Lessons learned from becoming CTO of a small startup

Update 2021: I first drafted this piece back in 2018, roughly eighteen months after I took over engineering at a 30-something-person startup. I’ve kept it around because people still stumble on it, but a few things have changed — title included. These days I run tech at a digital agency, give early-stage founders a reality check on their product plans, and publish the occasional guide for technical managers (plus a newsletter when caffeine levels allow).

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I’ll walk through what changed for me when I moved from senior engineer to CTO. Everything below is written for the person who suddenly has the organisational power to approve budgets, veto architectures, and — uncomfortable but true — fire people. That last bit matters more than any fancy title.

The usual story says you either stay on the individual-contributor track or “switch” to management. Reality is messier. Some companies run dual ladders, some experiment with Sociocracy where nobody really manages anyone, and a few seniors I know dodge the whole debate by joining tiny three-person startups where hierarchy can’t physically fit. Still, if you do take the formal management route, the power dynamics change overnight — ready or not.

I became CTO of a small company (just under forty people, most of them engineers) in 2017. For the first quarter my to-do list looked like a log file in tail-f mode — new lines every minute. It took me a year to wrestle that chaos into something that felt sustainable. Below are the lessons that would have saved me a few grey hairs. I could be wrong, but they’ve held up so far.

Moving up in the same company

When you step up from dev to manager inside the same organisation, you drag a lot of history with you. Some of it helps, some of it bites you later.

If you’re taking over the people you coded next to yesterday, earn technical credibility first.

Sounds obvious, yet I’ve seen career ladders that list “peer respect” as a checkbox item without explaining how anyone measures it. Those documents (often locked behind some HR portal) rarely mention that influence erodes fast the moment teammates suspect you’re phoning in the technical work. Get the respect before you get the title, otherwise every roadmap discussion turns into a quiet referendum on whether you still deserve the chair.

Your friendship with your teammates will suffer once you're their boss.

I tried to keep the Friday beer ritual going “like nothing changed” (spoiler: it changed). The moment performance reviews are part of your job, off-hours banter gets filtered through that lens. Even if you manage to separate work topics at the bar, the rest of the team may still assume bias. At some point you’ll have to give a difficult piece of feedback to the same person you shared dumb memes with the night before — fun times. Though it didn't fully fix things, I continue to navigate these challenges.

On the flip side, I know brilliant seniors who absolutely refused the management track for exactly this reason and instead went deep on architecture roles. That’s a valid move if you value peer camaraderie over organisational leverage. Just be clear which trade-off you’re making.

Habits to get rid of

The role change forces a surprising amount of unlearning. Below are the behaviours I had to actively kill — some are still undead and occasionally crawl back.

Desire to do everything yourself.

I spent the first months ripping interesting tickets out of Jira because “I can finish this tonight.” Short-term dopamine, long-term disaster. The team learned that if something looked hairy enough, the CTO would grab it anyway. Delegation isn’t just polite; it’s a signal that you trust people (and that they own their outcomes). Assume success by default; intervene only when reality disagrees.

(Side note: once you’ve rescued a critical task twice, congratulations, you’re the new default assignee. Better block that reflex early.)

Don't be a bottleneck. If a matter is not a decision for the President or you, delegate it… Donald Rumsfeld

Desire to be the know-it-all.

The first time I answered “I’m not sure, let’s find someone who knows” felt like signing my own competence death warrant. Nothing happened. In fact, the team picked up that it was okay to surface uncertainty early. You’re now the router, not the single source of truth.

None of us is as smart as all of us.

Closing up and working alone.

The tempting escape is to shut the laptop, put on headphones, and bang out code. That escape is gone. Your new deliverable is clarity — for your team, for stakeholders, sometimes for customers. Expect your calendar to look like a game of Tetris. I tried blocking two no-meeting afternoons per week; works about half the time, which is better than zero. Managing meetings remains an ongoing struggle.

If you don’t protect your devs from random Slack pings, nobody will. Be the buffer. Yes, it means more context switching for you. Welcome to the job.

Caring only about your part of the work.

“My service passes all tests, so it’s Ops’ problem now.” That mindset dies the day you join leadership meetings. If accounting delays an invoice and your AWS credits run out, guess whose incident post-mortem it becomes? Exactly.

Habits to improve

Enough doom and gloom. Here are the muscles you’ll need to train deliberately. I got most of them wrong for the first six months.

Communication

The volume goes up by an order of magnitude, sure, but the type changes too. High-impact CTO work is less about answering emails and more about stitching people together: pairing a junior with a domain expert, introducing the data team to a potential partner, coaching a senior on how to negotiate scope. If you treat communication as a chores list, you’ll miss the leverage it offers.

The art of communication is the language of leadership.

Stress management

Instead of one PM breathing down your neck, you now juggle marketing, sales, finance, the board, and occasionally the landlord (“the server room is too loud”). Each believes their ask is existential. I won’t pretend a 10-minute meditation fixes that, but it buys you the pause needed to respond instead of react. Sports help, as does a weekend phone drop — still working on that last one.

Paying attention to your body and taking care of yourself will help you deal with leadership stress.

Decision making

Every technical choice is now a people choice in disguise. Migrating to microservices? Great, who’s on pager duty for the extra six deployments? Firing up Kubernetes might be architecturally sound but politically impossible if Ops is already drowning. I still draw trade-off diagrams on a whiteboard because seeing the messy middle makes it easier to defend the call later.

(I should be upfront — this framework works for a 40-person shop. I’m not entirely sure it scales unchanged past a hundred.)

Ability to learn and adapt to new things

Your stack will evolve faster than your org chart. Keep a beginner’s mindset. I still block time for conference talks and the occasional Coursera binge on distributed systems. Not to become the deepest expert — that’s what your specialists are for — but to ask better questions.

Accept that you will be wrong.

Leadership myths say the boss is paid to be right. Real life: you’re paid to correct course quickly. When a junior pokes a hole in your architecture diagram, thank them publicly. You just saved three weeks of rework and modelled psychological safety in one go.

Caring about small things

No one wakes up excited to audit logging levels or chase flaky tests. Yet those “trivial” tasks grow into existential risks if you ignore them. Create a rotation, gamify it, whatever — just don’t let the hygiene backlog rot.

Good things about being in Management

You will meet a lot of interesting people.

The forced-conversation nature of the role turns into a super-power once you realise half your calendar is implicit networking. I’ve traded API war stories with product leads I’d never have met as an IC, and those relationships paid off later when we needed a friendly Beta customer.

You influence the direction of the company

Small orgs magnify every leadership decision. Pick Postgres over Dynamo early and you’ve set the hiring pipeline for years. That leverage feels great — just remember that structural authority means your casual opinions can become team mandates by accident. Use the power sparingly.

Experience!

I’ve learned more about finance, hiring, and (surprise) office acoustics in this role than in a decade of pure engineering. If variety fuels you, management is an all-inclusive buffet. If it doesn’t, maybe stay on the specialist track — the industry needs both.

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