When Remote Work Didn’t

Lockdowns Aren’t The Same As Remote Work

After a full year working remotely from home during the COVID lockdowns I thought I had a good handle on what “remote work” meant. So when Erik Troan and Todd Olson invited me to join Pendo.io and help it grow into its next phase, I jumped at the opportunity with both feet. In early 2021 Pendo was a 400 person company rapidly on its way to 1000 people, and made products that its customers truly needed and deeply loved. Like all rapidly growing companies they were experiencing some organizational growing pains in engineering and were looking for someone who had lived (and managed) through those inflections.

You Can’t Lead from the Back

After a while I started to notice that I would dial into meetings to discuss some decision only to find that the group had already informally discussed it via impromptu hallway conversations and made good progress. That was efficient and great for the business, but it meant I was constantly rushing to catch up to a discussion I was supposed to be leading. Over time I started to feel like I was holding the team back more than helping it forward — and that sucked.

Lessons Learned the Hard Way

Here’s the ugly truth; without knowing any better, I set myself up for failure.

  • A pretty substantial amount of discussion, debate, and consensus occurs outside of scheduled meetings and if you can’t be in it then you will be perpetually playing catch-up. “Hallway conversations” are real and the people who discount them are not being honest.
  • It’s hard to do good career development for people you never see in-person. It’s not impossible, but you shouldn’t underestimate the added friction. A Zoom call is not the same as a walk with someone who really needs your advice. They are qualitatively different experiences and you should plan accordingly.
  • I used to think I was a raging introvert but sitting everyday in the same chair for 12 hours — staring at the same screen — was super unhealthy for me. I still think a cocktail party is a special kind of hell, but I now recognize that I need a change of venue and the presence of other humans in my life. Maybe you don’t, but I bet you do…

Meanwhile, Back In the Real World..

It’s good to have options. More choice is better than less. But.. Never lose sight of the reality that everything costs something. Nothing is free.



Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store