Does a CEO really need a desk?

Episode #7
Nov 5, 2018

There was a time when employees' productivity was measured based on how long they've been sitting on their desk. This old school thinking has changed as entrepreneurs explored various ways to drive employee efficiency. Let's listen to Upsuite CEO Ben Wright as he enlightens us on how coworking spaces can help you get more ability and resource than you had before.

 “It's a leader's job to help his people do their best work.”

Ben Wright


2:23 – What is Upsuite?

5:09 – How coworking spaces can help you become agile

9:19 – The benefits of empowering your employees

11:35 – Limitations of working remotely

14:40 – You need to make an effort to meet other people

19:06 – The trait that helps create a community

31:19 – Why you should trust your people in making decisions




 Connect with Ben:


Jon Voigt:           Welcome to Agile Living, the entrepreneurs journey, a show dedicated to discovery and how entrepreneurs, digital leaders are doing more with less. I'm Jon Voigt, your host and CEO of Agility and we're on a journey across the country to learn from top digital entrepreneurs on how to live a more agile, adaptable, and fulfilling life. Thank you for joining me today, and let's dive in.

Jon Voigt:           Hi there. To celebrate the Agile Living podcast launch, I'm doing a massive giveaway and giving three lucky winners a chance to win some of my favorite things I use frequently. The first step in being Agile is your mindset, and these prizes all help you with that process. First, a box of bulletproof Instamix. These are high-octane oils to fuel your day. I add it to my coffee or my tea almost daily. Second, a Fitbit Charge 3. I don't even have one of these yet. It's not even being released and they look pretty cool. So it's coming out soon, and that'll be the second prize. Third, a microbiome test by Viome. This is a leading test in the U.S. that tests your gut biology and tells you exactly the foods you should be eating. It's pretty cool stuff. I did it about a year ago and saw the results and it was really amazing, the things I should and shouldn't be eating. Please note, this contest will only be open to those in Canada and the U.S. I'm really sorry for anyone internationally.

Jon Voigt:           And to win you have to do the following. Subscribe on iTunes to the show. Go to and enter your email so we have a way to contact you. And share the show with a friend who wants to start living a more agile lifestyle on Twitter or Facebook with the tag "Be more agile." That's it. Pretty simple. Can't wait for you to hear some of the episodes and hopefully you can start living a more agile life.

Jon Voigt:           I'm very pleased to be joined by Ben Wright. Ben is the founder and CEO of Upsuite. We met back in Denver when I was driving across the U.S. and we got into some really cool discussions about shared workspaces and the fact that I haven't had a desk all summer. And we started to ask the question between ourselves, does a CEO really even need a desk and how does that affect the company and himself? So Ben, maybe you can introduce yourself, what you're up to with Upsuite, and tell a little bit about your story about when you had a desk, when you didn't, and we can kind of go from there.

Ben Wright:       That's great. Thank you so much, Jon, and I want to give a huge shoutout to Jon for sending me a cold email and making it interesting enough that I really had to meet him. And so that's how we met.

Jon Voigt:           Well, I'm glad you replied.

Ben Wright:       I'm excited about ... And now I'm in Toronto in your hometown, which is even more-

Jon Voigt:           Yeah. Exactly.

Ben Wright:       Even more funny. So to give you a sense of what I'm doing now ... The three-time founder and somebody who's really gone from being a skill-doer to somebody who understands that it's a leader's job to help people really do their best work. And if you do that, you're going to be happier and more successful. So the business that I've started and am running now is called Upsuite. And Upsuite is for businesses looking to accelerate their search for the perfect coworking office. Upsuite really takes the guess work out of finding and selecting the office that's the perfect fit for their business. The alternative to what we do is Googling for coworking offices and not going to individual websites. And what we do is we're an online and human powered matchmaking service that's free to use for teams. So for me, that's an extension, that business and the purpose of the business is pretty exciting to me because we're in coworking, we have coworking operators as customers. So I've spent a lot of time in WeWork, I've spent a lot of time in Space Co. Control Collective. That is in Los Angeles in Denver and we have 25 other operator customers in the markets that we're in.

Ben Wright:       And I don't think coworking by itself helps solve the problem of teams doing their best work. I think leaders have a really important role in it too, and culture does too. But I think the environment of coworking really helps send us in the right direction. So I was hoping we could talk a little bit more about that, Jon.

Jon Voigt:           Definitely. Definitely. And I'm right there with you. We moved into, just so everyone knows, I moved into a coworking space with our company earlier this year. We work in Toronto and now we've just been able to expand into Vancouver very quickly because we already had a relationship with them and then they set us up over there, but we definitely would have talked to you guys as well. But it's just such a movement of people moving into these shared spaces so they don't have to worry about all these other things and you get a consistent culture and community that you can build up even if you're a couple people. So.

Ben Wright:       So what we found about that is there's some parallels in the actual software development world, where if you're a business and you're looking for an office, you have a waterfall approach, which would be "Let me start looking for space, let me develop a shortlist, with or without a broker, let me evaluate it, let me sign a five-year lease, let me build out the space, and then let me be in that for a while." That feels very akin to a waterfall development approach.

Jon Voigt:           Yep. Yep.

Ben Wright:       Whereas a more agile approach to this really feels quite different, where it would really start with "Yes, let's understand the requirement and really get to that, but then let's actually utilize the space. Let's literally jump right in. We might not need to sign a lease longer than a month. Let's review and integrate that with that space and then let's refine that space." And I think, so from an entrepreneur's perspective, like myself, that has felt like there's nothing wasted. And that we can really match the work environment, the vibe, the amenities to what our team really needs. As a result, we've been able to retain employees that are in very high demand and we've been able to improve collaboration. We've been able to improve flexibility and working from home as well. So it's been a great process from an entrepreneur's standpoint and a business owner's standpoint. From an individual's standpoint, myself, it's interesting. When we first signed our first coworking lease, I was told that I was not going to have a desk. Right?

Jon Voigt:           Right.

Ben Wright:       At first I said, "Well, why?" And it took me a little while to get used to it, and the truth is, what I've found is when I wasn't traveling or when I wasn't in meetings or when I wasn't meeting other people at the space, I actually preferred to work in the common area or in a quiet part of the common area or at home or wherever. And it allowed me, myself, to be a little bit more agile.

Jon Voigt:           Right.

Ben Wright:       And not stick into the paradigm that really suited me. But meet people, literally and figuratively, where they were. And be in the environment that suited the work. And I think that's been more interesting. It's been more invigorating, and it's felt a little bit more connected to myself and my business.

Jon Voigt:           Yeah, yeah, I had a very similar situation this summer, because I've been traveling all summer meeting people and across the country and I didn't have a desk either. I would stop at some cities and have a desk for a couple of days, but it wasn't a desk with the rest of my team. It was a bit more work to connect with anybody, and what I found was it made everyone else a little bit more flexible and adaptable because there was way more times when people couldn't just turn their head and ask me a question or they couldn't walk into my office. And they really had to make decisions quickly sometimes, and move on things that were in the past, maybe they would have came to me just for confirmation, just to feel a little bit more comfortable about something. But then as they started, in the summer, to make decisions quicker, by themselves, they were making better and better decisions and getting just more control themselves. So it kind of energized people, because they didn't feel they had to wait for an answer. So my team got much more, I would say accountable and took things on a lot more, which was a side that I didn't really think about. I was thinking about just myself, my flexibility, and I could do this here and I could do that there. But it affected the whole company. It was interesting.

Ben Wright:       One of the things we've seen is that being part of a coworking environment or a shared working environment actually allows people to feel like they've got more resources.

Jon Voigt:           Right.

Ben Wright:       So, Jon, the example that you gave, I think the temptation for entrepreneurs is to think, "Well sheesh, we have to have all the answers."

Jon Voigt:           Yeah.

Ben Wright:       And I think what you were alluding to is, well, you need to have some of the answers, but not all of them. And the more you can empower and connect employees with either their own skills or with a broader community that they can learn from, the better a business might perform. And I think there's a ... You can't tie all of this back to not having a desk, but you can certainly see the relationship there that instead of being locked into our own office where it's just us, if you're inherently part of a bigger community, you, as the entrepreneur, and staff can feel like they're not at work in a very simple way. And that they've got more ability and resources than they had before. And that's a softer side of what we're talking about with not having a desk, but there's some real power there.

Jon Voigt:           Yeah. I agree with the perception of the working space, even if the people aren't in your room, a lot of these spaces have glass walls, you see other people around you. We're a much smaller team since we sold half the business earlier this year and there's days where people have to work on the road or be out of the office or whatnot and when there's only a couple people in the office one day, you feel lonely but you don't when you see all these other people doing stuff. And you go to the kitchen and there's other people, even if you're not working or interacting with them, you feel like a bigger thing. And that perception is very powerful. A lot of our energy and movement and life is that we perceive things and the way we are believing things are. So if you change your surroundings and set them up so that you have a certain belief system, it can really help you stay more focused and aligned.

Ben Wright:       For sure.

Jon Voigt:           Yeah.

Ben Wright:       It's interesting, I think we've explored, as a business, that the opportunity and the limitations that come from working remotely. So we actually have a work policy where you can work remotely or from home as much as you see fit. And I think what we've found is there are ... It depends on the person and on the role, obviously, but I do think that are limits to working remotely. And we've actually read some research by the American Psychiatric Association that says that the cost of isolation isn't just emotional, it's physical as well.

Jon Voigt:           Interesting.

Ben Wright:       And they're starting to tie that back to life expectancy and relating it to other health issues, and so what I found, personally, is that I do like to work remotely from my home office one day a week if I can. I think there are other folks that can do as much as three, three and a half or four, but what I would say perpetual working from home has not just negative impacts on collaboration and inspiration, but also on your feeling of connectedness and on the downside, the feeling of isolation. I don't know if you've read into that as well, but-

Jon Voigt:           Oh, definitely. Yeah. When I was driving across the country, I was working on the road a lot. And other than my frustrations with internet, which can be a whole another thing when you're physically on the road and going from spot to spot. But when I got to Denver, when I got to Chicago, when I got to Vancouver, I used shared workspaces when I was there and I was the only employee from my company, obviously, only person there. But it was still a different feeling. And you felt a little bit more connected and back in with other people and it almost re-energized you again a little bit. So as much as I do like to work remote, do different things, I personally need to come back with people, whether they're right on my team or just other people doing stuff, right? So there is that connection part. Yeah.

Ben Wright:       One of the things I've been ... I'm not clear on that I would like to put out to you, Jon, is when you're working in a shared workspace or a coworking space such as the WeWork that I'm in as part of the Tech Stars, PropTech Accelerator that I'm in right now-

Jon Voigt:           Yeah.

Ben Wright:       Is-

Ben Wright:       A PropTech Accelerator that I'm in right now is it's nice to be around people but you don't always get to know who they are. I'm an extrovert and I will certainly talk to people in my environment but I have a little bit of discomfort to say, "Are these my coworkers?" Even if they're working for a different company in the same space. Do I have an obligation to get to know them? And how deeply will I get to know them? I think after about a year or so in a shared workspace I think I've found my happy-medium which is I'll certainly talk to people in a conversational way and maybe we'll develop a few ongoing jokes. It doesn't get that much deeper unless there's a very tangible collaboration benefit. I don't know what you've seen but that's been my personal experience.

Jon Voigt:           Yeah, it's a great point and it was really interesting. We moved into We Work in January and I've been in other shared spaces in the past and things like that but I find you really have to make an effort to meet other people in there which is weird because it's not what you'd think. You think of the community of these shared spaces and everyone's gonna be buddy-buddy and stuff but people are really busy and a lot of these, they're start-ups or smaller groups so they're very focused and they're not as distracted. If you go to the events that they have all the time you could definitely meet people. When you're getting coffee you could say hi to people but I think you're right, I have not had that many really, really deep connections with people.

Jon Voigt:           Now, the interesting thing is just because I've been in Toronto for so long and in business for so long, there's gotta be four businesses in the Richmond alone We Work space that I know. I know some people there already but I knew them from before. It's difficult when you go in there to work, you're working away and you have your own little group and things so yeah, I do find it difficult to reach out and meet more people. I know they do the community events but I don't think they hit enough people. Maybe it's just me. It'd be interesting to ask the employees what their perception is of that because I'm sure they interact a little bit more, but I'm running in and out pretty fast and doing stuff a lot pretty quick so it's tough to sit down and have a deep conversation with anyone.

Ben Wright:       Right. To me, this underscore's the power of context in terms of relationships that a space doesn't create that context for you, there's something else. There's online ways to create context like LinkedIn. There are physical ways to create context like, hey, if we work in the same space and we're all part of the same company, then there's context for us. I think that might be a missing piece of not having a desk that we lost a little bit of relational context.

Jon Voigt:           Yep.

Ben Wright:       I don't know that that's all bad, but I do think that there's something that's got to grow to replace it. If any of your listeners have a solution to relational context in a coworking environment, I would love to know it.

Jon Voigt:           I don't know how many coworking spaces I've been in but I think one huge, huge factor is that community manager that works there, they can post on the wall that there's a drinking event or coffee or whatever that afternoon. But, I've seen the ones that really engage people and they're walking around and talking to people and connecting with people and saying, "Are you coming tonight?" There is this person that almost needs to be that cheerleader who goes around and puts the spark to get the fire of people to communicate. I've seen that work pretty well, but it's a full-time job almost. These spaces aren't easy to manage.

Jon Voigt:           There's a lot of different demands, a lot of different needs, so it's pretty difficult to have someone who can just do that. We'll have to see the way that it works because I definitely see a huge shift of people moving from leasing their own offices to share. I think the shared space is gonna explode even more. It's like software going from paid software to software as a service. Everything is going in that direction, pay for what you need. Next month, maybe we'll double in size and we need a different space. The only problem I see in there right now is that even the shared working spaces, a lot of them are booked up. Even they're hard to get into. There's gonna be a big shift and that's gonna have to be something somebody's gonna take over, I'm sure.

Ben Wright:       From our vantage point, having about 200 different buildings and spaces on our site in the Denver market and the Toronto market, and getting to know the community managers at each one, I would highlight actually a few things that really help create the community and they're all human traits. There's some coworking operators that are really open about the fact that they're in the hospitality business. What that means is they hire people from hospitality and they understand that part of that role is to help people feel comfortable but also connected to where they are. We've seen that with a few of our operator customers that really get that right. Hospitality is a little bit intangible. It's one of those things you know it when you feel it, but you're not sure what it takes to create it. That's something that comes to mind and I think that's important. Jon, for the coworking growth data that you might be interested in, right now shared offices are about 2% of the North American office market. It's very small. Growing to roughly somewhere ... estimates vary but between 20 and 30%-

Jon Voigt:           Yeah, it's huge.

Ben Wright:       Of the office market. That's about a 10 to 15 X growth over the next 12 years. By 2030. There's a very big shift as you said and if this was a baseball game, we're in the first inning of it.

Jon Voigt:           That's good for you guys.

Ben Wright:       It is, yeah. It's a real change for the real estate industry. It's almost a convergence between the view of an office and the view of the way a hotelier might think of their business. I think it's good in general. Tying it back to should you have a desk or not, I think if offices are converging with hotels, that means we can work on the couch. We can still sign big deals but do it on comfortable furniture that may or may not look like the desk that we had. One of the things that drives the physical changes in spaces that we talk about a lot is when we worked with a lot of paper, we needed a big desk to put a lot of paper on it. Now that there is much less paper, our desks can be small and that means we can move around a lot more. It's really interesting to see how that is working and how it's candidly changing as entrepreneurs are. Relationship with our staffs, our customers and all of that.

Jon Voigt:           If you really look at the true definition of an entrepreneur of a CEO, really they're supposed to create the vision and hold people accountable. What I've found is every time I sit down at a desk, even if it's not in the office, and start working on something, if I'm on my computer and I'm face-down working away or doing emails or whatever, I hate to say it but most of that is not creating vision and holding people accountable. It is getting sucked into tasks or being escalated to, or doing projects and things that seem important and whatnot but really, if I don't have a desk and I'm on my phone or I'm standing there talking to someone or I'm in a meeting, there's much more of a chance that I'm actually working on vision. Giving people ideas of where to go, how to make direction changes.

Jon Voigt:           Making sure they're staying on target of what they have to do. Holding them more accountable. That's the big realization I've had this summer around the fact that when I do have a desk and I'm comfortable, I can sit back a little bit more and do tasks that maybe are easy to do for me, but probably isn't the best use of my time. That's where when you and I were talking, it shone a little light in my head. I was like, that is something that's happened to be this summer. I've been focusing on the higher priority items, not just all my items because I have limited time or limited time to sit in front of a computer so I'm gonna do the top, top priority things which surely are vision and accountability first.

Ben Wright:       It is important to ask you Jon, has the whole world crumbled around you? Or is everything okay? Or maybe even better now that you've done that.

Jon Voigt:           Yeah, I would say parts of me have felt like I crumbled but because it's just been an adjustment. It was so used to having a desk and sitting there and have everyone around you. Nothing really crumbled but my mindset, it was difficult at first. As I got into a groove with it, it's excelled both my focus and my company's actually because when I talk to them on the phone, I'm not sitting in the office so they can't talk to me at much. When we talk, we talk about the top priority things and because we're talking about it instills that that's the important thing. We've been able to drop some things that are lower priority and stay a little bit more focused. I'm seeing that improve and improve the longer I'm in this state.

Jon Voigt:           As I said, initially there was some same paper. It was rough a little bit like, "Oh, I need you," or, "We need to talk," or whatever. We'd start talking and we're like, "You know what? We didn't need to talk about this. This is an easy solution that you could've figured out or it's not really top priority. What's our top priority for the quarter?" It's been a forcing function if you will to push us into a more accountable, a responsible phase. It's been interesting. It's been good though. Really good. I have a desk in the We Work Vancouver office because we're opening that office and I'm actually scared to get too comfortable there. We don't have as many people there so it's not as distracting and whatnot, but I can sit down at my desk and I can do more task-based things which can limit me from staying focused on the vision and accountability stuff.

Ben Wright:       The story that I would share around that is we did a quarterly planning meeting at Upsuite and we have six employees at the company and then two contractors. I was starting to get a little bit overburdened. We're right in the thick of a tech starter's Proptech accelerator program that is very intense with lots and lots of new ideas that the business still has to run. I remember going into that meeting feeling like I needed to ask for help from my staff and wondering if I could. What was so helpful was for me to essentially admit that hey, if I'm in these different seats doing these seats, I'll become the limiter to the business and I don't want to be that.

Ben Wright:       What was so refreshing is yes, we agreed to make another senior hire but we had one person agree to step into a role that he had done before but was working part-time for us and agreed to up his time commitment. We had another junior staff person be able to take a few accountabilities from another role, and we actually adjusted a junior role that we're hiring for, or a mid-level role to make it a senior role. It was everybody solving that together. It was me asking I think for what you experienced Jon, in your road trip, which was ... and I need to get out of the middle of these things not necessarily just for my own sanity but for the health of the business. When I put it that way to the staff and the leadership they really responded and that, it sounds like you're experiencing some of that yourself?

Jon Voigt:           Yeah, and before I left, I did talk to people. I said, "You know what? You guys gotta watch my back. Hold my back. We need to team up and everyone's gotta take on different things because I'm doing this road trip, I'm doing a podcast, I'm meeting people, I'm gonna be on the road-

Jon Voigt:           Good. I'm doing a podcast. I'm meeting people. I'm going to be on the road. I'll need you guys to take over these different things. There was a discussion about it, as well, and it's thing about getting out of the way and letting them blossom, too. It gives them an opportunity and just like what you ... I love that you asked them and you set it down that way, because then they make the decision, and if they don't want to, they don't want to, but then you have to figure out a different solution, but if they want to, there's nothing better than giving someone an opportunity of something they want to do.

Ben Wright:       I think, for me, what it took to do that was to admit that I'm just as limited as anybody else and admit that my limitations will limit the business and admit that I've got a family at home and a wife at home and my own health to worry about, and, for me, I'm in my 18th year of being an entrepreneur. I don't know that I either have the confidence or the self-knowledge or the tools or just the words to do that until some years ago. I think I thought, "Okay, I'm a gap filler. I'm the leader. I need to ... That means I need to take on whatever comes," and I think this does tie back to having a desk is that you play a role, yes, you're a gap filler, but when you're filled up and there's still gaps, you've got to ask for help, and I think that came through to the positive just this week.

Jon Voigt:           Well, I think it's the book, Good to Greater ... I think it's that one. It's what got you here, what won't take you there. The idea is, as an entrepreneur, we normally get into this position because we're good at a lot of things, and we can answer a lot of problems and solve things, but that only goes so far in a business and in an entrepreneur's career because, eventually, you need to get other people and teach them how to do things.

Jon Voigt:           We just had dinner last night, and we were talking about how you teach others to take on things and to grow as leaders themselves, if you were just taking on everything, and helping others take on things.

Jon Voigt:           I think with the desk idea desk idea, the concept going back to that. When you do have a desk, it's very easy to get sucked into to just do those things, but when you're not there, people will step up and take things off you and allow you to help them and lead them, and they'll grow, and then they'll learn how to do the same thing for the people below them, and it rea

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