August 11, 2025 • 52 mins
Leif O'Leary, CEO of Alegeus and veteran sales leader, shares how strong leadership skills can translate into executive success through communication, consistency, and a commitment to developing talent.
- Leif explains how strong sales leadership requires both consistency and positive communication
- Leif emphasizes building connections with team members is essential for motivating performance
- Communication frameworks should include regular one-on-ones, steady outbound cadence, and team events
- Effective leaders understand three universal principles: people want to win, they want opportunity, and want others invested in their success
- The most successful leaders genuinely care about unlocking human potential and building teams
- Morning routines and consistent habits contribute significantly to leadership effectiveness
- Weekly communication to the entire organization creates alignment and accountability
Leif breaks down his communication framework—the regular one-on-ones that prioritize listening over talking, the weekly notes to his entire organization, and the meaningful events that bring teams together. But beyond these tactical approaches lies what Leif calls "the art" of leadership: the genuine caring and curiosity that transforms transactional relationships into meaningful connections.
Whether you're currently leading a sales team, aspiring to greater leadership responsibility, or considering the leap from sales leadership to executive roles, this episode offers invaluable insights into how exceptional leaders think and act. Tune in to discover why, as Leif puts it, "I have no greater sense of satisfaction than watching people that I've worked with go on to achieve their dreams."
Music by Ben Cina & Ayler Young
Mark as Played
Transcript
Episode Transcript
Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 2 (00:16):
Hello everyone and welcome to another episode of
Pillar Talk, where we build thefoundations of sales leadership
success and create clarity interms of what good looks like
for current and aspiring salesleaders.
Before we jump in, let's reviewthe six pillars of successful
sales leadership.
Starts with talentidentification and attraction.
Obviously, building the teamand attracting that type of
(00:38):
talent is incredibly difficult.
The operating rhythm.
For me, I love this inestablishing an environment
where you foster motivation andbalance that with accountability
and engagement, Businessplanning, the cross-functional
relationships that exist, so youcan play offense instead of
reacting to things that happento you.
In Leaf Talk, that is, make thenews instead of read the news.
(01:03):
Communication, ownership andmastering the craft.
How do we help the team win?
Today we are fortunate to haveas a guest Leif O'Leary.
Leif is the CEO of Allegius, aleading healthcare platform.
Leif has spent decades inleadership roles, primarily
leading sales and revenueorganizations, before rising to
(01:26):
the CEO role.
From my experience with Leif, Iknow him for his commitment to
great communication, for hisconsistency in leadership and
just for his pure hard workethic.
Leif brings a uniqueperspective on how strong sales
leadership skills can translateinto executive level success.
Speaker 1 (01:46):
So, leaf, welcome to pillar talk thanks, rick, it's
great to be here.
Um, I was honored to be askedto join.
I think this work you're doingto support the community I mean
this sincerely is maybe asimportant as any work being done
out there.
You know how I feel about thecriticality of sales leadership,
the importance of the role Evenyou capture in some of your
(02:11):
thoughts around this work you'redoing that it's one of the most
difficult roles.
I actually think it is the mostdifficult role and I think I
can say that with three-plusdecades of experiencing, having
done just about everything.
I think there's very littlemore challenging or rewarding
than building an extraordinaryteam and unlocking sort of
(02:32):
growth and impact in a businessthrough that team.
And so the fact that you'rebringing real world
practitioners together just toshare some thoughts I think is
awesome thoughts I think isawesome.
Speaker 2 (02:46):
Yeah, I mean I just see myself as a student trying
to learn and I've developedthese pillars as a way to try to
frame what I define assuccessful and how I will lead
and develop leaders within myorganization.
But I don't claim to have allthe answers.
So I love having these types ofconversations and trying to
learn from others and to sharethose learnings, obviously
through this podcast and thenewsletter.
(03:07):
You know, leif, one of myfavorite stories is in our time
working together is you weresharing about.
You know you would often getquestions around hey, how do I
one day get into your role orhow do I develop into be a more
elevated leader?
And we'd have those types ofconversations.
And you talked about earlier inyour career where you were
living a pretty far distanceaway from where your office was
(03:29):
and so you had quite an extendedcommute and please correct if I
get any of the details wronghere but you would leave like
way before the sun would come upin the morning and you would
then hit the gym when you got tosort of near the office and
then you would still get intothe office and start the day
really before everybody elseeven got there.
But you know, with thatextended commute it got to the
(03:50):
point where you had to specialorder some type of like stronger
dose coffee to maintain yourenergy levels and how that
dedication and years of likejust grinding through that
really helped you expand andgain experience and skills to
develop as a leader.
So I remember those storiesreally well.
I guess my question for you iswhat's your morning routine like
(04:12):
these days compared to then?
Speaker 1 (04:14):
Well, I will say a couple of quick notes and I
thank you for remembering Rick.
It's nice to know that some ofthe stories which you know,
fortunately or unfortunately,are completely based in fact in
that case stuck with you,fortunately or unfortunately,
are completely based in fact inthat case stuck with you.
And and I'll I'll answer yourquestion about kind of my
morning routine, because youknow a bit about me and you know
(04:36):
that I am a very habitualperson.
You know, I feel the bestpeople are really sort of
defined by their habits and sortof that's the way I live my
life.
But my morning routine now isnot all that dissimilar, absent
the two or three hour commutefrom.
Yes, you are correct, I wasliving in Connecticut but I had
this extraordinary connectionwith this unbelievable company
working for just amazing leaders.
(04:57):
At the same time, my wife and Iwere starting a family with
four kids and we were connectedto where we lived and I was.
I just felt like I was in thisreally unique spot working for
the right types of sales leadersthat could unlock what I felt
was the right types ofopportunities for me, and so it
was an important.
You know, yes, I left at 4amevery day.
(05:18):
Yes, I had to go find regularcoffee stopped keeping me awake
on the highway in the dark ofthe night.
So I did go find.
I'm not going to mention thename of the coffee because I'm
actually not.
I think I don't want to be anadvocate for that.
That's not really the bestmodel when your heart rate is,
you know, through your chest at5 am before you get to the gym.
But but that.
But that was actually a veryintentional decision because I
(05:41):
wanted to be there for my family, even if I was getting home at
nine or 10 o'clock at night andthen leaving at four the next
morning even though I wascatching a few minutes, I was
supporting that part of my life.
At the same time, I was reallyreally leaning into what I
thought was a unique opportunity, which actually comes back in
many ways this conversationbecause it was the opportunity
to work with some of the best,the best leaders, the best
(06:05):
salespeople, and that was what Iaspired to be and do, and so it
was important for me to do that.
So, yeah, my morning routinenow is exactly the same.
I get up every day at the sametime, I work out first and then
I'm in the office.
And well, it might not be asquite en vogue today with the
(06:26):
youngest generation, I'm still ahuge believer that you know,
working harder and being morepresent and leaning in more is
one of the greatestdifferentiators that you can
have in a career, and so it'sstill, sort of three decades
later, what I sort of lean on.
(06:46):
Maybe it's because I'm notsmart enough to differentiate
with my intellect and IQ.
Hard work is the mostcontrollable asset I have, and
so, you know, that's been sortof the way I've defined it from
the beginning.
Speaker 2 (06:58):
Well, I'm hoping that the start time is a little
later than 4 am.
Speaker 1 (07:03):
It's a little later than that because that was born
out of absolute necessity, butnot much later.
It's just a little more civil.
I'm not injecting sort of thewrong types of coffee into my
system.
Speaker 2 (07:15):
Yeah.
So I think about those storiesof hard work and I overlay that
with the world that we're intoday.
Like people have differentexpectations or even definitions
of what hard work is andthere's different types of
distractions that can take awayfrom hard work In your coming up
in your career or the earlierin mine.
(07:35):
Concepts like a smartphonesitting right next to you or
hybrid slash remote work thoseweren't really regularly applied
concepts.
Now we have a new generationwhere these are things that we
have to grapple with a bit andyou know there's always the like
.
Prior generation is alwaysjudging the newer generation and
(07:58):
saying that they're lesshardworking.
Or you know, back in my day wedidn't have this or that, but I
really wanted to get a sense ofnow, as you reflect, as someone
that lived hard work at a timeand place where that's just what
you had to do.
And now you are in a worldwhere you see people across a
large organization.
They're early in their career,they want to move up, like what
(08:20):
is hard work look like in a waytoday that creates opportunity
for folks in your organization?
Speaker 1 (08:26):
Yeah, yeah, rick, I think it's a, it's a really big
factor for leaders.
You know, whether you're asales leader or you're a leader
of other functions, we, we areall living a time of just
massive change.
It's funny, though, as I listento you sort of frame the
question, I have to say I'm I'mactually drawn back to some of
my first meetings with you andsome other leaders when we came
together many, many years agoand we're slightly different
(08:49):
generations I'm a little bitahead of you but we're sort of
close neighbors.
But you might or might notremember this, but one of my
very first trips down to our NewYork office at Intronix, when
we came together, you andanother leader there, you know,
were gracious enough to comeinto the office for a 7.30 am
(09:09):
meeting which, by the way, I hadflown down from Boston for but
you two sort of marched into theoffice and said we don't do
7.30 am meetings, like what isthis?
And it was this really funnymoment where, you know one, I
saw sort of the strength ofconviction in both of you and
(09:30):
that was a very truecharacteristic.
But it was also, I think,indicative of a really important
lesson for, I think, allleaders, certainly for me, and
one that I've learned inmultiple phases of my journey,
that one there's not onedefinition of hard work and, by
the way, I can say with absoluteconviction, knowing both of you
now for, I guess, 15 plus years, that there's few harder
(09:55):
workers than the two of you, butthat that the definition of
what that means is not alwaysthe same For me.
I'm a morning person, so for me,like you described, being out
the door at 4 am or 5 am, beingat the gym and being in the
office at 7 and turning thelights on that's how I started
my career at ADP.
Like I knew nothing when Ilanded in the Windsor
(10:15):
Connecticut office of ADP, asnothing but raw material.
You know somebody who'd neverbeen in a professional
white-collar setting and theonly thing I knew to do was turn
the lights on for everybodyelse.
So I wasn't losing ground tothe 50 or 60 salespeople in that
room with me.
But that was the way I definedit, and you all defined it in a
slightly different way, andthat's a really important thing
(10:36):
for leaders to understand theshape and form of the people you
hire, the way they're motivated, the way they work, is not
always going to be a reflectionof you and, frankly, the best
teams aren't just a mirror imageof their leaders.
Anyways, you want a mosaic ofskills and capabilities and
personalities and dynamics.
So I'm reminded of that,although your question is much
(11:00):
more framed.
In this current generation andI have four kids who are all in
their 20s you've met them andthey're all entering or in the
workforce now, and so I kind oflive every day like being a
little bit of this the old goat,old guard.
You know, just work hard, grindit out, and then I'm immersed
in a setting with people thathave lived just a totally
(11:26):
different experience.
You know they've lived, as youdescribed, instant access to
information all the time.
Like you know, when I and sortof we were growing up, you know
if you wanted to get an airlineticket book, you worked at it.
You know you went to a travelagent.
That's before your time, butyou went to a travel agent.
That's before your time, butyou went to a travel agent.
Or you know you made phonecalls or you did things.
(11:49):
Like you know today, you knowthat's two clicks of a button on
your phone and you're flying toNova Scotia to go golf for the
weekend and that's probably whatyou did, right?
So our kids have grown upconditioned to just a totally
different set of experiences.
In many ways, really good stuffsurrounds that access to
information, but it does changethe evolving dynamics in a
(12:10):
workplace and I certainly amlearning every day through this.
It's not like I have all theanswers.
I think one of your pillarsaround communication, though,
really starts to get to theheart of how you sort of thread
this needle of.
You still do need a hardworking, productive, engaged workforce.
If you're a sales leader, youneed a group of people who are
(12:32):
committed to the mission.
You know that want to go makethe news.
Thank you for using one of myphrases.
I think my current company getstired of sales.
Certainly the salesorganization here gets tired of
hearing that every day.
I need people to make the news,not report the news, which I
think I stole from somebody atPTC many, many decades ago.
But you know it's.
You know you need people towant to do that, but you've also
(12:54):
got to realize that you knowthe team you put together is
probably going to have peoplewho are closer to our generation
and maybe a little bit morethat mindset.
They're going to be people thatare morning people, and I'm
using simple, stupid examples,like the morning person versus
you and Pete, who, hey, we liketo work all night.
You know like, this is what wedo you get up at four, we'll get
up at eight and we'll get towork at nine.
(13:16):
You know like, and it's goingto be everything in between.
And so this idea of how youcommunicate and connect with
people becomes really critical,really critical.
And I'll tell you you're justjogging for me so many stories
from when we were together, butyou probably don't remember our
first meeting.
I do, though, and I rememberthese things.
Speaker 2 (13:37):
It was a breakfast.
Speaker 1 (13:39):
Yeah, it was a breakfast in Boston at the
Liberty Hotel.
You might or might not rememberthe first thing you said when
you sat down with me, but itstuck with me in a really good
way.
It was kind of an interestingmoment but it stuck with me.
And at the time I was a salesleader.
For those who don't know, I wasat that time sort of coming
into the business, sort ofrunning the Americas and then,
(13:59):
with this plan to move into theCRO role, and Rick had been a
long time, really, reallyimportant leader in this
business.
It really helped build thebusiness and had the requisite
amount of loyalty, connectionand commitment to this business.
And I think and I won't speakfor him, but I know this to be
(14:20):
true in some ways it's likelooked at him, looked at himself
as sort of a guardian of thiscompany and what it was and in
all the right ways.
And here I was a total outsider, like a guy who knew nothing
about this space, was fromBoston, and we had breakfast in
in Boston and Rick sat down withme and he said first thing he
said out of his mouth like afterthe pleasantry is like you know
(14:49):
, I don't work well with peoplewho aren't very smart.
That's what he said.
Very, very first thing Ricksaid and I, it was a really
interesting moment and and andyou know you have to you know
you realize that, as a leader,like I, knew enough to know,
even though I didn't know Rick,I knew that Rick was a very
important part of the mosaic ofthis business which you were and
(15:10):
you know I had.
You know there's decisions youmake in these moments.
Right, I could say you know whois this arrogant, cocksure guy
who starts a meeting with hisnew boss?
Like that.
It probably was something thatwent through my mind, but like
that, it probably was somethingthat went through my mind.
(15:31):
But I also saw in that thelevel of connection and how much
you cared about this business.
You weren't saying that becauseyou were trying to reject the
organ that was Leif O'Leary.
You were saying that becauseyou wanted to make sure the
standards that you had for whatyou had been building there were
going to be met and surpassedby new leaders.
And I mentioned that onlybecause, like those types of
(15:55):
moments where, clearly, at thatmoment in our journey, you and I
didn't know the things we havein common and there are many,
you know, a relentless love oflearning, love of leading
building teams.
You know very hard workerspassionate about supporting, you
know, our clients and buildingbusinesses.
Like there were so many thingsthat you and I ultimately had in
common but at that moment wewere just.
(16:18):
You know, I was an outsider andevery leader starts that way.
Every leader starts that way.
You have either hired somebodynew Now they are an outsider to
your team if you find them in,but you are an outsider to them
and building connection, whichfor me is currency with people
is everything and I know that'sa cliche, but like you've got to
(16:41):
figure out how to connect withpeople.
Like you've got to figure outhow to connect with people and
communication and the way you dothat is a critical sort of
facilitator of doing that.
And I do look back fondly onsort of the relationship we
ultimately built and the impactyou made in our business and
what you've gone on to do andsoar after your time at
Intralinks.
But there's these justinteresting moments and it's all
(17:03):
about human connection.
Speaker 2 (17:04):
You know it's really great.
I don't remember that specificcomment.
I remember the specificbreakfast.
To give you some context of whyI probably went in with a
little bit of a sharper elbowthan normal, and that situation
was our CRO at the time.
Reiner had made a commitment,so we had some leadership tumult
in that organization prior tohis arrival, your arrival.
That was like cartoonish thatwe don't need to get into the
(17:27):
details of, but so there was ahigh level of sensitivity, there
was a protective aspect andthen there was a commitment of
like, hey, and you know there'snever the right answer here if
you involve people in theinterview process for someone
that they'll be reporting to and, of course, when you are in a
role where that you know thehire is going to be the one
(17:48):
you're reporting to, of coursethe answer is yes, you should be
involved in that, because youknow you have a bias there, of
course, and you want to makesure that the leader is great.
In this particular situation,you were hired and then Reiner
kind of came to me and was like,look, I know I said you could
be involved, but like, trust me,when you leave you are going to
(18:10):
understand that we brought theright leader in.
So he took like a bit of a riskand, of course, like one of the
things that made me a topindividual contributor was that
swagger, was that attitude.
It's a little bit cringy to hearnow as now you know, almost 20
years into a leadership careerand realizing that that swagger
and that cockiness that makesyou a very strong individual
contributor has real riskassociated with leadership
(18:32):
dynamics and part of the journeyof trying to define what good
leadership is is on the back ofthat reality.
So I try to play into theswagger and that stuff where
applicable in bringing a winningmindset and those types of
elements.
But also try, try not alwayssucceed into being more
thoughtful about the words thatcould have an impact.
(18:53):
You were a real deal leadercoming into an organization and
off putting comment to initiatea conversation is not going to
phase you.
There are many people in theorganization that are far less
secure in their position, farless confident in their even fit
for a role and a higher levelof sensitivity to that, and that
could be a really bad situationwhen you are in an elevated.
So I laugh a bit at what you'resaying, but it also makes me
(19:15):
really sad, as the context oftheir even meaning well doesn't
necessarily translate into theright things.
But but whatever it was a it's afunny way to kind of you know,
talk about how we kick thingsoff, but I do like to reflect on
a then and now type of dynamic.
Speaker 1 (19:30):
Yeah, but.
But.
But, Rick, just just thinkabout what you just said.
I mean, that's the essence ofyour growth mindset personified,
and I think you capturedperfectly the reality.
Like your sense ofself-assuredness and your
swagger and your confidence hasbeen a defining characteristic
of what's made you great.
That's going to happen withpeople.
Just, they're going to be muchmore quiet, much more powerful
(19:53):
people who don't have thatexternal kind of sort of
projection of who they are, andthey're also extraordinary.
They can also beextraordinarily high performance
.
So you know, it's all part ofthe growth for all of us.
You know I probably learned asmuch in that moment as a leader
it's.
You know I'll remember thatforever.
You know, along with many otherstories, my journey with you
(20:13):
and others, that forever youknow, along with many other
stories, my journey with you andothers, but those are things
that help you grow as a leader.
You know I had to learn how tohandle that approach, just like
I did with you and Pete sittingthere in the New York office and
we don't do 730 meetings andI'm sitting here saying you
don't do 730 meetings, You're anhour and a half late to work.
I don't know what to tell you,Like I flew in here and beat you
to the office.
That's problem number one.
(20:34):
You know you, you walk to theoffice.
So so you've got to learn howto adapt.
And I just think communicationis just so critical because if
you don't connect and engage,and then if you can't
communicate which is both activeand reactive, listening, like
you, you know, communication isnot a one way street.
You've got to also listen,understand and connect.
Speaker 2 (20:57):
So well, it wasn't just pete and I that you were uh
had to establish thatcredibility with.
We had 200 people, 150 peoplein the organization, all uh.
Yes, we had offices and mostpeople were in the office, but
we also were a national teamwith, uh, you know, disparate
geographies and folks all overthe country and I think, as I
reflected on what made you sosuccessful in the role, it
(21:18):
really was like what I'd call aconsistent and positive
communication.
Consistent and positivecommunication and you would
include the rest of leadership.
Really, really well, this wasn'tjust coming from LEAF.
You made an explicit effort toensure that you would reference
Reiner a bunch and like, hey,reiner and I were talking like
(21:38):
establishing even more that thisisn't just you off the cuff
communicating a message or aninitiative or whatever it was.
There was a it felt to me likea real intent to make sure that
this isn't about you but it'sabout the organization and that
there's alignment across.
You know your leadershipinfrastructure there and I guess
I wanted to ask you about thedevelopment of that
(22:00):
communication skill, both from atone, that positive type of
element, and then theconsistency of it, and you know
how you have evolved that.
You know into where you aretoday.
Speaker 1 (22:12):
Yeah, I'll just say Rick, you know, first of all I
am the byproduct of the gifts ofso many incredible examples and
leaders through the years.
So like I think, first I wasblessed even from my earliest
days at ADP, like I worked forpeople, many of whom I'm still
close with today, 30 years later, and have worked with again and
(22:32):
have worked with again, whomodeled this level of sort of
clarity, vision, engagement,communication with their people,
you know, and so like I think,the first again remember when I
started my career I hadliterally zero frame of
reference as what it meant to bea leader in a professional
setting.
You know, any intrinsicleadership capabilities I might
have had were just born ofnecessity, of reference as what
it what it meant to be a leaderin a professional setting.
(22:55):
You know, any intrinsicleadership capabilities I might
have had were just born ofnecessity.
And athletic settings or schoolsettings, which you know are
valuable but totally different,and, you know, for a variety of
reasons.
And so for me, first andforemost, I think I saw that
modeled in exceptional ways atadp.
And then I went to ptc with alot of intentionality, by the
(23:17):
way, drawn there, you know, toone of your pillars around
attracting the right people.
If I can throw myself into thebucket of one of the right
people that went there throughthe years, I was drawn there by
Jamie Pappas, just an absolutelyextraordinary leader.
He called me and this is a realstory back to the start early.
It's funny how this story willconnect a little bit, and you've
(23:37):
heard this story before.
This is that before cell phoneswere a thing, you know, I was
sitting in my office, my firstoffice in my whole career.
I was sitting in that office inWindsor, connecticut.
It was 630 in the morning andmy phone rang.
Jamie doesn't even probablyremember this, but he called me
and he had this dynamic energyto him and he said Leif, I got
(24:00):
your name from the ADP RollingStone magazine.
It looks like you're the topsales leader in North America.
Blah, blah, blah.
You're in Hartford Connecticut.
I'm in Hartford Connecticut.
I'm looking for a salesdirector to come build this team
.
Blah, blah, blah, blah, boom.
And I was like I'm neverleaving ADP Jamie.
I this team.
Blah, blah, blah, blah, boom.
And I was like I'm neverleaving ADP Jamie.
I'm going to be here for 35years.
My entire career is mapped outin front of me.
And he said, okay, got it,perfect, but you need a network
(24:25):
in Hartford.
Why don't we go have coffee onemorning?
It seems like you're an earlyriser, I'm an early riser.
Let's get coffee one day beforeyou go in the office.
And I said you know what Ishould do, that you know.
He had an infectious energy tohim.
And I said I should do thatbecause I don't know anybody,
like I'm literally a babe in thewoods.
I know nobody.
I don't know anybody atHartford.
I moved here the day after Iwalked off my graduation stage
(24:47):
at BC and moved to sleep in abasement in Hartford and started
working the next morning.
That was the glamorous start tomy career.
That was the glamorous start tomy career and I had coffee with
Jamie and a month later I wasstarting a PTC and it was.
(25:09):
So.
I've been sort of seeing thismodel, this engagement,
connection, communicationcapability and the consistency
of it almost throughout mycareer.
So, first and foremost, I thinkthat's where sort of I
developed that mindset.
I think that's where sort of Ideveloped that mindset and I
just, I'm just a huge believerthat as a sales leader really
any leader, but certainly as asales leader you play this
critical role where you haveobviously a responsibility to
build the best team and create ateam of high performance impact
(25:34):
players who make the news.
You also have this enormousresponsibility to the
stakeholders around you, becauseif you're in a company that is
focused on growth, really kindof everybody around you is
nourished by or focused on arewe driving growth, and so you,
as a leader, have thisstakeholder responsibility to
create connectivity.
(25:55):
This is what's working to powergrowth.
This is how we're performingTransparency to say we
understand we're winning orwe're losing.
I know you've heard me say thisbefore in an actual work
setting, but, like peopleunderestimate in growth,
leadership roles sort of what Irefer to as the psychological
aura you have in a company and Iknow that sounds egotistical,
(26:18):
it's not what I mean.
People want to work for awinning company.
The simplest way to understandare we winning, are we losing Is
the sales organization showingup with a sense of we're winning
, and then is that backed up bypoints on the board.
And boy, that was an importantlesson for me to learn early on,
rick.
(26:38):
I think early on I was underplaying that.
So the stakeholders around you,they want to know one that they
understand what's happening,are we winning?
You know they want to know,they're lined up to support that
, and so you have this hugecommunication responsibility
there.
And then, of course, you allhave bosses, you know, and
whether you're the CEO, you'vegot bosses that are the board.
(27:00):
Whether you're a CRO first-linesales leader, everyone's got
bosses and and you also havethis sort of responsibility to
make sure they also are beingsupported with what they need.
They understand how the companyneeds to line up to support you
.
So it's like all of this, thissort of connective tissue, comes
back to, to being able tocommunicate effectively and draw
(27:22):
people together.
Um, and I like the way you frameit with positive intent and the
way I interpret what you'resaying.
It's not necessarily thateverything is just pollyanna and
rose-colored glasses, but it'sput in frame that's easy for
people to understand, that theycan connect with, and there's a
sense of clear vision and sortof positive direction behind
(27:44):
what we're doing.
Sometimes you have to deliververy tough messages, but I think
when people kind of put in theright context, people can really
believe in it.
And, by the way, all of what Ijust said sort of described
around the stakeholder ecosystemwe have to communicate with, I
think does come back to some ofthe things you referenced.
Like, most people don't want tojust hear that their leader
(28:08):
believes something or we'redoing something because of Leaf
or Rick.
What they want to believe in issomething bigger and they want
to feel connected to it.
They want to know the team andthe company are positioned to
win.
They want to know the team andthe company are lined up behind
what we're doing.
And you know, I think that'sreally important, you know.
So you're right.
Whether it be a Ryan or a Ronwho was our CEO at the time or
(28:30):
other members of the team, likeyou want to, the team wants to
believe that we're.
We're one team, one fight.
Speaker 2 (28:36):
You talk about like a little bit of concepts clarity,
engagement, connection,transparency.
Have you developed, like, isthere a framework that you use
for communication, or is it alittle more casual than that?
Like, how would you, you know,have you developed the both the
style, the frequency and mediumof how you approach
(28:57):
communication as a leader.
Speaker 1 (28:59):
Yeah, I'll say so.
To me it's a bit of an art anda science.
So let me start with thescience, which is kind of the
basis of your question.
I don't think there is like auniversal framework for
communication, but I do thinkthere's some really important
foundational elements which tome, are kind of non-negotiable.
You've seen these kind of playout in real life.
(29:20):
One is having a rhythm, aone-on-one rhythm with your
people.
And I'll tell you why I putthat in frame of a communication
framework because one-on-onesfor me are not an opportunity
for me to sit with one of mydirect reports and talk to them.
It's actually much more theirmeeting and my opportunity to
(29:42):
listen to what they need, what'shappening.
Where are we Through that?
Of course there's always thingsI want to maybe sort of touch
on or focus on, but to me it isestablishing the space, whether
it's weekly, biweekly, et cetera, and those things can vary
depending on the company and thestructure, but it's
establishing the space wheresomebody who works for me knows
(30:05):
they've got the platform toarticulate with me what they
need to.
Those might be personal things,those might be professional
things.
Personal things, those might beprofessional things, those
might be career aspirations,whatever it might be like.
Creating that space is really,really important.
So I'm a big believer in thatas sort of a first sort of
principle around buildingcommunication into your business
(30:28):
, into the leadership construct.
Second is I sort of believe youcreate a steady cadence of
outbound communication.
Those take the form for me, andI've evolved this over the
years I tend to do a weekly noteout to the team that I'm
working with, and this in mycurrent sort of span of
responsibility as the CEO ofAllegis.
(30:50):
There's a weekly launch.
It's the branding of the note,not the most exciting, I know,
but the weekly launch is a notethat goes out for me every
Monday or Tuesday to the entirecompany and it tends to capture
some thematic area that's top ofmind for me, something I want
to share with the team, might besome successes in there, might
(31:10):
be some lessons learned.
Then there's always a personalelement.
You know I'm a big reader.
You know my day starts the waywe described at the start of
this.
I won't bore people with thatagain, but I also do the exact
same thing.
It's the last thing I do everynight, which is I sit down and I
read.
Usually it's stuff focused inthe business and leadership area
, just because that's where mygreatest interest is and I tend
(31:32):
to love those stories, thosebooks.
But but it sort of it has onelast personal element in that
note every week which was on thebedside table and I'll be
sharing thoughts about whateverit is that I'm reading.
And I do that for two reasons.
Just you know.
To come back to thiscommunication framework.
One I love to share anyinteresting tidbits, like if
(31:53):
there's something I picked upI'm reading the new Stanley
McChrystal book right now oncharacter, which is an
unbelievable book and if I picksomething up along the way I
want to share.
So that's one thing.
But the second thing is it'salso for me embodying one of in
the company to say, oh Leaf hasit all figured out, which is the
reality.
Couldn't be further from thetruth.
(32:25):
You know, we live on atreadmill, you're constantly
learning new things.
There's a there's justgenerations of people in front
of me who've learned so muchmore than I have, and so like
I'm embodying that and then itjust creates some connection,
like it's, you know, readingabout what we did in the company
, the new wins we had, or thebig release we just had, or we
have our customer advisory boardhere in the office this week
and I'll talk about that nextweek, you know like.
But this creates a differenttype of connection.
(32:45):
So the second is create anoutbound sort of structure that
you're disciplined around.
Again, I do it weekly.
It doesn't have to be weekly,but just people.
You would be stunned, as Itravel, I might be in India or I
might be in one of our officeshere in the US and I'll bump
into somebody at the coffeemachine and say, oh, I was
reading your note last week andyou know I really love this.
Or oh, I just read that book,or I bought that book you're
(33:08):
reading Like.
Just create sort of a flow.
So that's the second thing.
And then I also am a hugebeliever in building, I'll just
say, sort of events.
But, like you know, you've gotto establish a cadence where you
are engaging your team.
So like might take the form ofa company all hands that I do
(33:30):
quarterly now and that you know.
Or, if you're a sales leader,maybe you have a monthly all
hands meeting you're doing tobring your whole team together
where you are able to share avery sort of in a consistent way
, kind of you know what are wetrying to accomplish, where are
we, what are the obstacles, whatare the things going well and
hopefully, if you do those wellwhich I try to always, include
(33:52):
time for active Q&A, even with athousand person company.
Today, like every one of ourquarterly all hands meetings,
you know, we have at least 30minutes of active Q&A where I
and other members of theleadership team just take
whatever questions on people'smind.
So, like I think I think thereare some things that that at
least I do, that I feel supportmy commitment to communication.
So that's kind of a little bit.
(34:13):
This is the way I think aboutthe science piece of it, but I
think the art around this is iswhere a lot of the magic really
happens.
Rick, I just thinkunderstanding how to get people.
Like there are some universalhuman principles, you know.
I just there's many of them andI won't I don't know them all,
(34:33):
but I know there's some thatmatter to me Like people want to
, people want to win, peoplewant opportunity.
You know, like I've traveledmany, many times over, I've been
blessed to do that and there'sso much more that connects us
around the world than thanseparates us.
But one of the most you knowsort of consistent things is
people just want an opportunityto show up, make an impact,
support their lives.
(34:54):
So, like you know, that'speople want to win, they want an
opportunity.
And I think the third, which isreally relevant here, is I think
every one of us wants tobelieve we have people who are
invested in our success.
And when I just think back overmy career, like I, you know I
(35:16):
referenced Jamie Pappas callingme at 630 in the morning, you
know, you know our then CEO atInterlinks, ron, who was willing
to sort of commit to helpingclose the loop on my desire to
ultimately be a CEO, like theseare investments people are
making in, you know, yoursuccess.
Yes, and of course it'ssupporting what they need.
But genuinely feeling.
(35:36):
Or our CEO of PTC for many ofthe years I was there, dick
Harrison, who really started meon the journey of sort of
shaping a vision to want to be aCEO and then investing in me
over a decade just giving meopportunities to go build a
portfolio of skills.
I could go on and on.
But people want to feel likethey're invested in their
success and so, as I think abouthow much I've benefited from
(35:59):
that, like I've really tried todefine who I am as a leader by
creating that level ofconnection with people and
trying to then back that up withreal actions.
You know, if somebody wants togo, you know, pursue a dream or
a vision, whether that'sprofessional or personal, how
can I, as a leader, and how canI, with the company, support
(36:22):
them doing that?
Because I think that art, theart that's there, rick is what
really unlocks people and Ithink it's what creates the
connection.
And you know I've got thisCaptain America shield over my
shoulder.
You know that's a gift, that'sthere, very intentionally, in my
office in Boston, ourheadquarters.
But that was a gift when I leftIntralinks from our team in
(36:45):
Latin America.
You know there was a funny phaseof the journey there, as I was
moving into the CEO role, wherethis Avengers theme became a
thing and sort ofinternationally, I developed
this playful sort of personawhich was Captain America and
this was such a thoughtful giftto me.
We had this big dinner when mydeparture had been announced and
(37:06):
two members of my staff, boband Ken, were taking over as
co-CEOs and Bob and I were inBrazil and the whole Latin
America leadership team wasthere and they had taken the
time to go buy this set usedshield from the Winter Soldier
movie, which they had this bigit was framed in this big gift.
(37:26):
It was a really emotionalmoment and they were.
And to me, the reason I keep itso prominently displayed in my
office is not because I'm someMarvel sycophant I do love the
Marvel movies but it's actuallyjust much more because it's
emblematic of like connection,and my connection with that team
was deep, as it is what it waswith most of the teams around
(37:47):
the world, and I'm still closewith many of those people today
and I know it meant a lot forthem and they really went out of
their way to think about a giftthat would be representative of
the way they thought about it.
So to me that's the art portionof it, right, rick?
It's like do people, when theyshow up they're working for leaf
or they're showing up workingfor rick, do they feel like this
(38:10):
is a leader who, yes, issupporting what's best for the
company that's all of our jobbut in that pursuit, is going to
take the time to make sure ifrick wants to ultimately, you
know, run his own company, be aceo, or wants to move into
larger, more expansive roles asa leader.
(38:30):
Is he supporting my ability todo that?
If I have these other personalambitions, am I being supported
in my ability to go unlock that?
Because, as I said earlier, Ijust think connection I know
it's cliche connection iscurrency, and in the right way,
like when you trust, youunderstand, you know.
And again, I look back fondlyon our first breakfast or my
(38:50):
first meeting with you and Peteat Intralinks in New York,
mostly because now I know youboth so well that I can see all
the best in those moments andthat's what matters.
Speaker 2 (39:04):
You know I love the kind of overlay between the
science and the art and you knowthe one-on-ones and it being
their meeting, the steady, theconsistency of steady outbound
communication on whatever thatfrequency is, Totally the work
involved in creating events andexperiences.
You know I've benefited fromthe importance I've probably
neglected that a little bit in,as I've, you know, moved up as a
(39:25):
senior leader, and so there's alot to think about around it.
The art, though, isparticularly interesting, and I
guess when I hear you talk aboutthe stories around it, do you
view like the trick to the artis just that innate caring and
curiosity, and like nothing more, and then it's the application
of that, or do you attribute anyother aspect around what makes
(39:45):
the art effective for you?
Speaker 1 (39:47):
Yeah, I think, listen , I think my general opinion
here is that it starts with afirst principle within the
leader, that is, you actually dogenuinely care about unlocking
human potential.
Like to me, like I know it's abit of a maybe it's a little bit
of a Pollyanna view onleadership, but, from what I
(40:09):
have found, the best leaders arepeople who are generally
genuinely energized by the forcemultiplier of building great
team and unlocking people, likethey're not just doing it
because they might make moremoney.
That I'm all for making money,I'm a huge supporter.
But but, like I have a lot ofnew leaders or people who are
(40:32):
pursuing leadership degrees, oreven sometimes my own kids, as
they talk about.
Oh yeah, I, I should get intomanagement as quickly as
possible and I would, I ask why,well, you make so much more
money in management?
Actually, not necessarily.
You know, the people whousually make the most are your
best salesperson and your bestengineer in a software company.
So if you're after just makingmore money maybe not, but if you
(40:57):
are really energized byunlocking human potential and
creating the force multiplier ofa great team, then I think
you're on the track, becausethen you know we all have our
different styles.
You know, it's just we do.
We have different personalities, so like there's no then one
art form around it.
But I think curiosity is a bigthing.
(41:19):
I think having the patience tospend time with people, being
there when times get tough.
You know, unfortunately, I'vebeen at this long enough to have
seen people go through somepretty traumatic and challenging
personal situations.
Early on in my career I had arep lose a baby.
I've had a leader I wasextraordinarily close with
(41:41):
unfortunately pass after a longbattle with cancer.
Like, and you know, you kind oflive through these journeys.
You know, and you've gotta, areyou there and, and I think
people genu genuinely know whensomething is transactional and
when, when a relationship ispurely transactional, hey, you
(42:04):
might make some magic happen.
I mean, there's all these hiredgun salespeople that love to
roll into a company, roll outsome big, do some big deals,
make some money, support thecompany might make me look good
as a leader, might make you lookgood as a leader.
So that happens, it's going tohappen, like you know.
Again, I'm not Pollyanna aboutthis stuff, but I think the most
successful, most sustained,high impact sales organizations
(42:29):
are where you're creating thatsort of cultural foundation that
is, we're here to unlock andmake an impact and then people
lean in in a really, really bigway and it's reciprocated.
I literally have no greatersense of satisfaction for my
(42:51):
professional career, and I cansay this with all sincerity.
Obviously, it's always beenabout providing for my family,
so I have to.
That is always first, likethat's why I've always done what
I've done.
But I have no greater sense ofsatisfaction and watching people
that I've worked with go on tobe CROs you know, building great
teams, ceos, whatever it isthat start their own companies,
(43:12):
like build a media empire whichyou might go do someday, you
know become a massive influencer, whatever it is Like that's
what I love most.
I mean, it's literally what Ilove most.
Speaker 2 (43:24):
Yeah well, great answer.
I mean you can tell from youknow your energy that how that
plays out in your interactionswith teams.
And answer I mean you can tellfrom your energy that how that
plays out in your interactionswith teams and how that results
in thoughtful gifts when thosemilestones come to an end, and
so on.
So really, really great stuff.
I got to ask you one question.
Around you know, as someone,most of sales leaders, when they
have a lot of experience, oneof the potential transitions
(43:46):
would be to CEO.
That's become a reality for you.
It's not for everyone, ofcourse, but what's really
different from being a salesleader to being a CEO?
Speaker 1 (43:56):
Yeah, yeah, you know it's a.
It's a great, great question,rick, and, and you, you actually
hit a very important point.
I don't think it's actually foreverybody and I look at it was
early in my journey because ofgreat models and seeing somebody
like a Dick Harrison who'd beena salesperson at PTC become CEO
, being surrounded by reallygreat leaders, who who I looked
(44:20):
and I said this is this is sortof the ultimate opportunity to
build the team, shape culture,build the vision and the
strategy for the business.
So I was really energized bythat.
But it's not for everybody,because as you transition to a
CEO role, that stakeholderecosystem that you are now sort
of you work for, like I tell andpresent to our new hire class
(44:43):
every week.
You know like a lot of it's Q&A, most of it is Q&A.
I just let them ask mewhatever's on their mind.
Ineptly, somebody will alwaysask me what do you do as a CEO?
I always say the same thing Iwork for three different
stakeholder communities.
I work for all of you, I workfor our board and I work for our
customers.
(45:03):
When you're in sales leadershipI described earlier, you still
have this stakeholder communitythat you kind of play, this
integral sort of central nervoussystem role to.
But you really know yourmission.
It's clear and you have a verywell-defined sort of model that
you need to go deliver againstwhen you move into the CEO role.
(45:25):
There is a very different sortof relationship with those
stakeholders.
Like, the employee community isone set of stakeholders.
They have much of which iswe've centered in this
conversation Like do they feel?
Like they believe, do theyunderstand where we're going?
Do they have a sense ofconnection and transparency?
Are we building the rightstrategy?
All those things you put it.
(45:46):
The other end of the spectrum,we have our customer advisory
board in with us today.
So, like that group ofstakeholders is looking at me as
a sort of indication of is thisa business we wanna continue to
bet on?
Do they have the sense ofunderstanding of who we are,
that we can believe that this isa partnership we wanna continue
(46:07):
to nourish?
So it's totally differentstakeholder community.
And then, of course, you've gotthe board dynamic and boards
and owners of businesses come inall shapes and sizes, as you
know well, but ultimately theyhave sort of this shared
responsibility.
I work on a privateequity-based environment.
They have a sense ofresponsibility to ensure they're
(46:28):
delivering for the stakeholders.
They serve the investors thathave trusted them with their
money, so they're focused onoutcomes.
They're also focused ongovernance.
So that's a very differentdynamic.
And then the other piece, whichsort of connects back into the
employee piece but is reallyalso very different, is, I think
, to make the transition fromCRO, for instance, to pick the
(46:48):
top sort of growth oriented roleinto a CEO role, you also have
to have real professional andpersonal curiosity around the
360 degree that is a businessLike.
I'm always a little skeptical ifsomebody moves actually from
any role in a business itdoesn't have to just be CRO, but
(47:09):
they aren't genuinely like,energized by the art of the
possible and product andtechnology or they don't really
want to lean into how do weunlock operational excellence
across the company and thepeople, of which I've just seen
many go through the transitionthat I just think of, soared, as
CEOs bring that growth mindsetand the connection to the market
and the ability to build, ofwhich I've just seen many go
through the transition that Ijust think of, sword, as ceos
bring that growth mindset andthe connection to the market and
(47:31):
the ability to build a greatsales team and they sort of
surround that with this sort ofreal passion and interest for
the rest of the company in a ina in a deeper way.
And and I I would just say myother observation is you can
always tell those leaders, likeI think of some of my closest
friends through the yearsthere's a group of them that all
(47:53):
went on to be CEOs or COOs thattwo different sort of ways to
think about an additional stepbeyond CRO.
And then there's a group ofthem that have just done
spectacularly well, have made aton of money, that have just
done spectacularly well, havemade a ton of money, have lived
a best life, who said I am nevergoing to leave the sales world
(48:18):
because I love it.
This is my sort of happy place,I'm in my groove swing, and
that to me is just as important,just as powerful.
You know people who get hung upon taking the next job for ego
or like it just it's.
It's always best to be in whatis the right role for you, and
so yeah Well, leif, I mean, thetime just flew by here.
Speaker 2 (48:41):
I could probably speak to you for hours, so
perhaps we do this again in thefuture, but I want to thank you
for joining us today.
Any other messages you want tosend before we wrap up?
Speaker 1 (48:51):
No, no, not nothing in particular.
Thank you for having me on.
Like I said, it was an honor.
I think you're doing somereally, really important work
here, rick, I want to make sureI get you some a nice long list
of guests you can draft in hereas well.
I think there's so many justextraordinary leaders who can
help this next generation ofleaders become the best version
of themselves.
Please use me as a resource.
(49:13):
I'm grateful, this time withyour community, and look forward
to talking again soon.
Speaker 2 (49:17):
Well, I appreciate that and I'll take you up on it.
And you shared some amazingthings today, so thank you.
Reflecting on the conversationthat we just had with Leif
(49:38):
O'Leary, I'm thinking about hisreference multiple times to
concepts like having a growthmindset, creating an environment
for winning, creatingmotivation for something beyond
just the paycheck.
Leaf puts a lot of emphasis onthese areas.
What he described in theinterview as like a
psychological aura.
I've always considered theseitems to be outputs, outputs
(49:58):
that are derived from tacticalinputs, of the actual day-to-day
work that is put in towardswinning winning the deal,
improving the process, designingthe campaign.
But for Leaf, I came away withthis impression that these areas
are part of the inputs thatplacing purpose in his
communication centered aroundwinning, and growth as an input
(50:23):
is a key that helps peopleperform at a level ahead of what
they would do on their own.
We've also broke down the artand the science of communication
.
What I just described, you knowjust there was the art side of
it.
On the science side, hiscommitment to weekly
communication at the org levelstood out to me.
Sharing successes, lessonslearned, personal learning and
(50:48):
development, modeling thebehavior you want to see in the
organization it's that kind ofconsistency in communication
that I think really helps anorganization stay aligned and
keeps leadership in some wayaccountable on ensuring there
are items to talk about otherthan just going through the
motions.
This is an area that I've hadfits and starts with.
(51:09):
I do a lot of communication butsimply not consistently enough.
If I change one thing on theback of this episode, it's going
to be an increase in thefrequency of org-wide
communication.
That one-to-many communicationhas such unbelievable ROI.
We all need to do it and we allneed to do it well.
The frequency can vary.
(51:30):
For example, in episode fivewith Kyle Norton, he broke down
his monthly communicationcadence, which was highly
structured and also highlyeffective.
To me this rhythm andconsistency is an example of
great leadership.
And lastly, you can hear Leif'spassion come through as he
responded to questions today andmentioned early in our
(51:53):
conversation the power of havinga routine.
Leaf is consistently energetic,consistently consistent in his
leadership and I attribute a lotof that to his discipline and
routine.
It keeps Leaf as the same guyyou're going to encounter
anytime, anyplace.
They get the same Leaf and themore senior you get in an
(52:15):
organization or in a role, themore important and valuable that
that becomes.
I want to thank Leaf for joiningtoday.
I want to thank Ari Smolin forproducing.
I love the music at thebeginning and end of this
podcast.
Isla Young and Sons of Summerput that together.
I hope you enjoy it too.
We will see you next time on.
Pillar Talk Hurts in me Likethe joke.
Speaker 1 (52:40):
I can't shake, I can't quit.
It's never really what you saidit was.
Hello everyone and welcome to another episode of
Pillar Talk, where we build thefoundations of sales leadership
success and create clarity interms of what good looks like
for current and aspiring salesleaders.
Before we jump in, let's reviewthe six pillars of successful
sales leadership.
Starts with talentidentification and attraction.
Obviously, building the teamand attracting that type of
(00:38):
talent is incredibly difficult.
The operating rhythm.
For me, I love this inestablishing an environment
where you foster motivation andbalance that with accountability
and engagement, Businessplanning, the cross-functional
relationships that exist, so youcan play offense instead of
reacting to things that happento you.
In Leaf Talk, that is, make thenews instead of read the news.
(01:03):
Communication, ownership andmastering the craft.
How do we help the team win?
Today we are fortunate to haveas a guest Leif O'Leary.
Leif is the CEO of Allegius, aleading healthcare platform.
Leif has spent decades inleadership roles, primarily
leading sales and revenueorganizations, before rising to
(01:26):
the CEO role.
From my experience with Leif, Iknow him for his commitment to
great communication, for hisconsistency in leadership and
just for his pure hard workethic.
Leif brings a uniqueperspective on how strong sales
leadership skills can translateinto executive level success.
Speaker 1 (01:46):
So, leaf, welcome to pillar talk thanks, rick, it's
great to be here.
Um, I was honored to be askedto join.
I think this work you're doingto support the community I mean
this sincerely is maybe asimportant as any work being done
out there.
You know how I feel about thecriticality of sales leadership,
the importance of the role Evenyou capture in some of your
(02:11):
thoughts around this work you'redoing that it's one of the most
difficult roles.
I actually think it is the mostdifficult role and I think I
can say that with three-plusdecades of experiencing, having
done just about everything.
I think there's very littlemore challenging or rewarding
than building an extraordinaryteam and unlocking sort of
(02:32):
growth and impact in a businessthrough that team.
And so the fact that you'rebringing real world
practitioners together just toshare some thoughts I think is
awesome thoughts I think isawesome.
Speaker 2 (02:46):
Yeah, I mean I just see myself as a student trying
to learn and I've developedthese pillars as a way to try to
frame what I define assuccessful and how I will lead
and develop leaders within myorganization.
But I don't claim to have allthe answers.
So I love having these types ofconversations and trying to
learn from others and to sharethose learnings, obviously
through this podcast and thenewsletter.
(03:07):
You know, leif, one of myfavorite stories is in our time
working together is you weresharing about.
You know you would often getquestions around hey, how do I
one day get into your role orhow do I develop into be a more
elevated leader?
And we'd have those types ofconversations.
And you talked about earlier inyour career where you were
living a pretty far distanceaway from where your office was
(03:29):
and so you had quite an extendedcommute and please correct if I
get any of the details wronghere but you would leave like
way before the sun would come upin the morning and you would
then hit the gym when you got tosort of near the office and
then you would still get intothe office and start the day
really before everybody elseeven got there.
But you know, with thatextended commute it got to the
(03:50):
point where you had to specialorder some type of like stronger
dose coffee to maintain yourenergy levels and how that
dedication and years of likejust grinding through that
really helped you expand andgain experience and skills to
develop as a leader.
So I remember those storiesreally well.
I guess my question for you iswhat's your morning routine like
(04:12):
these days compared to then?
Speaker 1 (04:14):
Well, I will say a couple of quick notes and I
thank you for remembering Rick.
It's nice to know that some ofthe stories which you know,
fortunately or unfortunately,are completely based in fact in
that case stuck with you,fortunately or unfortunately,
are completely based in fact inthat case stuck with you.
And and I'll I'll answer yourquestion about kind of my
morning routine, because youknow a bit about me and you know
(04:36):
that I am a very habitualperson.
You know, I feel the bestpeople are really sort of
defined by their habits and sortof that's the way I live my
life.
But my morning routine now isnot all that dissimilar, absent
the two or three hour commutefrom.
Yes, you are correct, I wasliving in Connecticut but I had
this extraordinary connectionwith this unbelievable company
working for just amazing leaders.
(04:57):
At the same time, my wife and Iwere starting a family with
four kids and we were connectedto where we lived and I was.
I just felt like I was in thisreally unique spot working for
the right types of sales leadersthat could unlock what I felt
was the right types ofopportunities for me, and so it
was an important.
You know, yes, I left at 4amevery day.
(05:18):
Yes, I had to go find regularcoffee stopped keeping me awake
on the highway in the dark ofthe night.
So I did go find.
I'm not going to mention thename of the coffee because I'm
actually not.
I think I don't want to be anadvocate for that.
That's not really the bestmodel when your heart rate is,
you know, through your chest at5 am before you get to the gym.
But but that.
But that was actually a veryintentional decision because I
(05:41):
wanted to be there for my family, even if I was getting home at
nine or 10 o'clock at night andthen leaving at four the next
morning even though I wascatching a few minutes, I was
supporting that part of my life.
At the same time, I was reallyreally leaning into what I
thought was a unique opportunity, which actually comes back in
many ways this conversationbecause it was the opportunity
to work with some of the best,the best leaders, the best
(06:05):
salespeople, and that was what Iaspired to be and do, and so it
was important for me to do that.
So, yeah, my morning routinenow is exactly the same.
I get up every day at the sametime, I work out first and then
I'm in the office.
And well, it might not be asquite en vogue today with the
(06:26):
youngest generation, I'm still ahuge believer that you know,
working harder and being morepresent and leaning in more is
one of the greatestdifferentiators that you can
have in a career, and so it'sstill, sort of three decades
later, what I sort of lean on.
(06:46):
Maybe it's because I'm notsmart enough to differentiate
with my intellect and IQ.
Hard work is the mostcontrollable asset I have, and
so, you know, that's been sortof the way I've defined it from
the beginning.
Speaker 2 (06:58):
Well, I'm hoping that the start time is a little
later than 4 am.
Speaker 1 (07:03):
It's a little later than that because that was born
out of absolute necessity, butnot much later.
It's just a little more civil.
I'm not injecting sort of thewrong types of coffee into my
system.
Speaker 2 (07:15):
Yeah.
So I think about those storiesof hard work and I overlay that
with the world that we're intoday.
Like people have differentexpectations or even definitions
of what hard work is andthere's different types of
distractions that can take awayfrom hard work In your coming up
in your career or the earlierin mine.
(07:35):
Concepts like a smartphonesitting right next to you or
hybrid slash remote work thoseweren't really regularly applied
concepts.
Now we have a new generationwhere these are things that we
have to grapple with a bit andyou know there's always the like
.
Prior generation is alwaysjudging the newer generation and
(07:58):
saying that they're lesshardworking.
Or you know, back in my day wedidn't have this or that, but I
really wanted to get a sense ofnow, as you reflect, as someone
that lived hard work at a timeand place where that's just what
you had to do.
And now you are in a worldwhere you see people across a
large organization.
They're early in their career,they want to move up, like what
(08:20):
is hard work look like in a waytoday that creates opportunity
for folks in your organization?
Speaker 1 (08:26):
Yeah, yeah, rick, I think it's a, it's a really big
factor for leaders.
You know, whether you're asales leader or you're a leader
of other functions, we, we areall living a time of just
massive change.
It's funny, though, as I listento you sort of frame the
question, I have to say I'm I'mactually drawn back to some of
my first meetings with you andsome other leaders when we came
together many, many years agoand we're slightly different
(08:49):
generations I'm a little bitahead of you but we're sort of
close neighbors.
But you might or might notremember this, but one of my
very first trips down to our NewYork office at Intronix, when
we came together, you andanother leader there, you know,
were gracious enough to comeinto the office for a 7.30 am
(09:09):
meeting which, by the way, I hadflown down from Boston for but
you two sort of marched into theoffice and said we don't do
7.30 am meetings, like what isthis?
And it was this really funnymoment where, you know one, I
saw sort of the strength ofconviction in both of you and
(09:30):
that was a very truecharacteristic.
But it was also, I think,indicative of a really important
lesson for, I think, allleaders, certainly for me, and
one that I've learned inmultiple phases of my journey,
that one there's not onedefinition of hard work and, by
the way, I can say with absoluteconviction, knowing both of you
now for, I guess, 15 plus years, that there's few harder
(09:55):
workers than the two of you, butthat that the definition of
what that means is not alwaysthe same For me.
I'm a morning person, so for me,like you described, being out
the door at 4 am or 5 am, beingat the gym and being in the
office at 7 and turning thelights on that's how I started
my career at ADP.
Like I knew nothing when Ilanded in the Windsor
(10:15):
Connecticut office of ADP, asnothing but raw material.
You know somebody who'd neverbeen in a professional
white-collar setting and theonly thing I knew to do was turn
the lights on for everybodyelse.
So I wasn't losing ground tothe 50 or 60 salespeople in that
room with me.
But that was the way I definedit, and you all defined it in a
slightly different way, andthat's a really important thing
(10:36):
for leaders to understand theshape and form of the people you
hire, the way they're motivated, the way they work, is not
always going to be a reflectionof you and, frankly, the best
teams aren't just a mirror imageof their leaders.
Anyways, you want a mosaic ofskills and capabilities and
personalities and dynamics.
So I'm reminded of that,although your question is much
(11:00):
more framed.
In this current generation andI have four kids who are all in
their 20s you've met them andthey're all entering or in the
workforce now, and so I kind oflive every day like being a
little bit of this the old goat,old guard.
You know, just work hard, grindit out, and then I'm immersed
in a setting with people thathave lived just a totally
(11:26):
different experience.
You know they've lived, as youdescribed, instant access to
information all the time.
Like you know, when I and sortof we were growing up, you know
if you wanted to get an airlineticket book, you worked at it.
You know you went to a travelagent.
That's before your time, butyou went to a travel agent.
That's before your time, butyou went to a travel agent.
Or you know you made phonecalls or you did things.
(11:49):
Like you know today, you knowthat's two clicks of a button on
your phone and you're flying toNova Scotia to go golf for the
weekend and that's probably whatyou did, right?
So our kids have grown upconditioned to just a totally
different set of experiences.
In many ways, really good stuffsurrounds that access to
information, but it does changethe evolving dynamics in a
(12:10):
workplace and I certainly amlearning every day through this.
It's not like I have all theanswers.
I think one of your pillarsaround communication, though,
really starts to get to theheart of how you sort of thread
this needle of.
You still do need a hardworking, productive, engaged workforce.
If you're a sales leader, youneed a group of people who are
(12:32):
committed to the mission.
You know that want to go makethe news.
Thank you for using one of myphrases.
I think my current company getstired of sales.
Certainly the salesorganization here gets tired of
hearing that every day.
I need people to make the news,not report the news, which I
think I stole from somebody atPTC many, many decades ago.
But you know it's.
You know you need people towant to do that, but you've also
(12:54):
got to realize that you knowthe team you put together is
probably going to have peoplewho are closer to our generation
and maybe a little bit morethat mindset.
They're going to be people thatare morning people, and I'm
using simple, stupid examples,like the morning person versus
you and Pete, who, hey, we liketo work all night.
You know like, this is what wedo you get up at four, we'll get
up at eight and we'll get towork at nine.
(13:16):
You know like, and it's goingto be everything in between.
And so this idea of how youcommunicate and connect with
people becomes really critical,really critical.
And I'll tell you you're justjogging for me so many stories
from when we were together, butyou probably don't remember our
first meeting.
I do, though, and I rememberthese things.
Speaker 2 (13:37):
It was a breakfast.
Speaker 1 (13:39):
Yeah, it was a breakfast in Boston at the
Liberty Hotel.
You might or might not rememberthe first thing you said when
you sat down with me, but itstuck with me in a really good
way.
It was kind of an interestingmoment but it stuck with me.
And at the time I was a salesleader.
For those who don't know, I wasat that time sort of coming
into the business, sort ofrunning the Americas and then,
(13:59):
with this plan to move into theCRO role, and Rick had been a
long time, really, reallyimportant leader in this
business.
It really helped build thebusiness and had the requisite
amount of loyalty, connectionand commitment to this business.
And I think and I won't speakfor him, but I know this to be
(14:20):
true in some ways it's likelooked at him, looked at himself
as sort of a guardian of thiscompany and what it was and in
all the right ways.
And here I was a total outsider, like a guy who knew nothing
about this space, was fromBoston, and we had breakfast in
in Boston and Rick sat down withme and he said first thing he
said out of his mouth like afterthe pleasantry is like you know
(14:49):
, I don't work well with peoplewho aren't very smart.
That's what he said.
Very, very first thing Ricksaid and I, it was a really
interesting moment and and andyou know you have to you know
you realize that, as a leader,like I, knew enough to know,
even though I didn't know Rick,I knew that Rick was a very
important part of the mosaic ofthis business which you were and
(15:10):
you know I had.
You know there's decisions youmake in these moments.
Right, I could say you know whois this arrogant, cocksure guy
who starts a meeting with hisnew boss?
Like that.
It probably was something thatwent through my mind, but like
that, it probably was somethingthat went through my mind.
(15:31):
But I also saw in that thelevel of connection and how much
you cared about this business.
You weren't saying that becauseyou were trying to reject the
organ that was Leif O'Leary.
You were saying that becauseyou wanted to make sure the
standards that you had for whatyou had been building there were
going to be met and surpassedby new leaders.
And I mentioned that onlybecause, like those types of
(15:55):
moments where, clearly, at thatmoment in our journey, you and I
didn't know the things we havein common and there are many,
you know, a relentless love oflearning, love of leading
building teams.
You know very hard workerspassionate about supporting, you
know, our clients and buildingbusinesses.
Like there were so many thingsthat you and I ultimately had in
common but at that moment wewere just.
(16:18):
You know, I was an outsider andevery leader starts that way.
Every leader starts that way.
You have either hired somebodynew Now they are an outsider to
your team if you find them in,but you are an outsider to them
and building connection, whichfor me is currency with people
is everything and I know that'sa cliche, but like you've got to
(16:41):
figure out how to connect withpeople.
Like you've got to figure outhow to connect with people and
communication and the way you dothat is a critical sort of
facilitator of doing that.
And I do look back fondly onsort of the relationship we
ultimately built and the impactyou made in our business and
what you've gone on to do andsoar after your time at
Intralinks.
But there's these justinteresting moments and it's all
(17:03):
about human connection.
Speaker 2 (17:04):
You know it's really great.
I don't remember that specificcomment.
I remember the specificbreakfast.
To give you some context of whyI probably went in with a
little bit of a sharper elbowthan normal, and that situation
was our CRO at the time.
Reiner had made a commitment,so we had some leadership tumult
in that organization prior tohis arrival, your arrival.
That was like cartoonish thatwe don't need to get into the
(17:27):
details of, but so there was ahigh level of sensitivity, there
was a protective aspect andthen there was a commitment of
like, hey, and you know there'snever the right answer here if
you involve people in theinterview process for someone
that they'll be reporting to and, of course, when you are in a
role where that you know thehire is going to be the one
(17:48):
you're reporting to, of coursethe answer is yes, you should be
involved in that, because youknow you have a bias there, of
course, and you want to makesure that the leader is great.
In this particular situation,you were hired and then Reiner
kind of came to me and was like,look, I know I said you could
be involved, but like, trust me,when you leave you are going to
(18:10):
understand that we brought theright leader in.
So he took like a bit of a riskand, of course, like one of the
things that made me a topindividual contributor was that
swagger, was that attitude.
It's a little bit cringy to hearnow as now you know, almost 20
years into a leadership careerand realizing that that swagger
and that cockiness that makesyou a very strong individual
contributor has real riskassociated with leadership
(18:32):
dynamics and part of the journeyof trying to define what good
leadership is is on the back ofthat reality.
So I try to play into theswagger and that stuff where
applicable in bringing a winningmindset and those types of
elements.
But also try, try not alwayssucceed into being more
thoughtful about the words thatcould have an impact.
(18:53):
You were a real deal leadercoming into an organization and
off putting comment to initiatea conversation is not going to
phase you.
There are many people in theorganization that are far less
secure in their position, farless confident in their even fit
for a role and a higher levelof sensitivity to that, and that
could be a really bad situationwhen you are in an elevated.
So I laugh a bit at what you'resaying, but it also makes me
(19:15):
really sad, as the context oftheir even meaning well doesn't
necessarily translate into theright things.
But but whatever it was a it's afunny way to kind of you know,
talk about how we kick thingsoff, but I do like to reflect on
a then and now type of dynamic.
Speaker 1 (19:30):
Yeah, but.
But.
But, Rick, just just thinkabout what you just said.
I mean, that's the essence ofyour growth mindset personified,
and I think you capturedperfectly the reality.
Like your sense ofself-assuredness and your
swagger and your confidence hasbeen a defining characteristic
of what's made you great.
That's going to happen withpeople.
Just, they're going to be muchmore quiet, much more powerful
(19:53):
people who don't have thatexternal kind of sort of
projection of who they are, andthey're also extraordinary.
They can also beextraordinarily high performance
.
So you know, it's all part ofthe growth for all of us.
You know I probably learned asmuch in that moment as a leader
it's.
You know I'll remember thatforever.
You know, along with many otherstories, my journey with you
(20:13):
and others, that forever youknow, along with many other
stories, my journey with you andothers, but those are things
that help you grow as a leader.
You know I had to learn how tohandle that approach, just like
I did with you and Pete sittingthere in the New York office and
we don't do 730 meetings andI'm sitting here saying you
don't do 730 meetings, You're anhour and a half late to work.
I don't know what to tell you,Like I flew in here and beat you
to the office.
That's problem number one.
(20:34):
You know you, you walk to theoffice.
So so you've got to learn howto adapt.
And I just think communicationis just so critical because if
you don't connect and engage,and then if you can't
communicate which is both activeand reactive, listening, like
you, you know, communication isnot a one way street.
You've got to also listen,understand and connect.
Speaker 2 (20:57):
So well, it wasn't just pete and I that you were uh
had to establish thatcredibility with.
We had 200 people, 150 peoplein the organization, all uh.
Yes, we had offices and mostpeople were in the office, but
we also were a national teamwith, uh, you know, disparate
geographies and folks all overthe country and I think, as I
reflected on what made you sosuccessful in the role, it
(21:18):
really was like what I'd call aconsistent and positive
communication.
Consistent and positivecommunication and you would
include the rest of leadership.
Really, really well, this wasn'tjust coming from LEAF.
You made an explicit effort toensure that you would reference
Reiner a bunch and like, hey,reiner and I were talking like
(21:38):
establishing even more that thisisn't just you off the cuff
communicating a message or aninitiative or whatever it was.
There was a it felt to me likea real intent to make sure that
this isn't about you but it'sabout the organization and that
there's alignment across.
You know your leadershipinfrastructure there and I guess
I wanted to ask you about thedevelopment of that
(22:00):
communication skill, both from atone, that positive type of
element, and then theconsistency of it, and you know
how you have evolved that.
You know into where you aretoday.
Speaker 1 (22:12):
Yeah, I'll just say Rick, you know, first of all I
am the byproduct of the gifts ofso many incredible examples and
leaders through the years.
So like I think, first I wasblessed even from my earliest
days at ADP, like I worked forpeople, many of whom I'm still
close with today, 30 years later, and have worked with again and
(22:32):
have worked with again, whomodeled this level of sort of
clarity, vision, engagement,communication with their people,
you know, and so like I think,the first again remember when I
started my career I hadliterally zero frame of
reference as what it meant to bea leader in a professional
setting.
You know, any intrinsicleadership capabilities I might
have had were just born ofnecessity, of reference as what
it what it meant to be a leaderin a professional setting.
(22:55):
You know, any intrinsicleadership capabilities I might
have had were just born ofnecessity.
And athletic settings or schoolsettings, which you know are
valuable but totally different,and, you know, for a variety of
reasons.
And so for me, first andforemost, I think I saw that
modeled in exceptional ways atadp.
And then I went to ptc with alot of intentionality, by the
(23:17):
way, drawn there, you know, toone of your pillars around
attracting the right people.
If I can throw myself into thebucket of one of the right
people that went there throughthe years, I was drawn there by
Jamie Pappas, just an absolutelyextraordinary leader.
He called me and this is a realstory back to the start early.
It's funny how this story willconnect a little bit, and you've
(23:37):
heard this story before.
This is that before cell phoneswere a thing, you know, I was
sitting in my office, my firstoffice in my whole career.
I was sitting in that office inWindsor, connecticut.
It was 630 in the morning andmy phone rang.
Jamie doesn't even probablyremember this, but he called me
and he had this dynamic energyto him and he said Leif, I got
(24:00):
your name from the ADP RollingStone magazine.
It looks like you're the topsales leader in North America.
Blah, blah, blah.
You're in Hartford Connecticut.
I'm in Hartford Connecticut.
I'm looking for a salesdirector to come build this team
.
Blah, blah, blah, blah, boom.
And I was like I'm neverleaving ADP Jamie.
I this team.
Blah, blah, blah, blah, boom.
And I was like I'm neverleaving ADP Jamie.
I'm going to be here for 35years.
My entire career is mapped outin front of me.
And he said, okay, got it,perfect, but you need a network
(24:25):
in Hartford.
Why don't we go have coffee onemorning?
It seems like you're an earlyriser, I'm an early riser.
Let's get coffee one day beforeyou go in the office.
And I said you know what Ishould do, that you know.
He had an infectious energy tohim.
And I said I should do thatbecause I don't know anybody,
like I'm literally a babe in thewoods.
I know nobody.
I don't know anybody atHartford.
I moved here the day after Iwalked off my graduation stage
(24:47):
at BC and moved to sleep in abasement in Hartford and started
working the next morning.
That was the glamorous start tomy career.
That was the glamorous start tomy career and I had coffee with
Jamie and a month later I wasstarting a PTC and it was.
(25:09):
So.
I've been sort of seeing thismodel, this engagement,
connection, communicationcapability and the consistency
of it almost throughout mycareer.
So, first and foremost, I thinkthat's where sort of I
developed that mindset.
I think that's where sort of Ideveloped that mindset and I
just, I'm just a huge believerthat as a sales leader really
any leader, but certainly as asales leader you play this
critical role where you haveobviously a responsibility to
build the best team and create ateam of high performance impact
(25:34):
players who make the news.
You also have this enormousresponsibility to the
stakeholders around you, becauseif you're in a company that is
focused on growth, really kindof everybody around you is
nourished by or focused on arewe driving growth, and so you,
as a leader, have thisstakeholder responsibility to
create connectivity.
(25:55):
This is what's working to powergrowth.
This is how we're performingTransparency to say we
understand we're winning orwe're losing.
I know you've heard me say thisbefore in an actual work
setting, but, like peopleunderestimate in growth,
leadership roles sort of what Irefer to as the psychological
aura you have in a company and Iknow that sounds egotistical,
(26:18):
it's not what I mean.
People want to work for awinning company.
The simplest way to understandare we winning, are we losing Is
the sales organization showingup with a sense of we're winning
, and then is that backed up bypoints on the board.
And boy, that was an importantlesson for me to learn early on,
rick.
(26:38):
I think early on I was underplaying that.
So the stakeholders around you,they want to know one that they
understand what's happening,are we winning?
You know they want to know,they're lined up to support that
, and so you have this hugecommunication responsibility
there.
And then, of course, you allhave bosses, you know, and
whether you're the CEO, you'vegot bosses that are the board.
(27:00):
Whether you're a CRO first-linesales leader, everyone's got
bosses and and you also havethis sort of responsibility to
make sure they also are beingsupported with what they need.
They understand how the companyneeds to line up to support you
.
So it's like all of this, thissort of connective tissue, comes
back to, to being able tocommunicate effectively and draw
(27:22):
people together.
Um, and I like the way you frameit with positive intent and the
way I interpret what you'resaying.
It's not necessarily thateverything is just pollyanna and
rose-colored glasses, but it'sput in frame that's easy for
people to understand, that theycan connect with, and there's a
sense of clear vision and sortof positive direction behind
(27:44):
what we're doing.
Sometimes you have to deliververy tough messages, but I think
when people kind of put in theright context, people can really
believe in it.
And, by the way, all of what Ijust said sort of described
around the stakeholder ecosystemwe have to communicate with, I
think does come back to some ofthe things you referenced.
Like, most people don't want tojust hear that their leader
(28:08):
believes something or we'redoing something because of Leaf
or Rick.
What they want to believe in issomething bigger and they want
to feel connected to it.
They want to know the team andthe company are positioned to
win.
They want to know the team andthe company are lined up behind
what we're doing.
And you know, I think that'sreally important, you know.
So you're right.
Whether it be a Ryan or a Ronwho was our CEO at the time or
(28:30):
other members of the team, likeyou want to, the team wants to
believe that we're.
We're one team, one fight.
Speaker 2 (28:36):
You talk about like a little bit of concepts clarity,
engagement, connection,transparency.
Have you developed, like, isthere a framework that you use
for communication, or is it alittle more casual than that?
Like, how would you, you know,have you developed the both the
style, the frequency and mediumof how you approach
(28:57):
communication as a leader.
Speaker 1 (28:59):
Yeah, I'll say so.
To me it's a bit of an art anda science.
So let me start with thescience, which is kind of the
basis of your question.
I don't think there is like auniversal framework for
communication, but I do thinkthere's some really important
foundational elements which tome, are kind of non-negotiable.
You've seen these kind of playout in real life.
(29:20):
One is having a rhythm, aone-on-one rhythm with your
people.
And I'll tell you why I putthat in frame of a communication
framework because one-on-onesfor me are not an opportunity
for me to sit with one of mydirect reports and talk to them.
It's actually much more theirmeeting and my opportunity to
(29:42):
listen to what they need, what'shappening.
Where are we Through that?
Of course there's always thingsI want to maybe sort of touch
on or focus on, but to me it isestablishing the space, whether
it's weekly, biweekly, et cetera, and those things can vary
depending on the company and thestructure, but it's
establishing the space wheresomebody who works for me knows
(30:05):
they've got the platform toarticulate with me what they
need to.
Those might be personal things,those might be professional
things.
Personal things, those might beprofessional things, those
might be career aspirations,whatever it might be like.
Creating that space is really,really important.
So I'm a big believer in thatas sort of a first sort of
principle around buildingcommunication into your business
(30:28):
, into the leadership construct.
Second is I sort of believe youcreate a steady cadence of
outbound communication.
Those take the form for me, andI've evolved this over the
years I tend to do a weekly noteout to the team that I'm
working with, and this in mycurrent sort of span of
responsibility as the CEO ofAllegis.
(30:50):
There's a weekly launch.
It's the branding of the note,not the most exciting, I know,
but the weekly launch is a notethat goes out for me every
Monday or Tuesday to the entirecompany and it tends to capture
some thematic area that's top ofmind for me, something I want
to share with the team, might besome successes in there, might
(31:10):
be some lessons learned.
Then there's always a personalelement.
You know I'm a big reader.
You know my day starts the waywe described at the start of
this.
I won't bore people with thatagain, but I also do the exact
same thing.
It's the last thing I do everynight, which is I sit down and I
read.
Usually it's stuff focused inthe business and leadership area
, just because that's where mygreatest interest is and I tend
(31:32):
to love those stories, thosebooks.
But but it sort of it has onelast personal element in that
note every week which was on thebedside table and I'll be
sharing thoughts about whateverit is that I'm reading.
And I do that for two reasons.
Just you know.
To come back to thiscommunication framework.
One I love to share anyinteresting tidbits, like if
(31:53):
there's something I picked upI'm reading the new Stanley
McChrystal book right now oncharacter, which is an
unbelievable book and if I picksomething up along the way I
want to share.
So that's one thing.
But the second thing is it'salso for me embodying one of in
the company to say, oh Leaf hasit all figured out, which is the
reality.
Couldn't be further from thetruth.
(32:25):
You know, we live on atreadmill, you're constantly
learning new things.
There's a there's justgenerations of people in front
of me who've learned so muchmore than I have, and so like
I'm embodying that and then itjust creates some connection,
like it's, you know, readingabout what we did in the company
, the new wins we had, or thebig release we just had, or we
have our customer advisory boardhere in the office this week
and I'll talk about that nextweek, you know like.
But this creates a differenttype of connection.
(32:45):
So the second is create anoutbound sort of structure that
you're disciplined around.
Again, I do it weekly.
It doesn't have to be weekly,but just people.
You would be stunned, as Itravel, I might be in India or I
might be in one of our officeshere in the US and I'll bump
into somebody at the coffeemachine and say, oh, I was
reading your note last week andyou know I really love this.
Or oh, I just read that book,or I bought that book you're
(33:08):
reading Like.
Just create sort of a flow.
So that's the second thing.
And then I also am a hugebeliever in building, I'll just
say, sort of events.
But, like you know, you've gotto establish a cadence where you
are engaging your team.
So like might take the form ofa company all hands that I do
(33:30):
quarterly now and that you know.
Or, if you're a sales leader,maybe you have a monthly all
hands meeting you're doing tobring your whole team together
where you are able to share avery sort of in a consistent way
, kind of you know what are wetrying to accomplish, where are
we, what are the obstacles, whatare the things going well and
hopefully, if you do those wellwhich I try to always, include
(33:52):
time for active Q&A, even with athousand person company.
Today, like every one of ourquarterly all hands meetings,
you know, we have at least 30minutes of active Q&A where I
and other members of theleadership team just take
whatever questions on people'smind.
So, like I think I think thereare some things that that at
least I do, that I feel supportmy commitment to communication.
So that's kind of a little bit.
(34:13):
This is the way I think aboutthe science piece of it, but I
think the art around this is iswhere a lot of the magic really
happens.
Rick, I just thinkunderstanding how to get people.
Like there are some universalhuman principles, you know.
I just there's many of them andI won't I don't know them all,
(34:33):
but I know there's some thatmatter to me Like people want to
, people want to win, peoplewant opportunity.
You know, like I've traveledmany, many times over, I've been
blessed to do that and there'sso much more that connects us
around the world than thanseparates us.
But one of the most you knowsort of consistent things is
people just want an opportunityto show up, make an impact,
support their lives.
(34:54):
So, like you know, that'speople want to win, they want an
opportunity.
And I think the third, which isreally relevant here, is I think
every one of us wants tobelieve we have people who are
invested in our success.
And when I just think back overmy career, like I, you know I
(35:16):
referenced Jamie Pappas callingme at 630 in the morning, you
know, you know our then CEO atInterlinks, ron, who was willing
to sort of commit to helpingclose the loop on my desire to
ultimately be a CEO, like theseare investments people are
making in, you know, yoursuccess.
Yes, and of course it'ssupporting what they need.
But genuinely feeling.
(35:36):
Or our CEO of PTC for many ofthe years I was there, dick
Harrison, who really started meon the journey of sort of
shaping a vision to want to be aCEO and then investing in me
over a decade just giving meopportunities to go build a
portfolio of skills.
I could go on and on.
But people want to feel likethey're invested in their
success and so, as I think abouthow much I've benefited from
(35:59):
that, like I've really tried todefine who I am as a leader by
creating that level ofconnection with people and
trying to then back that up withreal actions.
You know, if somebody wants togo, you know, pursue a dream or
a vision, whether that'sprofessional or personal, how
can I, as a leader, and how canI, with the company, support
(36:22):
them doing that?
Because I think that art, theart that's there, rick is what
really unlocks people and Ithink it's what creates the
connection.
And you know I've got thisCaptain America shield over my
shoulder.
You know that's a gift, that'sthere, very intentionally, in my
office in Boston, ourheadquarters.
But that was a gift when I leftIntralinks from our team in
(36:45):
Latin America.
You know there was a funny phaseof the journey there, as I was
moving into the CEO role, wherethis Avengers theme became a
thing and sort ofinternationally, I developed
this playful sort of personawhich was Captain America and
this was such a thoughtful giftto me.
We had this big dinner when mydeparture had been announced and
(37:06):
two members of my staff, boband Ken, were taking over as
co-CEOs and Bob and I were inBrazil and the whole Latin
America leadership team wasthere and they had taken the
time to go buy this set usedshield from the Winter Soldier
movie, which they had this bigit was framed in this big gift.
(37:26):
It was a really emotionalmoment and they were.
And to me, the reason I keep itso prominently displayed in my
office is not because I'm someMarvel sycophant I do love the
Marvel movies but it's actuallyjust much more because it's
emblematic of like connection,and my connection with that team
was deep, as it is what it waswith most of the teams around
(37:47):
the world, and I'm still closewith many of those people today
and I know it meant a lot forthem and they really went out of
their way to think about a giftthat would be representative of
the way they thought about it.
So to me that's the art portionof it, right, rick?
It's like do people, when theyshow up they're working for leaf
or they're showing up workingfor rick, do they feel like this
(38:10):
is a leader who, yes, issupporting what's best for the
company that's all of our jobbut in that pursuit, is going to
take the time to make sure ifrick wants to ultimately, you
know, run his own company, be aceo, or wants to move into
larger, more expansive roles asa leader.
(38:30):
Is he supporting my ability todo that?
If I have these other personalambitions, am I being supported
in my ability to go unlock that?
Because, as I said earlier, Ijust think connection I know
it's cliche connection iscurrency, and in the right way,
like when you trust, youunderstand, you know.
And again, I look back fondlyon our first breakfast or my
(38:50):
first meeting with you and Peteat Intralinks in New York,
mostly because now I know youboth so well that I can see all
the best in those moments andthat's what matters.
Speaker 2 (39:04):
You know I love the kind of overlay between the
science and the art and you knowthe one-on-ones and it being
their meeting, the steady, theconsistency of steady outbound
communication on whatever thatfrequency is, Totally the work
involved in creating events andexperiences.
You know I've benefited fromthe importance I've probably
neglected that a little bit in,as I've, you know, moved up as a
(39:25):
senior leader, and so there's alot to think about around it.
The art, though, isparticularly interesting, and I
guess when I hear you talk aboutthe stories around it, do you
view like the trick to the artis just that innate caring and
curiosity, and like nothing more, and then it's the application
of that, or do you attribute anyother aspect around what makes
(39:45):
the art effective for you?
Speaker 1 (39:47):
Yeah, I think, listen , I think my general opinion
here is that it starts with afirst principle within the
leader, that is, you actually dogenuinely care about unlocking
human potential.
Like to me, like I know it's abit of a maybe it's a little bit
of a Pollyanna view onleadership, but, from what I
(40:09):
have found, the best leaders arepeople who are generally
genuinely energized by the forcemultiplier of building great
team and unlocking people, likethey're not just doing it
because they might make moremoney.
That I'm all for making money,I'm a huge supporter.
But but, like I have a lot ofnew leaders or people who are
(40:32):
pursuing leadership degrees, oreven sometimes my own kids, as
they talk about.
Oh yeah, I, I should get intomanagement as quickly as
possible and I would, I ask why,well, you make so much more
money in management?
Actually, not necessarily.
You know, the people whousually make the most are your
best salesperson and your bestengineer in a software company.
So if you're after just makingmore money maybe not, but if you
(40:57):
are really energized byunlocking human potential and
creating the force multiplier ofa great team, then I think
you're on the track, becausethen you know we all have our
different styles.
You know, it's just we do.
We have different personalities, so like there's no then one
art form around it.
But I think curiosity is a bigthing.
(41:19):
I think having the patience tospend time with people, being
there when times get tough.
You know, unfortunately, I'vebeen at this long enough to have
seen people go through somepretty traumatic and challenging
personal situations.
Early on in my career I had arep lose a baby.
I've had a leader I wasextraordinarily close with
(41:41):
unfortunately pass after a longbattle with cancer.
Like, and you know, you kind oflive through these journeys.
You know, and you've gotta, areyou there and, and I think
people genu genuinely know whensomething is transactional and
when, when a relationship ispurely transactional, hey, you
(42:04):
might make some magic happen.
I mean, there's all these hiredgun salespeople that love to
roll into a company, roll outsome big, do some big deals,
make some money, support thecompany might make me look good
as a leader, might make you lookgood as a leader.
So that happens, it's going tohappen, like you know.
Again, I'm not Pollyanna aboutthis stuff, but I think the most
successful, most sustained,high impact sales organizations
(42:29):
are where you're creating thatsort of cultural foundation that
is, we're here to unlock andmake an impact and then people
lean in in a really, really bigway and it's reciprocated.
I literally have no greatersense of satisfaction for my
(42:51):
professional career, and I cansay this with all sincerity.
Obviously, it's always beenabout providing for my family,
so I have to.
That is always first, likethat's why I've always done what
I've done.
But I have no greater sense ofsatisfaction and watching people
that I've worked with go on tobe CROs you know, building great
teams, ceos, whatever it isthat start their own companies,
(43:12):
like build a media empire whichyou might go do someday, you
know become a massive influencer, whatever it is Like that's
what I love most.
I mean, it's literally what Ilove most.
Speaker 2 (43:24):
Yeah well, great answer.
I mean you can tell from youknow your energy that how that
plays out in your interactionswith teams.
And answer I mean you can tellfrom your energy that how that
plays out in your interactionswith teams and how that results
in thoughtful gifts when thosemilestones come to an end, and
so on.
So really, really great stuff.
I got to ask you one question.
Around you know, as someone,most of sales leaders, when they
have a lot of experience, oneof the potential transitions
(43:46):
would be to CEO.
That's become a reality for you.
It's not for everyone, ofcourse, but what's really
different from being a salesleader to being a CEO?
Speaker 1 (43:56):
Yeah, yeah, you know it's a.
It's a great, great question,rick, and, and you, you actually
hit a very important point.
I don't think it's actually foreverybody and I look at it was
early in my journey because ofgreat models and seeing somebody
like a Dick Harrison who'd beena salesperson at PTC become CEO
, being surrounded by reallygreat leaders, who who I looked
(44:20):
and I said this is this is sortof the ultimate opportunity to
build the team, shape culture,build the vision and the
strategy for the business.
So I was really energized bythat.
But it's not for everybody,because as you transition to a
CEO role, that stakeholderecosystem that you are now sort
of you work for, like I tell andpresent to our new hire class
(44:43):
every week.
You know like a lot of it's Q&A, most of it is Q&A.
I just let them ask mewhatever's on their mind.
Ineptly, somebody will alwaysask me what do you do as a CEO?
I always say the same thing Iwork for three different
stakeholder communities.
I work for all of you, I workfor our board and I work for our
customers.
(45:03):
When you're in sales leadershipI described earlier, you still
have this stakeholder communitythat you kind of play, this
integral sort of central nervoussystem role to.
But you really know yourmission.
It's clear and you have a verywell-defined sort of model that
you need to go deliver againstwhen you move into the CEO role.
(45:25):
There is a very different sortof relationship with those
stakeholders.
Like, the employee community isone set of stakeholders.
They have much of which iswe've centered in this
conversation Like do they feel?
Like they believe, do theyunderstand where we're going?
Do they have a sense ofconnection and transparency?
Are we building the rightstrategy?
All those things you put it.
(45:46):
The other end of the spectrum,we have our customer advisory
board in with us today.
So, like that group ofstakeholders is looking at me as
a sort of indication of is thisa business we wanna continue to
bet on?
Do they have the sense ofunderstanding of who we are,
that we can believe that this isa partnership we wanna continue
(46:07):
to nourish?
So it's totally differentstakeholder community.
And then, of course, you've gotthe board dynamic and boards
and owners of businesses come inall shapes and sizes, as you
know well, but ultimately theyhave sort of this shared
responsibility.
I work on a privateequity-based environment.
They have a sense ofresponsibility to ensure they're
(46:28):
delivering for the stakeholders.
They serve the investors thathave trusted them with their
money, so they're focused onoutcomes.
They're also focused ongovernance.
So that's a very differentdynamic.
And then the other piece, whichsort of connects back into the
employee piece but is reallyalso very different, is, I think
, to make the transition fromCRO, for instance, to pick the
(46:48):
top sort of growth oriented roleinto a CEO role, you also have
to have real professional andpersonal curiosity around the
360 degree that is a businessLike.
I'm always a little skeptical ifsomebody moves actually from
any role in a business itdoesn't have to just be CRO, but
(47:09):
they aren't genuinely like,energized by the art of the
possible and product andtechnology or they don't really
want to lean into how do weunlock operational excellence
across the company and thepeople, of which I've just seen
many go through the transitionthat I just think of, soared, as
CEOs bring that growth mindsetand the connection to the market
and the ability to build, ofwhich I've just seen many go
through the transition that Ijust think of, sword, as ceos
bring that growth mindset andthe connection to the market and
(47:31):
the ability to build a greatsales team and they sort of
surround that with this sort ofreal passion and interest for
the rest of the company in a ina in a deeper way.
And and I I would just say myother observation is you can
always tell those leaders, likeI think of some of my closest
friends through the yearsthere's a group of them that all
(47:53):
went on to be CEOs or COOs thattwo different sort of ways to
think about an additional stepbeyond CRO.
And then there's a group ofthem that have just done
spectacularly well, have made aton of money, that have just
done spectacularly well, havemade a ton of money, have lived
a best life, who said I am nevergoing to leave the sales world
(48:18):
because I love it.
This is my sort of happy place,I'm in my groove swing, and
that to me is just as important,just as powerful.
You know people who get hung upon taking the next job for ego
or like it just it's.
It's always best to be in whatis the right role for you, and
so yeah Well, leif, I mean, thetime just flew by here.
Speaker 2 (48:41):
I could probably speak to you for hours, so
perhaps we do this again in thefuture, but I want to thank you
for joining us today.
Any other messages you want tosend before we wrap up?
Speaker 1 (48:51):
No, no, not nothing in particular.
Thank you for having me on.
Like I said, it was an honor.
I think you're doing somereally, really important work
here, rick, I want to make sureI get you some a nice long list
of guests you can draft in hereas well.
I think there's so many justextraordinary leaders who can
help this next generation ofleaders become the best version
of themselves.
Please use me as a resource.
(49:13):
I'm grateful, this time withyour community, and look forward
to talking again soon.
Speaker 2 (49:17):
Well, I appreciate that and I'll take you up on it.
And you shared some amazingthings today, so thank you.
Reflecting on the conversationthat we just had with Leif
(49:38):
O'Leary, I'm thinking about hisreference multiple times to
concepts like having a growthmindset, creating an environment
for winning, creatingmotivation for something beyond
just the paycheck.
Leaf puts a lot of emphasis onthese areas.
What he described in theinterview as like a
psychological aura.
I've always considered theseitems to be outputs, outputs
(49:58):
that are derived from tacticalinputs, of the actual day-to-day
work that is put in towardswinning winning the deal,
improving the process, designingthe campaign.
But for Leaf, I came away withthis impression that these areas
are part of the inputs thatplacing purpose in his
communication centered aroundwinning, and growth as an input
(50:23):
is a key that helps peopleperform at a level ahead of what
they would do on their own.
We've also broke down the artand the science of communication
.
What I just described, you knowjust there was the art side of
it.
On the science side, hiscommitment to weekly
communication at the org levelstood out to me.
Sharing successes, lessonslearned, personal learning and
(50:48):
development, modeling thebehavior you want to see in the
organization it's that kind ofconsistency in communication
that I think really helps anorganization stay aligned and
keeps leadership in some wayaccountable on ensuring there
are items to talk about otherthan just going through the
motions.
This is an area that I've hadfits and starts with.
(51:09):
I do a lot of communication butsimply not consistently enough.
If I change one thing on theback of this episode, it's going
to be an increase in thefrequency of org-wide
communication.
That one-to-many communicationhas such unbelievable ROI.
We all need to do it and we allneed to do it well.
The frequency can vary.
(51:30):
For example, in episode fivewith Kyle Norton, he broke down
his monthly communicationcadence, which was highly
structured and also highlyeffective.
To me this rhythm andconsistency is an example of
great leadership.
And lastly, you can hear Leif'spassion come through as he
responded to questions today andmentioned early in our
(51:53):
conversation the power of havinga routine.
Leaf is consistently energetic,consistently consistent in his
leadership and I attribute a lotof that to his discipline and
routine.
It keeps Leaf as the same guyyou're going to encounter
anytime, anyplace.
They get the same Leaf and themore senior you get in an
(52:15):
organization or in a role, themore important and valuable that
that becomes.
I want to thank Leaf for joiningtoday.
I want to thank Ari Smolin forproducing.
I love the music at thebeginning and end of this
podcast.
Isla Young and Sons of Summerput that together.
I hope you enjoy it too.
We will see you next time on.
Pillar Talk Hurts in me Likethe joke.
Speaker 1 (52:40):
I can't shake, I can't quit.
It's never really what you saidit was.
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