How to Hold a Challenging Conversation

Tools for talking when it matters most

Why this?

Whether it’s dealing with a challenging client, boss or team member these crucial conversations have the potential to strengthen or weaken a relationship and need to be handled with skill and care. However many people avoid such conversations for fear of saying the wrong thing, too much or not enough. Yet the issue is rarely resolved by ignoring or inflaming it.

What will it cover?

The highly practical workshop focuses on the process, content and emotion of challenging conversations. Drawing on cutting-edge research from the Harvard Negotiation Project, delegates will leave with some practical tools and phrases to handle tough situations, thorny issues and heated moments.

By the end of the session delegates will be able to:

  • Clarify what they want to happen as a result of the conversation
  • Recognise their own unhelpful stories and thoughts which can exacerbate situations
  • Differentiate between a “battle of messages” and a “learning conversation”
  • Start awkward conversations and stop procrastinating
  • Describe the importance of facts, empathy and questions in holding challenging conversations
  • Use an easily-memorable 3 step framework with key phrases
  • Manage strong or suppressed emotions both in others and themselves.
  • Avoid saying the wrong things 

Please note: We won’t cover formal workplace conversations such as dealing with underperformance, redundancies and grievances as these are specific management development subjects and need a specific approach.

How long is it?

3.5 hours

How many delegates can attend?



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What have others said?

The Insurance Institute of Bristol have worked with Melissa on several occasions for various seminars and workshops in recent years. Her events are always very popular and well received but “How to have Challenging Conversations” was fully booked within five minutes! We ended up holding a second session to accommodate more members and still had a reserve list of over 20. The workshop received excellent feedback from delegates and I cannot recommend it highly enough.”

Ellie Rowland-Callanan, Area Marketing Administrator, Chartered Insurance Institute

“I would like to thank you for the training yesterday.  I admit I was a little skeptical beforehand but found it very interesting. I had my “challenging conversation” this morning and your training was invaluable.  The conversation went really well and not only do I feel better but I feel our working relationship will be stronger going forward.  We cleared the air, understood things from each other’s perspective, cleared up misunderstandings and worked out a plan going forward.  All in a calm and friendly, informal way – and in a neutral location.”

Team Leader Pensions Consultancy

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