The issue will not become clearer by avoiding it.

Difficult Conversations checklist

Prepare a fair, specific conversation about a workplace problem. Focus on observed behaviour, listen to the other perspective and agree a workable next step.

10 steps · 30 practical checks

Illustration of a presenter discussing a recommendation with an audience.
People Skills for Techies · Preparation for real work.

Prepare the next conversation, session or decision.

Work through these 10 steps and choose the actions relevant to your situation. The pitfalls are illustrative examples, not customer quotations. Use the checklist on screen or print it for your preparation.

Define the purpose

Illustrative pitfall

“The conversation was an opportunity to vent rather than resolve an issue.”

  • State the change or understanding you need.
  • Keep the purpose relevant to the working relationship.
  • Check whether another process or responsible person must be involved.

Gather specific evidence

Illustrative pitfall

“Always and never replaced examples the person could discuss.”

  • Identify observable actions and their context.
  • Separate facts from interpretations.
  • Choose a small number of relevant examples.

Check your assumptions

Illustrative pitfall

“We treated an inferred motive as an established fact.”

  • List what you do not yet know.
  • Consider plausible alternative explanations.
  • Prepare to revise your interpretation.

Choose the setting

Illustrative pitfall

“A sensitive issue was raised in front of the whole team.”

  • Arrange a private, appropriate channel.
  • Allow enough time for a two-way discussion.
  • Check any participation or support needs.

Prepare a clear opening

Illustrative pitfall

“The introduction was so vague that the issue never became clear.”

  • Describe the situation and observed behaviour.
  • Explain its effect without attacking the person.
  • State that you want to understand their perspective.

Listen before solving

Illustrative pitfall

“The action plan was ready before the other person spoke.”

  • Ask an open question about their view.
  • Let them explain without repeated interruption.
  • Summarise what you heard and check it.

Stay with the issue

Illustrative pitfall

“One concern turned into a list of everything that had ever gone wrong.”

  • Return to the agreed purpose when needed.
  • Distinguish new relevant information from unrelated grievances.
  • Pause if the discussion cannot remain constructive.

Explore a workable change

Illustrative pitfall

“The proposed solution ignored a genuine constraint.”

  • Ask what would help the work improve.
  • Discuss responsibilities and available support.
  • Check the change is within both parties' authority.

Agree specific actions

Illustrative pitfall

“Be more professional was the only instruction.”

  • Describe the behaviour or action required.
  • Agree who does what and by when.
  • Check both parties understand the agreement.

Review fairly

Illustrative pitfall

“The next meeting began as if no agreement had been made.”

  • Record the essential actions appropriately.
  • Review progress using relevant observations.
  • Acknowledge improvement and address remaining gaps.

Put it to work

Turn the checklist into focused practice.

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