Ep. 29: Guest Brian Wolff - Storytelling & Building Buyer Trust. - Software Sales Simplified: MOVE to Success

Episode Transcript
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(00:08):
Welcome everyone to Software Sales Simplified Move to
Success, your weekly podcast forsoftware sales professionals who
want to sell better. Whether you're a seasoned
professional or just starting out, make our podcast your home
for insights developments in theworld of software sales.
I'm Kevin Donville and I'm goingto be one of your hosts today.
I'm joined by my illustrious partner and good friend, Matt

(00:31):
Long and between the two of us, Matt and I have over 50 years
experience in the world of enterprise software sales.
Matt, how are you doing today? How has your how's your week
been? It's good we survived A tsunami
and now we have hurricane force winds.
I think there's a hurricane passing, passing South of us.
So, you know, just another day in paradise here.

(00:52):
Well, I'm glad that you're stillthere and you're doing well and
that that the island didn't get washed away with all of that.
But today we're going to be talking about a subject slightly
different than all of that. We're going to be talking about
emotional value, real discovery and authentic engagement and why
that wins deals in the world of enterprise software sales.
And in order to have that conversation, we are joined by a

(01:14):
good friend of both of ours, gentlemen, that we've both been
able to sell with in the past and have a lot of deep respect
for that is Brian Wolf. Brian, how are you Sir?
How you doing today? I'm doing wonderfully.
Thank you for the kind words Kevin and Matt.
It is so good to see the both ofyou and I obviously feel the
same about both of you. 2 of thesmartest, best professionals

(01:38):
that have had the pleasure of cooperating with in my career.
And we didn't have to pay him toeven say that, folks.
That was unsolicited. So that was like a wonderful
little add on for us. So folks, Matt and I know Brian
very, very well, but of course you guys don't.
So Brian, if you wouldn't mind, take a moment, take the floor
and introduce yourself to our audience.

(01:59):
Who are you? What's your claim to fame and
what do you do? Oh wow, a lot of expectations
there. So I and I am an enterprise
seller on the new logo side at Glass Box.
We provide digital experience and fraud solutions for BFSI and
major retailers. My also and the founder and head

(02:19):
of the Wolf Den, which is a revenue community and
consultancy that I built to share and spread best practices
among revenue professionals including marketing and sales.
I have been selling for over 15 years, multiple Presidents Club
awards. And I suppose my claim the fame

(02:40):
is that in the last couple of years I've made a concentrated
effort to document best practices and really understand
the psychology of sales and morespecifically why people buy,
what drives them to do that. And I know that we're going to
talk a little bit more about that today.
Definitely one of the topics we're going to be hitting up
today, Brian, I have joined yourWolf Pack there on the website

(03:03):
before and I've had the opportunity to to appreciate
some of the things that have been shared through that.
We're going to be talking a lot about that as well as not just
one, but two books that you haveactually authored.
Now, Matt and I are authors, so we know what goes into actually
writing a book and for you having to write 2 makes me feel
like an underachiever. Hopefully over the course of
today, we can reference both of those.

(03:24):
We're going to put the links to those documents to those books
so that people who are listeningto our podcast today can come in
and get their own copies of those.
We're going to put those in the description as well.
Just split ours in two and therewe go, 2 books.
We should have done it Part 1. We could have done a trilogy.
We could have done a trilogy, you know, three picture deal.
We could have called paramount and made that happen, but but we

(03:46):
didn't. So Brian, one of the things that
I know that inspired you to to write these books and it's
something that's driven a lot ofthe conversations you and I have
had, is this concept of value being broken a little or
misunderstood in the world of enterprise software sales,
misused and abused. That's probably a better way to

(04:08):
go and talk about that. And now I got to change the
title. I love it.
I'll be editor right now. You got them on speed.
They love last minute changes, don't they?
But in all seriousness, it's an area that and I share your Matt
and I both are very, very much attuned to the pain you're
talking about here. Why do sellers, and in many
cases sell sales leaders, get the idea of value wrong?

(04:32):
And what how can they be workingbetter to reframe that so it's
more effective than their conversations with buyers?
Yeah. So, you know, the book that
you're referring to I just released is Value Overrated and
Misunderstood. And you know, the kind of the
inspiration behind the book is that for 15 years, I've sat
through pipeline meetings and strategy sessions where leaders

(04:55):
have always said, have we proventhe value, the solution just
demonstrate the value you and you're looking at leaders who
are top voices in their field. They're obviously in positions
of power in their company. And it's not to say that they
don't know what they're doing orhave had great experience, but
I've never had a single leader definitively be able to point

(05:17):
out what that value is and specifically what it actually
means to the buyer. And I think that that value
differs among buyers. So you know, the first thing
that I immediately kind of tackle is, you know, we sit in
an industry where a 20% win rateis acceptable.
Why do we do that? We throw out these bulletproof

(05:39):
business cases to buyers. We expect that to close the
deal, but we really don't understand what they truly value
what how they're even processingthat.
I begin with the the definition of value that the regard that
something is held to deserve theimportance, worth or usefulness
of something that encompasses somuch more than an ROI business

(06:00):
case. And that really kind of sets the
stage for what we need to dive into.
What is it and how do buyers perceive it and react
differently in every single situation?
No, I get you there. And in fact, Matt, I'd love to
get your thoughts on this one. We just had somebody we were
talking with just a couple of weeks ago on the show, and that
whole misconception of value where when people are bringing

(06:24):
it up inside of the organization, in many cases they
don't really appreciate what thetrue value is.
That's manifest when the solution gets deployed for the
customers and it becomes almost like an academic conversation
with them. They just assume this is the
value that we can deliver. Have you shown that value
without being able to contextualize it with the person

(06:47):
that you're trying to sell to? If that value is meaningless to
them, then probably then the values not going to resonate.
If and when you actually prove it to them in the sales cycle,
is that kind of been your experience?
Yeah, I, I'm glad that you use the word contextual.
So before I dive into what I consider to be the two types of

(07:09):
value, I actually talk about value perceptions and, and 1 is
that contextual meaning? So I use the example you've been
given a bag of diamonds and you understand how much that's
worth. You're happy.
Like, hey, I want to be able to go sell those.
But contextually, what if you'reon a deserted island?
What is the value of those diamonds?

(07:29):
Now you'd rather have a fire starter or a bottle of water
than those diamonds. So one value perception through
context is really the circumstances of our current
environment. The second is experienced.
I use the example that McDonald's, we're all familiar
with the we're all old enough here, good thing or not, to

(07:50):
understand what the dollar menu used to be.
It was a dollar and now everything on there is $3 today.
But you know, logically it makessense that we can't get dollar
cheeseburgers anymore. So those are kind of the two
perceptions that I've seen in myexperience that people see value
from and that influences obviously their decision making.

(08:10):
And we need to just better understand that to do a better
job of communicating with the buyer.
I love that analogy about, you know, the desert island and
stuff, because we always thoughtthe same thing during the
apocalypse. What's going to have value is
like all these, all these dollars that I have or the fact
that I have matches or, or can opener or things like that,

(08:31):
right. So the value changes based upon
the the context And and that's the thing I've seen a lot as
well. You know, sellers come in like,
these are the things that we solve for.
These are the benefits that people get.
And then you just like hammer that home and it's like, yes,
we're all aligned and no one asks like, well, is this
important to you? I mean, what do you value the
most? Right?
So I'm sure you're going to get into that as well.

(08:52):
Yeah. So Brian, that's a really good
point that Matt brought up, which is, you know, the fact
that you have to kind of draw the alignment in a proper way.
How do you reframe that if you realize that the person you're
speaking with doesn't really understand or appreciate the
value you're bringing to the conversation?

(09:14):
I think it's understanding for them what is important to them,
and that's an easy thing to say,but this is something I know
that we've talked about in the past when we sell to a customer
and often times B2B sales strategies revolve around this.
I'll use Walmart as an example. We capture the Walmart logo but
have it we actually sold to the monolith that is Walmart.

(09:38):
Did Walmart sign their name on the contract?
When they have a problem, do they e-mail you
walmart.walmart@walmart.com or is it first name dot last name?
There's a person behind making that decision that is
representative of the company. We sell to people who are
employed by Walmart, not Walmartitself.
And what we need to do a better job of understanding what is the

(10:01):
personal win for that person to move forward.
What is the personal win for someone who is our champion, but
not the economic buyer to take that a solution that we have and
and move it upstream. And what I've done in my book is
categorized two types of value, the emotional value.
So the subjective importance that we place on something and

(10:22):
obviously the material value, what is the objective
importance, Emotional value I think is is more associated with
some of those personal wins, what we can personally gain out
of partnering with companies such as ours to fix problems.
Material value is obviously probably more relevant to the
business and what the business case would be drawn upon.

(10:43):
So I totally hear you there. That's actually an area that we
talk about in our book as well. We approach it from a slightly
different perspective and we talked about it from the
perspective of how you need to engage that in discovery.
How do you uncover these things and how do you realize whether
or not the person is explaining the problem to you?
Do they truly own that? Is it meaningful to them?

(11:04):
Is their life on the line with respect to solving this problem?
And you're, you're to explain back to them in a way that makes
sense to them and and has emotional impact.
I totally get what you're sayingthere.
So, you know, really good sellers, it's been my experience
that they kind of intuitively know how to how to phrase their
questions and do their discoveryin such a way to root that out.

(11:26):
But in your in your mind, what would be some tactics that maybe
a good seller should be using when they're going in and
talking with someone to find out, is this really the person
who owns the problem and will they care?
Yeah, I I've really spent a lot of time over the last couple of
months testing really how to identify what is that personal

(11:47):
win. And you know, it's something I
have more materials built aroundthat we'll talk about in a
future podcast. I'm sure understanding, you
know, why that person is going to take it forward.
It's a great disqualifying question because if I at the end
of a call say, you know, I flip off my recording, I say, hey,
you know, have I earned the right to ask you a really tough

(12:07):
question right now? And if you don't want to answer
it, that's totally OK. But what are you getting out of
this? What's the benefit for you so I
can ensure that I make you look like a hero internally if you
are going to take this forward? And I've had people go on for
three or 4 minutes talking aboutthings that are not relevant to
the overall business. And frankly, a lot of the

(12:28):
discovery and, and a lot of the momentum I've been able to
capture and deals just comes from that approach.
And it's all around this emotional value.
I, I believe so strongly and just understanding that because
I think a true champion with whom you build trust will be
candid and open up to you. Someone who doesn't trust you

(12:51):
and is not in a position to takesomething forward is going to
answer that. And you mentioned like, you
know, do we have the right person?
Does this actually matter to them in answering that question?
You can identify that pretty quick if you can work with that
individual successfully or if you're going to have to go find
someone else in the business. Yeah.

(13:12):
I mean, it's always such a, it'sa, it's a personal question for
sure, right? And one that requires a certain
level of trust and relationship building.
I mean, obviously after the first call you're not be asking
these questions, but when do you, when do you find that you
you are getting to a mode where these conversations and these
questions are easier to ask and easier to get answers?

(13:33):
Yeah. So sometimes it is at the end of
a first call, but that call would have needed to go well.
So, you know, obviously the way that I look at a first call, I'm
looking to first of all provide a great experience because you
never know where that person is going to end up, who they can
refer you to. I also think that if they're
taking time out of their day to talk to you, we just owe them

(13:55):
that and we can kind of pass it forward and making sure that we
improve upon their their buying experience in the future.
But I'm looking to disqualify ifwe can't solve a problem and I
really have to spend a lot of time connecting the dots and
they're really not connecting. It's just not worth the time.
But if we've been able to do that in certain situations, I
have asked that sometimes, you know, after that first call, one

(14:17):
tactic I deploy, I usually set up a virtual sales room.
I'm setting 15 minutes to reviewthat with the individuals so
they know exactly what they're getting to help them be able to
brief colleagues and their internal committee and just
really gauge are they actually going to do that or are they
being nice and just kind of brushing me off and asking that
question at the end of that callcan really help me solidify and

(14:41):
be able to project. We've got next steps here, which
probably involves some kind of demo or consulting session.
And if I'm not getting what I feel is a reciprocal interest,
then I can tell them, you know, it doesn't seem like this is a
priority or a fit. That's OK.
What's part is friends, and we can perhaps come back to this in
the future. Can you talk more?

(15:03):
What, what is the 15 minute sales room?
What it? What actually is that?
Well, so I think that you've kind of seen, you know, the rise
in virtual sales rooms and and being able to have a one stop
shop for company collateral, youknow, problem solving videos.
So I use one of those and the 15minute session that I schedule,
you know, rather than just send it over and say, hey, look

(15:25):
through this if you have the time, you know, figure out if
this is relevant to you. I actually walk through those
materials and why I've included those for that specific buyer
for that specific company. And that's just a way that
allows us to kind of reconnect after a couple days from the
discovery. It's a temperature check, it's a
pulse check. Are they still interested?
Are they still as excited knowing that excitement wears

(15:47):
off over time because it's emotional, not logical.
And if they are, what materials are resonating with them that I
know that they're going to take internally and spread?
Most of the selling as we know is done when we're not in the
room. So I need that person to be able
to do that. And if they're not, we're
probably not going to come closeto winning that opportunity.

(16:08):
So do you have a particular set of tools that you use for
building this virtual sales roomwith with your contact and your
champion? Yeah.
So I use aligned. There's other alternatives out
there, so I'll give them a plug because they've been very good
to me. I do see higher success in win
rates in my deals correlating tomore engagement with those

(16:29):
materials. There's other tactics I've
deployed, you know, I've, I've tinkered with creating custom
materials myself. So you know, I'm really big on
meeting people in the situation in the moment.
Understanding if you're going tomove this forward, what do you
specifically need to have confidence to be able to do this
because so many reasons will cause someone to not take it

(16:51):
forward in the business. The majority of conversations
that we have are with people at enterprise level who cannot sign
off on our solution. So we know that they have to
take it to someone in the business who's going to approve.
And frankly, the bulletproof business case around growth and
ROI is not enough to justify that decision for them versus

(17:13):
the risk they're processing it through.
The emotional value, what's in it for me specifically?
What risk mitigation can you give me to take this forward
that won't cost me my job or jeopardize my my reputation
internally? Right, moving up the food chain
as you're going through that sales cycle, that's one of the
most, I think one of the best litmus tests to find out if

(17:35):
you've got the right person who's going to champion your
product, your solution and fightfor it in committee, committee
to make sure that it gets through.
Because if you can find someone who can say to you, I need this,
I will fail without it, then you've you've got your internal
champ. That's the person who's going to
sell for you internally is goingto and also give you all the

(17:57):
information you need provided you're being authentic and
you're being clear with them andyou're building a partnership.
But what happens then when you get somebody who, when you start
to press on that, you begin to realize that while they are
personally concerned about something related to the
project, based on what you know about the organization, there's

(18:20):
not a compelling reason to move forward with that.
There's no stake in the ground, a line they need to cross where
if we don't do this by X, peopleare going to lose their jobs.
If you can't build that, I've seen some people get very
creative with some of the thingsthat they try to come up with to
try and artificially manifest that.
What's been your experience withrespect to that, and is there a

(18:43):
right way or a wrong way to go about trying to create that
urgency if it's not manifested correctly?
I think that there's wrong ways,but I also think that there's
multiple right ways. And I always kind of frame my
material as anyone is free to disagree with me anytime, right?
You know, my way is not the onlyright way.
There's multiple ways to get to success.

(19:05):
But you know, I come back to, you know, the inspiration for
the book. So what you're describing is
we're probably sitting around with leadership and we're
talking about tactics to deploy.Why are we talking about tactics
and strategies to deploy when wecan't understand what value is
and and how it works? So you know, my whole kind of

(19:26):
goal with this book is when you're in that situation, take a
step back and I look at 3 commonmistakes that we make before we
even look at deploying. And, and the first is we've all
heard that buyers buy an emotionand justify on logic.
So I make the case emotional value always Trump's material

(19:46):
value. So when we're speaking to a
buyer, our tactics and strategies need to be catered to
that individual and not the business.
So how do we make this person feel comfortable to move
forward? That's usually around personal
gains. We know always that, you know,
people are worried about their jobs.
They don't want to jeopardize that.

(20:07):
So what can we do for that person that motivates them to
share our idea with a larger committee?
The second mistake, When we do that, we usually present.
Material value information for them to take upstream and that
resonates with buyers generally more so at AVP level and above.

(20:28):
But we fail to realize that buyers are still processing the
material value through the emotional value.
The example that I give for thisis that, you know, Kevin, Matt,
if I, you know, it's said to you, I've got a near perfect
return. If you invest $10,000 with me, I
will get you $50,000 no questions asked.

(20:49):
We've done it for these companies and that sounds great
and that's the ROI and growth argument.
But what's really more effectiveit's the, you know, the cost of
inaction. And in doing that, I need to
mitigate the risk because you are looking at that and saying,
well, that's a home run on paper, But do I trust Brian to
give him $10,000? Is this really going to work?

(21:11):
Is this the one time it doesn't?And our buyers are thinking more
like that than they are, oh, this is a slam dunk and I'm
going to take it forward to make$50,000.
I think looking at those two mistakes in particular are
important. And before I talk about the
third dimension, getting to the right person is crucial.

(21:33):
And I don't know that we necessarily ask those questions
and identify those people through the emotional sense as
much as we do the material sense.
So I'm hoping that we can just focus and, and take our time
before we work with leadership and say, hey, what tactics do we
need to motivate this person? Why are we trying to do that in
the 1st place? What can we get this person to

(21:54):
achieve before we take it upstream?
Yeah. And that goes all the way back
to what we're talking about a moment ago about discovery,
right? This is where the discovery, the
diligence and the dedication to being a really good interviewer
of the people you're talking about and asking the questions
critically and evaluating the answers comes into play.
Because you need to determine whether or not the person you're
speaking with is really sharing with you information that is

(22:18):
that's creating a compelling story that will stand up under
scrutiny. And if that person clearly can't
articulate it correctly, either there's not really a compelling
reason or that's the wrong person for you to be talking
with, right? So it all starts with that due
diligence and doing the discovery on that front and then
challenging your own assumptionsas it goes along.

(22:38):
Let me ask you a quick question on that just to think about,
don't need an answer. But coming back to my example
with Walmart, we go into deals at this level knowing what
strategic priorities are. They're they're out in the open
for enterprise companies. We know the likely problems that
they have and how we can solve them and we have accompanying
social proof. So I would argue going through

(22:58):
the discovery process is discovery of the business
reasons and the impact. Are we going to spend as much
time on that or are we going to spend more time on doing
discovery with the actual buyersand what the impact is to them
and how they feel about it. And I would argue that that
ladder is becoming increasingly more important as we take a pre

(23:20):
built point of view into accounts and it's arguably more
effective at getting us to builda partnership and trust with
those buyers. It's 100% that's we often say in
a in our sessions, your discovery is also helping the
customer discover things about themselves, understanding
consequence, understand understanding scope things that

(23:41):
they don't even appreciate abouthow bad bad is with respect to
what the problem they're trying to solve.
And then bringing that to them in a way where you can also
constructively say, here's the consequence.
If you don't come with me. Here's what I can do to make
that happen. Here's the problem I make go
away and the threat that I take out of your life by being able
to do that because to to put it in a different way, anybody who

(24:03):
is championing for you inside ofan organization is staking their
career in many cases on your ability to deliver on the
promises you've made. So 100% totally get what you're
talking with from that. Matt, any any thoughts on your
side? Yeah.
I mean, one, one point of that really is people have been sold
to so much in terms of the promise and the outcomes and all

(24:24):
that stuff, yet they've been bitten so many times by not
delivering on those things. So I think your point about risk
mitigation is key. Like what is the risk of me
bringing this in is the chance of success?
Because we all, we all agree improving profits, decreasing
costs, that's our goal. That's important.

(24:44):
We all want to do that. But are you going to be able to
do that for me, right. And that's where I think really
digging in and understanding thegrounding elements that are
driving that person are key. So I love that aspect of your,
of, of your methodology. I also do want to just double
down on one point that you made,one tactic, which is near and

(25:06):
dear to my heart, which is a collaborative workspace to bring
everyone together. Because there's nothing worse
than a bunch of attachments flying around to individuals or
various distribution lists, and no one knows where the current 1
is, where you could just say, hey, here's where everything is.
You can just keep driving them back to that.
I just love that so much. I think that's so effective in

(25:29):
terms of I think it's managing, yeah.
Yeah, I, I think it's a big differentiator too.
It shows a level of professionalism that I think,
you know, most buyers are still surprised by, but they are
expecting in this process. We know that we have to really
lay it out for them and also investigate and balance that
with how they purchased before. But it really is incumbent on us

(25:51):
to go to that next level and seta new standard for them because,
as I said, most of them have hadpretty terrible experiences in
the past. We have to do better for them.
Yeah, I've been a buyer before and I can tell you that it
astonishes me the number of times that sellers have made it
hard for me to to understand whyI should buy their solution and

(26:13):
to gather together the materials.
I'm going to need to go fight for it internally.
Once I decide that that's the solution I want to want to work,
want to work with and is going to deliver on what we need.
And in that respect, I, I think that there's a fundamental
delivery that can happen in the sales cycle between the the
sales engineer and the salesperson.

(26:35):
And it really comes down to you've got all this information
now you know what, what's what, you know what's at stake and who
cares when you go to deliver that message, You've got to
deliver it in a way that's easy for them to understand so that
they can turn around and re articulated internally for you
and be that that voice of selling inside that

(26:57):
organization. Storytelling probably one of the
most fundamental things to beingable to make that message work,
don't you think? Yeah, I totally, I mean,
storytelling I think goes into, you know, partial seeing as
believing. We obviously know things like
demos and proof of concepts. I think that, you know, probably
those are the most three important things that we can do

(27:17):
to reinforce that, hey, we're making these claims and we can
back them up. I always try to kind of grow in
my storytelling. I'm not perfect in that regard.
What I will share with with people is, you know, we, we did
a, a storytelling exercise at one of my previous software
organizations. We just brought somebody in.

(27:38):
We didn't work in sales or software, but just to
articulate, actually worked in improv comedy and had a very
easy framework, she said. Remember every story in the
context of the fairy tale, and you probably remember those even
going back 20-30 years because how they're structured.
You have a beginning, you have amiddle, and you have an end.
So in the beginning, here's the current situation.

(27:59):
The problem that people are facing in the middle, it
impacted us so much that we had to make a change.
And in the end, we adopted this solution and it was able to help
us do XY and Z. And when you think of it like
that, not only can you tell clear, concise stories, but you
can really speak to anybody in the room and understand that,

(28:22):
again, the way that people are going to process those stories,
how they're going to calculate the value through EV and the
it's going to be different for every single person.
I agree with you. It is such a powerful tool to
use. And ultimately, that's what
people remember. They remember the stories that
you told or the conversation or the critical moment as you're
outlining that that's what sticks out, not the fact that

(28:45):
your solution, if I did this, itmoves forward to these things
faster down the pipeline. It's like, who cares, right?
But but that that, that visceralfeeling of someone coming to
that realization or that that breakthrough or whatever, if you
tell it right, that's what they're going to remember and
they're going to remember that with your solution.
Yeah, absolutely. I mean, one of the things that I

(29:07):
know we've actually done tests on and it's one of the things
that I try to bring in. It's funny.
You were talking about having the comedy troupe and we've
actually had people do that withus in the past as well.
But I. Always the comedy troupe.
I, I all my looks are funny. So we'll start there.
You know, definitely my face should be be on the side of a of
a comedy troupe that wagon, that's for sure.

(29:30):
But with respect to storytelling, the way that I've
always like when I was in sales enablement, I would always tell
people the person you're talkingto needs to go in at the end of
your meeting, needs to walk intothe next meeting and be able to
tell the story. So first of all, when you do the
storytelling, start with the things that are most important
to them. The things they've told you are

(29:51):
the most important to to actually solve and give it to
them in a narrative that uses their own terminology, use their
phrases, use their values. And so they can walk into the
next meeting and go, here's whatthey can do for us.
Isn't this awesome? No one's going to turn around
and point to them and say, well,OK, what what buttons do they

(30:11):
have and what widgets they have in the solution to make that
happen. That's never going to be the
challenging question. You might, you might get that
down at the user level. So from that perspective, the
technical demo versus the value demo, how do you prioritize the
two of them inside of your salescycle?
I think probably the biggest change I've made in my cycle in

(30:33):
the last couple of years on getting them to see the product
early and being able to make that assessment for themselves.
So I think that also works with pricing.
I know, I know that there's repeated conversations around
showing demos on the first call without having context and
without, you know, sharing pricing on that first call.

(30:54):
You know, the reality is as a buyer and think to the way that
we, you know, you individually buy things, you want to be able
to see it, you want to understand its value on its own
terms. And if I see something that I
don't like and, or I don't agreewith the pricing, you know, that
emotional value for me, how I'm processing it as as a seller,

(31:16):
I'm just not going to get myselfto move off of that.
It's very unlikely. I just haven't had an
opportunity to earn the right. So, you know, dragging that
person through a 2, three-step process, it's a waste of their
time. It's a waste of our time.
So I do want them to see pricingearly.
I want them to see a demo early and then to come back to your

(31:38):
tactical demo. I think at that point, probably
earn the right to do a deep diveand get that person to open up
and a, a, a tactic that I deploynow when I think I've identified
a champion. You've got to have a prep
meeting for everything with thatindividual.
Prep before that demo. If they're going to introduce

(31:58):
materials to the team, prep withthem.
If they're going to go to leadership and say we want to
discuss this internally, I'm I'mgoing to present this on your
behalf. Prep them on what they need to
do and say in order to do that. That is, that I think is one of
the biggest changes in helping me create better relationships
and ultimately just drive more success in in each of those

(32:22):
actions throughout the cycle. Yeah, I I agree.
The more FaceTime you get and the more time working together
with your champion, you know, toget them in the right frame of
mind as well as the comfortable to be able to articulate the
story and the value that you want and make them feeling
confident when they go into these meetings is great.
I'm just curious because a lot of times we all leave these busy

(32:45):
schedules, you know, how hard isit sometimes to get these prep
things going? I imagine after you get a couple
people are willing to take the extra time, but do you find it
difficult sometimes for that to schedule those types of things
or to make them sign up for thattype of activity?
They'll make time if they're committed and if they won't, I
don't think that you have a champion there.

(33:06):
And I think it is important, youknow, medic and other frameworks
try to define the champion. Oh, they've got power, you know,
over budget. They'll go sell on your behalf.
I don't disagree with any of those things.
I really focus on the ability tosell on her behalf and influence
leadership, not necessarily holdthe budget over that because I
mean, honestly, who has budget for anything?

(33:27):
You know, we're going to pull from different sources.
We're going to access pools and money that we don't necessarily
have access to right away, testing kind of that commitment
because I think you can be a champion of change and not
necessarily a specific product or vendor.
And we are selling change first because the biggest competitor
that we have is not other vendors, it's the status quo.

(33:50):
And then it becomes competing solutions and vendors, some of
which are not even in the same space.
So understanding, is this a champion of change?
And then is this person going tobe a champion of us?
And as they move closer to beingboth, I find it easier to get a
commitment on that time. And if I don't get commitment on

(34:11):
that time, I know I've got somebody who is very unlikely to
make those commitments moving forward unless I can get to the
core reason of why they won't. They won't.
And usually it's always associated with that risk
factor. Absolutely.
Well, there's a lot of interesting stuff here that
we're bouncing back and forth, but I want to kind of come back

(34:32):
to your books a little bit here because I, I totally follow
along. Matt and I are both lockstep
with you on your approach to selling and why these things are
important to do. But I want to talk a little bit
about the last the the book that'll be coming out just
before this podcast will post because I had a quick sneak peek

(34:55):
at it and it's an interesting perspective.
The problem not being sales, theproblem is all about the
execution and it's the reason why buyers hate sales.
Tell me a little bit about that.What if you could fix?
And I think your top ten list isright there, right?
Is that book kind of like a how to of how to fix your sales
organization that the the top problems there are with respect

(35:18):
to execution? Yeah, So, you know, the
inspiration of behind this, the book is 10 Things I Hate about
You sales. So just kind of of a clever play
on the the nice film. I wanted to build ideas that
would incorporate the buyer intothis, you know, into this
process and and really put something out to the audience

(35:38):
where they could understand our frame of thinking while calling
out sales, saying we need to do a better job of of understanding
them. So I'm hopeful this is the first
piece I've done that appeals both to a buying and selling
audience and and meets in the middle.
And what I looked at, you know, our selling process is pretty
much defined, especially when itcomes to B to B and software in

(36:01):
particular. There are commonalities in every
organization from messaging to objection handling to setting
next steps, demos and and pipeline management.
So I've taken what I feel are the 10 most common scenarios and
I've looked at those from, you know, using an example and then

(36:23):
being able to understand from a buyer perspective, why are they
frustrated with this? You know, what do we need to
know right away that would just cause them frustration, pain and
and not want to deal with us? I then provide an explanation
for the buyer, why sales does it, and then lessons for what

(36:44):
sales can learn from this and what buyers can learn.
And again, the whole idea here is just to create some
conversation in this mutual understanding with the hope that
both parties will be a little more amicable to working with
each other moving forward. Building bridges, building
bridges there, right. So if you had to pick though,
because I I've already read through it and part of I was

(37:06):
chuckling and cringing at the same time as I was reading the
list, if you had to pick one as being the one that stands out to
you as being the biggest guffaw of all that happens, which one
would it be? Think what I've seen in my
career and I should do like a power ranking of these.
I think that they're all important.
But I think what's kind of near and dear to me is, you know #4 I

(37:29):
call it out. Interrogative discovery, AKA
tell us what's wrong you, you have convinced someone to spend
time with you who probably does not have time in their day and
you go into a call whether it's inbound or outbound, there's
certain things that they want toknow there's certain things that
they want to see and the majority of sales will still

(37:49):
tell me your biggest problem, what's going on in the
organization what's the impact of that These just general
questions that we've been told to ask to basically fill out
sales force and and medic and other frameworks for a CRM.
It's just it's not buyer friendly.
No one wants to sit there under the light in a steel chair and

(38:11):
be asked all these things and come away with, you know,
absolutely no understanding of how we can help them.
I'd probably call that one out. Is the one that we probably
should work the most on. Wholeheartedly agree, but some
people pay extra for sitting in that chair with the hot light on
them. Let's be honest, right?
But that's a whole other podcast.
They're called, they're called industry conferences and preset

(38:32):
meetings. That's what they are.
Absolutely. You know, there's there's all
kinds of tactics you can use forit can actually be an
interrogation. But if the person walks away
feeling like it was the best 30-40 minutes they've spent of
their week, then yeah, that was a great tactic to use.
And there's all kinds of different ways you can make it
clear that they're investing. And I don't mean to say you're

(38:55):
like you're going to Tom Sawyer and fool them into it into that
process, but all about engaging them, making it about them and
making it about them in a way that's non threatening and clear
that I'm here to help. You know, you're offering.
That kind of goes right back to that thing we were you were
talking about in reference to your other book about building
that trust with the person that you're trying to make your

(39:17):
champion by establishing value and the reasons why it matters
to them. Yeah.
And and I think you know what you'll find in in some of my
materials, I'm less focused on the actual plays.
So going again, going back to that pipeline meeting example,
the emphasis is really for people to take a step back
critically, think about the situation in the buyer, think

(39:40):
about how you personally buy, think about what matters to whom
you're talking. And if you do that, if you
understand the psychology and how people think, then you can
execute an infinite number of plays for that individual.
It's, you know, I look at it toolike objection handling.
It is a great example of this. So we're cold calling people and

(40:03):
that we have lists of like what we should say, like to memorize
when they object. Why?
Understand when you're cold calling, they're objecting.
Primarily because in that momentyou are the biggest pain in
their day. You are interrupting them when
they were not expecting it, taking time away.
So if they object, they are not going to respond well to you

(40:24):
arguing with them or giving product.
You should acknowledge that objection and continue to work
from there on, focusing on a problem that you know that they
have. And if you do that, then you're
not going the route of making itpainful for them.
And you probably developed a conversation with a good amount
of individuals there. And that just comes from the

(40:44):
simple understanding. You can get any objection.
But if you understand, you know,acknowledge it and make them
feel heard, they're a human being.
And then kind of pivot to the problem that they care about
rather than just these memorizedlines that aren't going to stick
with the majority of people. So, you know, if you take one
thing away from all my materials, take a step back,

(41:04):
focus on why things are happening, why the buyer thinks
that way, and then you can put into action some of these
strategies, some of these plays much more effectively than what
you've just been thrown and toldto do in a playbook.
I think that every seller shouldbe forced to sit in on a buying

(41:25):
committee at least once in theircareers.
It's eye opening when you're sitting on the other side to see
how cold it can be right? How dispassionate and how
mechanical the process can be. Sometimes you're asking this
person to vouch for you and potentially even put their

(41:46):
career on the line. This is all about trust.
And the the way that I always position myself and I've gone
into those of those conversations is like, I'm here
to help you. Tell me what's broke.
You tell me where you're at risk, you tell me what's
threatening you and I'll tell you how I can help.
And if I can't, we'll part friends, right?
And to me, if you and a lot of what you're talking about in

(42:10):
your top ten list and even in the other book definitely
resonates with respect to anybody who's ever had to sit on
the other side of the table in those conversations.
We've all sat there and, you know, I've got to tell you,
sometimes I think I've got it down to a tee and what I want to
do. And I sit in one of those
account managers, CSM calls for software that we're using or

(42:32):
even the evaluation itself. And I'm just bored to tears by
the second slide. And it's just, I know those
people are making an effort. A lot of them are just doing
what they've been told. There's no real formal education
for this. It's replicating, you know, what
you see in people around you. And that's not always the best.
So I hope just as an industry, we start to move more to kind of

(42:53):
challenging that status quo. And again, let's bring a level
of professionalism and enthusiasm in working with our
buyers that's not only contagious for them, but, you
know, let's set, well, let's setsome blazes in the industry that
other sellers can pick up on as well.
Yeah. I really think, you know,
differentiating yourself throughyour sales team and your

(43:13):
relationship is really what matters because all the, there's
so many products out there, lot of them do pretty much the same
thing, maybe in slightly different ways.
It's very rare that you have something that just so different
than anything that people are just going to flock to it.
So what it comes down to is who executes better?
And I, and I always think about every, every interaction I have

(43:34):
in a sales thing, whether or notI'm buying some clothing or I'm
buying a car or whatever. I, I think about what
experiences did I enjoy, right? There's times when I'm super
motivated. I'll buy from anyone.
I don't care, right, because I want it and it's a good price.
I'm going to get it. A lot of times it's like, it's
what was that interaction like? And I reflect upon that a lot as

(43:55):
I'm selling because it makes me more empathetic to what it is on
the other side. So I, I love all these things
that you've been mentioning, Brian, and I really appreciate
the focus on the emotional side of selling for sure.
Yeah, I, I appreciate your enthusiasm for that, both of
you. You know, Matt, I just closed
one of the biggest deals in my career and product and

(44:16):
differentiators certainly came down to it.
But I know for a fact in talkingwith my customer and just in my
heart, it came down to those prep sessions.
It came down to building custom materials that we didn't have
and sitting down with that at the time prospect and making

(44:37):
that person feel comfortable that they could go in a room and
defend a higher price solution, sue their boss and having the
confidence to do that and know that that would not jeopardize
their standing or their career at that organization.
I know that made the difference.I deploy that in every deal that

(44:57):
I can. It looks a little bit different,
but that's how we how we've got to meet buyers in the moment.
But I'm absolutely sold that that's the right thing to do,
and sellers who do that will be more successful in the
community. I was just to say during proofs
of concept, never forget, folks,it's not just the product that's

(45:17):
being tested here. It's everything about what we
stand for. Everybody's in the VAT.
We're all getting tested here. So 100% on board.
I always get excited when I talkwith you about this.
As you can tell, I'm getting very excited now and I always
have been. And I really appreciate the fact
that we got a chance to talk with you here today.

(45:39):
I hate to say this, we do need to wrap this up or we'll be here
all afternoon talking about these topics and enjoying
ourselves immensely. But Brian, if someone wants to
reach out to you to talk a little bit more about the topics
that we've talked about today or, or go into any of the
elements that are in your books a little bit different, a little
bit deeper, how can they reach out to you?
What's the best way? Yes, so I mentioned the Wolf

(46:01):
Den, my consultancy and community for revenue
professionals. So that's the wolf. den.co Wolf
has 2FS like my last name. You can also reach me on
LinkedIn Wolf with two FS hyphenBrian, you can also reach out.
I will provide like an e-mail address.
You can contact me through the website.

(46:21):
But I encourage anyone who wantsto just talk about some of these
topics. If especially if you're new
salesperson, if you're a new SDR, I've got materials for you.
If you want to take 1520 minutesto talk about it, I am
absolutely happy to do that. I want people again to come away
doing a better job and it not necessarily taking the better

(46:42):
part of 20 years to get there. I want them to feel comfortable
and confident in their approach.So please reach out to me via my
website or LinkedIn. Very happy to talk to you.
And we will put all that information down in the
description. Diddly do I think it's what they
call it below the podcast and wherever it is that you happen

(47:03):
to be watching US on? I do want to take a moment now
to go and say, folks, we are coming to the end of our episode
today and I want to thank Brian for coming on to the show and
talking about things that are near and dear to Matt and mine's
heart. Matt, anything you would like to
share before we go and say goodbye today?
No, it's always a pleasure, Brian.
I always enjoyed working with you.

(47:24):
And since we had our onboarding in Paris a long time ago, that's
a bonding experience in itself. I'm looking forward to reading
your books and I'll look forwardto our next conversation.
And I hope. So much.
No, absolutely. Thank you, Sir.
It's it was a joy to talk to youtoday and I'm walking away with
a smile on my face as I always do whenever I've had a chance to

(47:45):
have a conversation with you. But folks, that does bring us to
the end of our episode today. If you guys liked what you
heard, please go ahead. Like subscribe, follow.
If you would like give us a comment, let us know what we got
right, what we got wrong, thingsyou'd like us to go into a
little bit more deeply, or things we missed entirely.
We want to hear back from you tomake these episodes as valuable
to you as we possibly can. Please take a moment also to go

(48:09):
to Brian's website, check out his books, check out the site
that he's got there. It's incredibly valuable for
sellers. I can't recommend it any
stronger than than that, but please go take a look at it.
And if you'd like to go and takea look at our book, go to our
website where you can go and buyyour own copy of our methodology
as well. But with that having been said,
folks, thank you for spending a little bit of time with us

(48:31):
today. It was great to see you and I
hope you we're going to see you back here next week.
Until then, take care.

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Ep. 29: Guest Brian Wolff - Storytelling & Building Buyer Trust.

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Ep. 29: Guest Brian Wolff - Storytelling & Building Buyer Trust.