Leadership Prompt Library
Ready-to-use AI prompts for engineering managers and tech leaders. Fill in the blanks, copy, and run in any AI assistant.
26 of 26 prompts
Preparing for a difficult 1-on-1 with an underperformer
Use before a 1-on-1 where you need to address performance issues directly but compassionately. Best used after you've already given informal feedback at least once.
View prompt →1-on-1 Prep30-day check-in with a new hire
Use at the 30-day mark for new hires. This is your best window to catch onboarding problems and set expectations before habits form.
View prompt →1-on-1 PrepSkip-level 1-on-1 question bank
Use quarterly or when you suspect information isn't flowing up properly. Critical when you're new to a role managing managers.
View prompt →1-on-1 PrepRe-onboarding someone returning from extended leave
Use before someone returns from parental leave, medical leave, sabbatical, or any absence longer than 4 weeks.
View prompt →Team HealthTeam health assessment after a rough quarter
Use after a rough quarter, reorg, layoffs, or when you sense morale is low but can't pinpoint why.
View prompt →Team HealthMediating conflict between two engineers
Use when conflict between team members is affecting team dynamics. Don't wait until it's a full crisis.
View prompt →Team HealthRebuilding trust after layoffs
Use within the first week after layoffs. Speed matters — silence from leadership gets filled with rumors.
View prompt →Team HealthDiagnosing remote team disconnection
Use when remote team engagement drops or when onboarding remote team members who seem isolated.
View prompt →Incident RetrospectivesBlameless post-mortem facilitation guide
Use within 48 hours of incident resolution while details are fresh. Send the async template immediately, schedule the meeting for 2-3 days out.
View prompt →Incident RetrospectivesIdentifying incident patterns across multiple post-mortems
Use quarterly when reviewing incident trends. Turns individual incidents into a strategic reliability narrative for leadership.
View prompt →Incident RetrospectivesExtracting and spreading learnings from an incident
Use after post-mortem is complete to spread learnings across the org. Most orgs do post-mortems but fail at cross-pollination.
View prompt →Technical StrategyTech debt prioritization framework
Use when planning a quarter and negotiating tech debt capacity with product. Having a framework prevents the annual 'we need to stop and rewrite everything' conversation.
View prompt →Technical StrategyBuild vs. buy decision framework
Use when evaluating vendors, considering building internal tools, or during architecture reviews. Forces structured thinking instead of engineer-default 'let's build it'.
View prompt →Technical StrategyArchitecture decision record (ADR) review
Use during architecture reviews or when a tech lead proposes a significant system change. Best used as async review before the meeting.
View prompt →Technical StrategyPlatform team pitch to leadership
Use when you've identified repeated toil across teams that a platform team could address. The pitch must speak business language, not engineer language.
View prompt →Hiring & InterviewsStructured interview rubric design
Use when opening a new role or when your current interview process has a high false-positive rate. Better signal = fewer mis-hires.
View prompt →Hiring & InterviewsHiring pipeline analysis and optimization
Use when a role has been open for >6 weeks or when you're not getting quality candidates. Data-driven hiring beats gut feel.
View prompt →Hiring & InterviewsClosing a strong candidate who's comparing offers
Use after a strong onsite when you know the candidate has competing offers. The sell phase is where many engineering orgs lose top talent.
View prompt →Career DevelopmentBuilding a promotion case
Use 2-3 months before a promotion cycle. A strong written case is the #1 factor in successful promotions — not the work itself.
View prompt →Career DevelopmentDelivering difficult but growth-oriented feedback
Use when you've observed a pattern that needs addressing. Don't wait for performance review season — timely feedback is kind feedback.
View prompt →Career DevelopmentCreating a growth framework for your team
Use when joining a new team without a clear ladder, or when your existing framework generates more confusion than clarity.
View prompt →Career DevelopmentRetaining a flight risk
Use when you notice disengagement signals in a key team member. Acting early gives you options; acting after they have an offer gives you none.
View prompt →Stakeholder CommunicationWriting an executive status update
Use weekly or bi-weekly for VP/C-level updates. The exec update is your team's marketing — it determines resourcing, attention, and air cover.
View prompt →Stakeholder CommunicationSaying no to a stakeholder request
Use when you get an urgent request that would derail your team's commitments. The skill of saying no is the most important and least taught management skill.
View prompt →Stakeholder CommunicationCross-functional alignment when priorities clash
Use when cross-team work is stuck due to conflicting priorities. Most alignment problems are really communication problems — everyone optimizes for their own local metrics.
View prompt →Stakeholder CommunicationCommunicating an org change to your team
Use before any reorg, team split/merge, manager change, or reporting structure change. People handle change better when they hear it from their direct manager with context, not via an all-hands Slack message.
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