AI roleplays
Practice that helps youhandle the conversations that matter at work: sales calls, tough feedback, incident updates, and more.
Practice with an AI character who pushes back like a real colleague, then see exactly which line didn't land.
More roleplays
21Disagreeing With Your Manager's Hiring Decision
A practical guide for raising a specific hiring concern with your manager, grounded in what you actually saw in the interview, and proposing a quick safeguard without overruling her or turning it into a fight.
Talking to: Dana Mitchell, Engineering Manager
Explaining a Production Incident to Customer Success
A practical guide for giving a client-safe incident update to a non-technical stakeholder without speculating, overpromising, or hiding behind technical details.
Talking to: Rachel Kim, Head of Customer Success
Explaining a Security Vulnerability to a Non-Technical Stakeholder
Practice turning a security flaw found before launch into plain business terms and one clear launch call that a non-technical product manager can act on today.
Talking to: Maya Chen, Product Manager
First 1:1 With a New Engineering Manager
A practical guide for introducing yourself to a new Engineering Manager in a way that goes beyond status updates.
Talking to: Dana Mitchell, Engineering Manager
Making the Case for a Checkout Refactor
A practical guide for proposing a technical refactor to an Engineering Manager by tying it to roadmap speed, delivery risk, and future feature work.
Talking to: Dana Mitchell, Engineering Manager
Making the Case for a Promotion
A practical guide for making a promotion case to your manager using evidence, impact, and a clear next-step ask.
Talking to: Dana Mitchell, Engineering Manager
Mentoring a Junior Engineer on Poor PR Quality
Jordan Lee, a junior engineer you mentor, thinks his large new pull request is ready to merge. You're meeting him 1:1 to help him make it easy for the team to review.
Talking to: Jordan Lee, Junior Software Engineer
Navigating a Code Review Disagreement
A practical guide for defending a technical decision in a visible code review without dismissing a senior engineer’s input.
Talking to: Ethan Rao, Principal Engineer
Negotiating API Contract Changes With Another Team
A practical guide for negotiating a change that creates work for another team, holding the one date that can't move while asking about their side and trading for a firm commitment, without pushing, blaming, or giving everything away.
Talking to: Ethan Rao, Principal Engineer
Negotiating Data Access With Security
A practical guide for negotiating access to sensitive customer data with Security, by asking about their concerns, narrowing your request to what the work truly needs, and agreeing on safe handling, without arguing urgency or asking for everything just in case.
Talking to: Omar Siddiqui, Security Engineer
Presenting LMS Integration Feasibility to Sales
A practical guide for giving Sales a technical feasibility answer under commercial pressure without either overcommitting or killing the deal.
Talking to: Adrian Malik, VP of Engineering
Principal TPM Bar Raiser Interview: Leadership Principles Deep Dive
Practice the round that can veto an offer: defend two of your own leadership stories under relentless follow-up questions on ownership, depth, disagreement, and results, and own a real failure without deflecting.
Talking to: Laura Bennett, Principal Engineer, Bar Raiser
Principal TPM Interview: AI Accelerator Infrastructure
Practice the round that decides principal-level TPM offers: defend a program you led under hard follow-up questions, steer a next-generation accelerator launch that is at risk, and brief executives with a decision-ready readout.
Talking to: Daniel Reyes, Director of Technical Program Management
Pushing Back on an Unrealistic Deadline
A practical guide for pushing back on an unrealistic deadline from a Vice President of Engineering without becoming defensive, passive, or unhelpful.
Talking to: Adrian Malik, VP of Engineering
Raising a Concern About an Architecture Decision
A practical guide for raising a technical concern about a senior architecture decision without making it sound like you are trying to overturn the decision.
Talking to: Ethan Rao, Principal Engineer
Re-estimating SSO Login Support Mid-Sprint
A practical guide for telling a Product Manager that a feature is taking longer than expected before they walk into a stakeholder update.
Talking to: Maya Chen, Product Manager
Recurring Payment Latency After Downgrade
A practical guide for handling a manager conversation when an incident was marked as mitigated, but the issue has started showing up again.
Talking to: Dana Mitchell, Engineering Manager
Redirecting an Over-Engineered Solution
A practical guide for redirecting a junior engineer who over-engineered a simple feature toward a simpler design, without dismissing their effort or crushing their motivation.
Talking to: Alex Morgan, Software Engineer
Responding to a Bug Your Code Introduced in Production
Own a checkout bug you shipped and give your manager a clear, honest update on the cause, the impact and the fix before she briefs leadership.
Talking to: Dana Mitchell, Engineering Manager
Running a Blameless Postmortem Meeting
A practical guide for running a blameless postmortem with the engineer whose change caused an outage, by making it safe to be specific, reconstructing what happened, and turning the real causes into owned fixes, without hunting for blame or letting the impact slide.
Talking to: Ryan Walsh, Software Engineer
Scoping a Vague Settings Brief
A practical guide for turning a vague Product Manager brief into something buildable without making the conversation feel like an interrogation.
Talking to: Maya Chen, Product Manager