Why the name 'cto.coffee'?

You mean, you need a reason to associate any term with coffee? Well, then, it’s a kinda long story, but you asked.

In my first job as a CTO, there was a time, when the team got too big for me to have regular 1on1s with everyone on the team. Which is a fancy way of saying, my management bandwidth wasn’t enough for the size of the team anymore. Which again, is a fancy way of saying, that I needed to do a reorganization.

My point being, when I introduced teamleads (the reorg itself), I stopped doing 1on1s with some in the tech organization. Some would say it’s good practice then to do skip-level 1on1s, but I have a very specific idea of what a 1on1 is and how it should generally be done, and it was important to me, to signal a clear distinction between what I did before and what I’d be doing after the reorganization.

A good way to clarify distinctions is by using different names for different things, so I needed a new name for what I planned to do with the people in my organization that weren’t my direct reports.
I was CTO and my 1on1s had basically always been done as walks to a nice café. So it kind of was a fitting to call these it’s-not-a-1on1 talk opportunities “CTO Coffee”, as the people were most likely to get coffee with me as the CTO.

At some point Robert pointed out to me, that the .coffee TLD was available and that cto.coffee was still for the taking.

This then was the perfect opportunity and name for a something I wanted to do for some while now:
Talking about the human side of software development, and especially about the challenges of the role Engineering Managers.

The “talking” part is really intended as a conversation with other people in such roles, and less so as a “I’ll tell you all about it”.

Because what really helped me in the past, as I fulfilled role as Engineering Manager, was talking to other people in similar positions, or generally to people who actually appreciated the humans they worked with. Nothing else helped as much as conversations with people who really cared about people.