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Difficult conversations at work

How do I raise something difficult with my manager or a colleague?

The conversation you keep putting off is usually the one costing you the most. Preparation turns it from a confrontation into a piece of work.

Session length
30 minutes
Cost
Free
Matched on
Your field
The short answer

Three things worth knowing.

  • Separate the facts from the story you have built around them. "The report came back to me twice after the deadline" can be discussed; "you do not respect my time" cannot.

  • Name what you want before you start. An apology, a change in process, clearer expectations, or simply to be heard are very different conversations.

  • Choose the time and place deliberately, keep it short, and end with something specific that both of you have agreed to do next.

What to do

A sequence that works.

  1. 01

    Write the facts down

    Dates, what happened, what the effect was. Nothing about intent.

  2. 02

    Decide the outcome you want

    One sentence, and a realistic version of it.

  3. 03

    Open plainly and then listen

    Say the issue in two sentences, then stop and let them answer.

  4. 04

    Agree a next step and confirm it

    A short follow-up message means both of you remember the same thing.

Common mistakes

What to avoid.

  • Raising it while still angry

  • Storing up months of examples for one conversation

  • Talking about character instead of behaviour

  • Having it in an open-plan office or a public channel

  • Leaving with no agreed action

Questions

The things people ask first.

What if my manager is the problem?

Prepare harder, stick to facts and effects, and know your escalation route before you start.

Should I put it in writing first?

A short note requesting time is useful. The conversation itself is better spoken.

Can I rehearse it with a mentor?

Yes, and it is one of the most useful ways to spend 30 minutes with someone outside your organisation.

Get this answered for your situation.

A mentor who does the job you are aiming at can tell you which of this applies to you.