, it's not allabout me, so it's a tough
balance to kind of strike itmight be.
Speaker 2 (26:05):
It might be all about you.
Here's my thing is that whetheryou come in with a list or not
is a data point.
Whether you're prepared or notcan be something separate.
If you come in and you'reunprepared, we're going to talk
about you coming in unprepared.
That's going to be theconversation.
But if you come in prepared andyou don't have a list, that's
(26:25):
okay.
Some people use lists For us.
I tell you one of the thingsthat we do on calls which is, I
think, really valuable and it'sdifferent than what we're
talking about.
But we started this pre-callbrief and it's like a pilot does
before they take off, and ourreps jump on a call five to 10
minutes before the prospect andthey talk about that call, what
(26:46):
they're preparing to do, whatthey're preparing to learn, and
they do that.
They do that out loud to therecording so that they've really
prepared themselves for that.
So I do think that prep isimportant.
Speaker 1 (26:57):
This sounds interesting.
Let's talk about this pre-callbrief.
Speaker 2 (27:01):
Yeah, I have not heard this before I know like it
is something new here.
So our ceo is a pilot, um, andone of the things he believes is
that, as a pilot, the importantpart of flying the plane is
doing that pre-flight brief,making sure that everything like
the checklist manifesto.
If you haven't read a toolgawande's checklist manifesto,
love the book very simple, butit's really about we do the
(27:23):
things that we have a checklistfor and we get better at that
repetition.
And so his point of view on thiswas if you go into a call and
haven't really thought about andarticulated what your goals are
for the call, then you likelyare going to miss something.
And so the fact of preparingfor that pre-call brief, saying
it out loud okay, this is thecall I'm going into with this
(27:43):
person in this title, this iswhat I need to learn, this is
what I need to understand, thisis my goals for the meeting.
Then that allows me, as aleader as well, when I do a call
review, to see what they saidthey were going to accomplish
and where they were going andhow they actually executed
against that and it's much, it'sreally helpful.
My team started to get out ofdoing it a couple of weeks ago
(28:04):
and I was like, guys, thismatters, get back to doing it
again.
And now they've raised the baragain and they're doing it every
call.
So it's huge.
Speaker 1 (28:11):
Just the mechanism with which this happens.
How do they?
Speaker 2 (28:15):
they do it they jump on their zoom call.
So we use zoom with ourcustomers.
It's the same.
Speaker 1 (28:19):
Okay, so they jump into the zoom link for the
meeting that's coming up.
Speaker 2 (28:23):
They just jump in five minutes before the the
scheduled time and we use awaiting room, we use the waiting
room feature in zoom, so wedon't let the customer, we don't
let the prospect in yet, and so, like sometimes, a prospect
will join three minutes earlyand you're like you don't want
to be caught in the middle ofyour preflag yeah, yeah, 100
weird, but yes, we jump in fiveminutes early, we record that
and then we let them into thecall and so, um, I think it's, I
(28:46):
think it helps us make surewe're prepared again back to a
culture of being prepared.
That's the way, one of the ways,we're being prepared for those
calls you mentioned what I needto learn, goals for the meeting,
what else so it is.
Who am I meeting with?
What do I know about thebusiness?
This is john from thisorganization.
They do this sort of thing fromthe lead.
(29:11):
I understand that they havethis type of problem.
I need to dig into that problemsome more to find out this,
that and the other, and they'lltalk about that.
And then my goal for themeeting is to learn this and to
get this type of problem.
I need to dig into that problemsome more to find out this,
that and the other, and they'lltalk about that.
And then my goal for themeeting is to learn this and to
get this sort of outcome so wecan have a next step.
And so that'll be the way welay it out when you get into
subsequent calls.
So that's for a sort of firstdiscovery For subsequent calls.
We in our CRM are using thewinning by design spiced as our
(29:35):
framework, with medic as a layerin it, and what I've asked them
to do is for each one of thosewithin situation and pain have
the discovery questions writtenthat they want to ask in the
next subsequent calls.
So in their pre-flight or theirpre-call brief, they're going
back through those to make surethey know hey, I've got these
six questions.
I'm going to try to ask thesethree today to make sure that I
(29:56):
can move the deal forward and dothat as well.
So it's sort of bringing intheir own deal analysis, their
own assessment of where they arein their deal lifecycle into
that to make sure that theythought about.
You can't ask 20 questions in acall.
It becomes an interrogation.
So what are the three or fourthat really matter to move your
deal to the next stage.
Speaker 1 (30:17):
Really interesting how long on average is this
pre-call brief?
Is it a minute?
Is it a few minutes?
It's like two to three minutes.
Speaker 2 (30:27):
When you do it, you sort of feel like there's only
so much Now.
Speaker 1 (30:32):
some of them may last a little longer, but two to
three minutes, yeah, sure, itdepends on the situation.
But as somebody then that is,reviewing a call or reviewing a
deal with someone I'm guessingthat you are finding just that
early setup helpful in howyou'll process and digest what
(30:55):
you observe in the meetingitself.
Speaker 2 (30:59):
Yeah, yeah, and it helps the rep do that, because
they've already thought aboutwhere they're going.
They've thought about the milemarkers in this call that
they're going to try to hit.
It helps me and my managersalso review it, because you know
you go into a call you don'tknow what you're going to get.
You say I'm going to listen tothis call and it's like five
minutes of them just talkingabout the weekend and then
(31:20):
you're like, okay, where do weget to the meet?
And at least if I know wherethey're going, I can then listen
for those sort of things and Ican use the AI to ask those
questions as well.
Speaker 1 (31:29):
Yeah, have you helped equip the team with like I
don't know how to mostefficiently prepare a pre-gall
brief, or is it's like let themfigure out the way that works
for them?
Speaker 2 (31:43):
we've been.
We've been working onstandardizing that, reviewing
those and standardizing, and Ithink that to this it's there's
a certain individual style to it, but again, you need to have it
laid out and we need tounderstand what your goals are
for the call.
What do you know?
What are your goals are for thecall, what do you know, what
are your goals are and how doyou know when you've
accomplished what you set out todo in that call.
Speaker 1 (32:04):
I keep asking questions because I observe the
same thing.
And, look, there's a humanelement to being in sales,
especially when you are gettinginbound inquiries, which
obviously not everybody isfortunate to receive.
But you get into a groove,you're comfortable, you know
your domain as an example, andit's fun to learn from the
(32:27):
individuals that you're about toengage with.
And a thing that can fall downby the wayside is that
preparation.
And so, on the one hand, howshould I prepare?
You're looking to standardizethat but, more importantly than
the how is just the effort.
It's just the effort, and Ithink my hypothesis here is just
by simply doing that, to allthe points you made, the sales
(32:51):
rep now has a bit of discipline,can enter the conversation,
having done some work, and youhave a verification element
around that.
And then, as it relates tocoaching, you now know what the
because.
Think about a coaching call inthe absence of this.
Now I'm kind of playing withthis concept.
Is you start?
The first half of the coachingcall is like what were you
trying to achieve?
What was the goal of themeeting?
(33:12):
What was, what were you hopingto learn?
Which is like meeting.
Speaker 2 (33:15):
What were you hoping to learn?
Which in?
Speaker 1 (33:16):
hindsight is a very different answer.
Speaker 2 (33:19):
Yeah right, exactly.
It's easy to re-engineer whereyou got to right.
Speaker 1 (33:32):
I love those fun little things that we can do to
a small change that can have abig ripple effect on how our
team goes to market.
Speaker 2 (33:35):
I think the third one is you mentioned two aspects
that it provided, but also itprovides a different mindset for
the rep going in, their mindsetis slightly different than if
they just come in cold.
They come in, yes, they'reprepared, yes, they have a plan,
but they're also then with amindset of okay, I'm settled.
I can now get into this and Iknow where I'm going Because, to
(33:56):
your point, we get all inboundleads.
We're blessed with an allinbound motion today.
I've never been anywhere withthat.
It's awesome, love it.
Now I get to build an outbound,but the inbound is such high
variability and again, gettingthat lead and trying to figure
out what is this person tryingto accomplish today and what.
Where do I want to take themand how do I take them from
where they are to where itpoints to our differentiation.
(34:19):
And that's part of thatconversation and you need to be
prepared for it.
Speaker 1 (34:24):
Wade, I imagine in a high inbound environment, that
one of the challenges associatedis with qualification and
there's probably a chance thatthere's a high volume of
opportunities that will getdisqualified after a call.
Is it your view that thatpreparation or that pre-call
brief is still just as relevantin a world where there might be
a decent size disqualificationrate, or is there some type of
(34:44):
factoring into that?
Speaker 2 (34:46):
No, in fact, part of the pre-call brief is hey look,
I don't think this is going tobe a good fit for us.
I'm going to try to figure thisout and disqualify this as soon
as possible.
Some of them that come to uswill be a 10-person company with
, like, they've just started andthey've got a small budget and
you know what?
They're a good customer for us,but they're a good customer
through our self-service channel, not through the direct channel
(35:07):
.
And what I'm trying to trainthe reps on is every deal is not
a great deal for you.
Just because they're a goodcustomer for filescom doesn't
mean they're a good one for youas a seller.
So let's try to get them to theself-service channel and do
that.
We try to catch that as theSDRs, but some of them go
through.
But yeah, it is very useful forthose that you want to
disqualify out early.
Speaker 1 (35:28):
Yeah, so what I'm hearing you say is relevancy to
all, even if just doing thatpreparation will lead to getting
clarity that this should bedisqualified or not.
Yeah, yeah exactly Superinteresting.
What other tools are you using,what other ways are you seeing
to be able to prepare the teamto win more?
Speaker 2 (35:49):
So I go back to the conversation.
One of the things that I'mworking on right now is win rate
.
So our win rate, again againstindustry metrics, is probably
about six, seven points off ofwhere it should be, and part of
that AI project was findingthose places where we are not
doing.
We're not executing the way weneed to, and, for now, what
(36:10):
we're working on right now is aset of sales plays to be able to
put the rep in the bestposition.
I've got this strong belief andI don't know if you've thought
about this.
So when an NFL team gets theirgame plan for a game, they
script the first 10 plays of thegame, no matter down and
distance.
I'm going to run these plays inthis order and then after that
(36:32):
they've learned what the defenseis giving them, how they align,
like all the things you need tolearn in those first 10 plays,
and then you run down indistance, and I think that for
us, what we're working on isgetting those first two to three
calls really well understoodand then running a set of
situational plays after that.
And so what we're working onnow is how do you sell value
(36:55):
before price?
We get a lot of people in thefirst call hey, can you give me
your price?
And our reps were like givethem price out.
And all that happens when yougive price out in the first call
is they disqualify you becausethey're like oh, you're too
expensive, you've done a bunchof discovery and you've given
them a price.
There's no reason for them tothink you're worth that.
And so we're working on somethings in those first two to
three calls that are morescripted again, not fully
(37:17):
scripted, but like we know wherewe want you to go, we know how
you want to handle each of thesescenarios, and then from that
we're putting in a set of playsthat are then more situational
so it's just like a discoveryguide.
Speaker 1 (37:30):
Is that essentially what you're trying to do?
More than that?
Speaker 2 (37:33):
it's more than that, because discovery so.
So there's a big component ofthis discovery.
So for us again, I said earlierwe do a lot of technical
discovery, not much businessdiscovery.
So then the question is how doyou do better business discovery
?
How are you not just thrashingaround in the pool and like
asking a bunch of randomquestions?
How are you really getting tothe right questions in the right
way?
But the second is is that?
(37:54):
How do you then start toarticulate value early and
differentiation early?
What is the way to do that?
We're working on our shifting,our positioning and our
messaging to help that.
But also, how do you arm therep in that moment to start to
shift the conversation from thediscovery into the value
conversation?
One of the things we've got abad habit of doing I'm sure a
lot of people do is you can hearit in sales calls is how many
(38:17):
users do you have, how many ofthis, how many of that?
And they're really askingpricing questions, right, and
they're veiling them asdiscovery.
And it's not really discovery,it's just really pricing.
Like I'm trying to figure outhow to price.
And I think that one of thethings I've observed is that
customers realize what you'redoing.
Therefore, they're like okay,now can you give me a price,
because you've conditioned them.
But wait, so you're spot on Helpme understand what you're doing
(38:42):
to change that.
So what I'm doing is actuallyso a couple things One, stop
asking price questions in thefirst call.
That's what I'm sayingscripting.
The second call will be aboutpricing questions.
So make the first call abouttechnical and business discovery
.
We are then putting in a smallvignette type demo.
Again, it's not a full demo,but it's a little bit of.
(39:03):
We compete against reallyclunky old SFTP managed file
transfer servers that are justhorrible to use.
So I want them to show a littlebit of our product, because if
we say it's easy to use, there'sno baseline or metric for you
are much easier to use and I cansee why that's valuable.
So I want them to show a littlebit of the product and then I
(39:24):
want them to be able to get intosome some value conversation to
the next step.
So differentiation a little bitof demo and get out of that in
the first call and the secondcall will set up okay, we'll do
a proper demo for you and thendo some pricing discovery and
then we can then get to a priceeither by the end of the second
call or the third call.
But at least we've been able togo through our version of the
(39:44):
story and how do you handlethose questions which is, hey,
can you give me your price?
How do you handle that in thatmoment?
Do you give them a price?
Do you dance around?
I want them to be veryconsistent in how to handle that
question and so that they don'tfeel slimy, they have empathy
and it's honest, it's like, look, we don't lose on price, but I
don't know enough yet about yourenvironment.
(40:05):
I'd like to get into a littlebit more before we, before we go
into that, is that okay withyou?
And then it's, then it'ssomething that is is in the
customers best interest, asopposed to something where
you're being being, we arewithholding information from
them.
Speaker 1 (40:20):
Level of like change that you're observing as you
work this through?
Like.
Is it a hard change or is it,like, not that complicated?
Like?
How would you rate that?
Speaker 2 (40:33):
Look for me.
My sales team are incredibleand they're taking it on and
they're learning and they'reapplying it immediately.
So, again, depending on yourenvironment, I'm blessed with a
team that is just the right typeof people who are learning it,
and they are thirsty for thissort of change because they want
their win rates Again.
This whole project is for us,win rates.
(40:53):
We're focused on win rates, andthat focuses on putting money
in their pockets, and so theyall know why we're doing it.
We're not doing it for anyother reason other than we want
them to earn more, and sothey're taking it on and they're
trying it, and they're comingback and saying, okay, this
worked, this didn't.
Can you listen to my call andtell me what I did wrong or what
I could have done differently?
And, frankly, we're adjustingour scripts and what we think
(41:19):
our hypotheses don't alwayssurvive right, we think we know
what it is, but the six footconversation that we have is
really where it plays out, andif we're good at that and we
learn from that, we can helpthem get it better and better.
So it's on me and my leadershipteam to adapt and change the
battle plan with them to be ableto do that better.
Speaker 1 (41:35):
But if I paraphrase what you've been talking about,
it's like hey, we have anobjective which is to improve
our win rates by six to sevenpoints.
One of the reasons that wethink our win rates are lower
than they could be the six toseven points is because we
aren't having the value-basedconversation early on.
We're sort of going right into,like, offering price and
(41:58):
answering their questions, andthere's a belief that if we can
just push off that aspect of theprocess until later and just
focus on, like, maybe, somebusiness discovery and some
technical discovery for fit andget permission from the customer
to do that, that that will setus up for the customer to better
(42:18):
understand the value that theywould get, which would provide a
different lens when they get tothe actual price point.
And if we just do that, wethink that will have the biggest
impact in terms of improvingwin rates.
Is that a right way to thinkabout it?
Speaker 2 (42:33):
It is.
The only thing I would add tothat is that we've also
identified champion.
Enablement is an area where wefall down as well.
So, yes, we can do all that,but when the person that you're
talking with goes and takes itback to the economic buyer, are
they prepared to have thatconversation?
And we're getting much betterat doing that.
That's something that'sdifficult for someone in an
(42:53):
organization to go sell thatinternally and we want to be
again shoulder to shoulder withthem, helping them get this
project funded and going,because it's good for their
career and it's good for thempersonally to be able to get
this going, so we want to be theone to go alongside of them.
I don't know, you and I weretalking about being a buyer.
As sales leaders, we don'toften get to be buyers.
(43:15):
I was a buyer once for anaccount-based marketing software
and I have to tell you, everysales pitch sounded the same,
every product and every one.
I wanted to say get me to theproduct demo.
And every time I got to theproduct demo I was like I don't
care about your product, I can'ttell the difference.
I wanted someone to tell meaccount-based marketing
initiatives fail for these threereasons, and we'll help you
(43:37):
make sure that it doesn't fail,because, as a as a revenue
leader, if I had gone after anaccount based marketing um
software package and program andit's gone belly up, it would
have looked bad on me and that'sreally all I cared about.
And I don't think we do enoughof that is making sure that
people understand what it feelslike to buy and what and the
(43:57):
risks that we have.
Speaker 1 (43:58):
And that part of champion enablement is making
sure that person's confidentthat this will be successful,
and I don't think we would spendenough time on that yeah, and
that plays into some of thethings you mentioned around the
jolt effect and customerindecision laid in a deal and
how you got to have bringconfidence that, like I got you,
it's no longer about it's about?
Speaker 2 (44:18):
it's about like, hey, we're gonna go do some great
things here and we're gonna makeit a win yeah, and look, I mean
, that book for me is one of thebest books that in in selling,
that I've read in many years,and I think that one of the
things that I try to model andthis goes back to coaching with
my team is I've got a stack ofbooks on my desk.
I always, always amrecommending one.
You and I work for a leader whowould always talk about the
(44:38):
book he's reading, and I askedhim about why he did it.
He said because I want everyoneto know that I am an avid
learner and I don't care whetheryou read my book or not, but I
want you to have a point of viewon.
You're an avid learner too, andwe share books that are great
for us great for us and so likethat's.
Speaker 1 (44:56):
That's the sort of culture that I want to encourage
.
Well, we've actually referredto a couple of books here
Checklist Manifesto.
We've got Jolt Effect.
What's one more that maybeyou'd recommend for aspiring
leaders that you've recentlyread that had an impact on you?
Speaker 2 (45:05):
You know the one is.
Let me get the right title ofit, it was Super Communicators,
I think.
Have you read SuperCommunicators?
Speaker 1 (45:12):
I'm not.
Speaker 2 (45:13):
You know, this was one that, as I came here, the
leadership here had read, andit's about those people who, in
the way they talk, open upinformation in people that other
people don't.
And these super communicators,you can spot them and they're
the ones who ask the insightfulquestion, the question behind
(45:35):
the question, and they're theone who don't start with, hey,
so like, what do you do for work?
Right, that's like one of thosemost the trite ones.
Speaker 1 (45:43):
They're the ones where you're based Exactly.
I'm weathering Milwaukee today.
Speaker 2 (45:48):
Yeah, there's a guy actually from our past that
would said the best open endeddiscovery questions.
Hey, tell me your life story,because in that way yeah that's
yeah.
Yeah, I mean it's.
Yeah, I mean, when Brian saysthat, you think yeah, because
what he's doing is he's gettingyou to stop and think where do I
start and how do I learn?
And I think that finding thosesort of super communicators and
(46:11):
those skills as being a supercommunicator has been huge.
So yeah, that's another one,awesome, all right.
Speaker 1 (46:17):
Well, now I have homework coming out of this Wade
.
Where can people find you ifthey have any questions?
They want to follow up onanything we discussed.
Speaker 2 (46:24):
Yeah, so obviously on LinkedIn, happy to connect with
anyone.
I love having a big communityon LinkedIn and I'm happy to be
a resource to people there, andthen obviously, we can connect
over email.
Also, I'm a member of Pavilion,so if anyone's in Pavilion you
can hit me up through Pavilionas well.
But happy to be a resource andif you've got something I can
learn from you, I'd love to dothat as well.
Speaker 1 (46:45):
Well, wade, I want to thank you for being on Pillar
Talk.
It was great catching up withyou.
I can't wait to read a new bookand to get into this pre-call
brief aspects and some of theother areas we covered.
We'll talk to you soon AwesomeThanks.
Reflecting on the conversationwith Wade Callison, you know
(47:08):
Wade's been in sales and salesleadership now for so many years
.
I think I had forgotten aboutthe fact that before sales, wade
came from a product backgroundand I loved how he described his
transition into sales and itreminded me that sales as a job
often looks so easy to those onthe outside, but it's a totally
(47:29):
different ballgame once you'reon the inside, and it makes
sense to me that what led toWade's success and what he
continues to lean on today ishis technical and domain skills
in order to succeed, and it'swhat he looks for in new team
members as well.
We got into coaching, which Ilove.
An aspect of the interview thatstood out in that area was that
(47:52):
tactic that they enabled calledthe pre-call brief.
As Wade had mentioned, the CEOof Files is a pilot, and I love
this connection between apre-flight plan that a pilot
sets up in order to succeed onthe flight and the quote-unquote
flight that a seller is goingto go through in the journey
(48:13):
with a buyer and that simpletactic of spending the time to
define what the rep is hoping tolearn and the goals for the
meeting, that simple change.
It's not a big ask it creates.
To me it creates two thingsMore consistency in the prep of
a seller, meaning sellers aremore consistently preparing for
(48:34):
the meeting, which is just animportant discipline that we
foster.
That translates to better salesconversations.
But it also accelerates theleader or the manager's ability
to coach, because now themanager knows, going in, what to
actually be coaching for.
And lastly, I enjoyed the focusWade described for looking to
(48:58):
enact change in the organizationbased on like a single metric
In this case he talked about winrate and that Wade has found
just two areas of coachingopportunities in order to
improve win rate.
The two areas that Wadedescribed are getting to value
early instead of thoseinterrogative pricing related
(49:18):
questions, and then championenablement to help towards the
end of the deal.
I kind of think about like ifyou were trying to coach
somebody on a golf swing and youtried to tell them to work on
six different things.
Of course that's not going towork.
You got to start with like oneor two things and that's sort of
what wade is doing here in hiscoaching in order to affect a
single metric.
So, you know, wade now putshimself in a position to
(49:41):
actually help his team improveand that result actually helping
the team get better.
Well, that's what this podcastis all about.
So I want to thank wadecallison for joining in this
episode of pillar talk.
Thanks to ari smolin forproducing.
I want to thank eiler young andsons of summerolin for
producing.
I want to thank Isler Young andSons of Summer for the tunes
and I want to thank you forjoining.
We will see you next time, onthe next episode of Pillar Talk
(50:13):
hurts in me like the joke Ican't shake, I can't quit.
Speaker 2 (50:17):
It's never really what you said it was.
All you're doing is break thetrust.
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