Communication skills for challenging conversations

How to have challenging conversations


This session has been run a number of times as an open course for CII members and also run internally for Trigon Pensions.


Whether it’s complaints from policy holders, objections about fees, underperforming staff or even colleagues with personal hygiene issues, financial services and insurance professionals can find themselves having challenging conversations on a daily basis.

These dialogues 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, saying too much or sometimes not enough. Yet the issue is rarely resolved by ignoring or inflaming it.


The highly practical workshop focuses on the process, content and emotion of challenging conversations. It takes delegates through the key stages and ensures they have useful phrases to handle tough situations, thorny issues and strategies to manage heated moments.


When asked what was the most useful part of the course, delegates’ comments included:

  • Explanation of the different steps within a conversation
  • The focus on planning a meeting and the useful phrases to use and what to avoid saying
  • The process, preparation for challenging conversations is key and the empathy issue is the area I need to work on
  • Breaking down the process helps to move forward with this tricky issues
  • The use of the right words and phrases
  • The reminder of the difference between truths and beliefs
  • The need to invest more time in understanding people’s situation
  • Remembering to breathe and say something nice to yourself in the heat of the moment to ride the emotional wave
  • Strategies to achieve a mutual goal
  • Avoiding the word but.


“Melissa was friendly, helpful and explained everything.  Her caring humble demeanour makes learning really easy and her examples and exercises are very useful.” Team Leader,  Bluefin

“I would like to thank you for the training yesterday.  I admit I was a little sceptical 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 Trigon Pensions Consultancy

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

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