Career Development

Retaining a flight risk

When to use

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.

Prompt Template

I think {name} ({role}, {tenure}) might be a flight risk. Signals: {signals}. They're critical to the team because: {why_critical}. Current comp: {comp_context}. Help me: 1. Validate whether these signals actually indicate flight risk or something else 2. Plan a conversation that doesn't tip my hand ('I know you're interviewing') 3. Identify what levers I have: comp, role change, new challenges, flexibility, visibility 4. Decide what I'm willing to offer proactively vs. reactively (counter-offer is usually too late) 5. If they do leave — transition plan to minimize blast radius

Fill & Run

Fill in the variables below, then copy the completed prompt ready to paste into any AI assistant.

Name

Role

Tenure

Signals

Why Critical

Comp Context

Fill in all fields above to enable copy.

Output Format

Flight risk assessment + retention conversation plan + contingency plan if they leave

More in Career Development

Building 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 →

Delivering 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 →

Creating 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 →

Back to PromptsLeadership Prompt