When Remote Work Didn’t

(Originally posted online here)

A staggering number of bits have been spent here (and elsewhere) extolling the virtues of remote work. No doubt it’s been a boon for some workers and companies but the hyperbole surrounding its benefits and its casting as a near-universal good stunts an important conversation.

Everything in this world costs something — including remote work — and it does no good to pretend otherwise.

In particular, the challenges facing a senior leader who works as a remote singleton are different than those faced by an individual contributor, or people earlier in their career. They are real, they are substantial, and they shouldn’t be glossed over.

I don’t claim any monopoly on truth, but the cost of being a senior remote singleton was high enough to cause me to recently leave a company and a team that I otherwise really loved.

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.

I spent time meeting with key engineers, execs, and board members and came to the conclusion that joining was an opportunity too good to pass up.

For the first year things went basically as I expected. Everyone was working from home so the only real reminder of the distance between us was managing the time zones. (I’m in California, the company HQ is in Raleigh, NC and has offices in Sheffield, UK and Tel Aviv, IL) The hours were long, but the work was super rewarding and the people really made it fun.

Then a strange thing started to happen…

The pandemic waned and people started returning to the office. Very slowly (and then very quickly) I could feel a gap growing between me and the people with whom I was working. Sometimes I would be the only person on a Zoom call with 10+ folks in an on-site conference room.

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.

Eventually the reality became obvious; to do the job to the standard I expected I needed to be full-time in the office in Raleigh. Since I have kids in high school, moving wasn’t an option right now — though we talked about it seriously.

That meant it was time to move on from a company I admire and a team I love.

Lessons Learned the Hard Way

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

If you’re a senior leader considering a remote singleton position then I encourage you to think very carefully — especially if big chunks of your team will be in-office and you won’t.

• 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.

In my opinion, the more senior you become the costlier that choices — so weigh your options soberly. If you are considering a senior role with a company that is “remote first” (ie. basically everyone is remote) then you can expect the costs to be evenly distributed across everyone and much of what I have written won’t apply.

However… If you will be a senior remote singleton leader then you really should ask yourself if you will be able to effectively lead teams who are in-person when you are not.

I couldn’t do it, and I tried really really hard.

If you figure out how to do it, I’d love to hear from you!

-dave :-)

p.s. Thank you to Rich Sanzi for encouraging me to share this. If you think I’m an idiot, please direct your pitchforks to him ;-)