AI for your role

AI for CTO / VP Eng

Lead engineering with AI doing the heavy lifting, not the thinking.

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The shift

How AI is changing the CTO / VP Eng role

In 2026, AI handles much of the first-draft work that used to fill an engineering leader's week: drafting architecture decision records, reviewing pull requests for risk, summarizing incident postmortems, and turning roadmap notes into structured tickets. The role shifts toward reviewing AI-generated technical proposals and catching the failure modes a model misses. Capacity planning, vendor evaluations, and hiring scorecards now start as AI drafts that you correct rather than write from scratch.

What AI can take off your plate

  • First drafts of architecture decision records, RFCs, and postmortems
  • Pull request triage and routine code review for style and obvious bugs
  • Converting roadmap and meeting notes into scoped, estimated tickets
  • Summarizing engineering metrics and incident trends for stakeholder updates
  • Drafting job descriptions, interview scorecards, and onboarding documentation

What stays distinctly human

  • Deciding which technical bets are worth the risk and when to say no
  • Reading the team and knowing who is burning out or ready to grow
  • Making the final call on architecture tradeoffs that have no clean answer
  • Building trust with peers in product, sales, and finance
  • Owning the consequences when a system or a hire does not work out
Tools

Five AI tools for CTO / VP Engs

GitHub Copilot
Use it to review pull requests across repos, generate test coverage for legacy modules, and spot security issues before they reach a human reviewer.
Try it →
Claude
Paste long incident timelines, RFCs, or vendor contracts and get structured summaries, risk assessments, and architecture critiques you can edit and circulate.
Try it →
Linear
Use its AI features to turn loose roadmap notes into scoped issues, auto-triage incoming bugs, and generate sprint summaries for stakeholders.
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Cursor
Pair with it directly in the codebase when you need to prototype a technical spike or validate a refactor approach before assigning it to a team.
Try it →
Notion AI
Draft engineering strategy docs, team OKRs, and onboarding guides from bullet points, then refine them for your specific org structure.
Try it →
Prompts

Five prompts to try today

Paste these into Claude or ChatGPT and replace the bracketed parts with your own details.

1. Architecture review
Review this proposed architecture for [system/feature]. Here are the requirements: [requirements]. Here is the design: [design]. List the top 5 failure modes, scaling limits, and operational risks, ranked by likelihood and impact.
2. Postmortem draft
Here is the incident timeline: [timeline]. Write a blameless postmortem with sections for impact, root cause, detection, and 3 concrete remediation items with suggested owners and priority.
3. Hiring scorecard
Create an interview scorecard for a [level] [role] on a team that owns [domain]. Include 5 competency areas, what strong vs weak looks like for each, and 2 sample questions per area.
4. Roadmap to tickets
Turn these roadmap notes into structured engineering tickets: [notes]. For each, give a title, acceptance criteria, rough effort estimate, and dependencies. Flag anything that needs a design doc first.
5. Build vs buy
We need [capability]. Compare building it in-house vs adopting [vendor options]. Estimate engineering cost, maintenance burden, and time to value for each, and give a recommendation with the main risk of each path.
The playbook

Every AI play for CTO / VP Eng

Your full AI playbook for your role — updated every week. Tap any card for a step-by-step walkthrough and examples.

✦  New AI plays are added every week — and go straight to subscribers in their morning brief. Skip the scrolling and get yours delivered free. Get my free brief →
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This is the kind of brief a CTO / VP Eng gets, every weekday morning.
Monday morning
✦ Personalized for: CTO / VP Eng
Your PlaybookFirst drafts
Turn a blank page into a solid first draft

The move that gets you past the hardest part of any task — starting. Works for an email, a plan, a report, a tricky reply. Free, no login.

ChatGPT  FREE  a free AI assistant that drafts, rewrites, and thinks through problems with you

1

Go to chatgpt.com (the free tier is fine) and describe what you need in plain words. Give it the goal, the audience, and any facts it should use:

I need to write [what]. It's for [who], and the goal is [what you want them to do or understand]. Here are the key points: [paste your rough notes]. Draft it in a clear, direct tone. Ask me anything that's missing first.
2

It drafts. Now make it yours — push back in the same chat:

Make it shorter and less formal. Cut anything that sounds generic. Keep the part about [X].

You go from staring at nothing to editing a real draft in two minutes. Editing is always easier than starting.

Your role, all in one place
  
Tools, prompts & tricks
Your full library, one tap away.
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Your playbook
Every entry, building each week.
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How AI is changing your role
Where your work is heading.
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