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.
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Claude
Paste long incident timelines, RFCs, or vendor contracts and get structured summaries, risk assessments, and architecture critiques you can edit and circulate.
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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.
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Notion AI
Draft engineering strategy docs, team OKRs, and onboarding guides from bullet points, then refine them for your specific org structure.
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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

The full library of tools, prompts, and tricks for your role — updated every week. Tap any card for a step-by-step walkthrough and examples.

✦  New tools, prompts, and tricks 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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A day in your inbox

This is the kind of brief a CTO / VP Eng gets, every weekday morning.
Monday morning
✦ Personalized for: CTO / VP Eng
Today's Tool
Try Claude for a vendor contract review
Paste a SaaS or infrastructure contract and ask for the renewal terms, liability caps, data handling clauses, and anything unusual. It catches the buried clauses you would otherwise skim past at 9pm.
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Today's Prompt
Pressure-test a scaling plan
Ask: Here is our current architecture and projected traffic growth: [details]. At what point does each component break, and what is the cheapest change that buys us 12 months of headroom?
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Today's Trick
Make AI argue against your decision
After drafting a technical proposal, ask the model to write the strongest case for the opposite choice. The counterargument surfaces assumptions you stopped questioning.
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Today’s three are just the start — go deeper on your role.
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