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How to Manage a Challenging Conversation

The Management Pocketbooks Pocket Correspondence Course

This is part of an extended management course. You can dip into it, or follow the course from the start. If you do that, you may want a course notebook, for the exercises and any notes you want to make.


As a manager, you will sometimes have to set up and have conversations you would really rather leave to someone else.  These challenging conversations can be about:

  • performance issues
  • personal issues
  • employment issues
  • terms and conditions
  • giving bad news
  • complaints
  • conduct issues

This is one of the least pleasant parts of your job, so it pays to prepare well and follow a process.

Exercise 1: Before You Go any Further

Take a moment to review the last module, Transactional Analysis for Managers. How does this apply to challenging conversations?  You know that an Adult state is ideal, but….

How would your being in Child state affect the way you manage a challenging conversation?

How would your being in Parent state affect the way you manage a challenging conversation?

What body language betrays Parent and Child state? How can you adjust your posture to support an Adult ego state?

Seven Steps

Let’s look at the Seven Steps for handling a challenging conversation.

Challenging Conversation

Preparation

Think through in advance how you want to conduct the conversation. Review the things you want to raise and identify those that are most important. Your conversation will be easier and more effective if you can focus it on the most substantive matters. Continually saying ‘and another thing’ can only make it harder.

Create Safety

Look for the right time and place to conduct the conversation and give the other person notice of what you want to talk about, so they can prepare, rather than react against you if they feel hijacked. Acknowledge that you and they may find the conversation difficult but express your desire to work through it openly and constructively. Demonstrate a relentless commitment to being respectful and maintain that even if the other person does not. If the emotional temperature rises to a level where you not feel emotionally or physically safe, call for a recess.

Setting-up the Conversation

If the relationship renders it appropriate to start with a short rapport building chat do so – otherwise stick to the courtesies that are standard in your culture. Too much pleasantry can come across as evasive – even manipulative.

So be honest without being blunt. Start by stating the nature of the conversation and what you want to achieve as a result.

Saying your Piece

Now say your prepared piece. Be clear, explicit and follow the facts concerned. Check understanding frequently and respond openly to questions and challenges.

If you are interrupted, listen to the interruption respectfully, deal with it and then resume where you left off – clarifying where you had got to if there was a long gap.

Listening to the Response

Listen carefully to the response, without interrupting. Note any misunderstandings and make the assumption that they are all inadvertent. Take responsibility for not explaining clearly enough and explain again, differently if possible.

Dialogue

Take responsibility for the structure and process of the dialogue, but do not try to control the other person’s responses. Listen hard when they are speaking and pause to consider your responses even if you think you know the answer immediately.

Ending the Conversation

Close the conversation by emphasising the next steps that either you have both agreed or that you can reasonably require of the other person.

Further Reading 

Tackling Difficult Conversations Pocketbook

The Problem Behaviour Pocketbook

The Resolving Conflict Pocketbook

The Handling Resistance Pocketbook

Blog: Conflict: As simple as AEIOU

Blog: Resistance to Negotiation

Blog: Is This Relationship Going To Work?

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