Distributed teams
Working with people you cannot see, in time zones that do not overlap with yours. The best preparation for agents that I did not know I was getting.
Also called offshore team, remote team, offshore engineering
For six years I led engineering across three continents: typically five engineers in India scaling to about fifteen, a support team in the Philippines, freelancers, and roughly fifteen US staff. Before that I was the technical lead for a team in Pune delivering for Adobe and Livefyre.
The constraint that shapes everything is that you get one round trip per day. You cannot look over a shoulder. You cannot clarify at 2 PM. Whatever ambiguity you left in the document, you will get back in the morning as work built on the wrong assumption, and you will have burned a day.
I learned to write specifications past the point that felt tedious and to define "done" before work started. I reviewed the artifact rather than trying to watch the process. When someone misunderstood the document, I treated that as my defect rather than theirs.
Those habits transfer directly to working with agents. I assumed my CTO years would be the least relevant part of my background for this work. So far, they have been the most useful.
See also Context engineering and Agentic operator.