December 31, 2024 • 28 mins
Get ready for an enlightening episode as we welcome Ben Cutler, the visionary leader behind Hushmail, to discuss the transformative power of leadership rooted in humility and transparency. Ben shares his unique approach, inspired by General Stanley McChrystal, where success takes precedence over always being right. Our conversation uncovers how radical transparency and psychological safety can empower frontline decision-making and foster a thriving team culture. Ben’s refreshing vulnerability demonstrates how personal growth, triggered by learning from mistakes, can drive organizational success.
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Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Carol Park (00:03):
Well, hi everyone, and welcome back to the Courage
Unmasked podcast, where ourguest today is Ben Cutler, and
I'm so happy that y'all aregoing to get to meet Ben.
I've known Ben for gosh since alot of years I'm thinking maybe
nine, 10 years, maybe 2013, 14,maybe 15.
(00:26):
We met in the kind ofentrepreneurial circuit of
starting companies he with hisand me with my cohort starting
ours and have just had such agreat time getting to know Ben.
So I'm glad y'all are going toget to hear from him and know
him.
So, welcome, ben, and tell us alittle bit just about your
(00:49):
company, your entrepreneurialjourney, kind of how you came to
be the leader of your company.
Ben Cutler (00:56):
Hi, carol, and thanks for having me on Sure.
So Hushmail.
We provide secure, hipaacompliant communication tools to
small healthcare practitioners.
A typical customer is a solepractitioner therapist, but we
serve customers all acrosshealthcare.
The service is primarily asecure email service.
We also have secure web formsthat support electronic
(01:19):
signatures, so our clients usethe service to communicate with
their clients and patients in aHIPAA compliant way.
They also use the secure formsfor things like intake and
patients in a HIPAA compliantway.
They also use the secure formsfor things like intake forms,
health history forms and fortheir practice, and the idea is
for the communication platformto be easy to use and just
generally help with theday-to-day running of small
practices.
(01:39):
I've been in the role for quitesome time.
I started off in a finance role.
I started off sort ofacademically as becoming an
accountant, but I think I foundmy calling in sort of the more
of a CEO role.
Carol Park (01:53):
Yeah, and I obviously I will vouch for
Hushmail because I use Hushmailand it has been fantastic in my
own private practice.
And again, we just kind of gotto know each other along the way
, going to conferences, havingbooths next to each other,
across from each other, spendingtime with our other cohorts in
(02:17):
the space to going to dinner.
So, as I've known you throughthe years, I definitely observe
you as a vulnerable and alsovery humble leader, like I just
observe you even working withthe people who work with you,
alongside of you.
So how do you think you came tobe this way as a leader?
Ben Cutler (02:41):
That's a great question.
I think part of it's just bakedinto who I am.
Leader that's a great question.
I think part of it's just bakedinto who I am.
Another aspect of that will befrom experience.
I've been in leadership formost of my career, but obviously
I didn't start there, so I dohave both sides of the equation
there.
One thing I think that it'squite important is I try to
focus on how to achieve asuccess as opposed to being
(03:01):
right.
Is I try to focus on how toachieve a success as opposed to
being right, and so I thinkthat's a different way of
looking at things, and I thinkin that scenario, you have to be
open to not always being right,and that's absolutely
appropriate.
In my role, I don't have all theanswers.
I want to get to the rightanswer.
I think also my style has justevolved through the years.
(03:22):
It's really a work in progress.
I work with some reallytalented, insightful individuals
.
I learn from them, which isalso really great.
And then a few years back I cameacross an article by General
Stanley McChrystal and it reallyresonated with me and he was
(03:47):
over in the Middle East and hehad some pretty significant
responsibilities and I knowmilitary is an interesting
comparison sort of kind ofsubject to this.
But he changed how they did ouroperations quite significantly.
And he had kind of threeprinciples to really kind of
resonate with me Radicaltransparency, so everybody knows
(04:08):
what the mission is.
I think that's applicable inall businesses.
If you've got people who havesiloed information, you're not
going to get the same outcome asif everybody understands what
the mission is.
The other thing that he does,he believes in, is that the
person closest to a decisionshould make the decision.
And you know, in a typicalorganization you know that's
(04:31):
kind of top down the CEO wouldmake all the most of the
decisions.
But I think it makes a lot ofsense.
So you know, if you've gotsomebody on the front line, they
can make a decision and it'smore efficient for them to make
a decision, it's more empoweringfor them to make that decision.
They should know when thatdecision needs to be deferred.
But I think that's a reallypowerful part of kind of the
equation because it really makespeople feel like they get to
(04:53):
contribute as opposed to doingtheir job written from a script.
And then the other kind of finalpoint that he said he made, and
this is really interestingbecause I think the uh the way
he described it is daily.
They would have a stand-up, azoom meeting, like we're doing,
but with a lot of people on it,and people would have to call
(05:14):
into this, go into this, calland explain why something they
had done hadn't worked out andhe goes.
You can't learn unless you makeit comfortable to talk about
the things that go wrong.
Uh, and I, to me that's justsort of those three points that
are really kind of lined up.
A lot of what I sort of hadsort of kind of come to in
(05:34):
various different ways but in avery nice and succinct way.
So that's sort of, I would say,a milestone on the evolution,
but it's still.
Carol Park (05:41):
It's still sort of a work in progress sure, sure,
we're all a work in progress,and I just think everything that
you just described is how Iperceive you as a leader, even
though I've never worked underyou or for you, with you, I've
just observed you, and so whatyou described there, too, is all
(06:05):
about psychological safety.
You know that people need toknow it's okay to fail and that
sometimes in the failing, weactually grow, become more
successful.
So that psychological safety,that those elements that you
(06:25):
touched on, I yeah, I couldn'tagree more.
(06:49):
It kind of has to start fromthe top down, but then the
people at the bottom have toknow, yeah, this is a safe place
.
Ben Cutler (07:03):
I can say, oh, I messed up or how can I do better
?
How do you, how do you makethat happen?
You can't say it.
You can't say it's a safe placeonce and expect people to
accept that.
You have to kind of create theconditions where people
understand that it is a safeplace.
And I would say, one place whereI uh do that a lot is where I
have people that manage thisreport directly to me and we'll
always talk about, um, kind ofdefining, kind of their
(07:27):
authority, and I'm alwaysencouraging them to, you know,
to really push up against theboundaries of their authority in
terms of their autonomy andagency, because I want them to
really feel that they have thatagency, that they have my
support and they have my trust.
And I always said well, if youoverstep your boundaries a
little bit, that's okay too,because we can learn from that,
we can understand.
Well, actually that was adecision that I probably should
(07:48):
have made, and then we can.
We've got some data there,we've got some understanding,
because that kind of puts somedefinition around that.
But I always encourage peopleto sort of to really really sort
of lean in to kind of theirrole and the authority that they
have, and I try when Icommunicate with with them, not
to tell them, but to sort ofhave a discussion about the
issues and then sort ofencourage them to sort of
(08:11):
formulate their response.
Because I think if I make thedecision for them or tell them
what they need to do, I'mrobbing them of the real value
of decision making, which is thecritical thinking around how do
I solve this problem If Iwasn't there?
If I wasn't there, they wouldhave to do this themselves, and
in another set of circumstancesthey would probably do this by
(08:32):
default.
And so I think the organization, the way I look at it, we
should be sort of creating theconditions where people can
exercise that authority.
Carol Park (08:50):
But the same token we want.
We want them to as well, and'vetalked at numerous times on the
podcast with different guestsabout psychological safety and
have touched on Google'sAristotle project, where they
went in to see what createssuccess.
They had predictions, hypotheses.
(09:12):
We think if you hire thesmartest people and put them in
a room, you're going to besuccessful.
And this was like a two-yearstudy and really what they found
at the end of the two-yearstudy is the number one element
of success that drove successwas psychological safety and, as
you said that, I was like, yeah, because what you said is when
(09:36):
people feel safe to be able tomake a decision, they can think
more critically, they can thinkoutside of the box, because
they're not afraid that theymight be shamed for their
response or criticized if itdoesn't work or whatever, and so
it gives them the freedom to bemore creative, to think outside
(09:56):
of the box, to use what theycan bring to the table, and I
hear in your leadership how youreally build that into people
and into your employees so thatthey can think outside the box.
So, yeah, you just put that sowell.
Ben Cutler (10:11):
I think so yeah, you just put that so well, I think.
Yeah, I think it's such animportant part.
You know, if I look back on mycareer, I've made, you know,
many, many mistakes.
Every one of them is a learningopportunity, and so it's okay
to make a mistake because it's alearning.
These are opportunities asopposed to mistake, and very
(10:34):
often the mistakes are notmaterial in the scheme of things
.
So they're not, you know,they're not going to end the
business, they're not going tohave dire consequences, but what
you can do is you can take sometime to kind of go what can we
learn from this?
What can we do better?
Is there a process that needsto change?
Or is there an area where, okay, we know that somebody needs to
(10:55):
kind of focus on sort of honingtheir skills in?
And I think, for me, when Ilook at, when I have these
conversations, I look at it aslike it's absolutely okay.
Where it can sometimes step outof being okay is the same thing,
the same issue recurs andrecurs and recurs, because then
you've got a pattern wherethere's no growth and I think
that can tell you something else.
But that doesn't typicallyhappen.
(11:15):
Typically, what happens is wesit down, we work out what we
can do better and that issuesolved.
And you know, within a littlebit of time another issue pops
up and then we just address itthat way.
But I think it kind of createsa the issue is not the issue,
it's kind of how do we solve theissue?
Carol Park (11:40):
Yeah, yeah, that's so well put and I know even as
you talk about that.
It's because you model thisfrom the top down and a lot of
times people think that you knowvulnerability and humility are
perceived as weaknesses,especially in leadership, where
you're supposed to be strong andhave all the answers and tell
people, and so you're modelingthis In your words.
(12:02):
How would you describe that?
Actually, vulnerability andhumility and leadership is
incredible strength, notweakness.
Ben Cutler (12:12):
Yeah, that's a really good question.
I think my view is that youwant people to support.
If you want people to supportyou, they have to feel like they
have some agency.
They got you know, they havesome control of the situation.
Talented people they reallywant a mission, they want to
know what the mission is, butthey also want the flexibility
to you know, do the mission.
You know, at times I need somesupport and sometimes I need
(12:36):
some understanding.
So I think when you take thatapproach it takes away from that
top-down model because you'resort of sharing that control
with other people.
Carol Park (12:50):
Yeah, it's really building a team right, because
they then feel like not okay,I'm tasked with this, I don't
have agency, I don't have anyfreedom to try things or
whatever.
I just have to do the task andespecially, as you said, for
talented people, that they kindof feel like they're pigeonholed
(13:12):
and probably won't stay verylong would be my guess.
Ben Cutler (13:16):
You've met some of the people that I work with.
These are phenomenally talentedpeople at different stages in
their career.
We absolutely want to maximizethe time that they stay with us,
knowing that at some point theywill move on to bigger and
better things, and when thosedays happen, I'll be sad but be
happy for them.
I think it's really though it'sreally important.
(13:37):
You've got to kind of createthose sort of conditions and I
think McChrystal's principlesreally apply here.
When you talk about you know heuses the word radical
transparency, but talk abouttransparency of the vision and
everything else If everybodyunderstands generally what
you're trying to do, whereyou're trying to go, I always
refer to it.
Well, you know the tank is goingto Europe and we're in Canada.
(13:59):
Right, we're on the East Coastof Canada, we're going to Europe
.
There's a lot of things thatcan happen on that journey that
are the control of other people,but we generally know where
we're going.
That's really important.
So if everybody understandswhat we're doing, then mission
is clearer.
Along that journey you then workout well, how do you handle the
(14:20):
decisions that need to be made?
You make those decisionsefficiently.
You make those those decisionsin ways that empower people and
empower growth, creativity andeverything else, because it's
the creativity and all of thethings that agency gives people
that really help move the needlein success.
And then you know, inevitably,if something goes wrong, you
(14:42):
have to make it safe to have theconversation about what did we
learn here and you look at thoseas opportunities, because I
think you have to take theapproach that if you've given
people the responsibility, youtrust them.
You know they have the skills,the skills.
Your job is to help maximizetheir success and that can be
through mentoring them,providing some support.
(15:03):
I play a variety of roles.
I play a lot of support roles,people in the organization and I
look at it as my, my obligation.
If somebody is doing somethingand I have some domain expertise
that can make their life alittle easier or make what
they're doing a little cleareror help expose the success a
little with a bit of clarity,that bit more clarity.
Carol Park (15:24):
It's absolutely incumbent on me to do that,
because that's my way ofencouraging what they're doing
yes, as, as you said, I haveseen some of the people that you
continue to grow and giveopportunities for, and have seen
you mentor, which is kind ofhow I started, like I've seen
your leadership ability and yourskills, which is why I think
(15:48):
your company has found so, somuch success, and the people who
work really with you.
I would say with you, not evenfor you, even though I know that
you're the leader, it reallyfeels more, even as you describe
it, that it's a team and, yes,you are the leader and they know
(16:09):
that, but it seems like it's somuch of a power with, not power
over.
Ben Cutler (16:15):
I think that's a really great way of describing
it Like I'm privileged to workwith such a talented team.
There are people that havedomain experience far in excess
of anything I can come close toin some areas and in some areas
I have a little bit ofexperience.
In some areas I have a littlebit of experience.
We have a phenomenal team andwe have to create the conditions
(16:35):
that allows the team to succeedin the best way they can.
Carol Park (16:42):
Yeah, yeah, absolutely, absolutely.
So, as a leader like you'vebeen vulnerable.
You've had times, I'm sure ofthings didn't go well, as we
allude to.
Are there any of those?
You can think of that, how itmaybe changed things or impacted
(17:04):
the culture in your company,your, your own ability to be
vulnerable and own own whenthings didn't go so well so off,
put me on the spot there.
Ben Cutler (17:18):
So I'm off the top of my head, I don't I can't come
up with any specific examples.
But one thing, um, I think youknow this I'm, I'm quite a
dyslexic.
I'm quite dyslexic, um, and youknow, being a little mature at
age, as a kid, that wasperceived something quite
differently than it is today.
Um, through my career, I'velearned to realize that my
(17:40):
dyslexia is actually more of asuperpower than a challenge.
But it does create challenges.
Sometimes when I, you know,read, read an email quickly or
read a Slack message quickly, Imight misinterpret it and give
the wrong answer.
And so you know, I think, for me, I'm very open about owning the
fact that I'm dyslexic.
I don't, I have no qualms aboutit.
I have no, I'm more than happyto the fact that I'm dyslexic.
I don't, I have no qualms aboutit.
Um, I have no, uh, I'm morethan happy to own the fact when
(18:04):
my dyslexia makes itself known,um, and I think that's a really
healthy thing.
It's like it's.
I'm okay, I'm very comfortable,um, with the limitations that I
have, because I know they'rebalanced out by some other, uh,
great strengths.
But every so often it uhdyslexia shows itself and
everybody's really understandingof it, which I appreciate.
But I know that I'm not.
I don't always get it right and, yeah, to me it just seems like
(18:27):
kind of the other side of theequation.
I think it's important for meto make it safe for everybody
else and but that also appliesto myself and everybody else in
leadership roles actually I knowyou said that was like oh, off
the top of your head.
Carol Park (18:43):
That's an incredible answer around how you being
vulnerable, you know, becausesometimes when we have our own
personal struggles and we allhave them for you it was and is
dyslexia, and so oftentimes wethink that we need to hide those
(19:05):
things that somehow people willperceive us as that makes me
weak, not strong, and you justown that.
And so you know, once again,the modeling which trickles down
to building that psychologicalsafety within your culture.
How do you think that thepsychological safety that the
(19:27):
employees that work with you,how do you think that
contributes to greater successor outcomes, and to the culture
as well, to the culture as well.
Ben Cutler (19:40):
So I think when you work with really smart and
talented people, they want tohave some agency, they want to
be able to contribute, they wantto know the mission, they want
to know the goals and if youtake that away from them,
they're not going to be happyand that's going to impact your
culture.
Yeah for sure.
If you have people that arehappy, that's going to
contribute to the culture.
Yeah for sure.
If you have people that arehappy, that's going to
(20:00):
contribute to the culture.
Obviously, hiring people thatare can do the role you know can
do, the role of generally agood fit to the culture helps.
But I think there's a symbioticcycle there.
If you have really talentedpeople and they're creative and
they're early on in their careerand they take on more
responsibility, they're keen todo all of that, but they're also
(20:23):
keen to grow and they can growin their professional lives and
when they do, they're going toachieve more success.
They're going to achieve moresuccess with the company,
they're going to achieve moresuccess within the company and
then, as a result, it's sort ofthis sort of feedback loop that
is created.
So the company wins, theemployees, the employees of the
team members win.
Carol Park (20:43):
Yeah, absolutely, absolutely so.
Direction like for your company, as you're creating this
psychological safety.
How much do the employees likeyou talked about you have the
meetings that y'all meet like inthis sense of agency on this
(21:07):
mission.
How much do they get tocontribute?
Obviously, you have kind of agiven but your missions I don't
know that the overall missionchanges, but maybe some of the
directions, or sometimes whenyou have to pivot, how much
input do your employees get togive with that?
Ben Cutler (21:27):
So I think, if you take kind of the overarching
vision and strategy, that's thatstuff that everybody gets to
contribute to because we sharelots and lots of information,
but that's sort of at the veryhigh level, the sort of the
stuff that's kind of cast instone but it gives a lot of
remit for flexibility andcreativity.
(21:47):
So I think everybody gets tokind of contribute in various
ways.
You know we share hey, this issome feedback we've got or this
is what we're thinking.
What do you think?
I know, sort of from a productside, sometimes there's a
(22:09):
one-on-one or groupconversations that are had and
all sorts of different ways ofsort of sharing that information
.
But I think the realopportunity comes is once we're
all on side with the mission andwe tend to get there really
easily.
Once we're clear on it is theexciting stuff then becomes sort
of like how do we execute onthat mission and sort of
creating those spaces wherepeople can be creative?
You know, there's an examplethis month where we sort of
changed one of our foundationaltech stacks which allowed us to
(22:30):
do something that we couldn't dobefore, and somebody who's not
very senior in the organizationstarted doing something.
That's sort of snowballing intosomething that's going to be
quite positive.
And that was to me a really,really exciting thing to see,
because it wasn't a top-downdecision.
It was quite the opposite.
Somebody who had a problem theywanted to solve saw that this
technology could solve thisproblem, had a little bit of
(22:53):
success, and then all of asudden we're saying, yeah, let's
see if we can roll this out andmake a fundamental change.
That's really neat to see,because that person has the
ability and is working in anenvironment where they can make
that change.
They don't have to run it upthe ladder you know two or three
levels and say well, ben, whatdo you think of this?
It just happens.
It happens in anon-consequential way.
We learn from it and then wecan.
We can, we can say, hey, that'sthe way we can sort of use that
(23:14):
knowledge in different ways forthe greater good.
Carol Park (23:21):
Yeah, that's that personal agency that people
actually believe that they havenot.
Just they're told that theyhave it, they know they have it,
and so they just do it and then, and then it starts to unfold,
and then the teamwork comes inbecause of this culture that
you've you've built within thecompany.
So, yeah, so any kind ofparting words of wisdom, advice
(23:48):
that you can leave us with today.
Ben Cutler (23:51):
So I think what I talked about is the stuff that I
think works for me.
For me, it's a journey.
I will be fine tuning andlearning until I'm not.
It will definitely evolve overtime.
I got some great feedback aboutbeing more direct earlier this
year or late last year, andthat's something I've
incorporated in into my style.
I sometimes I find it hard tobe to the point, indirect.
(24:15):
I've worked on how I can dothat, but in keeping with my the
other principles, and so beingopen to change, uh, evolving
over time is, uh, it's somethingthat you can expect should
happen.
I don't think you need to beperfect.
Um, you should expect to makemistakes.
That's okay.
You want to learn from them.
It's just like you expect fromyour team.
(24:37):
You expect them to learn, soyou know.
I don't think you need to getit right.
100 at the time it's sort of oh, that didn't go according to
plan or as I expected.
How could I handle thatdifferent?
Or is there a?
Is there a root cause?
I keep encountering thesethings.
I can modify that and I cansolve this issue going forward I
guess the last thing is there'slots of great resources
(24:58):
available to help you developyour leadership style.
A lot of them will tell youwhat you have to do.
This, I think picking andchoosing the things that really
resonate with you, and so yourstyle can kind of be the
compilation of the good, insteadof taking this really rigid.
Well, this book says I need todo these 10 things.
Five of them may be absolutelyrelevant and to to you, you to
(25:22):
your role, and resonate reallywell, and the other five maybe
feel like, oh, they feel likethey might, but they don't, so
just pick the ones that work.
Carol Park (25:32):
It's kind of where we started, where I was asking
about how you came to be thatway and you said part of it.
It's just, it's kind of built in.
It's just kind of who you areas a person which I believe that
to be true as well and beingable to be authentically you.
Again, we're still all growing,learning along the way, but
(25:57):
taking who you are and then theleadership tools that resonate,
that you may read about, but Ilove that you're staying
grounded in you.
You know what you know, andthen being open to growth.
And then being open to oh yeah,I could do that better.
And again then your employeessay, oh, he's open to that, I
(26:18):
can be too.
This feels really safe here.
And so, again, I know that yourcompany has been really
successful.
It's continued to grow.
You've grown the product,you've grown your employees.
So I really just want to saythank you again for taking time
out of your day to come on tothe Courage Unmasked podcast and
(26:39):
to share your wisdom andknowledge as a leader with us
today, ben, I so appreciate it.
Ben Cutler (26:47):
Thank you, Carol.
I really appreciate theopportunity.
It's been a lot of fun.
Carol Park (26:51):
Okay, well, take care.
Ben Cutler (26:53):
You as well.
Commix.io (26:55):
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Until next time, keep leadingwith courage.
Well, hi everyone, and welcome back to the Courage
Unmasked podcast, where ourguest today is Ben Cutler, and
I'm so happy that y'all aregoing to get to meet Ben.
I've known Ben for gosh since alot of years I'm thinking maybe
nine, 10 years, maybe 2013, 14,maybe 15.
(00:26):
We met in the kind ofentrepreneurial circuit of
starting companies he with hisand me with my cohort starting
ours and have just had such agreat time getting to know Ben.
So I'm glad y'all are going toget to hear from him and know
him.
So, welcome, ben, and tell us alittle bit just about your
(00:49):
company, your entrepreneurialjourney, kind of how you came to
be the leader of your company.
Ben Cutler (00:56):
Hi, carol, and thanks for having me on Sure.
So Hushmail.
We provide secure, hipaacompliant communication tools to
small healthcare practitioners.
A typical customer is a solepractitioner therapist, but we
serve customers all acrosshealthcare.
The service is primarily asecure email service.
We also have secure web formsthat support electronic
(01:19):
signatures, so our clients usethe service to communicate with
their clients and patients in aHIPAA compliant way.
They also use the secure formsfor things like intake and
patients in a HIPAA compliantway.
They also use the secure formsfor things like intake forms,
health history forms and fortheir practice, and the idea is
for the communication platformto be easy to use and just
generally help with theday-to-day running of small
practices.
(01:39):
I've been in the role for quitesome time.
I started off in a finance role.
I started off sort ofacademically as becoming an
accountant, but I think I foundmy calling in sort of the more
of a CEO role.
Carol Park (01:53):
Yeah, and I obviously I will vouch for
Hushmail because I use Hushmailand it has been fantastic in my
own private practice.
And again, we just kind of gotto know each other along the way
, going to conferences, havingbooths next to each other,
across from each other, spendingtime with our other cohorts in
(02:17):
the space to going to dinner.
So, as I've known you throughthe years, I definitely observe
you as a vulnerable and alsovery humble leader, like I just
observe you even working withthe people who work with you,
alongside of you.
So how do you think you came tobe this way as a leader?
Ben Cutler (02:41):
That's a great question.
I think part of it's just bakedinto who I am.
Leader that's a great question.
I think part of it's just bakedinto who I am.
Another aspect of that will befrom experience.
I've been in leadership formost of my career, but obviously
I didn't start there, so I dohave both sides of the equation
there.
One thing I think that it'squite important is I try to
focus on how to achieve asuccess as opposed to being
(03:01):
right.
Is I try to focus on how toachieve a success as opposed to
being right, and so I thinkthat's a different way of
looking at things, and I thinkin that scenario, you have to be
open to not always being right,and that's absolutely
appropriate.
In my role, I don't have all theanswers.
I want to get to the rightanswer.
I think also my style has justevolved through the years.
(03:22):
It's really a work in progress.
I work with some reallytalented, insightful individuals
.
I learn from them, which isalso really great.
And then a few years back I cameacross an article by General
Stanley McChrystal and it reallyresonated with me and he was
(03:47):
over in the Middle East and hehad some pretty significant
responsibilities and I knowmilitary is an interesting
comparison sort of kind ofsubject to this.
But he changed how they did ouroperations quite significantly.
And he had kind of threeprinciples to really kind of
resonate with me Radicaltransparency, so everybody knows
(04:08):
what the mission is.
I think that's applicable inall businesses.
If you've got people who havesiloed information, you're not
going to get the same outcome asif everybody understands what
the mission is.
The other thing that he does,he believes in, is that the
person closest to a decisionshould make the decision.
And you know, in a typicalorganization you know that's
(04:31):
kind of top down the CEO wouldmake all the most of the
decisions.
But I think it makes a lot ofsense.
So you know, if you've gotsomebody on the front line, they
can make a decision and it'smore efficient for them to make
a decision, it's more empoweringfor them to make that decision.
They should know when thatdecision needs to be deferred.
But I think that's a reallypowerful part of kind of the
equation because it really makespeople feel like they get to
(04:53):
contribute as opposed to doingtheir job written from a script.
And then the other kind of finalpoint that he said he made, and
this is really interestingbecause I think the uh the way
he described it is daily.
They would have a stand-up, azoom meeting, like we're doing,
but with a lot of people on it,and people would have to call
(05:14):
into this, go into this, calland explain why something they
had done hadn't worked out andhe goes.
You can't learn unless you makeit comfortable to talk about
the things that go wrong.
Uh, and I, to me that's justsort of those three points that
are really kind of lined up.
A lot of what I sort of hadsort of kind of come to in
(05:34):
various different ways but in avery nice and succinct way.
So that's sort of, I would say,a milestone on the evolution,
but it's still.
Carol Park (05:41):
It's still sort of a work in progress sure, sure,
we're all a work in progress,and I just think everything that
you just described is how Iperceive you as a leader, even
though I've never worked underyou or for you, with you, I've
just observed you, and so whatyou described there, too, is all
(06:05):
about psychological safety.
You know that people need toknow it's okay to fail and that
sometimes in the failing, weactually grow, become more
successful.
So that psychological safety,that those elements that you
(06:25):
touched on, I yeah, I couldn'tagree more.
(06:49):
It kind of has to start fromthe top down, but then the
people at the bottom have toknow, yeah, this is a safe place
.
Ben Cutler (07:03):
I can say, oh, I messed up or how can I do better
?
How do you, how do you makethat happen?
You can't say it.
You can't say it's a safe placeonce and expect people to
accept that.
You have to kind of create theconditions where people
understand that it is a safeplace.
And I would say, one place whereI uh do that a lot is where I
have people that manage thisreport directly to me and we'll
always talk about, um, kind ofdefining, kind of their
(07:27):
authority, and I'm alwaysencouraging them to, you know,
to really push up against theboundaries of their authority in
terms of their autonomy andagency, because I want them to
really feel that they have thatagency, that they have my
support and they have my trust.
And I always said well, if youoverstep your boundaries a
little bit, that's okay too,because we can learn from that,
we can understand.
Well, actually that was adecision that I probably should
(07:48):
have made, and then we can.
We've got some data there,we've got some understanding,
because that kind of puts somedefinition around that.
But I always encourage peopleto sort of to really really sort
of lean in to kind of theirrole and the authority that they
have, and I try when Icommunicate with with them, not
to tell them, but to sort ofhave a discussion about the
issues and then sort ofencourage them to sort of
(08:11):
formulate their response.
Because I think if I make thedecision for them or tell them
what they need to do, I'mrobbing them of the real value
of decision making, which is thecritical thinking around how do
I solve this problem If Iwasn't there?
If I wasn't there, they wouldhave to do this themselves, and
in another set of circumstancesthey would probably do this by
(08:32):
default.
And so I think the organization, the way I look at it, we
should be sort of creating theconditions where people can
exercise that authority.
Carol Park (08:50):
But the same token we want.
We want them to as well, and'vetalked at numerous times on the
podcast with different guestsabout psychological safety and
have touched on Google'sAristotle project, where they
went in to see what createssuccess.
They had predictions, hypotheses.
(09:12):
We think if you hire thesmartest people and put them in
a room, you're going to besuccessful.
And this was like a two-yearstudy and really what they found
at the end of the two-yearstudy is the number one element
of success that drove successwas psychological safety and, as
you said that, I was like, yeah, because what you said is when
(09:36):
people feel safe to be able tomake a decision, they can think
more critically, they can thinkoutside of the box, because
they're not afraid that theymight be shamed for their
response or criticized if itdoesn't work or whatever, and so
it gives them the freedom to bemore creative, to think outside
(09:56):
of the box, to use what theycan bring to the table, and I
hear in your leadership how youreally build that into people
and into your employees so thatthey can think outside the box.
So, yeah, you just put that sowell.
Ben Cutler (10:11):
I think so yeah, you just put that so well, I think.
Yeah, I think it's such animportant part.
You know, if I look back on mycareer, I've made, you know,
many, many mistakes.
Every one of them is a learningopportunity, and so it's okay
to make a mistake because it's alearning.
These are opportunities asopposed to mistake, and very
(10:34):
often the mistakes are notmaterial in the scheme of things
.
So they're not, you know,they're not going to end the
business, they're not going tohave dire consequences, but what
you can do is you can take sometime to kind of go what can we
learn from this?
What can we do better?
Is there a process that needsto change?
Or is there an area where, okay, we know that somebody needs to
(10:55):
kind of focus on sort of honingtheir skills in?
And I think, for me, when Ilook at, when I have these
conversations, I look at it aslike it's absolutely okay.
Where it can sometimes step outof being okay is the same thing,
the same issue recurs andrecurs and recurs, because then
you've got a pattern wherethere's no growth and I think
that can tell you something else.
But that doesn't typicallyhappen.
(11:15):
Typically, what happens is wesit down, we work out what we
can do better and that issuesolved.
And you know, within a littlebit of time another issue pops
up and then we just address itthat way.
But I think it kind of createsa the issue is not the issue,
it's kind of how do we solve theissue?
Carol Park (11:40):
Yeah, yeah, that's so well put and I know even as
you talk about that.
It's because you model thisfrom the top down and a lot of
times people think that you knowvulnerability and humility are
perceived as weaknesses,especially in leadership, where
you're supposed to be strong andhave all the answers and tell
people, and so you're modelingthis In your words.
(12:02):
How would you describe that?
Actually, vulnerability andhumility and leadership is
incredible strength, notweakness.
Ben Cutler (12:12):
Yeah, that's a really good question.
I think my view is that youwant people to support.
If you want people to supportyou, they have to feel like they
have some agency.
They got you know, they havesome control of the situation.
Talented people they reallywant a mission, they want to
know what the mission is, butthey also want the flexibility
to you know, do the mission.
You know, at times I need somesupport and sometimes I need
(12:36):
some understanding.
So I think when you take thatapproach it takes away from that
top-down model because you'resort of sharing that control
with other people.
Carol Park (12:50):
Yeah, it's really building a team right, because
they then feel like not okay,I'm tasked with this, I don't
have agency, I don't have anyfreedom to try things or
whatever.
I just have to do the task andespecially, as you said, for
talented people, that they kindof feel like they're pigeonholed
(13:12):
and probably won't stay verylong would be my guess.
Ben Cutler (13:16):
You've met some of the people that I work with.
These are phenomenally talentedpeople at different stages in
their career.
We absolutely want to maximizethe time that they stay with us,
knowing that at some point theywill move on to bigger and
better things, and when thosedays happen, I'll be sad but be
happy for them.
I think it's really though it'sreally important.
(13:37):
You've got to kind of createthose sort of conditions and I
think McChrystal's principlesreally apply here.
When you talk about you know heuses the word radical
transparency, but talk abouttransparency of the vision and
everything else If everybodyunderstands generally what
you're trying to do, whereyou're trying to go, I always
refer to it.
Well, you know the tank is goingto Europe and we're in Canada.
(13:59):
Right, we're on the East Coastof Canada, we're going to Europe
.
There's a lot of things thatcan happen on that journey that
are the control of other people,but we generally know where
we're going.
That's really important.
So if everybody understandswhat we're doing, then mission
is clearer.
Along that journey you then workout well, how do you handle the
(14:20):
decisions that need to be made?
You make those decisionsefficiently.
You make those those decisionsin ways that empower people and
empower growth, creativity andeverything else, because it's
the creativity and all of thethings that agency gives people
that really help move the needlein success.
And then you know, inevitably,if something goes wrong, you
(14:42):
have to make it safe to have theconversation about what did we
learn here and you look at thoseas opportunities, because I
think you have to take theapproach that if you've given
people the responsibility, youtrust them.
You know they have the skills,the skills.
Your job is to help maximizetheir success and that can be
through mentoring them,providing some support.
(15:03):
I play a variety of roles.
I play a lot of support roles,people in the organization and I
look at it as my, my obligation.
If somebody is doing somethingand I have some domain expertise
that can make their life alittle easier or make what
they're doing a little cleareror help expose the success a
little with a bit of clarity,that bit more clarity.
Carol Park (15:24):
It's absolutely incumbent on me to do that,
because that's my way ofencouraging what they're doing
yes, as, as you said, I haveseen some of the people that you
continue to grow and giveopportunities for, and have seen
you mentor, which is kind ofhow I started, like I've seen
your leadership ability and yourskills, which is why I think
(15:48):
your company has found so, somuch success, and the people who
work really with you.
I would say with you, not evenfor you, even though I know that
you're the leader, it reallyfeels more, even as you describe
it, that it's a team and, yes,you are the leader and they know
(16:09):
that, but it seems like it's somuch of a power with, not power
over.
Ben Cutler (16:15):
I think that's a really great way of describing
it Like I'm privileged to workwith such a talented team.
There are people that havedomain experience far in excess
of anything I can come close toin some areas and in some areas
I have a little bit ofexperience.
In some areas I have a littlebit of experience.
We have a phenomenal team andwe have to create the conditions
(16:35):
that allows the team to succeedin the best way they can.
Carol Park (16:42):
Yeah, yeah, absolutely, absolutely.
So, as a leader like you'vebeen vulnerable.
You've had times, I'm sure ofthings didn't go well, as we
allude to.
Are there any of those?
You can think of that, how itmaybe changed things or impacted
(17:04):
the culture in your company,your, your own ability to be
vulnerable and own own whenthings didn't go so well so off,
put me on the spot there.
Ben Cutler (17:18):
So I'm off the top of my head, I don't I can't come
up with any specific examples.
But one thing, um, I think youknow this I'm, I'm quite a
dyslexic.
I'm quite dyslexic, um, and youknow, being a little mature at
age, as a kid, that wasperceived something quite
differently than it is today.
Um, through my career, I'velearned to realize that my
(17:40):
dyslexia is actually more of asuperpower than a challenge.
But it does create challenges.
Sometimes when I, you know,read, read an email quickly or
read a Slack message quickly, Imight misinterpret it and give
the wrong answer.
And so you know, I think, for me, I'm very open about owning the
fact that I'm dyslexic.
I don't, I have no qualms aboutit.
I have no, I'm more than happyto the fact that I'm dyslexic.
I don't, I have no qualms aboutit.
Um, I have no, uh, I'm morethan happy to own the fact when
(18:04):
my dyslexia makes itself known,um, and I think that's a really
healthy thing.
It's like it's.
I'm okay, I'm very comfortable,um, with the limitations that I
have, because I know they'rebalanced out by some other, uh,
great strengths.
But every so often it uhdyslexia shows itself and
everybody's really understandingof it, which I appreciate.
But I know that I'm not.
I don't always get it right and, yeah, to me it just seems like
(18:27):
kind of the other side of theequation.
I think it's important for meto make it safe for everybody
else and but that also appliesto myself and everybody else in
leadership roles actually I knowyou said that was like oh, off
the top of your head.
Carol Park (18:43):
That's an incredible answer around how you being
vulnerable, you know, becausesometimes when we have our own
personal struggles and we allhave them for you it was and is
dyslexia, and so oftentimes wethink that we need to hide those
(19:05):
things that somehow people willperceive us as that makes me
weak, not strong, and you justown that.
And so you know, once again,the modeling which trickles down
to building that psychologicalsafety within your culture.
How do you think that thepsychological safety that the
(19:27):
employees that work with you,how do you think that
contributes to greater successor outcomes, and to the culture
as well, to the culture as well.
Ben Cutler (19:40):
So I think when you work with really smart and
talented people, they want tohave some agency, they want to
be able to contribute, they wantto know the mission, they want
to know the goals and if youtake that away from them,
they're not going to be happyand that's going to impact your
culture.
Yeah for sure.
If you have people that arehappy, that's going to
contribute to the culture.
Yeah for sure.
If you have people that arehappy, that's going to
(20:00):
contribute to the culture.
Obviously, hiring people thatare can do the role you know can
do, the role of generally agood fit to the culture helps.
But I think there's a symbioticcycle there.
If you have really talentedpeople and they're creative and
they're early on in their careerand they take on more
responsibility, they're keen todo all of that, but they're also
(20:23):
keen to grow and they can growin their professional lives and
when they do, they're going toachieve more success.
They're going to achieve moresuccess with the company,
they're going to achieve moresuccess within the company and
then, as a result, it's sort ofthis sort of feedback loop that
is created.
So the company wins, theemployees, the employees of the
team members win.
Carol Park (20:43):
Yeah, absolutely, absolutely so.
Direction like for your company, as you're creating this
psychological safety.
How much do the employees likeyou talked about you have the
meetings that y'all meet like inthis sense of agency on this
(21:07):
mission.
How much do they get tocontribute?
Obviously, you have kind of agiven but your missions I don't
know that the overall missionchanges, but maybe some of the
directions, or sometimes whenyou have to pivot, how much
input do your employees get togive with that?
Ben Cutler (21:27):
So I think, if you take kind of the overarching
vision and strategy, that's thatstuff that everybody gets to
contribute to because we sharelots and lots of information,
but that's sort of at the veryhigh level, the sort of the
stuff that's kind of cast instone but it gives a lot of
remit for flexibility andcreativity.
(21:47):
So I think everybody gets tokind of contribute in various
ways.
You know we share hey, this issome feedback we've got or this
is what we're thinking.
What do you think?
I know, sort of from a productside, sometimes there's a
(22:09):
one-on-one or groupconversations that are had and
all sorts of different ways ofsort of sharing that information
.
But I think the realopportunity comes is once we're
all on side with the mission andwe tend to get there really
easily.
Once we're clear on it is theexciting stuff then becomes sort
of like how do we execute onthat mission and sort of
creating those spaces wherepeople can be creative?
You know, there's an examplethis month where we sort of
changed one of our foundationaltech stacks which allowed us to
(22:30):
do something that we couldn't dobefore, and somebody who's not
very senior in the organizationstarted doing something.
That's sort of snowballing intosomething that's going to be
quite positive.
And that was to me a really,really exciting thing to see,
because it wasn't a top-downdecision.
It was quite the opposite.
Somebody who had a problem theywanted to solve saw that this
technology could solve thisproblem, had a little bit of
(22:53):
success, and then all of asudden we're saying, yeah, let's
see if we can roll this out andmake a fundamental change.
That's really neat to see,because that person has the
ability and is working in anenvironment where they can make
that change.
They don't have to run it upthe ladder you know two or three
levels and say well, ben, whatdo you think of this?
It just happens.
It happens in anon-consequential way.
We learn from it and then wecan.
We can, we can say, hey, that'sthe way we can sort of use that
(23:14):
knowledge in different ways forthe greater good.
Carol Park (23:21):
Yeah, that's that personal agency that people
actually believe that they havenot.
Just they're told that theyhave it, they know they have it,
and so they just do it and then, and then it starts to unfold,
and then the teamwork comes inbecause of this culture that
you've you've built within thecompany.
So, yeah, so any kind ofparting words of wisdom, advice
(23:48):
that you can leave us with today.
Ben Cutler (23:51):
So I think what I talked about is the stuff that I
think works for me.
For me, it's a journey.
I will be fine tuning andlearning until I'm not.
It will definitely evolve overtime.
I got some great feedback aboutbeing more direct earlier this
year or late last year, andthat's something I've
incorporated in into my style.
I sometimes I find it hard tobe to the point, indirect.
(24:15):
I've worked on how I can dothat, but in keeping with my the
other principles, and so beingopen to change, uh, evolving
over time is, uh, it's somethingthat you can expect should
happen.
I don't think you need to beperfect.
Um, you should expect to makemistakes.
That's okay.
You want to learn from them.
It's just like you expect fromyour team.
(24:37):
You expect them to learn, soyou know.
I don't think you need to getit right.
100 at the time it's sort of oh, that didn't go according to
plan or as I expected.
How could I handle thatdifferent?
Or is there a?
Is there a root cause?
I keep encountering thesethings.
I can modify that and I cansolve this issue going forward I
guess the last thing is there'slots of great resources
(24:58):
available to help you developyour leadership style.
A lot of them will tell youwhat you have to do.
This, I think picking andchoosing the things that really
resonate with you, and so yourstyle can kind of be the
compilation of the good, insteadof taking this really rigid.
Well, this book says I need todo these 10 things.
Five of them may be absolutelyrelevant and to to you, you to
(25:22):
your role, and resonate reallywell, and the other five maybe
feel like, oh, they feel likethey might, but they don't, so
just pick the ones that work.
Carol Park (25:32):
It's kind of where we started, where I was asking
about how you came to be thatway and you said part of it.
It's just, it's kind of built in.
It's just kind of who you areas a person which I believe that
to be true as well and beingable to be authentically you.
Again, we're still all growing,learning along the way, but
(25:57):
taking who you are and then theleadership tools that resonate,
that you may read about, but Ilove that you're staying
grounded in you.
You know what you know, andthen being open to growth.
And then being open to oh yeah,I could do that better.
And again then your employeessay, oh, he's open to that, I
(26:18):
can be too.
This feels really safe here.
And so, again, I know that yourcompany has been really
successful.
It's continued to grow.
You've grown the product,you've grown your employees.
So I really just want to saythank you again for taking time
out of your day to come on tothe Courage Unmasked podcast and
(26:39):
to share your wisdom andknowledge as a leader with us
today, ben, I so appreciate it.
Ben Cutler (26:47):
Thank you, Carol.
I really appreciate theopportunity.
It's been a lot of fun.
Carol Park (26:51):
Okay, well, take care.
Ben Cutler (26:53):
You as well.
Commix.io (26:55):
Thanks for tuning in to the Courage Unmasked podcast
If you enjoyed today's episode.
Thanks for tuning in to theCourage Unmasked podcast.
If you enjoyed today's episode,don't forget to subscribe and
leave a review.
It really helps us grow.
Follow us on social media forupdates and a look at what's
coming next, and a big thank youto our sponsor, Comixio, for
supporting this journey.
Until next time, keep leadingwith courage.
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