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Question to CTOs - are you happy? When I see what particular CTO does day to day, assuming he/she was an engineer before - it seems quite boring. It seems they've sacrificed their engineering side in exchange for a bigger salary.





The grind of constantly learning the latest technologies eventually got boring, and now I really enjoy managing developers. For me personally, helping an unhappy or under-performing developer get out of their slump is a really rewarding experience.

I don't enjoy long-winded, pointless meetings - but if you're organisation has so many of them, you'll get pulled into them anyway once you're senior enough.


> For me personally, helping an unhappy or under-performing developer get out of their slump is a really rewarding experience.

This is a pretty nice approach. Congrats.

Often people are chosen in senior positions because the sell themselves. They are articulate and have "executive presence" and they seem to know what to do, but often they don't. I wish more of them were chosen because they listen, and they knowledgable and thoughtful.


I'm generally aligned with this comment. I really enjoy helping others succeed. I also have a lot of input into the product strategy, and that is very rewarding for me also.

i think i am an under-performing developer. if you dont mind sharing some secret sauce... what are the first questions you think about asking to diagnose whats going on?

What makes you think you're under-performing?

I think the "secret" is simply to make sure people know what they're suppoesd to be doing, that they want to do it, and that they feel they have everything they need to do it. That won't necessarily always work, because not all under-performance is work-related - if you've just had a baby, going through divorce or bereavement, I'd expect you to be 'under-performing' and wouldn't try to fix it.

If you do want a chat, I'm available on email (it's on my profile page).


thanks, will drop an email (to be clear its not like i was expecting any solutions here, i just like learning about how managers manage).

Great, I'll reply to your email. As a manager, I wouldn't discuss any problems you're having in an open forum - and I'd try to do it face-to-face as much as possible. It takes time to build up trust, figure out what's going on - perhaps you already know but don't feel comfortable, perhaps you need to work it out.

I would look at three things.

- Do you have autonomy in your job ? You need to be able to do your job without having to ask for permission every five minutes. You should also have some freedom on how to do it.

- Do you feel you are getting better at your job ? Every day you need to have the feeling that you are becoming better at it. Is your job hard enough but not too hard. Too many unknowns may cause frustration. Too few unknowns make the jobs too easy and boring.

- Purpose - Do you feel that everyday you are making a difference? You need to feel that you are making somebody's life better.


ahh. 2 and 3 are killers. i need to go meditate on this.

to be fair tho, i don't expect most tech jobs to actually have a strong sense of purpose. it's that old SV trope of "we're making the world a better place through minimal message-oriented transport layers".

#2 is a great question. its kind of like looking at the job through game design. its true i dont feel like i'm becoming better and i dont see a clear path to becoming better. I will probably actually use this line of thinking to have a convo with my manager.


I'm not a manager, but I think I might have been where you are now a year ago. My agency and I ended up separating. At the time I felt a tremendous sense of relief, but now, I feel mostly regret because of the potential of that job and how ideal it had been in the first 2-3 years. I miss everyone terribly and wish I could magically go back to the good times because they were truly wonderful, like something out of a dream.

If I could do it all over again, I'd completely omit the technical from my decision making. Odds are that you're probably doing just fine and suffering from something like imposter syndrome. In my case, my billable hours had started to fall, which is the one thing that can't slide for long. I was having doubts about my project and my contribution to it, for personal reasons stemming from my financial troubles after the housing bubble popped. I should have asked for a sabbatical.

Maybe you can step back for a moment and imagine that if the technical needs of the project are being met, what is your vision for the future of the company and the prospects of the other employees? Have some of them been snatched up by Fortune 500 companies? Will some of them benefit greatly by having your company on their resume? Have some of them been able to grow as individuals, perhaps continuing their education or even finding happiness and love? If you feel a resonance with those types of things, you might be surprised to find an interest for it reflected in your own bosses. Maybe they are focused on making payroll and haven't had the support they need to consider those other things. If you have an HR person, maybe you can sway the conversation in those directions. If not, maybe you can talk management stuff long enough that people start to want you in that role. Please don't underestimate vision like I did.


thanks :) i definitely do have a bit of imposter syndrome, although i guess i actively seek it out. "if you're not the dumbest person in the room you may be in the wrong room" and all that.

i have rarely had a helpful convo with an HR person though. always hear the warnings at the back of my head that they're not on my side, they're on the company's side.


FWIW I've given up on trying to gauge my own performance. I've plainly been disappointing people when feeling like I'm working about has hard as I could. I've (over, and over, and over) been complimented on both the quantity and quality of my output when I feel like I'm half-assing it, at best. There doesn't seem to be a much relation between how I feel like I'm working and what others perceive.

Are you under performing due to lack of competence, or lack of motivation?

probably a little of columns A and B. i guess we're all like that? (we as in underperforming devs)

Sorry, not a manager myself, so I can't help with motivation. But competence can always be gained by practicing. Try a project on your free time. Make an app with ads. The bit of extra passive income can be your carrot on a stick.

haha, thanks for the idea :) i have no problem with passive income (i've done some teaching on the side, it generates passive income, it doesnt motivate me at all) but i do wanna work on a new app.

As CTO I'm trying to incorporate both sides: some hacking under the umbrella of a "Research Lab" and oversight/representation.

I definitely feel the lack of management training.

Being a nerd for decades doesn't mean you know how to lead a bunch of nerds ;)


I found the hardest thing to initially get my head around was going home at the end of the day wondering what I'd achieved.

Moving from tangible daily outputs (code etc), to longer term feedback loops can be just as rewarding, you just need to step back slightly.

Empowering others to achieve their potential, watching them grow. Watching great products evolve. Understanding and directly influencing tech decisions. Being able to look further than the next sprint. Interfacing with external parties, seeing how they approach similar / new problem spaces.

IMO, this never gets boring.


going home at the end of the day wondering what I'd achieved

Keep a log throughout the day. It helps.

Failing that, use email, issue trackers, repos, purchase orders, inventory logs or other major communications channels / process interfaces to retroactively summarize progress. I currently do this weekly, and use it as input to reporting and planning processes.


Hardly! It's about impact & working with people who complement your weaknesses - think about how much you don't know, even just as an engineer.

A more senior leader I very much respect - when I was about to make the transition - put it this way: "I was doing great as an engineer but had so much I needed to get done, so they helped me put together a team of 4, which was great, because I could accomplish almost twice as much; then it was 30 people and we had a whole product I was proud of. With 200 I know I'm changing the industry..."

You have to learn different skills - how to motivate people, how to see potential conflicts and roadblocks and use them constructively - but the technical skills you bring to the table can make your impact much stronger; and I think I get to learn new ones at a much faster pace at a compromise that I can't go as deep in more than a few spots compared to full-time engineering.


I suppose its partly how you perceive the work. Programming carbon-based neural networks can be an interesting technical challenge...

I really enjoy getting to influence projects at their genesis, being a CTO gives me a mandate to intercept & triage requirements. Trading off some day-to-day coding for this opportunity is a win for me.



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