Leading Remote Rockstars

Jenn Sydeski
2 min readMar 14, 2020

How to get the best out of talented people at a distance

One challenge of having a bunch of really talented high-performers who are fractional and not even all in the same city is coordinating digitally instead of the easier “in each others’ faces” office-style communication and progress.

0. Hire great people. As long as this is where are starting from, managing work and leading team at a distance is way easier. I know this is a bit of a cop-out entry, but, frankly, the rest doesn’t really work if you don’t start with great people. Having done this, you can:

  1. Offer space. While they figure out their literal space, you can offer them mental space. High performers know when they work best and are going to do the thing they are here to do best if they can avoid interruptions while in flow. Trust your people and let them work.
  2. Have a clear communications policy. Draft a version and open it up for discussion and iteration so you have the team’s need incorporated and their buy-in that this is something they can do and that if they can trust others to meet this policy, they can get done what they are trying to do. For example, we have a “once per day” check and response minimum for all email and Slack, meaning that nothing internal will sit for more than a day there, and we don’t encourage people to be in their email and Slack constantly, so we all have Google Hangouts on our computers and phones for any urgent communications. This gets used rarely, but gets noticed immediately.
  3. Have a well-organized file system. Make sure everyone knows how to navigate the company’s Google Drive or Dropbox or whatever. Are your permissions set appropriately? Do tools have tutorials and appropriate notes for use on anything people touch semi-regularly?
  4. Measure with care. It’s natural to unintentionally count the number of interactions or amount of time you seem to see coming from your remote team. Keep in mind that what you speak about, ask about, and reward for is what you will maximize. Ask about hours and email count, you’ll get more hours and emails flying. Ask about outcomes and progress, and that’s where their efforts will go.
  5. Expect greatness. Approach your remote workers as those who have more control over their environment and working conditions than they would otherwise. Performance (not just theirs- yours too) seeks to meet the expectations set for it. Expect greatness of each other, because you are confident in each others’ abilities and dedication.



Jenn Sydeski

CEO of Connect Wolf, professor, tinkerer, operations nerd, recovering scientist, and mama.