Best Practices for Structuring and Managing Distributed Workforces

Image credit:

Image credit:

When I couldn’t find a source of information on-line with best practices for managing distributed workforces—or guidance on how to transition from an in-office to a remote-work team, I reached out through my network and spent hours talking to other business owners and executives about how they did it and what I needed to know.

By the time I finished my one-on-one, in-depth conversations with about a dozen people, I had a massive OneNote file full of scribbles and bullets.

For anyone considering a distributed workforce in their organization, let me save you the time I spent. Here’s the how-to I sought on best practices for structuring and managing a distributed workforce.

Update Your Company Documentation

Let’s get the legal out of the way immediately, as everyone agrees you must have it, yet no one wants to dwell on it:

When you transition to a distributed workforce, in which all employees work remotely and you do not have a central corporate office, you should consult with your employment attorney and your information technology firm to update your employee handbook, your policies and procedures, and your company operations manuals and documentation. If you have employment contracts or any other human resources paperwork, you need to update these documents with your law firm as well.

Also, you should reach out to your insurance brokers to ensure you have all your bases covered when it comes to liability and property and all the rest as well.

Get the Right Technology in Place

Your current IT-services vender may not know much about what types of technology work best for distributed workforces, but you should find out if it has any expertise or guidance all the same. At the very least, as you assess technology for the transition, consult with your IT services company to ensure the software you have in mind marries well with the other technology your company has in play.

In short, distributed workforces will not work without solid, reliable, quality technology. All software and systems must live in the cloud, accessible via any Internet connection. To function ideally, distributed workforces rely on videoconferencing with screensharing, presentation, and collaboration capabilities; instant messaging and chat applications (for work conversations and for informal socializing); project management systems; and file storage and management platforms.

And every system you use needs to have an app for iPhone and Android. (Fortunately, these days, most established technologies do.)

Set Structure (and Rules)

Though you should treat the people you’ve hired like adults and give them responsibility, you should realize that everyone likes guide rails as well.

We all like to know what others expect of us and how we can succeed in our endeavors, and few employees feel more like they need guidance on what their companies expect than employees who work remotely. After all, they can’t glance around the office to take pointers from what everyone else does to succeed.

I set the following guidelines for the FrogDog crew:

  • During working hours (8:30 a.m. to 5:30 p.m., U.S. Central Time), all employees must respond to inquiries (including calls, instant messages, and e-mail messages) within fifteen minutes, unless they have meetings or calls on the calendar.

  • Keep your team apprised of your schedule. If you have a meeting or a call, put it on your calendar. If you will be out of pocket during normal business hours, let your team know. If you have time-intensive personal to-dos that need to take place during business hours, you must coordinate flex time with your manager or request paid time off.

  • All meetings and calls must take place via videoconference, unless you need to take a call or attend a meeting while in transit. In the latter case, make it a quick call. Meetings and substantial conversations require at least virtual face time.

  • All projects must have a dedicated, detailed project plan in the project management system to which you must link all billable time. All project documentation, discussion, and communication must live in the project management system, including call notes and e-mail exchanges. All final determinations must have a record in the associated project plan in the project management system. If you don’t have it in the project management system, you don’t have it.

We’d had the latter rule prior to transitioning to a distributed workforce, yet people continually drifted away from compliance in favor of the hallway-conversation habit, the determinations of which they forgot to write down no matter how many times we nagged them. These bad habits, even when everyone worked within the same office, meant that the entire team never had full information from the rest of the team at any given time and projects suffered as a result.

Once we transitioned to a work-remote model, rarely could someone have an “accidental” project-related conversation that they forgot to document because they didn’t have computers in front of them. As a result, everyone benefited.

Of course, we still needed to regularly remind everyone about the rules and enforce them when necessary. And we needed to ensure everyone used the technology we’d set up. They had a little leeway at the beginning to get used to the new systems and to acclimate to the new world order, yet we kept the grace period short.

We couldn’t afford to let things slide if we wanted to keep our work on point and our company effective and efficient.

Set Your Meetings

As mentioned in the caveats and benefits article, distributed workforces require intentionality not needed in an in-office environment.


Each manager sets a recurring monthly one-on-one meeting with each direct report. I designed the agenda-free meetings to capture the intangibles you miss when you don’t inhabit the same space for the bulk of your waking hours five days a week.

After all, you can see someone in meetings and talk to them via chats and e-mails and never pick up that something seems different about their demeanor. And if they only see you in structured formats, they may not feel they have the quiet time with you to bring up things that don’t feel worth setting a meeting, yet still have a lot of importance. Without intentionality around setting catch-up times, you may not know they got engaged over the weekend, or that a favorite aunt received a terminal diagnosis, or that their kid just won the spelling bee.

While these matters may not have critical importance to the work at hand, they have importance to the people you care a lot about. Agenda-free meetings bring these work-tangential-yet-important topics to the surface.

Doesn’t everyone want to be asked how they’re doing by someone who genuinely cares?


Don’t forget teambuilding events—they have more importance than ever in a distributed workforce structure.

We do a company book club, in which everyone reads the book and discusses it via videoconference. We’ve done team educational sessions, during which one of the team or someone outside the team gives a presentation to the group via videoconference. We’ve postmortemed projects, reviewed case studies, learned technical and nontechnical skills, and reviewed updates to our current technologies and received tutorials on new technologies.

I thought working remotely would prove hard on company culture, yet I’ve found it negligible. In fact, the team time turns out to have more importance and respect when it can’t get crammed into a happy-birthday dirge at lunchtime in the kitchen followed by a quick bite of cake. And I’ve discovered that distributed workforce structures have their own cultures—ones in which people work independently, with a team at their service when needed.

Strategic Planning

Annual or twice-annual events or retreats where all employees gather to think through the company’s bigger picture have more importance for distributed workforces, because they turn into concentrated team time. Ensure you build into them time and space for teams to work in tandem on existing projects, have fun together, and relax. (Trust falls optional.)

The Advent of the Distributed Workforce

Given that the technology making distributed workforces feasible only recently came to life—honestly, before the cloud, you just couldn’t work remotely more than occasionally—all but the newest companies work in offices because they came into existence in an office. Offices are the status quo.

However, as the cloud and our comfort within it gets more entrenched, and our entire world turns more digital, more companies will consider transitioning to a distributed workforce environment, just as FrogDog did. Transitioning from one structure to another has challenges that starting out in a structure doesn’t.

Next up: An article on how we managed the transition from an in-office team to an all-remote, distributed workforce. (Spoiler: I found it easier than I expected, yet I had a lot of preparation in place that made it so.)