Prompt Library
Precision-crafted prompts for the world's most senior leaders.
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Showing 1–20 of 20 prompts
Audit Invisible Work Consuming Engineering Capacity
Exposes hidden labour consuming engineering capacity — helping a CTO understand where effort is actually going and why delivery feels slower than headcount suggests it should.
Audit Senior Engineer Utilisation
Maps how senior engineers actually spend their time — diagnosing which responsibilities exist because the organisation is broken, and identifying one concrete change to restore their leverage and impact.
Coach Your Engineering Team on AI Adoption
Builds a CTO-led plan for introducing AI coding tools — covering rollout sequencing, fast-conviction use cases, code quality maintenance, and how to lead engineers who are simultaneously excited and threatened.
Decide: Build vs Buy vs Partner
A structured, commercially honest framework for making build/buy/partner decisions — and defending them to a CEO who wants cheaper and a board that always wants faster.
Deliver Bad Technical News to the CEO
Structures the message the right way: problem stated upfront, cause diagnosed honestly, recovery plan specific enough to be believed — calibrated to your CEO's communication style and relationship.
Diagnose the Innovation vs Delivery Balance
Reveals whether innovation capacity actually exists in your organisation — or whether it is structurally optimised for delivery while believing it is innovative.
Diagnose Why Engineering Feels Slow
Replaces subjective frustration with a systems-level diagnosis — separating delivery constraints, organisational friction, prioritisation problems, and genuine inefficiency to create alignment across product, engineering, and leadership.
Diagnose Your Engineering Culture
Runs a structured, unsparing diagnostic of the engineering culture you actually have — rather than the one you believe you have — and identifies what it means for quality, velocity, and retention.
Plan a Difficult Conversation as a CTO
Structures the conversation that needs to happen — whether it's an engineer who's become a bottleneck, a CEO pushing a damaging deadline, or a board that doesn't understand why the replatform costs what it does.
Plan Your First 90 Days as a New CTO
Builds a rigorous, phased playbook for a new CTO — covering early relationship priorities, team reads, cultural navigation, and first battles that establish credibility as a trusted strategic architect.
Prepare for Your CEO 1:1
Helps you think like the CEO before you're in the room — anticipating questions, surfacing background concerns, and showing up as a strategic peer rather than someone being managed.
Prioritise Technical Debt
Transforms your debt inventory into a ranked, commercially honest view of what to tackle, what to tolerate, and what to stop calling debt when it's actually just legacy.
Rate My CTO Comms
A blunt, outside-in assessment of how your communication lands with people who don't think like you. Paste any email, update, or board narrative and get an honest read on whether it works.
Reality-Check AI-Assisted Engineering Impact
Uncovers the true impact of AI on engineering output, quality, and skill distribution — revealing where it multiplies capability, creates hidden risks, or subtly reshapes workflow and decision-making.
Resolve Platform vs Product Engineering Tension
Helps a CTO diagnose what's causing friction between platform and product teams, structure governance that prevents recurrence, and have the conversations that usually don't happen until they're overdue.
Review a Major Architecture Decision
A structured adversarial review of a major architecture decision — exposing where the design solves the wrong problem, where operational assumptions are optimistic, and where today's solution becomes tomorrow's migration.
Run a Board Pre-Mortem on Your Technical Plans
Turns your technical plans into a sharp board member who asks hard questions, spots strategic fragility, and forces commercial clarity — before the real board does.
Run an Engineering Hiring Pre-Mortem
Goes beyond technical competence to test a candidate's judgment, collaboration instinct, and whether they'll make the team stronger or subtly more fragile. Paste in a CV and team context to get started.
Stress-Test Your Technology Roadmap
A rigorous adversarial review of your technology roadmap — exposing misaligned priorities, fragile delivery assumptions, and where the plan would collapse under realistic execution pressure.
Test Whether You Have a Hiring or a Systems Problem
Helps a CTO determine whether the real delivery bottleneck is capacity, coordination, clarity, or system design — before committing to hiring decisions that are expensive and difficult to reverse.