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> A CTO at even a small software company that is writing code is doing their job wrong if they aren't quickly evolving into a role where they don't even touch c

> A CTO at even a small software company that is writing code is doing their job wrong if they aren't quickly evolving into a role where they don't even touch code. hard disagree here. When I worked at Fastmail (less than 50 people), our entire leadership was technical. Even our least technical leadership person (CFO?) was more proficient than most junior developers. It's a beautiful thing, because business goals get aligned with programming goals, on a long lasting technical project that is very important. No more jostling over what some person with product vision wants versus what needs to happen, refactoring, etc. I actually think the biggest challenge for the leadership team at fastmail is the leadership part, not the programming part. A bunch of really really smart tenured developers suddenly navigating how to be managers, CEO, CTO, etc, is much more challenging than writing some fixes for a new Apple Calendar quirks. It was cool to see growth from the leadership who took the part of 'ok I am a real C level at a company with a growing headcount how do I do this right the first time?' I think, having a leadership that still keeps their hands in the dirt is a good thing. Plus they happened to all be the best programmers we had. Leapyears better than anyone else I think.

orev 4y ago
> I actually think the biggest challenge for the leadership team at fastmail is the leadership part …and you just identified why writing code in a leadership position is a problem, so actually it wasn’t working. There’s no doubt that leadership with previous experience in the trenches is a benefit, but they should not be actively doing it in that role. Leadership is a full time (or more) position, and coding is a distraction from that. We have the phrase “can’t see the forest from the trees” for a reason; Leadership needs to be looking at the forest almost all the time, and they can’t be effective if they’re stuck in day to day coding issues (the trees).
rmk 4y ago
Writing code is a different job from management. Of course you will be very successful if you have good management skills and you combine them with strong technical acumen. But writing code while being a manager is a recipe for failure. What you saw at Fastmail is pretty much standard in the industry: above average intelligence in the worker ranks but way below average ability and intelligence in the management ranks.
- calvinmorrison 4y ago
  > What you saw at Fastmail is pretty much standard in the industry: above average intelligence in the worker ranks but way below average ability and intelligence in the management ranks. No, the opposite. Most of the C level is extremely smart. Smarter than when I worked at a research lab with all PhD's and Professors. All are or have been leads on successful open source projects, contribute to IETF, one guy ran the Perl project for years, and so forth. Very smart crew. One of the best things about working there was being around people smarter than me

orev 4y ago

> I actually think the biggest challenge for the leadership team at fastmail is the leadership part …and you just identified why writing code in a leadership position is a problem, so actually it wasn’t working. There’s no doubt that leadership with previous experience in the trenches is a benefit, but they should not be actively doing it in that role. Leadership is a full time (or more) position, and coding is a distraction from that. We have the phrase “can’t see the forest from the trees” for a reason; Leadership needs to be looking at the forest almost all the time, and they can’t be effective if they’re stuck in day to day coding issues (the trees).

rmk 4y ago

Writing code is a different job from management. Of course you will be very successful if you have good management skills and you combine them with strong technical acumen. But writing code while being a manager is a recipe for failure. What you saw at Fastmail is pretty much standard in the industry: above average intelligence in the worker ranks but way below average ability and intelligence in the management ranks.

calvinmorrison 4y ago
> What you saw at Fastmail is pretty much standard in the industry: above average intelligence in the worker ranks but way below average ability and intelligence in the management ranks. No, the opposite. Most of the C level is extremely smart. Smarter than when I worked at a research lab with all PhD's and Professors. All are or have been leads on successful open source projects, contribute to IETF, one guy ran the Perl project for years, and so forth. Very smart crew. One of the best things about working there was being around people smarter than me