New CTO: Your First 90 Days as a First-time CTO

Meet your peers and your reports, in that order of difficulty. Your peers on the exec team decide whether engineering gets heard; your reports decide whether anything you say later gets done. Twenty to thirty conversations is plenty, and after the first eight you'll hear the same four problems in different words. Write those four down. That list is the start of your roadmap proposal.

Understand the business model and the roadmap before you have an opinion on either. Where the revenue comes from, which customers pay for which features, what the current roadmap promises and to whom, and what it costs the company when engineering is late. A CTO who can't say what a quarter of delay costs in money will usually lose the budget conversation to the sales leader who can.

Build your own roadmap proposal for the improvements you'd make. A proposal, as opposed to a rewrite plan: three to five changes, each with a cost, a time horizon and the business number it moves. This is the document you take to the CEO around day 60 to 75, and it's the first thing that shows the exec team what kind of CTO they hired.

Two things to leave alone. Don't make big changes yet: no reorg, no platform migration, no cancelling the project the previous CTO loved, however tempting. You don't know yet what's holding the place together. And stay rather quiet at first. The new CTO who announces a vision in week two is the one the org remembers in month six for the vision that didn't happen. The quiet one who asks questions and then brings a costed proposal gets the budget.

What the quarter of mentoring covers. The pack is called One quarter: six 60-minute sessions over three months, every two weeks, weekly while something burns. Session one is a diagnostic, where you really stand, your top three goals for the quarter and two KPIs we'll measure them by. Sessions two and four take whatever is on fire that week and work it against those goals; in a first quarter that's usually the stakeholder map and the first hard conversation with a director who is interviewing elsewhere. Session three is a checkpoint: progress on the KPIs, and are we working on the right things. Session five moves from operational to strategic, org design, talent moves, the bigger bets, which for you means the roadmap proposal before it goes to the CEO. Session six is the closing review, scored against the definition of success we wrote down in session one.

Jiří Petržilka, CTO at PalmApp, three months into our work: “How to build a quarterly roadmap that survives contact with the board. How to get budget approved instead of just asking for it.” And later in the same note: “Three months in, I'm calmer about the situation at hand and a lot clearer on what I bring to the table.” The full text is on the testimonials page.

What is a 90-day plan for a new CTO?

Three outputs by day 90: a stakeholder map with the four problems you heard most, a written understanding of the business model and the current roadmap commitments, and a costed proposal of three to five improvements with owners and dates. No reorg, no migration, no vision speech. The plan is the proposal; the first 60 days exist to earn the right to present it.

Does the 30-60-90 rule for managers work for a CTO?

Roughly. Thirty days of listening, thirty of diagnosing, thirty of deciding is a reasonable shape, with one change: a CTO's deciding phase ends in a document for the CEO, not in changes to the org. The changes come in the second quarter, once the proposal has been argued and funded.

Who is the boss of a CTO?

The CEO, in most companies, alongside the other C-level roles. A founding CTO who co-owns the company reports to the CEO on paper and negotiates as a shareholder in practice. If you're a hired first-time CTO, assume the paper version and build the CEO relationship first, before any other on the exec team.

What does founding CTO mean, and is it a different first job?

A founding CTO is the technical co-founder who built the first product, usually hands-on in the code, and grew into the title as the company grew. A hired first-time CTO inherits an org someone else built. The second job is harder in the first quarter, because nothing is yours yet and everything is visible. This page is written for the second one.