How To Hold A Challenging Conversation

Many managers and employees find it difficult to hold a challenging conversation.

The need to have a difficult conversation could arise when disagreeing with or challenging someone’s opinion, providing difficult feedback either about performance or behaviour, saying “no”, having conversations about personal problems such as sickness, or handling an emotional meeting.

This workshop provides tips and proven techniques to confidently hold a challenging conversation.

In 90 minutes participants will learn how to hold a challenging conversation by:

  • identifying what we mean by a “challenging conversation”
  • becoming familiar with the 4-Step Challenging Conversation Model
  • identifying your typical behaviour when faced with a challenging situation
  • learning techniques to show empathy and seeking first to understand.

Face-to-Face Workshop Content

In this workshop participants identify when they have to have challenging conversations, what a challenging conversation might look like and why it is important to have such conversations.

The workshop focuses on the 4-Step Challenging Conversation Model – creating the right environment, giving information, gathering information, and action planning.

Using a short profile, participants identify their preferred style when holding a challenging conversation – aggressive, assertive or passive.

We also explore the key skills of showing empathy, asking great questions and creating the context for being a good listener.

The workshop concludes with a practical challenging conversation work-related role-play.

“People almost never change without first feeling understood”

Douglas Stone

If you would like to talk to us about this or any other course
you are more than welcome to get in touch.

Call us on 01727 898 332 or email us at

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