How I keep the best remote employees all to myself

They are my remote superstars and you can’t have them without knowing their secret of success.

Many successful companies have made the leap to distributed remote teams but how do they keep the best employees happy?

You have undoubtedly seen the headlines. A giant enterprise recalls thousands of remote workers and another established tech company orders entire remote divisions to report to the nearest regional headquarters or be terminated. You might think that remote work has lost its shine or finally been exposed as a trendy fraud.

Nothing could be further from the truth. Converting an entire division or company from an office-based workforce to a collection of cohesive remote teams requires planning, substantial re-interviewing, critical assessment and difficult staffing decisions. When none of that happens, failure is inevitable. You might as well order an accounting division in Omaha to relocate to Lisbon without teaching anyone Portuguese.

Silent Success

Casting an eye on the current state of the remote work landscape, you will notice that at the same time as these poorly conceived remote conversions are crashing, entire companies are thriving with completely remote workforces and intelligent senior managers are quietly assembling distributed teams of highly qualified remote professionals. These companies have it figured out.

These senior managers know how to organize business units to work efficiently without a central office. They know how to hire just the right type of employee who thrives at home or bouncing from one island paradise to another, and they know how to keep those employees happy and productive. The management skills required to identify these gem-like remote employees is widely discussed and most books and articles get it nearly right.

But, in my experience, identifying and hiring is the easy part. It’s keeping them that gets tricky.

The Two-way Street

To keep the best remote employees happily meeting goals and deadlines, project after project and quarter after quarter, it takes more than paying them a fair wage and tasking interesting work. It takes exceptionally good management.

No one jumps ship faster than a great remote employee under bad management. They have learned to spot the signs early even if they missed them (or were lied to) during the interview process, and they know that it isn’t worth waiting around for it to get better.

Why is this? What is it that excellent remote employees know in their bones that some company executives are apparently clueless about. After all, middle managers (the ones directly over those doing the revenue generating work) only supervise their teams under the direction of upper management. So what causes these fantastic remote human revenue machines to stay or walk away?


Trust is the super glue that holds remote teams together and binds them willingly, and in some cases fanatically, to their managers. The best remote managers don’t micromanage. They don’t bungee boss. They don’t suddenly call developers into a video conference and demand to know what they are working on.

Instead, they set intelligent goals for each member of their team. They use regular group check-ins to assess the progress that each is making toward those goals without interrogation techniques and use milestones as… milestones: meaningful points on a progress bar. This means that experienced remote managers don’t give a fig about when someone started working today or exactly how many hours they put in on Thursday or if they took a two hour lunch on Monday to go for a long run. Such indicators are even less meaningful when applied to distributed workforces than cubicle denizens.

Call me The Sweeper!

Grab a Broom

Remote managers set individual goals, inform each team member, then trust that they will be reached. They still keep a close eye on progress, not out of suspicion, but in the interest of obstacle clearing. Great remote managers are the sweepers and mine clearers for their teams. The more efficiently each team member reaches their next goal, they better everyone looks, especially the manager.

Remote Secret #23
Great remote managers are the sweepers and mine clearers for their teams.

Of course, trust goes both ways. If an experienced remote employee suspects that the status questions in the daily standup have a big brother agenda behind them and managers are trying to exert control over how each chunk of the sausage is made, then rebellion is inevitable. But instead of taking to the streets, the best remote ninjas quietly turn to job boards where they are eagerly snapped up.

Hire carefully and trust comes easily. Check in regularly with the intention of identifying and removing obstacles, not micromanaging. And if your trust isn’t being paid back with solid results, move quickly to resolve the issue, if possible, or rehire if necessary with lessons learned from the experience foremost in your mind. Each member of your team is trusting you to hold everyone to the same standard. Don’t disappoint them.