I’m listening to the sound of a spoon clinking against a cereal bowl. Robert Jolly chats with me, making sure his little boy is getting his mushed bananas into his mouth and not all over his face. He tells me about his latest role as a freelance project manager with Simply Accessible, another flat team based in the great north of Canada.

Jolly is the kind of guy you’d hang out with and within a half hour, offer a best friends bracelet. When he’s not overheating during 24 hour marathons, he’s balancing the fun of four kids and a beautiful wife with four to eight projects at work—with more long distance training padded on each side for good measure. He’s funny, he’s honest about the fact that he lives in Wilmington, Delaware (which takes guts), and he’s doing this whole work thing a little differently.

Project management isn’t something you typically think of as remote freelance work, but Robert’s got things down to a science, and as such, has unique perspectives on what it’s like to work for a range of companies, including flat ones. I have to say, I was close to buying him tickets to a Celine Dion concert as a token of my Canadian appreciation. But I couldn’t because she sucks.

Rachel: So Robert, how long have you been freelancing with Simply Accessible?

Robert: I’ve been freelancing with Simply Accessible for about ten months now. Started in April of 2012.

Rachel: How did you first hear about it, and how did you transition into that role?

Robert: Derek Featherstone tweeted that he was looking for a project manager and wanted some recommendations. I direct messaged him because we’re friends, and he knows me, and I told him, “You know I did project management for Happy Cog before I left them.” He says, “No, I didn’t.” Because he remembered me as the client services director there. We talked on the phone and decided that it would be done. He needed somebody, he thought, for some part-time help, and it worked out perfectly in terms of his need and my availability.

Rachel: Is there anything you’re working on right now that has got you really excited?

Robert: Yes, we’re working on the launch of a major retailer’s presence in Canada. Our work is accessibility focused, so we’re working with them prelaunch to identify and resolve any design and code issues as they relate to accessibility. We’re actually bringing a lot to the project in terms of overall usability as well. Just by its nature, the accessibility has parallels with usability.

Rachel: Would you say that Simply Accessible is completely distributed—does anyone have an office, or anyone at a central location, or are you completely decentralized?

Robert: It’s completely decentralized. I’ll take that back. It is mostly decentralized. There is at the office space in Ottawa: Derek and Katherine (who is the president of the company). Derek is the accessibility lead. They also have an office manager that helps with bookkeeping and things of that nature that comes in. But there’s no main headquarters where we have a lot of the project work getting done by people in the same location.

The Jollies

The Jollies know what’s important.

Rachel: Do you find it challenging working remotely in a flat team?

Robert: Sometimes not knowing what the progress is with a specific task is tricky, so again that revolves around communication. And making sure you have a way of checking in when you need to know something. That’s one of the issues with remote teams, just making sure that everyone knows what’s going on and what’s coming up next. So as a project manager what I try to do is make sure we all talk about that stuff at the beginning of the week, and then almost—I wouldn’t say over communicate, but communicate some of the things that may be obvious to me or someone else, but may not be obvious to everyone on the team, like we have this milestone coming up, or we need to do this. And kind of checking in occasionally to make sure that everybody is on track with what they’re responsible for.

I read something today about project manager roles being ones that look after the team members as much as possible so they can focus on getting things done. I liked that in terms of how I try to approach things with our team. Make sure we have all the information in front of us but not be like a taskmaster about it; not stress people out about where we are with certain things—unless I know we’re falling behind. Then I’d have to start singing a different tune.

Rachel: The slightly more violent whistle.

Robert: That’s right, animated GIFs would become a lot more hostile.

Dr. McCoy and Captian Kirk approve.

Jolly approves of this message.

I definitely think I prefer the distributed environment. I do miss some of the in-person collaboration and camaraderie that happens when you go into an office and you share a space and a set of work hours with other individuals. I do think there are benefits to that but I think if you have the right team and the right ability to communicate, you can overcome those issues.

Rachel: It’s interesting, I was talking with someone recently about the same thing and he said both of those things; you need the right people on the team, and you need the right tools to be able to communicate.

I’ve also heard the argument that it’s not about the team members so much as the willingness to be able to adapt and evolve into that fit.

Robert: I think it’s true. If you can’t adapt then you’re probably not the right person for it. But it does take some flexibility, especially when you have people in multiple time zones.

Rachel: Do you think if you had a small company that was still considered a corporation, it is possible to transition to a flat structure?

Robert: I think it’s possible. I think what makes it difficult would be the resistance to change. If that idea wasn’t embraced by everyone on the team, from the top down or bottom up—you could say it both ways—I think the change has to really be wanted by everyone that’s there to make it work, or people that don’t like it have to leave. The people that want it have to create their own thing. I could even see there being flat departments within larger enterprise organizations, if that makes sense, just by virtue of how they decided they’re going to run their particular shop.

Rachel: Talk a little about what you might look for in your teammates as far as qualities go.

Robert: I guess being self-starters, being able to openly and freely contribute and also to give and receive criticism or feedback on the team. The ability to communicate is going to be pretty important with a flat team. It’s not that everyone has to feel comfortable speaking in a room or something like that, but just being able to tell your teammates what’s going on when you’re working and being able to jump in and help out when it’s needed is going to be important in a flat team.

Locrosse, Persia 1987 team

Robert and pals lacrossing Persian Gulf style, 1987.

Rachel: How do you think that differs from people who aren’t working in a flat team, but in a more traditional model? What sort of qualities do you think their senior employers look for in them?

Robert: I think they’re going to look for all of those things, but I think that work is maybe more siloed in those organizations. You may have people that if they aren’t wearing them when they come to the organization, they may end up putting on blinders where they’re really only concerned about what they’re supposed to be doing, what’s immediately in front of them, and maybe not necessarily what other folks in the organization are doing that is not directly impacting their job.

Rachel: We just talked about what kinds of qualities flat teams require. Then we asked, “What do traditional hierarchies look for?” The interesting thing is you said they look for the same qualities in people. But you also said the silos in hierarchical teams isolate people, which is fascinating considering many people think that same issue applies to distributed teams. What is the thing that you think ties people into this idea of “let’s be flat, let’s not haggle over our roles here”? What is that ‘common vision’?

Robert: I think that common vision is this dedication to do—especially in a small organization—whatever it takes to get the job done, to succeed, help the business succeed, help your customers succeed. Does that make sense?

There are more hierarchical organizations that really do try to honor work/life balance, but what I’ve seen with flat organizations is a real desire to recognize when something isn’t right, and then take steps as a team to fix that. Like if we work on a project and we have a crazy deadline with way too many deliverables to get it done in the amount of time that we need to without sacrificing our home life, we all recognize that and say what can we do differently next time to change that. I’m not saying that doesn’t happen in bigger organizations, but I think it’s harder to effect that change, or at least it’s been my experience that it’s harder to do that. You don’t have everyone feel like their voice is being heard and valued at the same level as everyone else.

At that point, you’re then lobbying for something, for what you need, to someone with more power than you have. That versus discussing things as a group and making the necessary adjustments, either consciously or subconsciously. I’m thinking now of a flock of birds. They don’t talk to each other and say we all have to turn right, right now this instant, then discuss it and decide to do it. They just do it as one.

[Jolly’s statement made me think of this starling video]

Robert singing the praises of project management back in the big hair days. I think.

Rachel: How does transparency come into play in flat organizations?

Robert: If you’re not clear about how your team is made up, who’s on your team, and the approach that you take, then it doesn’t build trust with the client. In the end, I think what really matters to the client is; are you going to be able to do the work, and do they trust it’s going to be great. I think some of that is evident from past projects, but the trust comes from just showing them we’re a little different; we’re a flat company. And if you want to read more about it, here it is. Transparency is really important and it can overcome almost any objection, I believe.

Rachel: When you sit down and look at the last however many years you’ve been working, and where you’re sitting today; what do you take away from our discussion, and where you’re at?

Robert: My takeaways from doing this for a while and after talking with you are that it’s good to hear there are a lot of other people doing this. I had no idea there were that many. So there are people that really are turning this almost into a bona fide science. Although I’ve known it has worked, I didn’t think it was magical or anything, but it is pretty special.

Robert Jolly Stickers at your service.

You get happy just looking at them.

It’s special indeed, Jolly. It was a real treat to be able to chat with you about a new perspective on freelance project management and flat teams—almost as much as it was to find out you weren’t hurt about the Celine Dion tickets. I’ll make it up to you, buddy.

Tools At Work

Some expert tools Simply Accessible uses to get the job done.

Basecamp (Classic)

The “old standby,” Basecamp is our main repository for project communication. I can’t imagine life as a PM without it.


TeamGantt’s a newcomer to our tool chest, but it’s proving to be wonderfully suited for us. It offers at-a-glance views of project tasks, progress, and resourcing which is really valuable for our remote team.


Git is the shit! We’re often developing accessible code prototypes and solutions for client projects and seminar examples, and this allows our team to develop, test, and revise work iteratively and cohesively.

Google Apps

Google Apps. So calendars. Email. Documents (Drive). And now Hangouts all help us be more efficient.


GoToMeeting, Skype, Google Hangouts/Chat/Voice, Phones, and IM apps. Basically, we need solid, affordable options for communicating since we don’t sit in the same room for most of our discussions. Google Hangouts is fast becoming one of my favorites for impromptu discussions—with or without the Pirate Hat.