Ask HN: CTO contemplating returning to developer role – seeking advice | Hacker News Reader

Ask HN: CTO contemplating returning to developer role – seeking advice

12 pointsvappolinario15 comments

I've been grappling with a significant career decision, and I could use your insights and advice. I'm currently serving as a Chief Technology Officer (CTO) at a tech company, but I've been seriously considering a move back into a hands-on developer role. However, my apprehension stems from the fact that I've spent the last six years primarily focused on leadership and management rather than coding.

I'd like to hear from anyone who has experienced a similar career transition, or from developers who have worked with CTOs who made the switch back to coding. How did you navigate this transition, and what were the challenges you faced?

Here are a few specific questions I have in mind:

    Skill Gap: I'm concerned about the gap in my coding skills. How can I efficiently catch up on the latest technologies and best practices after being away from the keyboard for six years? I've worked mostly with C# and .net, but I do have some experience with JavaScript.

    Balancing Act: How can I balance my current leadership responsibilities with the goal of transitioning back to a developer role? Any advice on time management and setting realistic expectations?

    Company Culture: For those who've been in a similar situation, how did your team and organization react to your decision? Were there any issues or concerns that arose during the transition?

    Personal Satisfaction: Ultimately, what has been your experience in terms of personal job satisfaction and fulfillment after making a similar switch? Do you regret the decision, or are you content with your new role?

I'm really torn about this decision and would greatly appreciate any advice, anecdotes, or insights you can provide. I understand that individual experiences can vary, but hearing from the HN community would be invaluable in helping me make an informed choice.

You may want to consider being hands on for a week or two in your current company. Best way would be to start a hackathon within the company or participate in outside hackathon, build something that can be useful to the company is some different tangent. Don’t just build features but something on a tangential lines or something that your team can use as a fun project.

After two weeks, you’ll likely work on it to complete the project. You can later decide if you like this more.

Few things to note with transition comes different pay scale. You may have less say in overall direction or even the best practices and standards.

I had transitioned from leading teams to IC role and had observed these things, so I can only imagine it for being a CTO to a contributor.

> Few things to note with transition comes different pay scale. You may have less say in overall direction or even the best practices and standards.

Definitely be prepared to be paid less and have your opinion matter less.

But that may be okay. With less authority comes less responsibility. That may even be what you are seeking.

I've experienced this at my current org, where sometimes I'll just give a suggestion based on my experience. I am in a peer dept of the engineering org and see and hear a lot, but am not an engineer. My suggestion may or may not be heard and acted on. Which, to be fair, is exactly the same position when an engineer makes a suggestion about something in my wheelhouse.

I also think that performing this transition coupled with a move to a new company is probably a good idea. While it is fine to trial this with your current company, moving companies means a clean break. I can see folks deferring to you in the old org, making the new CTO's life more difficult.

I'll give it a try. Thanks.

Such a great idea

First off, you're not alone - https://charity.wtf/2017/05/11/the-engineer-manager-pendulum.

I haven't made quite the same transition, but I did start coding again last year after 10 years in non-coding leadership roles. Assuming you had decent technical chops in the first place (probably the case given your current role), I would not worry at all about getting back into it. I have a similar .NET background, and I was able to build a product from scratch that did pretty well on Show HN a couple of days back. Used .NET 6 (nice to come back to), React with Tailwind (no prior experience), AWS infra (no prior hands-on experience), etc. Not a big deal, and SUPER enjoyable to be coding again!

Good luck! This decision is not irreversible by any means.

I did this. I was a developer my whole adult life and jumped from that to law school in my 30's. Graduated, become an attorney, decided I wanted to code again after a few years, and became a developer again. By the time I made the decision to switch back, I was out of hands-on development for about the same amount of time as you. I worked on a lot of different things as a developer, so it was hard to pick just one thing to brush up on. I figured I would try to get an interview for something I was interested in, then brush up on whatever tech stack the company was looking for. I applied for a job that required a niche skill I had and was surprised I got a call after my first job application. I got past the HR phone screen and had about a two-week gap to prepare between the HR phone screen and the first technical interview. I was doing well on the technical parts of the interview, but the hiring manager was noticeably checked out the entire time (he even took a phone call during the interview). I got the feeling he didn't review my resume before the interview and was annoyed I got past the initial phone screen since I hadn't coded professionally in years. The team member he had on the interview with him was much more interested and kept the interview going.

A week later, the HR person called back and said the hiring manager was concerned by how long it had been since I was a developer. That's what I expected would be the problem, so I changed strategies. I decided to get my foot in the door and work my way back up to the level I was at before I went to law school. That worked and I got a job that paid way less than my attorney salary and about 25% less than I was making as a developer at my last position (not accounting for inflation). I've enjoyed the job enough that I put "working my back up" on hold.

I don't know your situation and how big a pay cut you're willing to take, but that worked for me. Don't get discouraged, it's definitely possible. I'm "caught up" in my tech stack and feel comfortable enough to interview elsewhere, but I don't want to right now.

do you want to transition to IC role within the same company? if so, then dont. IMHO. - tough to reset power equations. people may not be comfortable around folks they have reported to many levels above. - 6 years of mgmt role is good experience to leverage for something else. - if you've just had a kid, an IC role might be tough to manage. - if you still want to do it, one way could be to take on small tasks that dont hold uyp the release almost independently for some time. and then when you think you are ready, do it.

but honestly, im not even sure how mgmt will see this. companies usually dont like people demoting themselves. best look for a new company. all IMHO

I did something similar to this last year. Went from site Engineering manager at a multi-national aerospace company to IC role and don’t regret it.

I did resign, and started in a software architect role at a smaller company. Did that for a bit and then moved to become their lead data scientist.

I was in the eng. management role for nearly 10 years but kept my skills relevant by working on lots of side projects.

Trying to manage a team remotely through lockdown and the never ending dance of aerospace mergers and acquisitions followed by the inevitable reorganisation was largely what prompted the change.

How big of an engineering org are you in charge of? If you're the "CTO" of a 5 person org then this is no different than transitioning from an engineering management role. There are lots and lots of former posts on HN that give good advice for dealing with this sort of move.

oh! I am a CTO, and, I code everyday. so, you don't need to step back (actually, anything you choose, it should be a step forward). no-one can stop the things you love to do. also, no-one can justice on the things you do to feed yourself too. find the thing you love, the thing can feed yourself, do it, both. at the end, goodluck with your choose.

big question, why? personal choice or is your team downsizing?

Re: skills - my standard advice is, every engineer should learn Next.js and launch a personal project using it. That builds familiarity with some modern tools.

Re: career development - just make sure you have a plan for where you're trying to go long term. Going back to being a contributor is fine if that's what you want, but don't sell yourself short as a leader.

I'm a mid-level engineering manager in a Fortune 1000 company, I spend about half my time doing "manager stuff" (mentoring, leading meetings, high level architecting) and half my time coding (mostly behind-the-scenes platform stuff like tooling, devops, testing). I was unfamiliar with much of our tech stack when I started, but started making small improvements where I saw they were needed, and slowly have been making my way thru the app and learning more.

hope this helps!

Both, personal as I have a child now and I want to spent more time with her and be more present. On the other hand, I'm rethinking my career choices as I'm not sure that my actions as a CTO are as impactful as I would like to be. When I was a developer or even as EM my actions seemed more relevant.

Probably try changing company, not the role? It depends, per my experience being TL is not harder than being a dev, probably CTO is more loaded, just try a smaller company then, so you have less people/tasks under your management.

how is that, being a manager but then still have to code and deliver? you have to constantly switch?

why move back into an IC role after being in leadership?

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