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Real questions from someone who has been leading remote teams for awhile:

Which one helped you better focus on your role and deliver what you needed to help the company?

Hearing all these things in-person can definitely be good context, but there is also a risk that you hear something wrong, succumb to gossip, or lose focus based on worries that may not be necessary. (Of course I’d argue it’s best for the employee to judge rather than be left in the dark, but I’m curious here specifically)

Part of this comes down to company culture as well - getting remote comms channels down is really hard, and takes a LOT of effort from senior management, especially for things that are nuanced or may change. How do you not panic anyone but also let them know there may be a need for urgency, etc (in-person works well for that)

When you were remote, was the CEO remote as well, or just you?




Something to consider about scalability is in the long term either the company will figure out how to scale beyond all workers sitting within five feet of the CEO or it'll go out of business or they'll somehow have over a hundred employees per square foot. So over a long enough timescale the problem kinda fixes itself.

As I moved up in the industry it eventually became normal for my peers to be two floors away and I never see them IRL, or later on, for my boss or peers to be 100 to 2000 miles away.

If my closest (in the sense of daily peer cooperation) coworker is three hundred miles away, does it matter if I'm at home or in an office with 600 people that I don't directly work with in it?

Not ever job will forever be entry level with a dozen IRL peers within a dozen feet. Companies that can't scale, do not survive long term.


It's an interesting question- which one helped me focus on my role and deliver? I can see in the abstract that distributed work can both demand and benefit from strong focus. In my case, when I was a "distributed" worker I had a much narrower scope of responsibility and along with that, less ability to gauge whether something was "good enough" to ship and perfectionism/procrastination and poor remote communication on my part really hampered my work. As an in-person worker, when we were betting the company I was able to constantly assess all work being done by all the company and pivot us and others to what was the most risk-mitigating thing we needed to do. When distributed, I suppose that was the role my Engineering VP was supposed to do and I was just focused on my narrow domain, but overall the company wasn't able to leverage my problem solving and triaging strengths and I was just a remote coder/designer resource with a task. When it was late, I knew it was bad, but I didn't have a sense of the consequences to the broader team (just my own job). In hindsight I think management was trying to shelter me from the stress and I respect that but I was really stunned at the end of the day how out of the loop I was. I was East Coast, CEO was East Coast but four hours away, some execs were West Coast, Engineering Lead was UK. I did a great job for them with engineering for in-person clients, but when I switched to being managed from overseas it really didn't work out. I always didn't want to interrupt the UK VP since he was so busy and/or because I was behind but the communication dynamic was ultimately dysfunctional for which I take more than half the responsibility. (I have since been on the flip side of that coin with a remote worker! It's an interesting challenge.)


Thanks for these answers - super interesting and helpful. Much appreciated!


By definition the CEO is not remote, right?


Fair enough - I meant was the CEO in an office with others, or was everyone distributed. I find that when it's "a few folks are remote" vs. "everyone is remote" (even culturally) this makes a big difference in how context is provided to an organization.




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