An interview with an NHL player turned CEO
From a Princeton pizza shop to the NHL, from Goldman Sachs to software solutions, Mike McKee, CEO and Director of ObserveIT, has worked on and led teams of every flavor. But whether it’s delivering pizzas or developing security software, it always comes down to people.
The Predictive Index Senior Director of Marketing, Thad Peterson, sat down with Mike to talk about what lessons he’s learned on his fascinating career journey.
Interviewer: So, Mike, first of all, thanks for taking time to chat with us.
Mike: No problem. Happy to be here, Thad. Huge fan of PI, happy to talk about it.
Interviewer: Awesome. Well, let’s talk about you. We’ll talk about you.
Mike: Sure. All right. I mean, it’s useful. My PI rating or what?
Interviewer: No, no no, let’s talk about your background. So first of all, you’re Canadian?
Interviewer: Where are you from in Canada?
Mike: From Toronto.
Interviewer: From Toronto, okay.
Mike: The accent gets a little stronger when I’m back in the homeland. I’m sure you’ll hear it this afternoon.
Interviewer: Yeah, it comes out a tiny bit.
Mike: Probably a little bit, the outs and abouts.
Interviewer: And like all good Canadians, you played hockey growing up.
Mike: I did, yeah. I did. I started at the age of eight which is actually late for Canadians, played a bunch, was kind of a late bloomer, almost gave it up when I was about 14, 15, but then went through a huge growth spurt and went onto college hockey and ended up playing for a few years after that.
Interviewer: Yeah. Let’s talk about that. On paper, you’ve got kind of a fairytale life. You went to Princeton.
Mike: Yes, I did. Which is, basketball is much bigger at Princeton than hockey. I found out when I got there. And I went to Princeton because I didn’t really expect to be able to do much with hockey, and I figured if I wasn’t going to go to Canadian school, I might as well go to one with a very good education. So I was education first, hockey second.
“I was education first, hockey second.”
Interviewer: Oh, that’s interesting. Okay. But as it turned out, hockey worked out okay because you went on to play in the NHL, no?
Mike: I did, yeah. I got drafted after my sophomore year and we had a couple good seasons at Princeton. And then when I graduated my senior year, I got a contract offer to go up to the Quebec Nordiques, and went to training camp, got knocked out my first day at training camp.
Interviewer: Literally knocked out?
Mike: Literally knocked out. I kind of crawled across the ice. By the time I got off the ice, I was sent down to the minors where I spent the first season in Halifax and down in Greensboro, North Carolina for the old enough people that know slapshot, they did slapshot down there. I lived that life for a little while. And then my second year, I had a really good training camp, got called up early in the season and stuck for most of the year. And then unfortunately, my third season was the lockout, and I got my last concussion. So I retired at the ripe old age of 26.
Interviewer: And then, as I understand it, you finished up with hockey, went and got your MBA at Harvard?
Mike: Between hockey and my MBA, worked down to New York at Goldman Sachs for a couple years. I was actually in the Canada group within corporate finance at Goldman Sachs, had a great experience working there. I got to see a lot of different businesses over the couple years, but really one day wanted to ideally run a business. And as a result, decided to go back to business school to broaden my exposure to different areas of business.
Interviewer: Got it. And then consulting after …
Mike: Consulting for summer, yes. I was at McKinsey for a summer, which was good. The tricky part about being a summer consultant is, all of a sudden there’s these MBA students showing up, and there isn’t a surge of projects in the summer, so they kind of have to give you what they have. And actually, I was sent back to Canada again, must be the accent. I was doing a post merger plan between two big Canadian banks, and no one thought the merger was gonna go through, and it didn’t go through, and no one on the banks really wanted to talk about it because it meant losing jobs. So it wasn’t the best study. I mean, great firm and stuff like that, but much like banking and consulting, when I was there, I always wanted to be on the other side of the table, wanting to know what the client did with the money and with the advice as opposed to just giving money, giving advice.
“[At McKinsey] I always wanted to be on the other side of the table, wanting to know what the client did with the money and with the advice as opposed to just giving money, giving advice.”
Interviewer: And then, as I understand it, you got into sales.
Mike: A couple of steps along the path. I went to a dot com startup where we raised 40 million dollars and spent 42, so I missed some class in business school. But I was doing business development there, and then I was temporarily the CFO for a little bit. I was the last employee signing off the assets when it was all said and done, and then I went to a bigger technology company, PTC, where I went in in finance and then shortly after being there, I went into sales for 15 quarters. When you’re at PTC in sales, you remember every one. I had a great experience there, and then went into the services organization, was overseas for a few years and then came back.
Interviewer: Okay. And I wanna jump back for a second, back to your Princeton days. You also had an experience, as I understand it, running a pizza shop?
Mike: Yeah, great experience. I was on financial aid and my first couple of years, that meant showing films for like seven bucks an hour. And I’m thinking to myself, “There’s gotta be a better way.” And at Princeton, there’s a bunch of student agencies, one of which was the Student Pizza Agency. And my roommate and I submitted an application to take it over. It’s all student run, sold to students. And we turned a business that would sell a hundred pizzas a week into a hundred pizzas a night. It was actually 25 thousand dollars in revenue, when I took it over it was 150. By the time we ended, when we started there were 10 student employees, when we finished there were 50. So it was actually the first time outside of sports that I had gotten that adrenaline rush, and it was actually that experience that led me to one day want to help run a company. It was a great experience. It was really exciting.
“We turned a business that would sell a hundred pizzas a week into a hundred pizzas a night.”
Interviewer: Really cool stuff. So, again, on paper, bit of a fairytale story or at least it feels that way, but every fairytale-
Mike: The dark spots aren’t up there.
Interviewer: What’s that?
Mike: I’m just kidding. Some of the downs aren’t on there, but I’ve been lucky.
Interviewer: Well that’s exactly what I was gonna ask about. You don’t see the trials and tribulations and the struggles on the resume, necessarily. So, as you think about, you’ve got this very interesting career arc, what are sort of some epiphanies you had along the way? Be it running the pizza shop, playing in the NHL, now you’re CEO of a company called ObserveIT. Talk about that a little bit.
Mike: Yeah. I remember actually, my college roommate who also did play in the NHL with me, also played in high school with me, had this sign on the wall saying, “Don’t get too high in the highs, don’t get too low in the lows.” And it was from Mario Lemieux, great hockey player. And I would say that’s really, really important in life and in business, in that there’s always gonna be highs and there’s always gonna be lows.
“That’s really, really important in life and in business, in that there’s always gonna be highs and there’s always gonna be lows.”
Mike: And I can remember when I got sent down from the minors to the sub minors my first year playing professional hockey, and it’s a long story but I showed up, first of all, the owner greets me at the airport and says, “Hey Mark, how are you doing?” And I’m like, “Actually, it’s Mike.”
Mike: He then takes me back to the hotel, there’s no rooms for me, so I get doubled up with the team goon who’s on steroids, he’s all tatted out and stuff like that. And I decide not to have a pregame nap with him in the bed beside him. And I’m walking along the side of the highway and I go to Mr Omelet’s, have my pregame meal. So I have my pregame meal at Mr Omelet, didn’t go to the rink. Another guy who got sent down greets me by saying, “Welcome to Hell.”
Mike: And there’s points like that, you know? I’ve had points like that in business where you have those dark moments, but you can’t get too low. And in the high points, you can’t get too high. You gotta just keep persevering, keep working hard, and hopefully things will work out.
Interviewer: What about, let’s talk a little bit about the people management side of things. Because I know, from what I understand, when I talk to people who work here, they say about you that for you, it’s all about people, it’s all about culture. Those are the things that you hammer on. Talk about that a little bit.
Mike: So my first work experience, as I mentioned, was at Goldman Sachs in New York. And there was a really strong culture there. And I can still remember the 10 principles of the firm back then, before iPhones, it was a little paper book that you’d write down your calendar, your scheduling book, stuff like that. So I often say that I learned as much about culture at Goldman Sachs as I did finance, in that it was something that was in the hiring process, it was in the review process, it was in the way that people acted. And it permeates the whole organization. So that was very, very—it left a large impression in my mind. And then before coming to Observe IT, I was at Rapid7, which was huge on culture. And that’s where I got introduced to PI.
Mike: And at the end of the day, it is all about people, in that, you know, especially in today’s day and age, especially in security, especially in cybersecurity, there’s probably 40 cybersecurity companies people can go work for. And if the majority of employees can’t go make more money somewhere else, then you don’t have good enough employees. And what’s gonna keep people, and what’s gonna keep people excited, is a good culture. And I remember at that dot com startup I was at, one of the managers, Tim Bernstein, said that, “If you can find yourself in a situation where you’re learning, contributing and having fun, you’re doing pretty well.”
“What’s gonna keep people, and what’s gonna keep people excited, is a good culture.”
Mike: And we have a grow, perform, succeed performance management plan here, but it’s very much along those lines of creating an environment where people feel like they’re contributing, they feel like they’re learning something, and they’re having fun. And that’s a good environment to be part of. So it’s, I say to people, I said it this week, every day it either gets better or worse. If it’s not getting better, then it’s getting worse. So it’s something you gotta keep working at day in and day out, but it makes you excited to come to work every day. And I think if you’re excited to come to work every day, then you’re gonna contribute more and the company’s gonna do better.
Interviewer: That whole philosophy of continuous improvement at both the organizational and the individual level is the common thread of great companies.
Mike: It is, and all of these things can be words or they can be real. And I remember from the CEO of Rapid7, Corey Thomas, he was a phenomenal leader, I’ve never seen someone so committed to self improvement. He’s a phenomenally capable person. I remember in the interview process, he said that he fires himself every six months and he goes over all the things he did badly over the last six months. And I would absolutely say since joining ObserveIT, the thing that I’ve learned the most is how much I have to learn. And I feel like the more I learn, the more I realize how much I have to learn. And I’m part of a CEO forum with Katelyn, which is amazing. And once again, it’s just incredibly humbling because you realize what you don’t know. But I think that if that’s generally accepted and generally believed by a lot of people, one of our five corporate values is always improving because everybody can improve.
Mike: And by the way, it feels good to get better at something and it feels good to learn new things. So it’s something that I know I need, a lot of things I need to work on, and I think people realize the same for themselves.
Interviewer: You said when you were at Rapid7, that’s when you got introduced to PI.
Interviewer: Tell me a little bit about your experience.
Mike: Yes I must’ve done the PI, actually I did do it, so I remember doing the PI because I remember trying to figure out the difference between question one and question two, which means I didn’t read the instructions well enough, which means I’m low C and wanna get things done quickly, and afterwards being like, “Gosh, I hope I did that right.” But like a lot of people, and literally this happened yesterday with a candidate here, you read the report, the three page report, after taking less than five minutes to fill out two questions, and you can’t believe it.
Mike: And you know, I heard the genesis of us using it at Rapid7 was from Aron Ain, the CEO of Kronos, who took a look at everybody who made Presidents Club over the years and had one of two profiles. And actually, the head of recruiting at Rapid7, Ed Nathanson, was huge on Predictive Index. And he sort of taught me all about it. And I remember I would sit down with him, at least on a monthly basis, and just learn little nuggets. Because he knew everything. Because the thing about, that’s the fact about PI, is the report’s actually quite complimentary. You have to know the second level of where the gotchas are in the personalities, and it is just phenomenally accurate. So the deeper I got into it at Rapid 7, ’cause actually, my first month at Rapid7, we had a management team offsite, and we all exchanged each other’s PIs.
Mike: So I started to get more deeply into it with Ed to understand all the members of the management team, and I would tell Ed’s stories, and he would know how people reacted in different situations ’cause of their PIs. So I just became entranced by the power of it, and then started using it on applicants coming in. And once again, it had the same basically 100 percent predictive accuracy around what that person was gonna be like in a different role.
“[PI] had the same basically 100 percent predictive accuracy around what that person was gonna be like in a different role.”
Interviewer: Yeah. It is pretty amazing that, especially like you said, when you consider that it only takes six minutes or so to take. And so now, fast forward to ObserveIT, talk a little bit about during the hiring process, how you use it. And by the way, one of your employees planted this question with me. She said I should ask you if it ever slows you down when you’re hiring people.”
Mike: Sure, yeah, for sure.
Interviewer: So talk about that.
Mike: Well I’ll go one step back. So when I got to ObserveIT, we have a hundred employees, and walking in and not knowing everyone’s PI, I just felt naked. Literally, I didn’t know how to deal with people because I didn’t know what their PI was and therefore I didn’t know how driven they were, how impatient they were, how process oriented they were, how collaborative they were. And as a result, it was certainly within the first month, it might’ve been the first two weeks, I asked everybody in the whole company to do the PI. And I said, “Hey, listen, here’s my PI.”
“When I got to ObserveIT … walking in and not knowing everyone’s PI, I just felt naked. Literally, I didn’t know how to deal with people because I didn’t know what their PI was.”
Mike: And I do the same thing with candidates. I’m like, “Listen, I’ll send you mine. I have no problem.” We actually use it internally to understand communication better and how to communicate with people. And, like you said before, everyone can improve, everyone’s got their weaknesses, and everyone’s wired a certain way. Just knowing how you’re wired, back to the low C, I have to be careful I don’t speak too quickly. I’m probably speaking too quickly now because I’m low C and I wanna get stuff done. But knowing that helps you sort of keep yourself in check as well as understand how to keep other people in check.
Mike: So started using it initially just to get to know everybody. Then, people always think you’re a little freaky at first when you tell them how accurate it is, and they’re a little bit skeptical. But they were following along anyway, just because I was pretty adamant about it. But once they start seeing how accurate it is and what a good predictor of how people will react or perform in different roles, once they see the light, they’re like, “Oh my god, I can’t imagine living without this.”
Interviewer: It’s so funny, I was talking to somebody at PI recently and we were talking about the fact, when you’re hiring somebody, you really wanna hire a great person. It’s always really important. And when there’s a candidate you’re kind of excited about, and you get the email that they’ve taken the behavioral assessment, you wanna open that thing, right? You’re anxious to see it.
Mike: Oh yeah, right away, for sure. And to your point, that sort of jab, it sounds like it’s slowing the process down, yeah. I mean, I’m a huge believer—exactly, both directions—meaning, I’ve never put a blow up date on a offer that we’ve put out there, and similarly, we don’t rush the process. One of our board members Ben Nye has this line, “Don’t squint.” It’s easy to squint, it’s easy to get tired, be like, “Okay, hire that person.” But I find two way digging, ’cause, in the same way that I don’t wanna squint and hire someone, I don’t want someone coming in the organization that’s not totally excited to come in. So we’re big believers in no surprises. And that should be at the personality level, and that should be at the job level and the function level overall.
“I don’t want to squint and hire someone … we’re big believers in no surprises.”
Mike: So yeah, it might slow the process down, but if a candidate’s not willing to go through a slower process so that both sides can evaluate each other more, then they’re not the right candidate in my mind.
Interviewer: Yeah. And I’m not sure if you hinted at this, but do you also, to what extent do you use your knowledge about somebody’s behavioral drives in how you manage them?
Mike: A lot, a lot for sure. I mean, our head of sales here in North America’s a low B. He’s a high A and he’s low C. And that profile is, I’m gonna get what I’m gonna get. I don’t care if there’s bodies in the wake. I literally had this conversation this week, because he’s low B, you have to draw information out of him. Because he’s thinking about stuff in his head, but he feels no need to talk it through with other folks. I don’t wanna say, “Be collaborative,” but talk it through.
Mike: I, on the other hand, am a high B, I’ll sometimes talk for too long and go on and on. I know I have to sometimes be more decisive even though I wanna talk it through with everybody, get everybody on board, get everybody behind it. So I know myself. I have to fight that natural tendency. And I know other people, I’m trying to remember who it was, but had a very high D. I was like, “Fight the high D, fight the high D, you’ve gotta move.” You know what I mean?
Mike: So definitely in managing people, it’s something I think about a lot, and frankly, I wish I thought about more because it’s just such a useful way to just understand the way people are wired. It doesn’t mean you can’t change.
Mike: And the other huge epiphany I had is, and I had this conversation with a candidate last night, a low B person can be collaborative, but it takes energy. And that doesn’t mean they’re not gonna put out that energy and make that effort, but just know that it’s gonna take them energy, and therefore, make sure they’re up for it, and make sure that it’s not a bridge too far. Because, you want to be at a job that everything you’re doing is the way that you’re wired. ‘Cause that’s energizing as opposed to taking energy.
“You want to be at a job that everything you’re doing is the way that you’re wired. ‘Cause that’s energizing as opposed to taking energy.”
Interviewer: Yeah. You know, one of the things that we talk about at PI is, we have this term, “Working in preference.” So if you’re trying to work out of preference, if you’re trying to do a job that requires behavioral drives that you don’t have, it’s like trying to write with your left hand all day long when you’re a righty. Conversely, if you’re working in preference, and your behavioral drives line up with the job, it’s like writing with your right hand. It’s fine. It feels natural.
Mike: Yeah. I haven’t used that metaphor, but it’s good. It’s very good.
Interviewer: So let me, you’ve been gracious with your time and I appreciate it, I’m kind of curious because you know, it’s a long way coming from running a pizza …
Mike: I do have one more story too on the CEO group.
Interviewer: Oh, bring it.
Mike: So for the CEO group that I mentioned, you know, we meet once a quarter for two days, phenomenal group of people, they hear me raving about PI, and it probably took three or four meetings, ’cause I was like, “Hey guys,” I would send them the link, I probably shouldn’t tell you this, but they used the ObserveIT account to get their PI profile. So I sent it to them, and they wouldn’t do it. And finally on the third or fourth meeting, a couple people did it. And I sent them the report. And I can still remember capital letters, “OH MY GOD.” And they get the report and they just cannot believe the accuracy of it. And it’s still surprising me to date.
Mike: I mean, I think sales is an example. I would never hire a sales person without doing it. Never. And sometimes, these people still hire sales people without doing it. I mean, it’s just, if you have the answer book to the exam, why not take a look at the answers? And it’s not the be all and the end all. It’s one factor in the decision making process. But it’s a major factor. And you’re just nuts, in my view, for not incorporating it into your decision making process.
“I would never hire a sales person without doing [a PI Behavioral Assessment].”
Interviewer: That’s awesome. All right, I wanna ask you my last question. Long way from running that pizza store at Princeton to running, how big is ObserveIT now?
Mike: 150 people.
Interviewer: 150 people, high-tech, high-growth company. What are some of the things that are the same, whether you’re running a pizza shop versus a high-tech company, and what are some things that are drastically different?
Mike: Wow. I haven’t connected those two dots in a while. So in the same way we talk about it’s all about people, scaling an organization and growing is all about letting go and empowering people to run the business. So my first year running the pizza business was grueling, ’cause we went from 10 employees to 50 employees, selling a hundred pizzas a week to 700 pizzas a week. And basically, my roommate and I were always the buffer. We were the extra driver, we were the extra cook, we were the extra phone operator. We were trying to hire people every night. Then we got this really smart idea before our senior year, “Why don’t we have a head cook each night? And we’ll pay that head cook a whopping hundred dollar bonus at the end of the semester if they have the right number of people each night that they’re supposed to have.” You know, seven for Sundays, five for Thursdays, whatever. And it worked magically. And they got their hundred dollar bill in December, and they were ecstatic.
“Scaling an organization and growing is all about letting go and empowering people to run the business.”
Mike: So, it’s the same thing in a business. Meaning, getting the right head of marketing, getting the right head of people, getting the right head of sales, getting the right head of product, engineering, whatever it might be. That’s how you scale as an organization. And obviously, making sure they’re aligned and the incentives are good. And then they have to do the same thing. But there’s this whole process, I talk about it in management all the time, of, you gotta let go. And you know, you might not be happy with the drivers that the Sunday night cook gets, but you gotta let that go and let that person figure out how to get good drivers and phone operators and cooks and stuff like that in the same way they exist in marketing.
Mike: But, you know, making sure you’re bringing in good people and then giving them responsibility is the same in both situations. And then also, I was actually writing an email on this this morning. Momentum matters. And, if you have momentum and a good direction, it creates energy and, just this week, the concept of small winds, you know, you always have to be very balanced between areas that you’re working on and always improving and celebrating those small wins. It’s easy to get fixated with all the things that could be better, and lose sight of the progress that you’ve made. So making sure that, and I could do much better at this, making sure that your balanced between celebrating those small wins and always being fixated on what you can do better. So there’s tons of parallels.
Interviewer: Awesome. Hey, thank you for your time.
Mike: Listen, thank you for helping us out so much here and in past lives. So, cool.
Interviewer: Good job.
Mike: All right.