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22 min watch with captions and full transcript

Sam Dunn heads Robin–a tech company with the mission of scheduling the people, places, and things in your workplace. Glenn spoke with Sam to find out how he attracts the right talent to Robin, and how he fosters a culture of transparency.

In this interview, Sam shares how he has built a high-performance culture based on talent and transparency:

  • How to look past tenure to find your best talent
  • How transparency spreads the weight and the work
  • The top three questions you need to ask in every interview


Catch more of Sam’s rebel wisdom, like:
  • Bundle the good news and the bad news to be transparent
  • Hire people with an internal locus of control
  • Distinguish your culture from a stop on a recruitment tour
  • Everyone has their own highlight reel
  • Let your employees do the recruiting
Our favourite quotes:

The most important thing for me is to hire people who have an internal locus of control versus an external locus of control. You happen to the world, the world doesn't happen to you.

You have to be okay with bringing people on to accomplish a specific goal. That's not to say that you should have a turn-and-burn organization. It's the idea that when people come on board it's because they're saying yes to your company being the best possible thing for them to accomplish whatever their goal is at the given time.

Sam's interview:

GLENN ELLIOTT: Hi it's Glenn Elliott here, today I'm in Boston with Sam Dunn who is co-founder and CEO at Robin, the software that helps you schedule everything in the office. So Sam thanks for having us around.

SAM DUNN: Absolutely.

GLENN ELLIOTT: So you're running Robin, a tech company now, but you didn't always run Robin. You also ran a digital agency before. Tell me what it's like, what the differences like in how you treat people and how people interact.

SAM DUNN: I think the nature of the agencies is little bit more project-based. That's nice because you get to work on a lot of stuff. But, also that stuff evaporates after the project is done. So, in terms of project ownership, it's very unlikely that you're gonna get to hang on to something long enough to iterate on it. So, that was something that in the agency days we had a hunger for doing a product of our own so we could iterate on it and keep it with us.

GLENN ELLIOTT: Do you find ... I know that at RG I used to find that some engineers missed the change of having a new project all the time. Do you find that at all or do you find that that excites you more by the ownership and the capability of perfecting of something?

SAM DUNN: I think it narrows down to if they're working on a big enough problem. I know an equal number of engineers that love the idea of using best practices for everything, having the codes so neat that anyone coming in would drool over it. But, I think that by in large the types of people that enjoy product are the types of people that are excited to get new features out the door, rather than iterate on one specific feature again and again and again. I can see how that would get boring.

GLENN ELLIOTT: Yeah. What's it like manager engineers? Is it enough after a lot of [inaudible 00:02:02] amounts of success?

SAM DUNN: Well, I can tell you that I have the luxury of sitting more on the sales and marketing side of the house, so what I've heard from my colleagues are at a certain point engineers want the ability to kind of remove ego from the equation. I think that that is the one thing that we've really focused on, which is you can be pragmatic, but you can't have an ego that makes you required to always be right. So that's been nice from a recruiting mechanism and what it's allowed us to do is have the quality of engineer consistently good and now be able to recruit themselves more than we recruit them. We actually don't have a shortage of engineers. That's a rarer thing in the area I think.

GLENN ELLIOTT: What do you do to keep marketing and sales and engineering connected? You found a way of getting the feedback from the sales to the finding of market into engineering in a good way.

SAM DUNN: So we used Slack in our daily methoding and apps like that. What we do is we make support requests and live chat all publicly available so there's that feedback from the customer in real time. So it's always a sales person coming over and saying hey I had this objection on my call, engineering please deal with this. There's actually seeing the emotional responses from the actual customers, which I think is an important way of making it real.

GLENN ELLIOTT: Do you put your engineers in front of customers?

SAM DUNN: We ha ... sparingly. That's not to say that they couldn't and that's actually something I'm proud of. They could be in front of customers, but it's just at the point where they might help draft a response to customers, but you know a lot of them don't necessarily strive to interact directly.

We work with some cool companies that they're fans of so they of course want to see those offices or interact, but more video game based companies.

GLENN ELLIOTT: Of course. So Robin's up to nearly 40 staff now.


GLENN ELLIOTT: Tell me a bit about recruitment because getting the right people into your business is obviously crucially important. How have you developed your recruiting strategy or your interviewing techniques in your assessment of [inaudible 00:04:18].

SAM DUNN: In the early days it was, we did everything from job boards to meeting people at events. We still do those things. We've introduced incentive programs to if you refer someone that we hire you get a kickback then you get a kickback after 90 days or a year of them being here, which actually double incents because then the person has to be here to actually collect it.

GLENN ELLIOTT: So does that encourage people to support the person?

SAM DUNN: Yeah. I think we've already seen that happen. One of our engineers here within the first 90 days of him joining, he recruited two of his friends so he's actually the top recruiter here all in the past year. So that's been a fun mechanism for us.

GLENN ELLIOTT: That's interesting. What about kind of a successful [inaudible 00:05:08] you got an effective approach?

SAM DUNN: So I've asked a lot a questions over the years and I think that at this point I really only boil it down to three things. I wanna know what the typically in the best room at, that shows what they think they're ... it shows what they think they're best at. Then you ask well what do other people in your current organization come to you for. That shows what other people think they're good at. It might not necessarily line with what they think they're the best person in the room at. Then the third is what do you want to be the best person in the room at. That's more of the aspirational one and I try to make it as narrow as possible. If someone comes in and says, "I'm the best person in marketing." No you are not. You might be the best person in the room at email, but you need to make it as concrete as possible. Those three questions normally boost confidence because they realize what they're good at as well as combine it with some sort of actual thing where I know what they want to accomplish while they're here.

GLENN ELLIOTT: that's interesting that you ask them what their aspiration is. What they wanna do at the interview stage. Tell me more about that. Why did you do that?

SAM DUNN: I think the question what do you want to do in five years is pretty lame. I think that when you frame more like what do you wanna be known for. When people in town talk about you the marketer or you the engineer what does that mean? You gotta bring that person in if you have this problem. You've gotta bring this person in if you're having a really hard time with email campaigns, if no one's opening your emails. Things like that.

GLENN ELLIOTT: That's interesting. The language you use in there kind of like what you're gonna be known in town for sounds like you're very much kind of reinforcing the idea that people should be thinking about their personal ground and how do they themselves as individuals how do I look to employers and other people.

SAM DUNN: That's actually an offshoot of who's in town. I've talked to a lot of my friends who also have companies in kind of peer groups and I've noticed that it's very rare that we refer to hires as oh this is a really good mobile person. It's almost never that generic. It's like I need a sales person who's really good at onsite meetings or I need a sales person who's really good at getting through the door. Who do you know? That helps us very quickly arrive on who to refer to both our friends companies as well as who want to track down. It's a good way when they show up on the first day too. It's a difference from Hello this is GLENN ELLIOTT and he'll be joining you in the marketing team. He's good at marketing obviously, that's why we hired him verses, this is GLENN ELLIOTT he's really good at doing outbound email campaigns. Talk to him about it. Gives you a brand from day one verses down the road.

GLENN ELLIOTT: Let's talk about tenure. I'm curious because we've been talking to lots of the people that are in the block to kind of re-understand and re-explore the idea of is there a permanent job anymore? Has that all gone and how do we feel about tenure? Is long service and tenure something we should be striving for or is that an outdated concept?

SAM DUNN: I think that tenure is obviously getting shorter and shorter. I think that you have to be okay with bringing people on to accomplish a specific goal. That's not to say that you should have a turn and burn organization. It's the idea that when people come on board it's because they're saying yes to your company being the best possible thing for them to accomplish whatever their goal is at the given time. If that takes 12 months if that takes two years, if that takes five years, everyone's gonna have a different tenure because the goals are gonna change and all you have to make sure is that your company is currently the best vehicle to get that done. What I like to do is make sure when people come into the organization, that's why that third question matter, which is the what do you want to be known for. If we're the best vehicle for that, great. We'll set up checkpoints because we've agreed on the goal together. The checkpoints that we're hitting while you're here, if they don't feel like they're moving you towards the goal, that doesn't mean that our goal of you developing professionally in the organization has changed. That means that my view of what checkpoints get you there might be a little different than yours.

So, the end result is that we rarely have someone leave without telling us or making it a conversation first. We're rarely surprised by it.

GLENN ELLIOTT: It's interesting isn't it. It feels like a very different way to think about work than maybe your kind of used to. Or maybe some people still do where they kind of think I've got a job in marketing and it's the company's job to develop me verses I wanna be known to be an expert in this part of marketing and my job is to chose the company that's gonna help me accelerate that and deliver that in the next two years and then it'll be my job to think about my next goal. It's a much more personal approach isn't it?

SAM DUNN: I think that kind of helps upend a few folks who might come in thinking, "Well I just got a do a couple years as an entry level engineer so I can be promoted so I can then get this job that I really want and then the next one." I think that making it more about developing a skillset rather than developing job titles on a resume is much more interesting.

GLENN ELLIOTT: Awesome. Since you bring up resume, I'm also curious about how we interpret where someone works on a resume. Do you think it's important to know that someone's worked at Expedia or [inaudible 00:11:06] or Hubspot or do we read too much into that? I don't know. How do you feel about that?

SAM DUNN: I feel like it really depends on the stage they came into the company. I think that it's a toss up. There's certain companies that are very good at developing, and you know if you pull someone from Acquia or Hubspot you know they've been trained really well on the sales and marketing side. So, they have the reputation there, but also you've gotta kind of ask a lot of questions to figure out whether or not they were the driving cause of certain development or they were just present while it happened around them. I think that the longer someone's been at a company and the later stage they started there often time resumes reflect grew revenue to 20 million and it's really not that person. They were just part of the team. It's really for things like that it's the I verse we and how they talk about it.

GLENN ELLIOTT: There's a great quote I read recently, but I can't remember it word for word but it's kind of "Success has an awful lot of people part of it, but a failure has nobody." Like no one ever ... When a company's done badly no ones says, "Yeah I was there. I was part of that. I was part of the team that screwed that up and this is what I learned." No one says that though. They kind of just like, "Yeah that [inaudible 00:12:23] was successful. I Played a leading role." And you've no idea if -

SAM DUNN: Everyone has their own highlight reel right?

GLENN ELLIOTT: Yeah. That's pretty interesting. So getting people into the business is really, really important to think about. When people are here how do you keep them connected to that mission. Kind of keep them motivated and engaged, what do you do here? What does it feel like to part of Robin?

SAM DUNN: I think the most important part is that we ... you know you can have your company vision. You can have, you know for us we wanna make sure that we're developing. We started with a scheduling product as a mechanism to help better coordinate the workplace and reduce friction and all of the things that might get in your way when you're trying to do work. So there's that kind of banner that we can all rally under. The difference is I think that when you hide information and only show the good stuff you loose credibility over time. I think transparency comes in a couple different ways. One is that you wanna be ... if you hire the right types of folks in my view and you give them the same information that you're acting on and the same problems, the same advantages to think about, that spreads the weight and you're able to all adapt to it. I think that sharing bad news is equally as important as sharing good news. For us, it's been a delicate balance between as we grown. It's harder and harder to make sure that everyone has equal amounts of information just because of the sheer number of conversations.

I find myself trying to figure out the best ways to bundle both the good and the bad news so that we're remaining transparent while also not giving limited views of things that might cause undo panic or celebration.

GLENN ELLIOTT: Yeah, it's tough. I've been criticized often for not giving out all the bad news, without ever consciously not giving out the bad news. I just did not realize it.

SAM DUNN: You're just really good at [inaudible 00:14:26].

GLENN ELLIOTT: Yeah, it's interesting. Sharing information is kind of key. Do you share business results? Do people kind of know what you're doing on terms of sales and revenue and that kind of stuff?

SAM DUNN: Yes. So people ... We have every two weeks we have something called the Mighty Meeting, which is an ohmage to our agency days, which our agency was called One Might Roar and we just thought the brand. Yeah, so it's an all hands meeting where we talk about different topics. It's at least once a month. Everyone knows what the revenue is, what the churn, customers that said no, customers that said yes. Then on the other side it's also a platform for perhaps sales to talk about what they've worked on that month that might have flown under the radar of engineers. So it's a way to bring visibility to wins, loses, and all of the other things that happen around you when your head down and working.

GLENN ELLIOTT: It was amazing writing the book how many companies we spoke to that had success in kind of involving everybody, people centric culture, done all the work on open, honest communication. [inaudible 00:15:34] it was a really big piece.

SAM DUNN: I think that the most important thing for me is if you hire people who have an internal locus of control verses an external locus of control, so internal is basically you happen to the world. The world doesn't happen to you. I was driving too fast, that's why I got a speeding ticket verses the cops are bored and they gave me a ticket. People who have an internal locus of control are able to take bad news and then react to it in a way that could correct it. The other ones you very quickly see a level of helplessness or complaints rather than action. I think that that is the one thing that business can't have a tolerance for in the early stage.

GLENN ELLIOTT: It reminds me of Arianna Huffington Cort actually. She talks about ... She says bad things are gonna happen to all of us. Things that we don't wanna happen are gonna happen. Some people they take them in and become bigger than those things and some people kind of shrink and become smaller than those things. It just kind of resonates with your locus of control.

SAM DUNN: It's really kind of like is this gonna be the thing that cuts you at the knees? Is this gonna be the thing that finally makes you buckle? Odds are no because most of the folks out here are less than 10 years into their career. The question becomes is this the biggest problem you're ever gonna face in your career or are you peaking right now? The answer to those should be no on both fronts.

GLENN ELLIOTT: Interesting. So we're here in the Robin office.


GLENN ELLIOTT: Which, I beautiful, newish office in Boston. This is the Whiskey Room. Tell us the story of how the rooms got designed and got their names and things. Kind of tell us about work space.

SAM DUNN: Okay so, this is our third office. Every single time we've at least doubled the space. There's about 40 of us here. The Whiskey Room actually hails from our previous office, which was obviously much more agency focused and we loved Mad Men so we had that touched of the romanticized leather furniture, whiskey drinks and that's where business goes. As we've grown we've wanted to make sure that we weren't a culture that necessarily celebrated drinking. We wanna make sure we're respectful to all folks. So it became less and less about the beverage and more and more about just the head nod to the past.

In our new office all of our conference rooms are named after time zones. We were delighted that whiskey is actually a time zone in military time for Hawaii. So it goes all the way around. They're not in order, but you know close enough.

GLENN ELLIOTT: Well you've got kind of you know we've got nice sofas here. There's like lots of different types of seating in the office. There's different places people can go depending on if they're reading or working or engineering or whatever. How important is it to create an office that feels kind of different to the traditional corporate office view?

SAM DUNN: I think it's pretty important, but I also think that you need to distinguish between what's a stop on a tour for recruitment, like ping pong tables, pool tables, video games verses what's actually gonna keep people coming back and people find useful. I think a lot of start ups tend to be stereotyped to have, you know this is Red Bull kegs, Nerf guns, ball pits, video games all of those were if that's what's driving recruitment you probably have a larger culture deficiency that you're just trying to mask with that. I mean we run a scheduling product so we see a lot of this data and I'll tell you putting a video game room gets the lowest amount of use. If people really wanna sit and play video games they're gonna go home and do it.

For us, we wanna make sure that we kind of cover our basis for the types of things that people need to do throughout the day. I don't wanna hear about is, "Hey I just worked from home this morning because I needed a quiet place to grind out emails." If you hear a lot of that you're probably just don't have the right space in your office for them and that's an adjustment you can make.

GLENN ELLIOTT: So, your advice is to focus on creating spaces where people can do all different types of work you need to do rather than creating spaces that just look exciting on an offer.

SAM DUNN: Yes and I think that if your goal is to do maximize your space it's easy to just do kind of a cafeteria style open floor plan, but then the noise kicks in and people don't really have variety throughout their day so they feel like they don't have a common space they can kind of use. So, the whiskey room here was the idea here is that it would be modeled very much after kind of hotel lobby, which is where people can congregate, be social but also do their own thing and break apart.

GLENN ELLIOTT: Well thanks so much Sam it's been a really great place to sit and chat with you. So Robin, scheduling software for all the things in your office, especially meeting rooms and like I said we use it ourselves at Reward Gateway and we love it. So that's it for our time with SAM DUNN. There's more interviews like this all at Rebelplaybook.com. And of course we're covering all the chapters in the book Rebel Playbook from Employee Engagement so I hope to see you back there soon.