AMA (Ask Me Anything) with Adam Robinson: Sharing lessons in leadership, hiring, and stand-up comedy

This week on the podcast we opened up the floor to Hireology to ask me anything, check out the results below.

























Max: Okay, hello and welcome to The Best Team Wins podcast. My name is Max Lowenbaum, not Adam Robinson. I am the Vice President of Sales here at Hireology and I’m joined by Adam for a very special additional podcast. Today, we are doing Ask Me Anything with Adam Robinson. We have reached out to the 115 employees that we have here at Hireology and asked them for burning questions that they have for Adam, everything about his experience at the company to his philosophy on leadership, hiring and retaining the best people and some fun questions sprinkled in. Adam, are you ready?


Adam: I’m ready. Tables have been turned, so excited to see how this turns out. Hopefully, I’m a good guest on my own show here today.


Max: I think you’re going to do just fine. Okay, Adam. We’re going to start with a tough one. How many people have you hired in your lifetime?


Adam: On behalf of other companies, upwards of 3,000 at least. I would say for my own companies, somewhere between 500 and 600 people.


Max: Wow, and I’m sure you’ve learned a lot, which is where a lot of these other questions will go. If you could kind of define your philosophy for managing people, how do you define it?


Adam: When I think about the people side of any business, what I’ve developed as a philosophy is number one, that you have to hire great people. You have to hire the best person for the role and let the role go unfilled until you find that one best person and then when you do find that person, you need to let them do their job, and so I would describe that as hire great people and get the heck out of their way.


Max: Yeah, and there are a lot of questions here about what you’ve learned. I assume you learned that lesson the hard way.


Adam: Nobody wants to, few high performing individuals want to be hired into a role and then be told exactly what to do by prescription, and you run into this issue in so many founder-led organizations where they’re not relinquishing control over the important things that they used to need relinquish control over and that’s how businesses stall. I’ve paid close attention to make sure it didn’t happen. I’ve made that mistake in the past.


Max: It’s a great lesson. Here’s a really interesting question. How much of who you are is what you do at work?


Adam: So I’ll interpret that question to be what percentage of my own self reflection or self worth do I attribute to what I do professionally?


Max: Yup.


Adam: There’s this notion of work and life balance and work-life and just personal life and I don’t subscribe to that way of thinking. I think it’s just life and what I do during the hours I’m working, I’m the same person that I am outside the office. I mean I don’t put on a game face to come into the office. I’m pretty much who I am when I’m around this place. If the company exploded tomorrow and there was nothing left of it and I had to start over, I would be the exact same person I am now. There’s no difference. I don’t subscribe to worth equals how big the business is or if financial success of it or any of that. I mean it just happens to be what I’m doing today. That’s how I feel about it.


Max: Do you feel like you have to draw a line or do you bring things from home to work? How do you sort of separate the two?


Adam: Well, life, I just believe it’s integrated. In today’s workforce, you’ve got to have an understanding that lives are complicated and they move quick and especially if you’re like us, we’re raising a family, as an example. Today, I spent the better part of the morning sitting in a room full of 4 year olds at my son’s class doing a parent observation of the classroom, and then made it downtown Chicago to finish the day and I’ll do what I need to do today and tonight to make that happen, but I didn’t really think about work versus personal life. It was just the day I was going to have. I need to get some things done today. One of those things that I needed to do was spend time with our son Alex in his classroom, which he’s really excited about.


For me, it comes down to planning the day and what you want to get out of everyday and sometimes, personal things are the majority and sometimes, they’re not.


Max: Yeah, it’s interesting, I made the transition to come into Hireology. I think I noticed that right away that our culture is really intentional about not drawing a hard line between life and work and instead having our leadership team, many of which have families, take time and spend time at both work and life and be really intentional at how they spend their time but kind of go full force at both, and so I think that has a really nice trickle down effect on our culture.


Adam: Sure, and if we want that culture, the leadership team has to live that culture and I can’t say it’s okay to do it and then not do it and secretly feel, frown upon if I see other people taking 10 to 2 to go do something with their kids. We just don’t try to even think about it here.


Max: Okay, here’s a question I’m really looking forward to hearing the answer to. What is the most awkward interview you’ve ever conducted?


Adam: As we said before we started rolling, I had to think about that. I had an interview early in my career when I was in the IT staffing business where one of our candidates was interviewing with Director of IT at one of the large companies here in Chicago in the suburbs, suburban Chicago, and that company, they would encourage us to sit it on interviews if we could, like bring the candidate in and kind of babysit the interview, and we’re in the middle of this interview and I think at this point, I’m 23 years old. It’s my first job out of college and bring in a Cobalt DB2 programmer in for some Y2K project at some mega company, it’s ’98 or ’99 and I’m sitting in this room and the interview’s not going well. I mean the guy’s a little off and we get a knock on the door and a security guy comes in and he says, “Excuse me, are you so and so?”, and our candidate says yes. He said, “Do you have a dog tied to the bumper of your car in our parking lot?” The guy said, “Yeah, I do.” I immediately, like okay, not getting hired.


Max: Yeah, interview’s over.


Adam: Here goes the commission and he has to excuse himself to go untie his dog that apparently, I respect it. He didn’t want to keep the dog in the hot car and so he took the dog out of the car in the middle of a corporate parking lot and tied this dog to the bumper, which was trying to bite because he parked in the visitor’s space right up front, literally trying to kill everybody who walked past this dog, and you could hear the dog barking as we walked out to the lobby and it was just, you don’t see that often. I think it maybe speaks to judgment but that was weird.


Max: Oh man.


Adam: That was weird. You go back in after the candidate’s excused himself and you call your hiring manager and you say, “Well that was awkward. I’m taking this is a no, that I’m wrong with our guy.” It was bizarre.


Max: You didn’t spend that commission check.


Adam: Nope, that was weird.


Max: That’s great. Well, a lot of questions about your interview style. What’s your favorite interview question?


Adam: My favorite interview question is what is the biggest misperception that people have of you? I like that question because you can’t prepare for that and you can’t help but give an honest answer to that question and what it shows are a couple of things. Number one, I want to see self awareness and I want to see confidence. If you have the confidence to explain the thing that you know other people think of you that’s not true, there’s a thought process. You can’t wing that one. That’s going to be an authentic answer, and it’s also, it turns out that the thing that the candidate says is almost always the impression that I’ve got in the back of my mind that they’re going to verify or not, and what I found is if someone says, I’ll give a real life example and I have Erin’s permission to do this. Erin Borgerson, who’s been with us darn since the beginning, is one of our first 10 employees, so I asked her the question in the interview, what’s the biggest misperception people have of you and the answer she gave me was people think that as happy I am, they think it’s an act. People think that this whole cheerful demeanor is a put on, it’s an act, but it’s not. I really am this happy. This is how I am. I act this way.


I had this thought. I was thinking in the back of my mind.


Max: You were asking yourself that question?


Adam: I have never seen someone sitting before me in an interview with a bigger smile on their face, more excited about talking about a job and I was thinking-


Max: Erin’s one of the pillars of our marketing team. She’s responsible for the message we put out.


Adam: Yeah, yeah.


Max: You hired the most positive person you can find.


Adam: She said it and she nailed it. I thought okay. That’s why I liked the question.


Max: I like that and I really like your explanation of like how to interpret their answer as well. We have that in our Hireology database and now I know how to ask it correctly.


Adam: Yeah, exactly.


Max: Talk about some leaders who inspire you. Who are some of your favorite leaders?


Adam: There are leaders that you think about you never had experience with and there are lots of names there but as I think about the leaders that I’ve had direct experience with that they’ve just been inspirational in the way that I’ve watched them grow their companies. Jeff Lawson is the CEO of Twilio. He’s actually a friend of my co-founders and was an advisor to the company in the early days actually. I think what Jeff, so back in 2010 when he was working with us in 2011, Twilio was still in its infancy and it’s gone on to be the most successful IPO the last 12 months and the company’s just amazingly well run and he’s got a philosophy about how to run a business that’s very intentional and it’s accountable and it’s transparent and it’s really culture focused and I just think he’s doing a great job running the business. To go from founder to public company CEO and execute at that level is just — not everybody can do that. That is very tough.


Max: Not an easy road.


Adam: Admirable, and I would say another leader I greatly admire from the Chicago technology community is Jai Shekhawat, who is the founder and CEO of a company called Fieldglass that was acquired by SAP and one of Chicago’s tech success stories and he, over the course of 15-plus years, built that business, took it through the first dot-com tech bust and through a couple other cycles and had just a great exit and he thinks so clearly about the problems that he’s trying to solve that when I’ve had the opportunity to sit down with him and I asked what I perceived to be a pretty tough question, what I find is, he’s a McKinsey guy, and so he can distill it down to an essential question. He’ll just ask me the question and damned if every time I don’t walk away with the most important insight I’ve ever gained in the last six months will come out of the conversation I’ve had with him where he just asked me the question or say the one thing and I’ll go, “Yeah, you’re absolutely right. Wow, thank you very much.”


He gives back to the community and it’s about helping others and the next generation, and I admire that greatly.


Max: That’s really interesting because I know you named two leaders that have had really successful exits, either selling or IPO but I’m sure both of them have also had a lot of failure.


Adam: Correct.


Max: Talk a little bit, one of the questions that came up was talk about some things you learned and some mistakes that you’ve made over your time at Hireology and elsewhere, building businesses and hiring folks.


Adam: Yeah, on the business front, the mistake I have made in the past is waiting too long to course correct. I think in the past, I have held on too long, waiting for something to happen that I expected to happen that just isn’t going to happen and so in its simplest form, it’s staying too heavy on a team when you don’t need the staffing level that you’ve got because the productivity’s not there and taken to the extreme, it’s waiting too long on a business model such that you get yourself back into a corner and it’s really hard to dig out of. I’ve had experience with both of those things in a prior business. What it has taught me is that facts are the facts. Your interpretation of them is what really matters, and so you’ve got to be honest with yourself about what the facts are telling you and act quickly and be deliberate, be careful, but act.


Max: Have a bias for action.


Adam: That’s correct, yeah that’s correct.


Max: This goes into a little bit of how we run our business but talk about the integrator role in our business and what it’s like having a true integrator on our team.


Adam: We follow an operating, management operating system called EOS or Entrepreneurs Operating System. We’ve had Dan Heuertz on this show. He’s an EOS implementer. Thousands of high growth companies use this system built by a guy named Gino Wickman out of Detroit. It’s a step by step process really for strategic planning all the way through what you’re focused on today and it’s a great system. One of the core tenets of Traction or EOS is this notion that there are really two people at the top of the organization. There’s the CEO and the COO but we don’t talk about in those terms. It’s the concept of the visionary and the integrator, the big idea person, the evangelist, big relationship development, the keeper of the culture, big R&D projects, where we’re headed five years from now, and this notion of the integrator, which is process driven, okay sounds good but here’s the reality. How do we make that happen? Identify the gaps. Lock everything down and actually let’s have a plan and see if this is reasonable.


If you’ve got a founder-led business, often the visionary role and the integrator role are the same role. It’s combined and that’s the way it was in Hireology for a good five years, and you get to a point right around I would say between $5 million and $10 million of run rate where you really have to pick as the founder which are you. Are you the idea person or are you the execution person? Because you can’t really do both. I would say when I’ve asked Gino this question, about 15% of CEOs can be CEO and the integrator and do it well, because it’s just, you’re not wired for both. Most people are not wired to be both things. I am not wired to build operating processes that I then manage every single day. That’s not the best use of my skillset, and for great integrators, the best use of their skillset’s not putting them out on the road, building brand recognition and inspiring the market with whatever your idea is.


For me personally, having somebody in that role has unlocked my ability to scale and invest that. That’s the best value to the business is for me to do what I’m best at. The more I can do what I’m best at and the less I can do what somebody else is best at, that’s going to provide shareholder value and customer value and that’s what I need to be doing.


Max: Did you get the feedback from which seat you should be in from other business leaders or did you know that internally?


Adam: I knew that. I mean I think anybody at least you need to think about yourself in those terms. Am I a better visionary or am I a better integrator? You’re going to know. You’re going to know. When somebody brings an idea to you, if your first response immediately is okay, based on what resources and people we have, how can I build a plan to make that happen? That’s an integrator mindset. It just is, if you’re sitting around dreaming up ideas that are long on vision and short on planning, you’re probably more of a visionary than an integrator. That’s okay, understanding what you are is pretty good.


Max: Then having somebody who can round out your skillset can really help your business.


Adam: Sure. I mean that’s a partnership that when it works, unlocks some pretty incredible growth.


Max: A question here, as I know you know, there’s been some controversy at Uber recently because of their treatment of some female engineers. How do you recommend that companies make sure they’re hiring and keeping their best employees while avoiding issues that may be cultural and can be poisonous in situations like this?


Adam: Unfortunately, the early stage and growth stage technology scene has developed a reputation, I think deservedly so, for being a tough culture for diversity. It’s unfortunate and certainly I’ve read the material, a blog post and it sounds like a lot of things went the wrong way. That kind of stuff, that starts at the top. You as the CEO of the business have to decide what’s acceptable culturally, and would you fire your best engineer, your best salesperson or producer, your top manager for violating a core value? If the answer is no, okay, you’re making that choice. You’ve decided that the result’s more important than equitable treatment or diversity. That’s just a fact. Leaders have to decide what they stand for. Any time I read anything like that, that’s not a reflection of HR. It’s not a reflection of middle management, it’s not a reflection of the person alleging the situation or complaint. That’s on the CEO and it’s your job very publicly, internally and externally in a high profile company like that especially, to let everyone know what you stand for.


I don’t know their CEO personally, but performance probably is a higher priority than inclusion. I think everybody can see that, not that that’s, I don’t want to judge good or bad, that’s just not for me.


Max: Yeah, so you mentioned core values. How do you choose core values and then once you’ve chosen them, how do you really make them more than just words in the handbook or something you put on the wall but something really actionable and as you mentioned, that the business is built upon?


Adam: Core values are the blueprint for the business. I mean I think for Hireology, the first thing we did was sit down the three of us and decide what they were. We’ve all been a part of starting businesses or growing businesses where the core values weren’t authentic or weren’t even defined and we just decided this time we were going to start there and we worked on it for weeks to get down to what do we think, what do we stand for, what do we believe in, what’s the kind of company we want to be a part of, and for us, we came up with our five core values, which for us, it’s pathological optimism, eager to improve, own the result, create wow moments and we have a no assholes core value and that is for employees and customers and vendors, frankly. Those things, how do you make those real, you have to manage it. You have to measure it. What we do here is evaluate every six months folks along measurements and core values adherence. Do they do it all the time? Sometimes or rarely?


We put people on performance plans based on core values violations. Every week in our all company standup on Tuesday morning, we’re letting people peer to peer nominate each other for core value shout outs, name the core value and what the person did that exemplified that. You’ve got to make that a part of the fabric of how you manage the business, and I think I haven’t always done that. In this business, we’ve done it from day one.


Max: You were in comedy, many people may not know this but you had a standing comedy and talk about how that’s helped you in public speaking and in business development and in running a company.


Adam: Thankfully, I was in standup before YouTube, so nobody will find evidence of this ever. It exists on 8 millimeter tape I’m sure somewhere, but it can’t get any worse than bombing on stage in a standup set in a room full of hundreds of people.


Max: Yeah, Adam set the stage because this wasn’t like you went to do an open mic or two. You were serious about comedy and you were traveling and you were doing a lot of shows for a while.


Adam: Yeah, you know it’s funny, I end up inevitably trying to start and organize and grow something great, so we started off doing open mic nights, which turned into meeting a couple of people I thought were good and then I quickly realized I was a better emcee opener and organizer than I was a featured comic. I was just never going to be that. We started, contact the local drinking establishment and say, “Hey, you give me Tuesday night every week, I’ll fill the room. Give me 50% of the door. We’ll sell some beer and blah blah.” We did. We end up with the Four Thieves Comedy Showcase Tuesdays at Hog Head McDunna’s in Chicago, and had a couple of big shows at a place called Joe’s on Weed Street in a room with hundreds of people. What was great was we got to work with some Chicago up and comers like TJ Miller and Kumail Nanjiani, who’s on Silicon Valley, it’s fun to watch those guys, or Pete Holmes, who has a show on TBS.


Those are all guys on the standup scene in Chicago in the early 2000s doing my open mic night at Hog Head McDunna’s. It was a lot of fun but you got to warm the room up and yeah, you go out there and you think your stuff is good.


Max: You’ve worked on it, you practice.


Adam: Let’s say you do 10 shows, and nine times it kills and one time, the temperature’s a little too warm. The seating is just a little too spaced. Some dynamic in the room changes and it’s just not funny and it’s crickets. You can get in front of the most important sales meeting of my life and I would never be more nervous than I would be going up to a microphone and trying to open a comedy show because it’s just you. It’s like be funny, Max. Go be funny. Is this guy funny? It’s hard.


Max: It’s really tough and you’re on your own and you have to wing it.


Adam: It’s fun though. It’s great. It’s the best, what I mean, of course, speaking training and situational awareness and communication training you can put yourself through. It’s Navy SEAL training for public speaking is go try standup comedy.


Max: All right, Adam. We’ve got one more question. It’s kind of a broad one but what is the greatest people lesson you’ve learned since starting Hireology?


Adam: I think back to some advice I got back around the time of, it was a famous HBS article which turned into a book called The Founder’s Dilemma and the question is do you want to be rich or do you want to be king? As the founder of the business, do you want to be the center of attention or do you want to actually scale something? What the research shows and experience bears out almost every time is that you’re not going to scale something if you need to maintain control and be the most important person in that organization. The most important lesson I’ve learned is the more I can set the direction and then get out of the way, the better we do, the better I do. I’m a better manager if people are doing more. The less I do, the better off we are. I need to be living five years into the future and I can’t do that if I need everybody to come in here and ask me for my approval on every little thing.


That ship has sailed. So many companies including previous companies that I’ve led, I sat there and I needed a hold on everything because I don’t, I either don’t trust the person in the role or I don’t trust myself to give it up or whatever it is so what I now know is that I either need to change the person or change my approach and I can identify when one of those two things is happening now. That has helped us grow here. I mean it’s the only reason we’ve grown really and we’re better off with that philosophy.


Max: The lesson there is delegate to others, know when to get out of the way, take a partner, bring other people in to the business.


Adam: All of the above, whatever the situation is. I guess recognize your strengths and know when you are responsible for holding your business back by doing too much.


Max: All right, and this has been great Adam. I’m not going to ask you to close with a joke but we may get some requests for you to do some standup here on the podcast but thank you so much, Adam for all of your insights and for answering the questions of Hireologists everywhere. For The Best Team Wins podcast, this is Max Lowenbaum here with Adam Robinson. Have a great week and we will talk to you soon.