Pillar Talk: Building Sales Leadership with Rick Smolen

Communication is Currency: How Great Leaders Connect and Inspire with Leif O'Leary

Rick Smolen

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

Speaker 2:

Hello everyone and welcome to another episode of Pillar Talk, where we build the foundations of sales leadership success and create clarity in terms of what good looks like for current and aspiring sales leaders. Before we jump in, let's review the six pillars of successful sales leadership. Starts with talent identification and attraction. Obviously, building the team and attracting that type of talent is incredibly difficult. The operating rhythm.

Speaker 2:

For me, I love this in establishing an environment where you foster motivation and balance that with accountability and engagement, Business planning, the cross-functional relationships that exist, so you can play offense instead of reacting to things that happen to you. In Leaf Talk, that is, make the news instead of read the news. Communication, ownership and mastering the craft. How do we help the team win? Today we are fortunate to have as a guest Leif O'Leary. Leif is the CEO of Allegius, a leading healthcare platform. Leif has spent decades in leadership roles, primarily leading sales and revenue organizations, before rising to the CEO role. From my experience with Leif, I know him for his commitment to great communication, for his consistency in leadership and just for his pure hard work ethic. Leif brings a unique perspective on how strong sales leadership skills can translate into executive level success.

Speaker 1:

So, leaf, welcome to pillar talk thanks, rick, it's great to be here. Um, I was honored to be asked to join. I think this work you're doing to support the community I mean this sincerely is maybe as important as any work being done out there. You know how I feel about the criticality of sales leadership, the importance of the role Even you capture in some of your thoughts around this work you're doing that it's one of the most difficult roles. I actually think it is the most difficult role and I think I can say that with three-plus decades of experiencing, having done just about everything. I think there's very little more challenging or rewarding than building an extraordinary team and unlocking sort of growth and impact in a business through that team. And so the fact that you're bringing real world practitioners together just to share some thoughts I think is awesome thoughts I think is awesome.

Speaker 2:

Yeah, I mean I just see myself as a student trying to learn and I've developed these pillars as a way to try to frame what I define as successful and how I will lead and develop leaders within my organization. But I don't claim to have all the answers. So I love having these types of conversations and trying to learn from others and to share those learnings, obviously through this podcast and the newsletter. You know, leif, one of my favorite stories is in our time working together is you were sharing about. You know you would often get questions around hey, how do I one day get into your role or how do I develop into be a more elevated leader? And we'd have those types of conversations.

Speaker 2:

And you talked about earlier in your career where you were living a pretty far distance away from where your office was and so you had quite an extended commute and please correct if I get any of the details wrong here but you would leave like way before the sun would come up in the morning and you would then hit the gym when you got to sort of near the office and then you would still get into the office and start the day really before everybody else even got there. But you know, with that extended commute it got to the point where you had to special order some type of like stronger dose coffee to maintain your energy levels and how that dedication and years of like just grinding through that really helped you expand and gain experience and skills to develop as a leader. So I remember those stories really well. I guess my question for you is what's your morning routine like these days compared to then?

Speaker 1:

Well, I will say a couple of quick notes and I thank you for remembering Rick. It's nice to know that some of the 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 in that case stuck with you. And and I'll I'll answer your question about kind of my morning routine, because you know a bit about me and you know that I am a very habitual person. You know, I feel the best people are really sort of defined by their habits and sort of that's the way I live my life. But my morning routine now is not all that dissimilar, absent the two or three hour commute from.

Speaker 1:

Yes, you are correct, I was living in Connecticut but I had this extraordinary connection with this unbelievable company working for just amazing leaders. At the same time, my wife and I were starting a family with four kids and we were connected to where we lived and I was. I just felt like I was in this really unique spot working for the right types of sales leaders that could unlock what I felt was the right types of opportunities for me, and so it was an important. You know, yes, I left at 4am every day. Yes, I had to go find regular coffee stopped keeping me awake on the highway in the dark of the night. So I did go find.

Speaker 1:

I'm not going to mention the name of the coffee because I'm actually not. I think I don't want to be an advocate for that. That's not really the best model when your heart rate is, you know, through your chest at 5 am before you get to the gym. But but that. But that was actually a very intentional decision because I wanted to be there for my family, even if I was getting home at nine or 10 o'clock at night and then leaving at four the next morning even though I was catching a few minutes, I was supporting that part of my life.

Speaker 1:

At the same time, I was really really leaning into what I thought was a unique opportunity, which actually comes back in many ways this conversation because it was the opportunity to work with some of the best, the best leaders, the best salespeople, and that was what I aspired to be and do, and so it was important for me to do that. So, yeah, my morning routine now is exactly the same. I get up every day at the same time, I work out first and then I'm in the office. And well, it might not be as quite en vogue today with the youngest generation, I'm still a huge believer that you know, working harder and being more present and leaning in more is one of the greatest differentiators that you can have in a career, and so it's still, sort of three decades later, what I sort of lean on. Maybe it's because I'm not smart enough to differentiate with my intellect and IQ. Hard work is the most controllable asset I have, and so, you know, that's been sort of the way I've defined it from the beginning.

Speaker 2:

Well, I'm hoping that the start time is a little later than 4 am.

Speaker 1:

It's a little later than that because that was born out of absolute necessity, but not much later. It's just a little more civil. I'm not injecting sort of the wrong types of coffee into my system.

Speaker 2:

Yeah. So I think about those stories of hard work and I overlay that with the world that we're in today. Like people have different expectations or even definitions of what hard work is and there's different types of distractions that can take away from hard work In your coming up in your career or the earlier in mine. Concepts like a smartphone sitting right next to you or hybrid slash remote work those weren't really regularly applied concepts. Now we have a new generation where these are things that we have to grapple with a bit and you know there's always the like.

Speaker 2:

Prior generation is always judging the newer generation and saying that they're less hardworking. Or you know, back in my day we didn't have this or that, but I really wanted to get a sense of now, as you reflect, as someone that lived hard work at a time and place where that's just what you had to do. And now you are in a world where you see people across a large organization. They're early in their career, they want to move up, like what is hard work look like in a way today that creates opportunity for folks in your organization?

Speaker 1:

Yeah, yeah, rick, I think it's a, it's a really big factor for leaders. You know, whether you're a sales leader or you're a leader of other functions, we, we are all living a time of just massive change. It's funny, though, as I listen to you sort of frame the question, I have to say I'm I'm actually drawn back to some of my first meetings with you and some other leaders when we came together many, many years ago and we're slightly different generations I'm a little bit ahead of you but we're sort of close neighbors. But you might or might not remember this, but one of my very first trips down to our New York office at Intronix, when we came together, you and another leader there, you know, were gracious enough to come into the office for a 7.30 am meeting which, by the way, I had flown down from Boston for but you two sort of marched into the office and said we don't do 7.30 am meetings, like what is this? And it was this really funny moment where, you know one, I saw sort of the strength of conviction in both of you and that was a very true characteristic.

Speaker 1:

But it was also, I think, indicative of a really important lesson for, I think, all leaders, certainly for me, and one that I've learned in multiple phases of my journey, that one there's not one definition of hard work and, by the way, I can say with absolute conviction, knowing both of you now for, I guess, 15 plus years, that there's few harder workers than the two of you, but that that the definition of what that means is not always the same For me.

Speaker 1:

I'm a morning person, so for me, like you described, being out the door at 4 am or 5 am, being at the gym and being in the office at 7 and turning the lights on that's how I started my career at ADP. Like I knew nothing when I landed in the Windsor Connecticut office of ADP, as nothing but raw material. You know somebody who'd never been in a professional white-collar setting and the only thing I knew to do was turn the lights on for everybody else. So I wasn't losing ground to the 50 or 60 salespeople in that room with me. But that was the way I defined it, and you all defined it in a slightly different way, and that's a really important thing for leaders to understand the shape and form of the people you hire, the way they're motivated, the way they work, is not always going to be a reflection of you and, frankly, the best teams aren't just a mirror image of their leaders.

Speaker 1:

Anyways, you want a mosaic of skills and capabilities and personalities and dynamics. So I'm reminded of that, although your question is much more framed. In this current generation and I have four kids who are all in their 20s you've met them and they're all entering or in the workforce now, and so I kind of live every day like being a little bit of this the old goat, old guard. You know, just work hard, grind it out, and then I'm immersed in a setting with people that have lived just a totally different experience. You know they've lived, as you described, instant access to information all the time. Like you know, when I and sort of we were growing up, you know if you wanted to get an airline ticket book, you worked at it. You know you went to a travel agent. That's before your time, but you went to a travel agent. That's before your time, but you went to a travel agent. Or you know you made phone calls or you did things. Like you know today, you know that's two clicks of a button on your phone and you're flying to Nova Scotia to go golf for the weekend and that's probably what you did, right? So our kids have grown up conditioned to just a totally different set of experiences. In many ways, really good stuff surrounds that access to information, but it does change the evolving dynamics in a workplace and I certainly am learning every day through this. It's not like I have all the answers.

Speaker 1:

I think one of your pillars around communication, though, really starts to get to the heart of how you sort of thread this needle of. You still do need a hardworking, productive, engaged workforce. If you're a sales leader, you need a group of people who are committed to the mission. You know that want to go make the news. Thank you for using one of my phrases.

Speaker 1:

I think my current company gets tired of sales. Certainly the sales organization 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 at PTC many, many decades ago. But you know it's. You know you need people to want to do that, but you've also got to realize that you know the team you put together is probably going to have people who are closer to our generation and maybe a little bit more that mindset. They're going to be people that are morning people, and I'm using simple, stupid examples, like the morning person versus you and Pete, who, hey, we like to work all night. You know like, this is what we do you get up at four, we'll get up at eight and we'll get to work at nine. You know like, and it's going to be everything in between. And so this idea of how you communicate and connect with people becomes really critical, really critical.

Speaker 1:

And I'll tell you you're just jogging for me so many stories from when we were together, but you probably don't remember our first meeting. I do, though, and I remember these things.

Speaker 2:

It was a breakfast.

Speaker 1:

Yeah, it was a breakfast in Boston at the Liberty Hotel. You might or might not remember the first thing you said when you sat down with me, but it stuck with me in a really good way. It was kind of an interesting moment but it stuck with me. And at the time I was a sales leader. For those who don't know, I was at that time sort of coming into the business, sort of running the Americas and then, with this plan to move into the CRO role, and Rick had been a long time, really, really important leader in this business. It really helped build the business and had the requisite amount of loyalty, connection and commitment to this business. And I think and I won't speak for him, but I know this to be true in some ways it's like looked at him, looked at himself as sort of a guardian of this company 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 from Boston, and we had breakfast in in Boston and Rick sat down with me and he said first thing he said out of his mouth like after the pleasantry is like you know, I don't work well with people who aren't very smart. That's what he said. Very, very first thing Rick said and I, it was a really interesting moment and and and you 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 of this business which you were and you know I had. You know there's decisions you make in these moments. Right, I could say you know who is this arrogant, cocksure guy who starts a meeting with his new boss? Like that. It probably was something that went through my mind, but like that, it probably was something that went through my mind. But I also saw in that the level of connection and how much you cared about this business. You weren't saying that because you were trying to reject the organ that was Leif O'Leary. You were saying that because you wanted to make sure the standards that you had for what you had been building there were going to be met and surpassed by new leaders.

Speaker 1:

And I mentioned that only because, like those types of moments where, clearly, at that moment in our journey, you and I didn't know the things we have in common and there are many, you know, a relentless love of learning, love of leading building teams. You know very hard workers passionate about supporting, you know, our clients and building businesses. Like there were so many things that you and I ultimately had in common but at that moment we were just. You know, I was an outsider and every leader starts that way. Every leader starts that way.

Speaker 1:

You have either hired somebody new Now they are an outsider to your team if you find them in, but you are an outsider to them and building connection, which for me is currency with people is everything and I know that's a cliche, but like you've got to figure out how to connect with people. Like you've got to figure out how to connect with people and communication and the way you do that is a critical sort of facilitator of doing that. And I do look back fondly on sort of the relationship we ultimately built and the impact you made in our business and what you've gone on to do and soar after your time at Intralinks. But there's these just interesting moments and it's all about human connection.

Speaker 2:

You know it's really great. I don't remember that specific comment. I remember the specific breakfast. To give you some context of why I probably went in with a little bit of a sharper elbow than 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 to his arrival, your arrival. That was like cartoonish that we don't need to get into the details of, but so there was a high level of sensitivity, there was a protective aspect and then there was a commitment of like, hey, and you know there's never the right answer here if you involve people in the interview process for someone that they'll be reporting to and, of course, when you are in a role where that you know the hire is going to be the one you're reporting to, of course the answer is yes, you should be involved in that, because you know you have a bias there, of course, and you want to make sure that the leader is great.

Speaker 2:

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 understand that we brought the right leader in.

Speaker 2:

So he took like a bit of a risk and, of course, like one of the things that made me a top individual contributor was that swagger, was that attitude.

Speaker 2:

It's a little bit cringy to hear now as now you know, almost 20 years into a leadership career and realizing that that swagger and that cockiness that makes you a very strong individual contributor has real risk associated with leadership dynamics and part of the journey of trying to define what good leadership is is on the back of that reality.

Speaker 2:

So I try to play into the swagger and that stuff where applicable in bringing a winning mindset and those types of elements. But also try, try not always succeed into being more thoughtful about the words that could have an impact. You were a real deal leader coming into an organization and off putting comment to initiate a conversation is not going to phase you. There are many people in the organization that are far less secure in their position, far less confident in their even fit for a role and a higher level of sensitivity to that, and that could be a really bad situation when you are in an elevated. So I laugh a bit at what you're saying, but it also makes me really sad, as the context of their even meaning well doesn't necessarily translate into the right things.

Speaker 2:

But but whatever it was a it's a funny way to kind of you know, talk about how we kick things off, but I do like to reflect on a then and now type of dynamic.

Speaker 1:

Yeah, but. But. But, Rick, just just think about what you just said. I mean, that's the essence of your growth mindset personified, and I think you captured perfectly the reality. Like your sense of self-assuredness and your swagger and your confidence has been a defining characteristic of what's made you great. That's going to happen with people. Just, they're going to be much more quiet, much more powerful people who don't have that external kind of sort of projection of who they are, and they're also extraordinary. They can also be extraordinarily high performance. So you know, it's all part of the growth for all of us.

Speaker 1:

You know I probably learned as much in that moment as a leader it's. You know I'll remember that forever. You know, along with many other stories, my journey with you and others, that forever you know, along with many other stories, my journey with you and others, but those are things that help you grow as a leader. You know I had to learn how to handle that approach, just like I did with you and Pete sitting there in the New York office and we don't do 730 meetings and I'm sitting here saying you don't do 730 meetings, You're an hour 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. You know you, you walk to the office. So so you've got to learn how to adapt. And I just think communication is just so critical because if you don't connect and engage, and then if you can't communicate which is both active and reactive, listening, like you, you know, communication is not a one way street. You've got to also listen, understand and connect.

Speaker 2:

So well, it wasn't just pete and I that you were uh had to establish that credibility with. We had 200 people, 150 people in the organization, all uh. Yes, we had offices and most people were in the office, but we also were a national team with, uh, you know, disparate geographies and folks all over the country and I think, as I reflected on what made you so successful in the role, it really was like what I'd call a consistent and positive communication. Consistent and positive communication and you would include the rest of leadership.

Speaker 2:

Really, really well, this wasn't just coming from LEAF. You made an explicit effort to ensure that you would reference Reiner a bunch and like, hey, reiner and I were talking like establishing even more that this isn't just you off the cuff communicating a message or an initiative or whatever it was. There was a it felt to me like a real intent to make sure that this isn't about you but it's about the organization and that there's alignment across. You know your leadership infrastructure there and I guess I wanted to ask you about the development of that communication skill, both from a tone, that positive type of element, and then the consistency of it, and you know how you have evolved that. You know into where you are today.

Speaker 1:

Yeah, I'll just say Rick, you know, first of all I am the byproduct of the gifts of so many incredible examples and leaders through the years. So like I think, first I was blessed even from my earliest days at ADP, like I worked for people, many of whom I'm still close with today, 30 years later, and have worked with again and have worked with again, who modeled 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 had literally zero frame of reference as what it meant to be a leader in a professional setting. You know, any intrinsic leadership capabilities I might have had were just born of necessity, of reference as what it what it meant to be a leader in a professional setting. You know, any intrinsic leadership capabilities I might have had were just born of necessity. And athletic settings or school settings, which you know are valuable but totally different, and, you know, for a variety of reasons. And so for me, first and foremost, I think I saw that modeled in exceptional ways at adp. And then I went to ptc with a lot of intentionality, by the way, drawn there, you know, to one of your pillars around attracting the right people. If I can throw myself into the bucket of one of the right people that went there through the years, I was drawn there by Jamie Pappas, just an absolutely extraordinary leader. He called me and this is a real story back to the start early.

Speaker 1:

It's funny how this story will connect a little bit, and you've heard this story before. This is that before cell phones were a thing, you know, I was sitting in my office, my first office in my whole career. I was sitting in that office in Windsor, connecticut. It was 630 in the morning and my phone rang. Jamie doesn't even probably remember this, but he called me and he had this dynamic energy to him and he said Leif, I got your name from the ADP Rolling Stone magazine. It looks like you're the top sales leader in North America. Blah, blah, blah. You're in Hartford Connecticut. I'm in Hartford Connecticut. I'm looking for a sales director to come build this team. Blah, blah, blah, blah, boom. And I was like I'm never leaving ADP Jamie. I this team. Blah, blah, blah, blah, boom. And I was like I'm never leaving ADP Jamie. I'm going to be here for 35 years. My entire career is mapped out in front of me. And he said, okay, got it, perfect, but you need a network in Hartford. Why don't we go have coffee one morning? It seems like you're an early riser, I'm an early riser. Let's get coffee one day before you go in the office. And I said you know what I should do, that you know. He had an infectious energy to him. And I said I should do that because I don't know anybody, like I'm literally a babe in the woods. I know nobody. I don't know anybody at Hartford.

Speaker 1:

I moved here the day after I walked off my graduation stage at BC and moved to sleep in a basement in Hartford and started working the next morning. That was the glamorous start to my career. That was the glamorous start to my career and I had coffee with Jamie and a month later I was starting a PTC and it was. So. I've been sort of seeing this model, this engagement, connection, communication capability and the consistency of it almost throughout my career. So, first and foremost, I think that's where sort of I developed that mindset.

Speaker 1:

I think that's where sort of I developed that mindset and I just, I'm just a huge believer that as a sales leader really any leader, but certainly as a sales leader you play this critical role where you have obviously a responsibility to build the best team and create a team of high performance impact players who make the news. You also have this enormous responsibility to the stakeholders around you, because if you're in a company that is focused on growth, really kind of everybody around you is nourished by or focused on are we driving growth, and so you, as a leader, have this stakeholder responsibility to create connectivity. This is what's working to power growth. This is how we're performing Transparency to say we understand we're winning or we're losing. I know you've heard me say this before in an actual work setting, but, like people underestimate in growth, leadership roles sort of what I refer to as the psychological aura you have in a company and I know that sounds egotistical, it's not what I mean. People want to work for a winning company.

Speaker 1:

The simplest way to understand are we winning, are we losing Is the sales organization showing up with a sense of we're winning, and then is that backed up by points on the board. And boy, that was an important lesson for me to learn early on, rick. I think early on I was under playing 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 huge communication responsibility there. And then, of course, you all have bosses, you know, and whether you're the CEO, you've got bosses that are the board. Whether you're a CRO first-line sales leader, everyone's got bosses and and you also have this sort of responsibility to make sure they also are being supported with what they need. They understand how the company needs to line up to support you. So it's like all of this, this sort of connective tissue, comes back to, to being able to communicate effectively and draw people together.

Speaker 1:

Um, and I like the way you frame it with positive intent and the way I interpret what you're saying. It's not necessarily that everything is just pollyanna and rose-colored glasses, but it's put in frame that's easy for people to understand, that they can connect with, and there's a sense of clear vision and sort of positive direction behind what we're doing. Sometimes you have to deliver very tough messages, but I think when people kind of put in the right context, people can really believe in it. And, by the way, all of what I just said sort of described around the stakeholder ecosystem we have to communicate with, I think does come back to some of the things you referenced.

Speaker 1:

Like, most people don't want to just hear that their leader believes something or we're doing something because of Leaf or Rick. What they want to believe in is something bigger and they want to feel connected to it. They want to know the team and the company are positioned to win. They want to know the team and the company are lined up behind what we're doing. And you know, I think that's really important, you know. So you're right. Whether it be a Ryan or a Ron who was our CEO at the time or other members of the team, like you want to, the team wants to believe that we're. We're one team, one fight.

Speaker 2:

You talk about like a little bit of concepts clarity, engagement, connection, transparency. Have you developed, like, is there a framework that you use for communication, or is it a little more casual than that? Like, how would you, you know, have you developed the both the style, the frequency and medium of how you approach communication as a leader.

Speaker 1:

Yeah, I'll say so. To me it's a bit of an art and a science. So let me start with the science, which is kind of the basis of your question. I don't think there is like a universal framework for communication, but I do think there's some really important foundational elements which to me, are kind of non-negotiable. You've seen these kind of play out in real life. One is having a rhythm, a one-on-one rhythm with your people. And I'll tell you why I put that in frame of a communication framework because one-on-ones for me are not an opportunity for me to sit with one of my direct reports and talk to them. It's actually much more their meeting and my opportunity to listen to what they need, what's happening. Where are we Through that? Of course there's always things I want to maybe sort of touch on or focus on, but to me it is establishing the space, whether it's weekly, biweekly, et cetera, and those things can vary depending on the company and the structure, but it's establishing the space where somebody who works for me knows they've got the platform to articulate with me what they need to. Those might be personal things, those might be professional things. Personal things, those might be professional 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 that as sort of a first sort of principle around building communication into your business, into the leadership construct. Second is I sort of believe you create a steady cadence of outbound communication. Those take the form for me, and I've evolved this over the years I tend to do a weekly note out to the team that I'm working with, and this in my current sort of span of responsibility as the CEO of Allegis. There's a weekly launch. It's the branding of the note, not the most exciting, I know, but the weekly launch is a note that goes out for me every Monday or Tuesday to the entire company and it tends to capture some thematic area that's top of mind for me, something I want to share with the team, might be some successes in there, might be some lessons learned.

Speaker 1:

Then there's always a personal element. You know I'm a big reader. You know my day starts the way we described at the start of this. I won't bore people with that again, but I also do the exact same thing. It's the last thing I do every night, which is I sit down and I read. Usually it's stuff focused in the business and leadership area, just because that's where my greatest interest is and I tend to love those stories, those books. But but it sort of it has one last personal element in that note every week which was on the bedside table and I'll be sharing thoughts about whatever it is that I'm reading. And I do that for two reasons. Just you know.

Speaker 1:

To come back to this communication framework. One I love to share any interesting tidbits, like if there's something I picked up I'm reading the new Stanley McChrystal book right now on character, which is an unbelievable book and if I pick something up along the way I want to share. So that's one thing. But the second thing is it's also for me embodying one of in the company to say, oh Leaf has it all figured out, which is the reality. Couldn't be further from the truth. You know, we live on a treadmill, you're constantly learning new things. There's a there's just generations of people in front of me who've learned so much more than I have, and so like I'm embodying that and then it just creates some connection, like it's, you know, reading about what we did in the company, the new wins we had, or the big release we just had, or we have our customer advisory board here in the office this week and I'll talk about that next week, you know like. But this creates a different type of connection.

Speaker 1:

So the second is create an outbound 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 I travel, I might be in India or I might be in one of our offices here in the US and I'll bump into somebody at the coffee machine and say, oh, I was reading your note last week and you know I really love this. Or oh, I just read that book, or I bought that book you're reading Like. Just create sort of a flow. So that's the second thing.

Speaker 1:

And then I also am a huge believer in building, I'll just say, sort of events. But, like you know, you've got to establish a cadence where you are engaging your team. So like might take the form of a company all hands that I do quarterly now and that you know. Or, if you're a sales leader, maybe you have a monthly all hands meeting you're doing to bring your whole team together where you are able to share a very sort of in a consistent way, kind of you know what are we trying to accomplish, where are we, what are the obstacles, what are the things going well and hopefully, if you do those well which I try to always, include time for active Q&A, even with a thousand person company. Today, like every one of our quarterly all hands meetings, you know, we have at least 30 minutes of active Q&A where I and other members of the leadership team just take whatever questions on people's mind. So, like I think I think there are some things that that at least I do, that I feel support my commitment to communication. So that's kind of a little bit.

Speaker 1:

This is the way I think about the science piece of it, but I think the art around this is is where a lot of the magic really happens. Rick, I just think understanding how to get people. Like there are some universal human principles, you know. I just there's many of them and I won't I don't know them all, but I know there's some that matter to me Like people want to, people want to win, people want opportunity. You know, like I've traveled many, many times over, I've been blessed to do that and there's so much more that connects us around the world than than separates us. But one of the most you know sort of consistent things is people just want an opportunity to show up, make an impact, support their lives. So, like you know, that's people want to win, they want an opportunity.

Speaker 1:

And I think the third, which is really relevant here, is I think every one of us wants to believe we have people who are invested in our success. And when I just think back over my career, like I, you know I referenced Jamie Pappas calling me at 630 in the morning, you know, you know our then CEO at Interlinks, ron, who was willing to sort of commit to helping close the loop on my desire to ultimately be a CEO, like these are investments people are making in, you know, your success. Yes, and of course it's supporting what they need. But genuinely feeling. Or our CEO of PTC for many of the years I was there, dick Harrison, who really started me on the journey of sort of shaping a vision to want to be a CEO and then investing in me over a decade just giving me opportunities to go build a portfolio of skills. I could go on and on.

Speaker 1:

But people want to feel like they're invested in their success and so, as I think about how much I've benefited from that, like I've really tried to define who I am as a leader by creating that level of connection with people and trying to then back that up with real actions. You know, if somebody wants to go, you know, pursue a dream or a vision, whether that's professional or personal, how can I, as a leader, and how can I, with the company, support them doing that? Because I think that art, the art that's there, rick is what really unlocks people and I think it's what creates the connection. And you know I've got this Captain America shield over my shoulder. You know that's a gift, that's there, very intentionally, in my office in Boston, our headquarters. But that was a gift when I left Intralinks from our team in Latin America.

Speaker 1:

You know there was a funny phase of the journey there, as I was moving into the CEO role, where this Avengers theme became a thing and sort of internationally, I developed this playful sort of persona which was Captain America and this was such a thoughtful gift to me. We had this big dinner when my departure had been announced and two members of my staff, bob and Ken, were taking over as co-CEOs and Bob and I were in Brazil and the whole Latin America leadership team was there and they had taken the time to go buy this set used shield from the Winter Soldier movie, which they had this big it was framed in this big gift. It was a really emotional moment and they were. And to me, the reason I keep it so prominently displayed in my office is not because I'm some Marvel sycophant I do love the Marvel movies but it's actually just much more because it's emblematic of like connection, and my connection with that team was deep, as it is what it was with most of the teams around the world, and I'm still close with many of those people today and I know it meant a lot for them and they really went out of their way to think about a gift that would be representative of the way they thought about it.

Speaker 1:

So to me that's the art portion of it, right, rick? It's like do people, when they show up they're working for leaf or they're showing up working for rick, do they feel like this is a leader who, yes, is supporting what's best for the company that's all of our job but in that pursuit, is going to take the time to make sure if rick wants to ultimately, you know, run his own company, be a ceo, or wants to move into larger, more expansive roles as a leader. Is he supporting my ability to do that? If I have these other personal ambitions, am I being supported in my ability to go unlock that? Because, as I said earlier, I just think connection I know it's cliche connection is currency, and in the right way, like when you trust, you understand, you know. And again, I look back fondly on our first breakfast or my first meeting with you and Pete at Intralinks in New York, mostly because now I know you both so well that I can see all the best in those moments and that's what matters.

Speaker 2:

You know I love the kind of overlay between the science and the art and you know the one-on-ones and it being their meeting, the steady, the consistency of steady outbound communication on whatever that frequency is, Totally the work involved in creating events and experiences. You know I've benefited from the importance I've probably neglected that a little bit in, as I've, you know, moved up as a senior leader, and so there's a lot to think about around it. The art, though, is particularly interesting, and I guess when I hear you talk about the stories around it, do you view like the trick to the art is just that innate caring and curiosity, and like nothing more, and then it's the application of that, or do you attribute any other aspect around what makes the art effective for you?

Speaker 1:

Yeah, I think, listen, I think my general opinion here is that it starts with a first principle within the leader, that is, you actually do genuinely care about unlocking human potential. Like to me, like I know it's a bit of a maybe it's a little bit of a Pollyanna view on leadership, but, from what I have found, the best leaders are people who are generally genuinely energized by the force multiplier of building great team and unlocking people, like they're not just doing it because they might make more money. That I'm all for making money, I'm a huge supporter. But but, like I have a lot of new leaders or people who are pursuing leadership degrees, or even sometimes my own kids, as they talk about. Oh yeah, I, I should get into management 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 who usually make the most are your best salesperson and your best engineer in a software company. So if you're after just making more money maybe not, but if you are really energized by unlocking human potential and creating the force multiplier of a great team, then I think you're on the track, because then 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.

Speaker 1:

But I think curiosity is a big thing. I think having the patience to spend time with people, being there when times get tough. You know, unfortunately, I've been at this long enough to have seen people go through some pretty traumatic and challenging personal situations. Early on in my career I had a rep lose a baby. I've had a leader I was extraordinarily close with unfortunately pass after a long battle with cancer. Like, and you know, you kind of live through these journeys. You know, and you've gotta, are you there and, and I think people genu genuinely know when something is transactional and when, when a relationship is purely transactional, hey, you might make some magic happen. I mean, there's all these hired gun salespeople that love to roll into a company, roll out some big, do some big deals, make some money, support the company might make me look good as a leader, might make you look good as a leader. So that happens, it's going to happen, like you know. Again, I'm not Pollyanna about this stuff, but I think the most successful, most sustained, high impact sales organizations are where you're creating that sort of cultural foundation that is, we're here to unlock and make an impact and then people lean in in a really, really big way and it's reciprocated.

Speaker 1:

I literally have no greater sense of satisfaction for my professional career, and I can say this with all sincerity. Obviously, it's always been about providing for my family, so I have to. That is always first, like that's why I've always done what I've done. But I have no greater sense of satisfaction and watching people that I've worked with go on to be CROs you know, building great teams, ceos, whatever it is that start their own companies, like build a media empire which you 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 I love most.

Speaker 2:

Yeah well, great answer. I mean you can tell from you know your energy that how that plays out in your interactions with teams. And answer I mean you can tell from your energy that how that plays out in your interactions with teams and how that results in thoughtful gifts when those milestones 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, one of the potential transitions would be to CEO. That's become a reality for you. It's not for everyone, of course, but what's really different from being a sales leader to being a CEO?

Speaker 1:

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 for everybody and I look at it was early in my journey because of great models and seeing somebody like a Dick Harrison who'd been a salesperson at PTC become CEO, being surrounded by really great leaders, who who I looked and I said this is this is sort of the ultimate opportunity to build the team, shape culture, build the vision and the strategy for the business. So I was really energized by that. But it's not for everybody, because as you transition to a CEO role, that stakeholder ecosystem that you are now sort of you work for, like I tell and present to our new hire class every week. You know like a lot of it's Q&A, most of it is Q&A. I just let them ask me whatever's on their mind. Ineptly, somebody will always ask me what do you do as a CEO? I always say the same thing I work for three different stakeholder communities. I work for all of you, I work for our board and I work for our customers. When you're in sales leadership I described earlier, you still have this stakeholder community that you kind of play, this integral sort of central nervous system role to. But you really know your mission. It's clear and you have a very well-defined sort of model that you need to go deliver against when you move into the CEO role.

Speaker 1:

There is a very different sort of relationship with those stakeholders. Like, the employee community is one set of stakeholders. They have much of which is we've centered in this conversation Like do they feel? Like they believe, do they understand where we're going? Do they have a sense of connection and transparency? Are we building the right strategy? All those things you put it. The other end of the spectrum, we have our customer advisory board in with us today. So, like that group of stakeholders is looking at me as a sort of indication of is this a business we wanna continue to bet on? Do they have the sense of understanding of who we are, that we can believe that this is a partnership we wanna continue to nourish? So it's totally different stakeholder community. And then, of course, you've got the board dynamic and boards and owners of businesses come in all shapes and sizes, as you know well, but ultimately they have sort of this shared responsibility. I work on a private equity-based environment. They have a sense of responsibility to ensure they're delivering for the stakeholders. They serve the investors that have trusted them with their money, so they're focused on outcomes. They're also focused on governance. So that's a very different dynamic.

Speaker 1:

And then the other piece, which sort of connects back into the employee piece but is really also very different, is, I think, to make the transition from CRO, for instance, to pick the top sort of growth oriented role into a CEO role, you also have to have real professional and personal curiosity around the 360 degree that is a business Like.

Speaker 1:

I'm always a little skeptical if somebody moves actually from any role in a business it doesn't have to just be CRO, but they aren't genuinely like, energized by the art of the possible and product and technology or they don't really want to lean into how do we unlock operational excellence across the company and the people, of which I've just seen many go through the transition that I just think of, soared, as CEOs bring that growth mindset and the connection to the market and the ability to build, of which I've just seen many go through the transition that I just think of, sword, as ceos bring that growth mindset and the connection to the market and the ability to build a great sales team and they sort of surround that with this sort of real passion and interest for the rest of the company in a in a in a deeper way.

Speaker 1:

And and I I would just say my other observation is you can always tell those leaders, like I think of some of my closest friends through the years there's a group of them that all went on to be CEOs or COOs that two different sort of ways to think about an additional step beyond CRO. And then there's a group of them that have just done spectacularly well, have made a ton of money, that have just done spectacularly well, have made a ton of money, have lived a best life, who said I am never going to leave the sales world 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 up on taking the next job for ego or like it just it's. It's always best to be in what is the right role for you, and so yeah Well, leif, I mean, the time just flew by here.

Speaker 2:

I could probably speak to you for hours, so perhaps we do this again in the future, but I want to thank you for joining us today. Any other messages you want to send before we wrap up?

Speaker 1:

No, no, not nothing in particular. Thank you for having me on. Like I said, it was an honor. I think you're doing some really, really important work here, rick, I want to make sure I get you some a nice long list of guests you can draft in here as well. I think there's so many just extraordinary leaders who can help this next generation of leaders become the best version of themselves. Please use me as a resource. I'm grateful, this time with your community, and look forward to talking again soon.

Speaker 2:

Well, I appreciate that and I'll take you up on it. And you shared some amazing things today, so thank you. Reflecting on the conversation that we just had with Leif O'Leary, I'm thinking about his reference multiple times to concepts like having a growth mindset, creating an environment for winning, creating motivation for something beyond just the paycheck. Leaf puts a lot of emphasis on these areas. What he described in the interview as like a psychological aura. I've always considered these items to be outputs, outputs that are derived from tactical inputs, of the actual day-to-day work that is put in towards winning winning the deal, improving the process, designing the campaign. But for Leaf, I came away with this impression that these areas are part of the inputs that placing purpose in his communication centered around winning, and growth as an input is a key that helps people perform at a level ahead of what they would do on their own. We've also broke down the art and the science of communication. What I just described, you know just there was the art side of it. On the science side, his commitment to weekly communication at the org level stood out to me. Sharing successes, lessons learned, personal learning and development, modeling the behavior you want to see in the organization it's that kind of consistency in communication that I think really helps an organization stay aligned and keeps leadership in some way accountable on ensuring there are items to talk about other than just going through the motions.

Speaker 2:

This is an area that I've had fits and starts with. I do a lot of communication but simply not consistently enough. If I change one thing on the back of this episode, it's going to be an increase in the frequency of org-wide communication. That one-to-many communication has such unbelievable ROI. We all need to do it and we all need to do it well. The frequency can vary. For example, in episode five with Kyle Norton, he broke down his monthly communication cadence, which was highly structured and also highly effective. To me this rhythm and consistency is an example of great leadership. And lastly, you can hear Leif's passion come through as he responded to questions today and mentioned early in our conversation the power of having a routine. Leaf is consistently energetic, consistently consistent in his leadership and I attribute a lot of that to his discipline and routine. It keeps Leaf as the same guy you're going to encounter anytime, anyplace. They get the same Leaf and the more senior you get in an organization or in a role, the more important and valuable that that becomes.

Speaker 2:

I want to thank Leaf for joining today. I want to thank Ari Smolin for producing. I love the music at the beginning and end of this podcast. Isla Young and Sons of Summer put that together. I hope you enjoy it too. We will see you next time on. Pillar Talk Hurts in me Like the joke.

Speaker 1:

I can't shake, I can't quit. It's never really what you said it was.