How to Transition from In-Office Teams to Remote-Work Teams or a Distributed Workforce

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As I mentioned in my article on the benefits and caveats of having a distributed workforce, and in my article sharing the advice and insights I gathered on setting up a successful distributed workforce, I didn’t feel at all confident in making the transition seamless.

I can’t say I succeeded in making the transition from an in-office team to a distributed workforce seamless, exactly, yet I don’t doubt that the advice I gathered from people who’d gone there before me and shared their learnings from making a few mistakes helped set me on a better path than I would have made for myself.

In the spirit of helping others as others helped me—especially as I found no other resources on-line from perspectives of employers who had made this transition—let me share what I learned from other CEOs and executives and through my own experience (so far).

Set a Work-Remote Trial Period

From jump, I made it clear to the FrogDog team that we trialed the distributed workforce structure. In fact, I truly did think we would move back into an office environment in the beginning. So when I told my team that the remote-work period wouldn’t last, I meant that it might not last the expected three months—not that it might not last long-term. We could easily get into a furnished, work-ready office (even a temporary one) if needed.

However, even after I decided to keep the distributed workforce structure long term, I let everyone know that we could move back into an office environment in the future, if the company changed in such a way that we needed an office or if the team stopped functioning optimally in a remote-work format.

I meant it—and still do.

Any company trying a distributed workforce structure for its employees has to acknowledge that it may not work for the organization or the team and should set expectations accordingly. If the distributed workforce structure doesn’t work, the in-office format will return.

Be Vulnerable (After All, You Are Vulnerable)

Change makes leaders vulnerable. Any shift from the status quo opens possibilities for mistakes, problems, failures—and their associated embarrassments.

As a leader, own the vulnerability. Remind your team that the work structure is new for you, too. Assure them that you’ll do your best during the transition, and yet still you’ll make mistakes. Ask for their patience as you—and they—adjust. Promise you’ll do the same for them in turn. Request their benefit of the doubt with each other, too.

Here’s what I wrote to the FrogDog team:

Be patient with your team (especially me)! This is new for all of us. It will be stressful for some. I may change things up a few—or even several—times as we work to get this right for our crew. I am trying to be thoughtful and intentional about this, but I may miss something important and you may need to nudge me. Your team member may get upset by “tone” in an e-mail when there was no tone. Someone may seem silent or standoffish when she’s just focused and working. Give everyone the benefit of the doubt, ask questions, forgive. FrogDog is a team and we support and enjoy each other. Remember that.

Just reminding people that you want to do the best you can, yet may flub it sometimes, helps them cut you a little slack and helps create a safe space for them to share their ideas and observations as the transitions get underway.

Start with Too Much Structure

At the outset, we had a daily schedule. The daily schedule transitioned into a weekly schedule after sixty days. After ninety days, we evaluated the program to see what we should adjust. You can always more easily decide that you have too much structure and back off a bit than you can realize that you have too little structure and try to impose it after you’ve gotten underway.

In the first month, we had scrum-style check-ins at the end of each day. For these check-ins, the entire team got on a call for thirty minutes or less with quick updates on work underway, especially any changes, roadblocks, and wins. Per our distributed workforce guidelines, we conducted all meetings via videoconference.

Each week, we met in person for three hours one afternoon in the middle of the week. All of us living in the same metro area made this possible. (Obviously, if your team starts out in offices in different geographic areas, you can’t swing a gathering on a weekly basis, even at the beginning.) I called these work-in-tandem meetings, or WIT meetings. In some WIT meetings, someone presented to the entire group; in others, we had our company book club gathering; in most WITs, subsets carved off into side discussions on projects or tasks for part of the time; and in almost every WIT, we worked together separately for a bit, just in the same place. The WIT meetings helped reduce the feeling that we went cold-turkey on team time.

At the one-month mark, we dropped the daily end-of-day check-ins. We met and chatted all day already, so they’d begun to feel redundant.

At the ninety-day mark, we decided that weekly WIT meetings disrupted our productivity more than we’d like. We rescheduled them to take place every other week instead, with the alternate week including an all-team virtual meeting via videoconference, with agendas that shifted based on the week’s needs.

Later, we moved to all-virtual team meetings, with spot WITs in person when the team wanted one; shifting to ad hoc WITs happened almost organically, and not until eight months after the distributed workforce transition. By then, the team and the workflow hummed nicely; working remotely felt normal, and the workflow operated without new hitches.

Expect Pitfalls

In any transition, no matter how carefully you plan, you’ll experience hiccups—and transitioning to a distributed workforce makes for a huge transition.

As with any change, some people will never buy in. Some team members will look for and find new job opportunities. If you’ve run a company for a while and managed people for a while, you’ll expect this.

Also, especially with the intense structure you should set at the beginning of the transition, some people will grumble. Stay positive, and they’ll get through it. At the beginning, some of the crew didn’t think they’d like the videoconferencing requirement. Yet pretty quickly, they realized that videoconferencing was critical for feeling like a connected team made up of people, not disembodied voices. You feel like you know everyone better when you can comment on their new haircuts and chat about the bibelots on their desks.

A lot of the team felt completely overwhelmed by the amount of check-ins and meetings at the outset of the transition. I emphasized that we needed them at least temporarily, and everyone hung in there and got through them. I still believe that we needed them at the beginning and, by the time we didn’t need them, we knew what we needed instead.

Finally, everyone will feel a lot of change-related anxiety at first. They’ll wonder how certain things will work. They’ll check in about basic things they didn’t need to question when they worked in an office, such as how to handle office supplies, whether they’ll get home-office printers, and when something qualifies as paid time off and when it gets categorized as flex time.

Your request and reminder for patience with each other will help here—as will your vulnerability and plea for some slack at the outset of the initiative.

After the Transition, Then What?

Since the transition to a remote-work model, I’ve added new team members; though I didn’t know how hiring would work before I did it, I think it went well enough. (In fact, the newbies said they appreciated not feeling the awkwardness of the first few weeks in an office setting, when you have to be “on” all the time and don’t know what you can and can’t do with the stuff in the kitchen, the walls in your office, and so on.)

Also, I need to get my retreat-planning groove on; though we’ve all met so often in person and virtually over our first twelve months as a distributed workforce, we now need a different type of time together to relax (not just work) in tandem and think about the company’s big picture. And that sounds like a lot of fun to me, too. Now that I can’t take for granted seeing them in person every day in the regular course of the work, I appreciate in-person time with them more.

One year in, I still have no plans to move the team back into an office. Of course, the option still exists (though I hope we don’t have to take it). I’ll see how the workflow and structure evolves from here—every day always brings new adventures. And I’ll keep you posted.

Update: I’ve had a few questions since this article posted, to which I’ve responded in a follow-up article.