HR's Hardest 1:1s

Coaching Managers Through Difficult Conversations

A practical template for preparing managers for difficult conversations without replacing them.

HR won't be in every difficult conversation. But great preparation can still shape how those conversations happen.

Use this template before you coach a manager.

What's at stake

Every coaching conversation should answer three questions:

Is the manager prepared?
Do they know what good looks like?
Do they know what happens after the conversation?

If the manager leaves with uncertainty, the coaching isn't finished.

The context
Phase 01

Before you walk into the room

Understand the situation

Review:
The purpose of the conversation
Previous feedback or documentation
Desired outcome
Any HR or policy considerations

Coach the manager—not the script

Help them think through:
What facts they'll share
Questions they'll ask
How they'll respond if emotions run high
What they'll need to document afterwards

Check yourself

Ask:
Am I preparing the manager or taking over the conversation?
Have I made expectations clear?
Does the manager know when to involve HR?
Phase 02

During the conversation

Focus on preparation

You don't need to tell the manager exactly what to say.

Instead, help them think through:

What's the purpose of this conversation?
What outcome are you aiming for?
What concerns do you have going into it?
How will you know the conversation was successful?
Phase 03

Before you finish

Confirm:

The manager understands the objective
Key messages are clear
Follow-up actions are understood
HR support is available if needed
Phase 04

After the conversation

Document

Guidance provided
Risks discussed
Agreed approach
HR support required
Follow-up plan
If someone reads these notes six months later, they should understand exactly what happened.
What to avoid
Don't take over the conversation — prepare the manager. Preparation doesn't guarantee a perfect conversation, but it helps managers walk in with a plan. Your job is to coach them, not replace them.

Should HR be in the room?

Managers should lead most difficult conversations. HR's role is to prepare them, not replace them.

The context
Managers can usually lead the conversation if...
It's routine performance or development feedback.
Expectations have been discussed before.
There are no employee relations or policy concerns.
The manager is confident leading the conversation.
HR should consider joining if...
The conversation could lead to formal disciplinary action.
There's an employee relations concern or workplace complaint.
An accommodation request or other sensitive issue is involved.
The manager is handling this type of conversation for the first time.
Company policy requires HR to be present.
Workspace

Prep checklist

Tick as you go. Add notes you'll want in the room.
Timeline confirmed
Internal alignment completed
Key messages prepared
Employee questions anticipated
Transition plan reviewed
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