Sean Ford, CMO at LogMeIn on Mantras, Vulnerability, and Working on Yourself

Show Notes

W. Sean Ford serves as LogMeIn’s Chief Marketing Officer. Sean is responsible for leading all aspects of LogMeIn's global marketing organization including product marketing, field marketing, demand generation, communications, brand, and e-commerce. Sean previously was at Avid, where he led worldwide marketing strategy, he has also held executive positions with Zmags, Syncsort, and Oracle.

Sean offers an introspective take on leadership in this episode of SEEKING EXCELLENCE.

Topics we cover include:

  • What Sean learned to become a leader from his Grandfather.
  • The importance of standing up for what you believe.
  • How Sean learned to have candid conversations.
  • Why Sean uses mantras and what his five mantras are.
  • How working in an addiction recovery center changed his perspective.
  • What Sean does to hold himself and other accountable.

 

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You can follow Brett Pinegar on:

 

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Podcast Transcript

I have a series of mantras and one of the things I'll always use with the team is, secrets keep you sick, and that doesn't mean, that doesn't mean that you don't have privacy, obviously people have privacy and that's completely fine, but you know, why sit there and suffer because you know something's wrong versus get out in front of it and have a conversation so that other people can jump in and help you make it better.

Welcome to Seeking Excellence. I'm Brett Pinegar. This podcast is all about understanding the experiences, the mindsets and the skills of people who are working hard to make a difference as leaders, people who are seeking to live up to their full potential. We work to get to the root of who they are, what makes them tick, and to draw out insights we can all use as we seek to live and lead with excellence. I hope you're inspired and motivated by what you hear. My work is all about helping leaders and teams become their best. The results I've observed are dramatic and tangible: increased productivity, higher levels of engagement, less stress, and frankly, a lot more fun. You can find out more about my work and get the show notes to each episode at brettpinegar.com. You can also follow me on social media @brettpinegar. Check the show notes for all the specifics. In this episode, I interview Sean Ford, the Chief Marketing Officer at LogMeIn, a leading provider of cloud based connectivity solutions. Sean is a remarkably thoughtful leader. You can feel his leadership flow from the inside out. There's an intentionality to it that is incredibly impressive. I love what he has to say about vulnerability, mantras, and getting yourself figured out. I'm also inspired by the courageous decisions he's made, and the impact they've had on his leadership. There's tons of good stuff here, so let's jump right in. Well Sean, it is a pleasure to be with you today. It's been a very long time since we've last seen each other.

Yeah, thank you so much Brett for inviting me.

Oh it's a pleasure to have you. Sean, I wondered if you could help the audience better understand the scope and structure of your responsibilities as Chief Marketing Officer at LogMeIn to kind of start our conversation off today.

Sure, well, so LogMeIn top ten SaaS company, 6 1/2 billion dollar market cap, you know, north of a billion in revenues, about 3,000 employees globally, just to give people a sense of the scale and scope of the company. So my job as Chief Marketing Officer involves you know, all of the aspects that you would traditionally put into a marketing function, product marketing, you know, demand generation, events, communications, brand, on a global basis across all of our businesses and products, and over 200 people in the team. So, it's a fairly large role.

Fantastic. How many direct reports do you have, Sean?

I have right now, four.

Fantastic. You know as I talk to many leaders, they're often struggling with having too many direct reports and four sounds like a really good number. Is that a number you've been at for a while?

No, it's fairly recent. I think that the way you get fewer direct reports is you get you know, stronger direct reports. And so if you can do that, it makes it easier to roll those folks up.

Indeed, indeed. Well I'm wondering if we can kind of take a step back here. Leadership, talents, abilities, and approaches sort of evolve over time, and I'm wondering if you could help us better understand what were some of the key milestones for you in becoming the leader you are today? Maybe events or experiences you had that really helped set the tone, either good or bad?

Sure, so you know, it's funny. I kind of come from the school of thought that you learn most of what you need to know about being a leader before you actually become a leader, sort of you know, in the formative years. I would say a few things. One, a very powerful influence in my life was my grandfather. He was a grocer, never went to college, but very quick minded and would always say, "I'm smart enough to know that I'm not that smart," so I think you know, that general principle was something that I carried with me, I still carry with me, and I think you know, really forms one of the foundational ideas that I bring to bear most of the time. I always have smarter people around me and I'm not so grandiose to think I always have the answers. So that's one part of my childhood. You know, the other thing I would point to, I think I remember the first time I really sort of stood up for someone and that was when I was playing hockey in college and there was a freshman that wasn't you know, getting a lot of play time, was sort of in a separate locker room, and I remember stepping up and going to talk to the coach and saying, "Look, I want him to sit by me," I was a more experienced person on the team and gave him a place rather than having him sit by himself for the entire year, and ruffled a few feathers because people have their space that they like, and again, it may seem trivial, but that's something I also believe in. You know, stepping up for people, making sure that nobody's left behind.

Where do you think that came from? What was the genesis of that courage or that desire to stand up for somebody? Can you trace it back?

Yeah, of course, well in that one, look, I think that I always, growing up, had you know, a high sensitivity to kind of the environment I was in, I think I was always pretty sensitive as a kid. I think that I've been in places, growing up, where I felt like maybe no one stepped up for me when I had hoped they would, and might have been in a position to do so, to make my life a little bit better, and I think that it just triggered that I was in a position of authority at that moment, even though it was, you know, just college hockey team, to be able to make a better difference for someone where I could appreciate how they might have felt.

You mentioned the fallout of that was that there was several people that kind of looked down at you or gave you a hard time for that.

Yup.

Do you remember your reaction? I realize this is a long time ago, but did that toughen your resolve, or did you feel like, oh man, did I do the right thing here?

Oh no, I absolutely felt justified. I felt really good about the decision. The people were just upset because they had to give up a space and move and it just, it seemed like they were trying to teach a lesson to this kid, and I didn't like the lesson they were teaching, but for the most part I think, again, I felt like I was in a position to be able to do it, and not have a lot of pushback because I had sort of earned my spot. So I felt like it was the right thing to do at the time, and I know that this person, when I ran into him six years later, brought it up out of the blue and thanked me for it, so you don't get much, it doesn't happen often in life, but in that particular moment, you know, I look back at that as a pretty nice part, at least one nice thing I've done, and feel like it was the right thing to do.

So maybe describe for a second here your first professional leadership opportunity and what that felt like. Was that a good experience, bad experience, give us a little bit of background.

Yup, so for me, I think this is another foundational core, and you'll appreciate this because it comes from, you know, cutting my teeth at Monitor company, and I remember in this particular environment, which you know, talked a lot about giving productive feedback and being direct, and having difficult conversations. I remember being an early consultant and having a particularly intimidating case team leader who was not known to be particularly extroverted and very smart, good guy, no one wanted to give him feedback and I remember being there with some of my colleagues and saying, you know look, I'm going to take this company up on its word, and I'm going to go talk to this person about the fact that maybe because of their style, people aren't relating to them, aren't communicating with them, and I know I wasn't. And I remember being very nervous, and sweating a bit as I knocked on the door. He turned very stoically with a face that I only read as what's this guy doing here, because he's a junior first year consultant, and I proceeded to have a really good conversation, and said, "I don't know if you know this, "but this is what I'm struggling with in the relationship "I have with you, here's the two things. "It may be that you know that, "and you're okay with it, but I wish it was better. "And, I just wanted you to know." After I left with sweat drenched down my shirt, I think I wore a light blue shirt, which was a bad wardrobe choice that time, I felt better about it but at the end of the day, what ended up happening was a couple of weeks, it was within weeks, I was all of a sudden moved up to then manage a team of people with that same account. And I really feel like that was a sign of him saying, "This guy's mature enough to deal with as a manager, "and he's mature enough "to deal with more client responsibility," and again, it might not have been a seismic moment, but for me, I always think back to that one as a first professional leadership experience by stepping out in front and taking a risk by being direct.

Well it sounds like having candid conversations is something you learned early in life, whether it was the experience on the hockey team or as an early consultant at Monitor. When you think about that, is that something that was modeled well in your growing up years? Did you see other people interact in a candid way, or when you think about your candidness and your willingness just to have the frank honest conversation, where did you gain those skills?

Well, it was definitely not a part of my upbringing. It was I think, you know, I was Irish Catholic, you know, everybody keep your lips zipped and mind your business, and so, it was a very unlikely environment to learn that. I think that part of it did come from the experiences that I shared with you. I do give a lot of credit to being a consultant in a place, in a company where, like Monitor, where the product of Monitor was really the people. I mean, every company will say that you know, the people are our biggest asset, and I do believe that companies largely think that, though a lot of those companies make widgets and devices and so they're actually selling that. Well a consulting firm has to do that if they're gonna improve their product, which is the ability of their people to think and execute and really sort of relate. So I think that was maybe the best proving ground for me, where I cut my teeth.

Yeah, love it, love it. Besides your family and other direct people that you've interacted with, are there any sort of leadership heroes you have that have influenced your approach to leadership?

You know, it's funny, so aside from family, which is a tough one for me, I would say, 'cause my father was a particularly big influence on me, he was a very successful executive with British Petroleum, and I think that you know, I take a lot of my leadership nods from sort of history, which is one of my personal interests. Again, I think that there's a lot of counterintuitive examples of people, if you can find little nuggets of leadership. One in particular, a little bit esoteric, there was a person who was the first sort of Native American captain of a US warship, his name was Ernest Evans, World War II, and he was in charge of the USS Johnston, which a lot of people haven't heard of, but he was a guy who ended up in a fairly seismic battle in World War II where there was overwhelming odds, the entire Japanese fleet against him and he proceeded to announce over the loudspeaker to all of his crew that this was a situation where they were facing overwhelming odds and they were unlikely to survive, but they were a fighting ship and they were going to do everything they could to you know, to help the fleet. And so out of that, just a simple nugget, there's a level of you know, certain things I try to emulate not at that dramatic level, but one is, it's a clear direct communication of the environment you're in, and what to expect. In this case, pretty dire, but no matter what, it's an understanding that you're there for the greater good of the broader team, it's not about the glory in this case of the SS Johnston, it's how do you win the war, and there's sort of that bigger picture view that at some time you have to play a role that seems like a small part that is a larger part to contributing towards a greater end. I think that there's a part of him that was a willingness to take risks and if you read about this in the book that's written about that particular battle, by Hornfischer, you find that he knew that he had to make some pretty daring choices in order to survive as long as he could, and maybe change the nature of the battle again, to create the greater good. So you see those things in leadership. I really look up to people that take risks, healthy risks, people that are in it for the bigger good versus themselves, and that are just direct, regardless of whether the news is good or not so good, with the people that they work with and set those expectations accordingly.

Wow, well what a great example. It reminds me a little bit of The Darkest Hour, this Academy Award winning movie with Winston Churchill and in an obviously, a much more public big way, but facing the risks, doing the right thing.

Yup.

Making sure that you give a reality to the people that you're dealing with, and understanding the consequences of that reality, but fighting nonetheless.

That's right, and great credibility comes from that, and great respect and loyalty comes from that because people I do believe, they know when someone being honest with them, it deepens the relationship and it knows that essentially, you're going to be able to trust, build trust, and minimize surprises at the other end.

Indeed, indeed, well thank you. What a great example, and we'll get the information on that book in the show notes, so that people who are listening can take a look at it and read it. Sounds like a very interesting book.

Yeah, it's great.

Well Sean, let's pivot and talk a little bit about your leadership approach. Obviously, candid communication is central to the way you approach leadership. What are the other kind of key elements that you would use to describe your approach to leading your teams?

So, I think, I guess it's a few things. One, I would say, direct, we talked about, you know, I sort of take things directly and you know, don't carry a lot of baggage. Try to stay fairly clean in terms of whether something is a big issue or a small issue. You just want to get it out and move on, so there's a directness there. I think approachability, which you know, I didn't talk about my father in the discussion of people I admire, but you know, he was always a very down-to-earth approachable guy and as a result, both at home and in the work environment, and I think that approachability, that non-threatening willingness to have a human conversation is something that has people open up, they're willing to tell you if there's a situation. They know that you care about them, you listen to them, so that's a second big one. I think a third one is the transparency. You know, I'm happy if someone, we always say in our family, if you're old enough to ask the question, you're old enough to get an answer and I think that there's a transparency level of you know the same sort of principle applies to organizational leadership. If someone asks you a question, you know, they deserve to have a straight answer and you need to be transparent with them. And then I think underpinning all of it is really just, accountability. I genuinely will you know, try to step up and own what I have done wrong, or own what I could do better and also hopefully share in the success the team delivers in an appropriate level but I do think it's people knowing that you're in the trenches and that you've rolled up your sleeves and whatever the outcome, you're equally accountable to it. It is one of the sort of central things that I try to do.

Well I love the sort of connection between accountability and approachability.

Yes.

And the possibility that creates for real, true feedback to you as a leader. Sometimes we as leaders don't get the feedback we really need to get. What have you done in order to become not just open door approachable, but to have the real conversations where you learn what you need to know? It's the unknown unknowns that often get us into trouble as leaders, so is there something beyond having an open door that allows people to come to you and confront either things that you've said or to give you information that may disappoint you but that you really need to know?

Yeah, well, I think you know, part of it Brett, is an amalgamation of the characteristics I just described, right, so if you're direct with people, they know that you respect them. If you're transparent, if you have a generally engaging personality where interactions like that you and I have, for example, this interaction to me doesn't feel like a transactive interaction. It's relational interaction and when you can try to you know, calibrate how many of your relationships or conversations that you're having are purely transactive, versus somewhat mixed, versus relational, if you can start swinging those over to the relational side, you'll find that people get to know you and then they feel comfortable enough coming up there. Plus I have a series of you know, mantras and one of the things I'll always use with the team is, secrets keep you sick, and that doesn't mean that you don't have privacy, obviously, people have privacy, and that's completely fine, but you know, why sit there and suffer because you know something's wrong, versus get out in front of it and have a conversation so that other people can jump in and help you make it better? And that might just be to process, and not do anything but process it, but it certainly helps to get out of your head and make the things that are you know, you're suffering with, take the power away by kind of bringing them into the light.

Love it, love it. So, you've got a very strong leadership style. I'm sure you've worked with people that have different leadership styles than you do. When you think about people that report to you or have reported to you in the past here that maybe have had a different style or maybe came from a place of distrust or protectiveness or closed sort of sharing the good news and avoiding the bad news and those sorts of things, is it the mantras that bring it out, is it your example, do you sit down and do you have a frank conversation, how do you bring people into this new world, besides or in addition to your example?

Yeah, it's a great, great question. I think that, well the first thing, and there's some of the other things I think we can talk about but the first thing that I'll do is, I lead with vulnerability. You know again, one of the things that a lot of people believe as leaders is that there's a sign of sort of you know, imperious self confidence and strength promotes confidence in the employee base, and the irony is that leading with vulnerability is actually I think probably the bigger strength. It takes more courage to do that, right, you become more open, and open yourself up. And if that's true, then what better way to start breaking down the barriers with others if you do two things: one, you lead with that vulnerability by saying simple words like "I don't know the answer to that," or by saying "I made a mistake here," and that's half the equation. The other half of the equation is that then you either amend the behavior or you apologize if something happens, and I... What are the things that you're doing to become the leader that you are today? How do you get up for each day? What do you do to make each day a great day?

Well, I think a few things. So, again, I've tried to spend a fair bit of time understanding you know, in a very hopefully candid way, sort of what my triggers are and where I'm not my best self, right, and I think, so everybody has those and so what I've got is five mantras, I actually have five mantras. I have a little note. They're all in code so people don't think they're particularly great, you know, they don't think I'm a crazy with a sticky note, but I've got five mantras, so what I'll do every day is, I've got 'em on my laptop or on my computer screen, and I just look at them, and I know what they mean, and that'll sort of center me at the start of every day. I don't know if you want to hear what they are?

I'd love to hear 'em, that'd be great.

So, the first one is letter R, but it stands for remember, and what that means, there's an exclamation on that. So, what does that mean, it means that what I say as a leader can have a disproportionate ripple effect on everybody else around me, so I have to be very careful with what I say and how I say it, and the language I choose. Remember at times that I like to think I'm just Sean and I've got a good sense of humor and I like to talk about movies and trivia but actually I'm the Chief Marketing Officer of a public company and so, again, remember that you have a position of authority and it's a physical position. So just lots of reminders when I go, remember what you want to do in this meeting, the tone you want to set, so remember's a good one. The second one is choose to be great. So, C-T-B-G, and that is, that for me is that I go in and my footprint, my personality, I can oftentimes you know, I can attach to comments others make. I'd love to tell you I have super thick skin but I'm probably a little more sensitive than some people, and I can't let that get in the way of me not being my best self, or being great in a meeting, in a session, et cetera. So, choose to be great. The third one is tough for me, and that's don't take the bait, D-T-T-B, so what does that mean? Look, I'm always good with the quick comeback, was a defense mechanism growing up. I've got a fairly quick rhetoric I would say and so there are times something will happen in a meeting and boy, the filter in my brain doesn't quite work, and I say something, but it might just be for funny, just happen because it's an amusing anecdote, but I gotta be careful about indulging myself, that's the third one. The fourth one is thoughts become things, so for me, TBT is you go into the day thinking it's going to be a bad day, it's probably going to be a bad day. You go into that classic you know, just visualize the outcome, which I have not mastered in golf, by the way, but I've gotten better at it, and the last one is confidence, and the funny thing on that one is, it isn't so much you know, I've told people that and there's a lot of, "Well you seem like you're a pretty confident guy," and I would say, I am, I think I'm pretty confident. For me, confidence means the confidence to say I don't know the answer to something. I always feel like I'm kind of walking on that precipice of someone uncovering that I'm not particularly smart and I don't deserve the job I have, so therefore, you know, I need to be confident enough to show that I'm human, say I don't know, and know that I'm not going to end up living on a street you know, without any home or food or blankets or anything. So, for me that's what confidence is. Those are my five, and that's what--

I love it, and you know, the old imposter syndrome gets many of us here, as we think about growing up and becoming leaders. I'd love to unpack the five, I mean these are incredibly interesting mantras, but before we talk about the individual mantras more, how'd you come about, I mean what was the process where you decided that you needed mantras? When did you first put one together here and you know, how do you actually sort of think about them every day?

Well, you know, it's funny Brett. One of the things that isn't on you know, I don't really talk a lot about, but after I left Upromise I was like, well look, I gotta re-attach to the family and kind of recommit to making sure I have balance in my life, and I've got my priorities lined back up. Upromise start up, it was the 80 hour work week, you know, dollar and a dream, that kind of thing. And part of what I did, was I took on a job to turn around a foundation, which was in the field of addiction research, and that's not really something I talk a lot about, I'm happy to, but it doesn't you know, kind of line right up. But as a part of that, I also became an addiction family counselor for about a year and a half, and so why am I sharing all this, why is that relevant, back to what the moment was, and when I started thinking about this? Well I worked so much with people that were incredibly successful professionals, founded companies, billionaires, couple of them, right? 'Cause this was a very high end place, and celebrities, and they all had these significant flaws like we all do, and the goal of this work was to try to not, you know, diminish the flaw necessarily, but acknowledge what the flaw was, make it discussable, and then do something about it. And so, that pattern over a year and a half of working with maybe 150 different people, that had all been you know, in the startup world, the business world, the you know, sort of celebrity spotlight, really had me do a ton of reflection on well look, I mean I've gotta eat my own dog food, what are the things that I should really be honest about myself and the way I operate, and then how can I start to do something about it? So I know it's maybe orthoganal to what you were looking for, but that was sort of the seminal moment for me, to say, this is the best work these people are ever going to do, and they're wildly successful, but they sabotaged themselves. I don't want that to happen to me. How do I dig in?

Very interesting. Well I think that at some level, we all suffer from one form of addiction or another here, and in many ways we all are self-sabotaging our success. Better said, we all succeed in spite of ourselves here.

Absolutely.

When you think about sort of the approaches that you use there, here, are there approaches that you use beyond just the mantras that you bring into your leadership as well?

Yeah, I think, well, look, I think you know, there's a certain, there's a certain level of, I mean you could, we've known each other for a while, I definitely have a strong sense of play and amusement, so I mean you know, there's simple little moments to bond that you look for. You know, in my staff meetings, I've taken to having someone choose the opening song to which the agenda is then read, so-- If you think about it, we've had Metallica, we've had Prince, we've had you know, I think we've had a whole slew, but then you have to announce it, so I think beyond it, it's find a common sense of joy and understanding that gives you your own unique traditions as a team, and have fun with those, so I think that's part of it, 'cause we spend a lot of time at work, you might as well mix things up. I often wonder, would this be good on an Office episode? You know, that kind of a thing, so. I think we got inappropriate, by the way, and then this would be kind of a funny scene, so let's just do it, right?

Awesome.

It's a little bit of that.

Well playfulness certainly is an important part of leadership. So often we get stuck in the seriousness of our work, that we don't have fun, and yet we're spending at least a third of our lives doing what we're doing here. We've got to have some fun doing it.

That's right, exactly.

So let's go back--

And there's lots of ways.

Yeah, let's go back to these mantras here. So the first one was all about remember, and we talked a little bit about what that meant. The second mantra you brought up was?

Choose to be great.

So, when you think about that choice to be great here, and having that visual picture of what you want to become, for you, is that more a set of accomplishments, or is it more a set of actions, or what are you visualizing when you think choose to be great?

For me, it's actions. For me, it's demonstrable actions. It really, it comes down to you know, not to just you know, demystify this, but for me it comes down to, you know, if I were being watched by people I cared about, how would they describe my behavior? And would it be done in a way that I could hold my head up and have a straight conversation and say, I might not have been perfect, I might have screwed that up, but I did it the best I possibly could and I didn't let the snipes, jabs, or my perceptions of impressions that others have get in the way. I did it in a way that I could feel good about it, and really that's what it is that, the work itself, Brett, there's so many things that you or I or people work on, on a daily basis. To me, you know, those are so varied it's impossible to do all scenario planning, but there's a certain attitude and style around choose to be great that you know, you can take to anything we do. And that's how I think about that.

I think this is brilliant. This is such a great concept. How do you juxtapose that choose to be great with your recognition that sometimes people around you or even yourself don't live up to that standard? There's a sense of choose to be great, which all serve a tribute to excellence, be your best self, but oftentimes we fall short. How do you, in an accountability environment, help somebody maybe up their game when they're clearly not performing at their capabilities?

Well I think you know, I think you get into a well first, you know, I will share my mantras with people, right, so they're not hidden, so you know, I will sit down with folks and have a version of the conversation we've had, and say it, again, within the bounds of being professional and letting people have their privacy, there's a little bit of you know, hey Brett, go home and think about like, what are the things that you really feel like you're either afraid of, or what you're you know, excited about, or what you think you could be better at, but don't tell me what they are. Don't tell me what they are, happy to talk about 'em, but you don't have to tell me. And what would it take to flip those on their head, just to do them better? So why don't you think about it, and at some point if you want to get together, let's have a conversation about those mantras, and let's see what you think they are. I'd love to do that with you. I had all of my team work on two or three mantras and many of them haven't shared them with me, I haven't asked, but I know they have. So I think that that to me is a good first step, and really it comes back to that core of leading with vulnerability. Saying I'm not perfect, I have all these issues, look at all the baggage I'm carrying around.

Yeah, yeah. Well, there's this fine line in it there, in the world of a leader becoming a therapist.

That's right!

Especially if you have some experience, as you have, in providing recovery therapy to people who need help, so not crossing that line and getting into their personal business but still helping people figure out what it is that's causing them to maybe perform sub-optimally.

Well you're right and the other line I use is, you can't fix their childhood, like, I'll draw the line there, right?

Indeed, indeed. All right, let's go on to your third mantra.

Yeah, the third one is don't take the bait, and that's more of a you know, and so that's the third mantra. I don't know if you want me to talk about it.

Yeah I do, yeah, sort of like, I think you'd mentioned that was the one that was sort of hard for you. That that's sort of an easy sort of place to get sucked into.

Yup. So for me, again, most of the time I come from a place where a lot of those behaviors or the fears or the anxieties that anybody has, is tied to their experience when they're young, whether or not they're aware of it or not. You know, for me, you know, I was able to use humor and my ability to you know, quick retorts and quips as a defense mechanism. It also gave me I think a pretty cynical lens on the world and one that at times could be more sarcastic and caustic than it need to be, and so, it's just a deep-seated groove of behavior that became a crutch for me, to be able to either deflect the feeling of embarrassment or fear in a way that people found either lighthearted or funny or just made me feel better about myself for putting someone in their place, and I've never been a harsh person, but that was underneath what was going on, even if it was done with a veiled you know, sense of humor. And so, that one runs deep because it's how I learned to survive, growing up, at least as a kid, as I wrapped my head around it, and it's a very strong pull for me to still want to be funny or seen as the quick-witted guy and also put people on notice at times, to say, oh jeez, I don't want to get into it with Ford, because you know, he's gonna run circles around me with the comebacks, and so forget it, and so I have to be careful because it will shut down discussion, and it just is, it's just easy, it's just an indulgent thing.

Do you think that sarcasm has a place at work, I mean, 'cause that, sarcasm's often very tricky here, I mean obviously a quick wit can be fun, but what's your sense here, is it always trouble for you, or can you be a little sarcastic and have it be playful and not get you into trouble?

Yeah, fortunately, I'm more of an improv rather than a sort of one-trick sarcasm guy. I don't think, I don't like sarcasm. I think it's, it veils a lot of, it's sort of the many a truth is said in jest, you know, strategy is to be sarcastic. I think if you're sitting around and you're doing sarcasm as funny because it's sarcasm, maybe there's a moment there but to use it as a technique, that and passive aggressive comments are just ultimately destructive, they really are, they're a weakness. It's a lack of courage, I think, when those things are used. I don't think I'm, I don't think there's much of a place for that, no.

Perfect, perfect. All right, let's go on to number four.

So the fourth one is, it's just your classic thoughts become things, I mean, that's just you know, I do believe that whatever attitude or situation you're in, a lot of times it's very easy, I know for me, I'll talk about myself, but I think human beings, to fall back into the perspective that this is being done to me, or I'm in a situation that is happening to me, without recognizing that somehow, I've made choices to put myself in this situation, but as an adult, I have the ability to get up and leave the situation if I want, or change the situation. That doesn't mean bad things don't happen, but no one's trapped, very few people, I'm sorry, very few people are trapped or really stuck. And so, for me, if you get to choose something, why not choose to have the outlook that says, things will work out. I can do this, I'm going to have a good day, I'm going to find you know, two or three new things to learn today. I know it sounds very Pollyanna, but it is really simple. The alternative is, you know, I've gotten up and said "This is going to be a miserable day," and guess what? It's usually a miserable day! So, it's just a reminder that I have control over what I select and how I think, even in the midst of days that maybe aren't going as well as I would want.

You know, there's a lot of research done by some folks that suggests that there's something even below thoughts, they call the mindsets, they're core beliefs, or premises upon which we build our thoughts. It's the way in which we evaluate what happens to us. Carol Dweck wrote the book Mindsets and talks a lot about children and how children develop these mindsets that like, "I'll never be good enough," or that life is a zero sum game. I only get ahead if somebody else loses, and those sorts of things here. When you think about kind of the underlying mindset below this thought that you have, thoughts become actions here, clearly there's this notion of abundance that flows from you, this sense of I can create the future that I envision, that I want to create, and I have the power as I surround myself with good people to do that. Is that something you've always had, or is that something you think that's developed over time?

Oh it's developed over time. Again, I grew up in the Irish Catholic sort of you know, very heavy you know, lots of easy to point out flaws, and fall into that mindset. I think that look, I mean I've read a bunch of books, and feel like, I do think that the pie's getting bigger, it's not a finite size, that you know, I'm a big believer in karma, and I've really tried to expand out even from that example I gave that the person I played hockey with, you know, doing the things that ultimately maybe not on your time, but will come back to you, and so no, I really have gotten I think, really evolved as I've gotten older and maybe been more reflective you know, looking back and saying, double down on that idea.

Fantastic. All right, let's go on to number five.

Number five is just confidence, and that's your imposter syndrome. No matter I think where anyone is, if the light goes out and they're in the dark, and they're thinking about themselves, or their abilities, if they've done any sort of personal work or exploration, there's something pinging them in the back of their head and it shakes their ability to feel like they really have it all together, right? It's a fair statement. And so, if that's true, it's just, I have to be confident that if I own something, I make a mistake, I don't know the answer, that the world doesn't come tumbling down, and obviously it doesn't. I've done that a lot, and I'm still here, and so it's an irrational thought, but it is one that comes from I think you know, a place where you know, you're expected to have the answers as a leader, you're looked to to have the answers, so it's almost like, the difference between a real leader, a human leader, and a leader you saw on television. The real leader needs that pump every once in a while to say no, you can do this and then yeah, it's okay to not have the answer and the television person always has the perfect script and perfect dialogue.

Well it's the confidence to be humble, it's the confidence to be vulnerable, it's not the confidence to be full of hubris or ego, but to sort of be that human, that real person that people can look to and respect and appreciate, because of your humanity. Love these mantras, they're powerful. We'll make sure they're in the show notes for everybody here. I think they're good advice for me and for all of us here as we listen to this conversation here. Let's now take these mantras and turn them into some challenges. Obviously, as a leader, not everything is roses, we have challenges. I'm wondering if you can share maybe a challenge from your past as a leader here, where you'd go like, man, it didn't go real well, and I learned from it, and I've changed as a result of that, but share with us maybe a challenge from your past that allowed you to evolve as a leader.

Yeah, I think you know, one of them for me was I did a small start up. It didn't amount to anything 'cause it ended up blowing up and it was one that on the backs of largely friends and family, my reputation as well as the reputation of an individual, a sort of pioneer in this particular field, we raised a couple million dollars. After about three weeks, we closed the books, found that this individual had been misappropriating funds from the money we had raised to pay off some personal debts, and I had to you know, get the board and this is my first gig really kind of running the whole show, knowing that if I called out this individual, this would be the end of the business, because he had the IP for this particular idea, and he was known, et cetera et cetera, it would get very ugly. And I decided, ultimately my reputation at this point was worth far more than trying to stick it out. It wasn't a significant amount of money, but that wasn't really the point. So, I blew it up, and out of two million, re-issued about 1.9 million back to the investors, and did this big mea culpa, and you know, I think it was the right decision but for me, what I learned was there's absolutely no situation where it is worth compromising your reputation as a leader, or as a person. It may not be the outcome you want to have happen at the time, it certainly wasn't what I wanted, but I would tell you that what I've gained from that in terms of connecting still with the people who were involved and knowing that again, they'd be treated honestly and directly, has been well worth it, but it was pretty scary, with no job to fall back on at the time.

Can imagine. When you did that, I'm sure there were moments where you were maybe second-guessing yourself, and wondering, is this really the right thing to do, am I handling it correctly? Did you have a support network, or people that you turn to for courage or for advice, or how did you surround yourself so that you're not isolated? Sometimes as leaders we feel very isolated. We're surrounded by people, yet feel very alone. Anything you did there during that time to kind of bring some support into your decision making process?

Well, the head of finance that we brought in was a really really solid guy and he was a great source of support on an ongoing basis. He agreed with the decision and that helped. My wife obviously, was a big supporter. Once she knew that I was going to have find something else, and she was way more confident than I was that I would. That was helpful, and then I think one of the investors was a friend, and I told him and his comment was, "Look man, just get out, get out, do what you need to do, "I invested because of you. "If you think this isn't right, "give me back 90% or whatever, "and it's a lesson well learned." So just again, being honest with the people that at least understood the situation, with the people who matter most to you, your family, you know, that was a deep source of strength for me.

That's fantastic. And the sense that you chose to share, I mean that you were vulnerable enough to say, hey, man, this is happening, this concept of secrets and how secrets are nothing but burn a hole in our head if we're not careful.

Right, 100%.

So let's talk about a success. What are you most proud of as a leader? What's happened recently or in the not too distant past, you go wow, I'm really grateful and appreciative for what happened here.

Yup. I think you know, for me, well I could talk about LogMeIn, so you know joining LogMeIn a little over 200 million in revenue, you know, we're over 1.1 billion, you know, projected for this year in revenue.

Congratulations.

Thank you you know, and by the way, again it comes down to what I feel good about, which is really sort of trying to find that balance of all the things that we talked about earlier, that I think are strengths, that at least I've been told are strengths, with the ability to scale an organization up, you know a few hundred people and have it be a global, a global team, is one of the things that I feel incredibly proud of. The caliber of the people that I've been able to bring in and hire into the company, and the successes that they've had as part of their careers, and their growth, I would point to that as a fairly big one for me, and so that's probably, that's a fairly significant one, I'd say.

So when you think about kind of the mentoring and the growth and seeing other people be successful in this regard here, what kind of advice do you give to people at LogMeIn or at other organizations you've worked with for how they can help themselves? Obviously it's a two way street, you need to help them as leader, they need to help themselves. What suggestions or encouragement would you give to aspiring leaders?

Well I would give this to aspiring leaders. I'd also give it to you know, my former self, right? I think it's you have to be in charge of your own career. There's no one ultimately that is going to take care of you in your career. There's you know, angels in your life that may come along and give you a piece of advice or help you at key moments and that's great, but if you think that you're not getting an opportunity, then maybe you need to advocate for that opportunity. If you feel like you're stuck, or not getting trained in something, there's a little bit of go take control of it and do it. It's very easy to order off the menu at companies that say they have a training program and here's how you connect the dots, and that's super helpful, like that's not belittling that, it's a great structure. It isn't sufficient though. It isn't often, I doesn't often work on your timetable, and so I think there's a real sort of step up and own your experience and don't assume you can't own it. A lot of assumption, there's a lot of reasons people will come up with to say why they're terminally unique, or why the situation doesn't apply to them, and it's oftentimes a defense mechanism for taking those risks and stepping out there. It's no the right time, it's not the right environment, it's not the right place, and I think that really being able to just throw that off to the side and just say, I'm in charge of making my decisions. I'm going to be honest about it and I'm going to speak up. That's really the best advice that I could give to anybody, whether it's a big company, a small company, or whether it's somebody just starting out in their career.

I love that. I think that's such, it's such good advice here. Obviously beyond the kind of having the right mindset, you know, believing you can do it, taking control of your actions here, what are the skills of leadership that you feel are most missing in up and coming leaders? Things that you wish that people had that they don't have, that they need to develop, I mean, maybe it's communication skills, or maybe it's decision making skills, or you know, what are the practical skills that you see missing in people that prevent them from leading as effectively as they could?

Boy that's a good one. I think it's really hard to generalize, 'cause everybody's so different and everybody has their own unique footprint. I do think you know, one thing is an openness to being wrong, so especially, and I know, I don't know if it was like this when you started out, Brett, or when we were at Monitor, but there's definitely a you know, a fear of having the wrong answer or getting the wrong answer and admitting that, and we've talked about this a fair bit today, but I do think that there is a belief that somehow, always being right is a sure fire rocket ship to the top, and that is something that I still think happens, people put their armor on, and they aren't you know, as relatable as they should be, because sometimes the environment demands it. And again, you know again it varies. I do think that there's, you know, from my perspective, I think people need to really appreciate not wallowing in the trenches and the hard work, but I think it's appreciate the benefit of digging in and working hard at something for an extended period of time, rather than, you know we've trained and I know with my kids, it's just this, the instant gratification that can come from always having the answer, so sometimes there's a degree of frustration that can come very quickly when something requires a little bit more work, again this is a generalization, not a you know, not true for everyone, But I do think there is that appreciation for the struggle you know, appreciation for the journey as the reward and I think, again, I feel lik I sound like someone who said I wrote uphill both ways to school, but I do remember digging through the insurance library in Massachusetts when I was at Monitor and there was no more of a bleak place than that, I will tell you, and so there is some of those things that I think still do apply, that when people try to be successful and maybe's missing a little bit more than it used to be.

Yeah. Takes a while to become a good leader, and you need to sort of pay your dues here. At the same time, there are great opportunities for young people to do remarkable things. I think the internet, the environment we live in gives the ability for somebody straight out of college or even before college to do some pretty remarkable things and so often, we see just tremendous activities coming. I've got close friends and family members that are doing tremendous things at a very young age.

Yup.

It's great, but, I think the challenge there is that, at some level, they're fully formed in so many aspects of their leadership, they're naturally talented, and yet there's a blind spot, and it's the thing they don't know they don't know that really sort of becomes that Achilles' heel. If I broaden the question I asked earlier here, to more generally, what advice would you give to people here about getting the truth about yourself and trying to remove those blind spots? What are advice or ideas or suggestions you have for somebody who wants to become more whole or complete as a leader, and wants to do the work that you've talked a lot about, good resources for them?

Yeah well, I would tell you, you're never, oftentimes, gonna get more honest answers than starting with the family. So I will tell you that you know, there's a great question parents can ask and I've used this at work with different language, but you know, what's the hardest part about living with Dad? Or, what's the hardest part about working with me? And you start again, in a safe environment, could be your team, right, but there's a little bit of prompting for, with the notion that there's something that needs to be better, rather than saying, do you have any feedback? Because that goes directly to the, oh you were really inspirational and oh, it was such a good meeting, no no no no, so you sort of take that off the table, and say, what's the hardest part? I need to know. That's one. I think that you know, I found that that's incredibly helpful, and I think that there's also a little bit of if there isn't a response, say well here's a couple of the things that I would throw out there, that would be hard if I was working with myself, and you sort of throw those in, and you essentially become a thought starter for criticism, hopefully productive for yourself. Again, there's no, it's being willing to be human and have flaws, and acknowledge them and do something. And again, that's just, that is it.

That's brilliant, that's brilliant. Well Sean, let's go ahead and wrap it up here with a series of just quick sort of one versus another question here, describe yourself as a leader with these questions here. Would you say you lead more from the front or from the back?

From the back.

And why is that?

Well, I think that, when I've got you know, people in place that I've you know, spent a lot of time with and developed, I think one of the greatest joys is to see them succeed?

Awesome, awesome. So are you more of a big picture person, or more detail-oriented?

Oh Brett. These are so easy, it always depends. I'm just going to say this once, you realize this depends.

Of course!

I think I'm both.

Where are you more comfortable? What's your default position?

Here's what I would say. If I've gotten to a point where the work I believe is at the right level of you know, quality and detail, then I'm absolutely more comfortable with the big. I'd rather think about what's the next big thing that we want to do, how should we break out of the you know, sort of our standard operating cadence and really change things up, so I like that. I don't like that if I'm not confident of the details though, so...

Got it, I got you. Risk averse or risk loving?

I would say I'm healthy risk loving, how's that? So again, within bounds, I love it if people take a chance, I love it if they try something new and again, healthy risks, meaning that it's not, you know, this, so crazy it just might work, if I hear that, that makes me nervous, but risk-- Then I know we're in big trouble! But that's it.

That's great, that's great to hear. Would you say that you're more internally or externally motivated?

I would say internally, absolutely internally.

That's come out loud and clear in our discussion so far today, I mean--

Easy, go overweight on that one.

You got a strong inner compass that guides a lot of what you've done here, and that's a very compelling part of your approach to leadership, and it's great to see that. One last question for you here on the one versus another here.

Yup.

We talked a lot about candid communication. Hard-hitting direct versus diplomatic versus indirect? Where do you tend to fall on that spectrum?

I overweighed on direct. I would say the thing, the hard-hitting part, I think one of the key things for me as a leader is to know that the goal isn't to impose my messaging style onto someone, but it's to know that the job is to be heard, I just wanna be heard, I don't have to be right, and so if that's the goal, there has to be sort of a nuanced way that that directness is applied, because you might hear something differently than someone else might hear it, and so my job, and really the Rubik's cube of this one, is to figure out what's the right delivery mechanism whilst still being direct.

Oh that's fantastic. Well, Sean, thank you so much for your time today. I think we've just been overwhelmed with good advice and insights into your leadership style. What's the best way for people to follow you online or through social media?

Yeah so, I'm @wsford on Twitter. Obviously, I'm on LinkedIn and I'm not, I would say not a huge social media person, but those are the two best ways.

Fantastic. Well Sean, thank you so much for your time today. Make it a great day, and thanks for sharing your leadership style with us.

Thanks Brett.

Leader InterviewsBrett Pinegar