CTO 30-60-90 day plan generator
Answer five questions about your company and how you got the seat. You get a plan that changes with your stage, team size and route into the job, ready to print or copy. No signup, nothing stored.
By the CTO Coach Team · Last updated 2026-10-11 · How this plan is generated
Still to answer: company stage, team size, how you got the seat, at least one problem, whether you have engineering managers.
How to use this plan
Treat the checklist as a starting draft, not a script. Cross out what does not fit, add what your CEO has asked for, and keep the order: listen first, decide second, deliver third. The most common mistake is to skip to delivery because it feels like progress.
Share the plan with your CEO in week one. Agreeing it early is itself part of the plan, because it makes your first 90 days a shared commitment rather than a private project.
Days 1-30: the listening tour
Questions worth asking each group. Take notes in the same format for everyone, so you can compare answers later.
- The CEO
- What does a good first year look like to you? What is the one thing engineering must not get wrong? What have you been reluctant to ask?
- Board members or investors
- What do you want to hear from engineering each quarter? What worries you about our technical risk? What did the last engineering update miss?
- Product and design leads
- Where does engineering slow you down, and where do you slow engineering down? Which decisions are made by whom when we disagree?
- Engineers
- What slows you down most? What would you fix first if you could? What did we try before that failed, and why?
- Support and customer success
- What do customers complain about? Which problems come back? What would you want engineering to know that you cannot easily tell them?
- Finance
- What is the cloud and tooling bill, and what is growing fastest? How is engineering headcount planned against revenue?
Days 31-60: the first decisions
Convert what you heard into a short list. A useful test for each decision: can you explain it in two sentences to someone outside engineering, and name what you are choosing not to do? Write each decision down with the options you rejected. That record is what you will present at day 90, and it protects you when someone asks why six months later.
Days 61-90: the first readout
The readout is five short parts: what you learned, what you decided, where the measures stand, the top risks, and what you need. Lead with the honest misses. A CEO who hears your bad news first will believe the good news. For help translating engineering status into board language, see board-ready CTO communication.
Why plans fail
Most 90-day plans fail for three reasons: they are written once and never reviewed, they promise more than a calendar can hold, and they ignore the relationships that decide whether anything ships. Review yours every Friday for five minutes and move what slipped. For the longer version, read your first 90 days as CTO, and see the wider first-time CTO playbook. Leadership workload is a real constraint too: in LeadDev's 2025 survey, 65% of engineering leaders reported expanded responsibilities, so protect time for the plan itself.
How this plan is generated
The plan comes from a fixed rules table of 86 checklist items, each tagged by company stage, team size, route into the job, problem area, or whether you have engineering managers. Every phase always includes three core items. The rest are chosen by how closely their tags match your answers, up to seven per phase. The same answers always produce the same plan. It runs entirely in your browser: no data is sent or stored, and the only record is the link you can copy. Method and sourcing standards: methodology.
Frequently asked questions
Is 90 days realistic at a startup?
Yes, if you treat it as three jobs rather than one deadline: about a month to listen, a month to decide, and a month to show results. At a startup the plan is shorter on process and heavier on the CEO relationship and the one or two outcomes the company needs soonest. Do not expect to fix everything; expect to leave day 90 with a ranked list, one visible win and an agreed next quarter.
Should a founding CTO do a listening tour?
Yes, but a different one. You already know the system, so spend the time on what you do not know: how the team experiences you, which parts of the system only you can maintain, and what the CEO and board now need that you were not asked for before. The plan for founding CTOs focuses on handoffs and on moving yourself out of the critical path.
What should a CTO deliver by day 90?
A written readout for the CEO covering what you learned and decided, one or two outcomes the company would notice, starting measures for delivery, reliability and hiring, a short list of top risks with owners, and goals for the next quarter. Delivering all of that matters less than being honest about what slipped.
How do I present my 90-day plan to the CEO?
Share the plan before you start, then present the readout at day 90 in five parts: what you learned, what you decided, where the measures stand, the top risks, and what you need from the CEO. Agree in advance how you will be assessed at six and twelve months, so the readout is a checkpoint rather than a verdict.
Sources
- Scaling your engineering team from one to 50 and beyond Bessemer Venture Partners Atlas, Current
- Engineering burnout rising as 2025 layoffs reshape tech industry LeadDev Engineering Leadership Report 2025, as reported by LeadDev, 2025
How we source and check figures: Methodology.