Tips for Small Businesses Managing Remote or Hybrid Workers


Editor’s Note: Each week, Maynard Webb, former CEO of LiveOps and former COO of eBay, will offer candid, practical and sometimes surprising advice to entrepreneurs and founders. To submit a question, write to Webb at [email protected].

Q. We have a small team. Someone is on extended leave and another person is traveling a long way and working remotely. How do you make sure that everything continues without a bullet falling?

-General partner in a successful boutique business

Dear General Partner,

We live in a new world of work where people work from all over the world and we have to cover different time zones and collaborate without being in the same office. I have long liked that people work from anywhere, so I think there are ways to deal with this effectively. Yes, it will be riskier than usual, and maybe out of your comfort zone, but you can do it all successfully. Also, what matters are the results, not the wait time.

The best approach here is to plan everything: think about what happens now and anticipate what will happen next.. In other words: on plan. Think about each eventuality and have a game plan for all of them. It starts with having visibility into the current workload, as well as seeing what’s coming up as much as possible.

Then on communicate. It is necessary to have open lines of communication and frequent checks. Be prepared to connect more than if you were in the same physical space. Often the bullets dropped are not things that weren’t done but things that weren’t communicated. It’s easy to solve: communicate more than you think necessary.

Be ready to adapt. Think ahead about what success looks like and what you will do if you don’t meet your requirements. How are you going to reconcile if this doesn’t work? What steps can you take to get things back on track? What is the deadline for this leave and this trip? Is it finished or undefined? It helps to know exactly what you are up against so that of course you can correct it if necessary. Seems like it’s not an eternal thing, which means it will be in your rearview mirror soon. Take the learnings and lessons for the next time.

Plan to be successful. Have good intentions about where this is going. A positive attitude helps unleash more creativity in problem solving and fosters more grace through the inevitable bumps along the way.

Doing this work comes down to planning and communicating and having empathy on all sides. It is also a matter of patience and trust. I believe this experience will build confidence by allowing people to work the way they want and see how much you can still accomplish. I hope you will be reminded that the team is amazing and resilient, and that you get through this new situation successfully. And if not, having an adjustment plan can ensure that you’ll be able to stay the course.


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