HR's Hardest 1:1s

Career & Retention Conversations

A practical template for conversations that help employees grow, and help you understand when they're at risk of leaving.

The best retention conversations often start as career conversations.

Use this template to prepare before you walk into the room.

What's at stake

Every career or retention conversation should answer three questions:

What does the employee want next?
What's getting in the way?
What happens next?

If you leave without understanding all three, the conversation isn't finished.

The context
Phase 01

Before you walk into the room

Career and retention conversations often begin the same way.The difference is what you're trying to understand.

If the conversation is about growth...

Prepare to discuss:
Career aspirations
Skills they'd like to develop
Growth opportunities
Internal mobility

If the conversation is about retention...

Prepare to understand:
What's changed?
What's frustrating them?
What's keeping them here?
What might cause them to leave?

Check yourself

Ask:
Am I listening more than I'm solving?
Am I prepared to hear something unexpected?
Can I commit to realistic next steps?
Phase 02

During the conversation

Open with facts

Start with curiosity. The first half of the conversation is usually the same. You're understanding the employee's experience, what's motivating them, and what's getting in the way. Where the conversation goes next depends on what you hear.

Ask

What's energising you most right now?
What would you like to do more of?
What's been frustrating lately?
What support would make the biggest difference?
What would make the next year feel like a success?
Phase 03

Before you finish

Confirm:

What you heard
Agreed actions
Support you'll provide
Follow-up date
Phase 04

After the conversation

Document

Career goals discussed
Retention risks identified
Development opportunities explored
Commitments made
Next steps
Follow-up timeline
If someone reads these notes six months later, they should understand exactly what happened.
What to avoid
End the conversation with a plan, not assumptions.
Workspace

Prep checklist

Tick as you go. Add notes you'll want in the room.
Previous development conversations reviewed
Growth opportunities considered
Potential retention risks considered
Open-ended questions prepared
Follow-up planned
Documentation ready
New
Meet Haven

Don't let your notes become another task.

You've prepared for the conversation. Haven takes care of what comes after.
Leave every conversation with:
Conversation summary
A structured summary of what was discussed.
Action items
Clear next steps, owners, and follow-ups.
Confidential record
A secure record you can revisit whenever you need it.
See Haven in action