How to Have a Difficult Conversation


Why am I unable to have a difficult conversation? It’s because I see them every day!

An article in the Financial Times further raises the question of why it is difficult for managers and colleagues to engage in a difficult conversation.  The article discusses how even the most skilled managers or entrepreneurs, are unable to start a conversation when they fear it will become difficult.

In our experience, working with both large and small organisations, one thing is consistent: the conversation with a colleague, line-report or peer, is the one that individuals dread the most.  Many people seem to hope that the conversation will just disappear, while some even hope that they or the other person would just disappear!

Another common constant is the fear of the unknown, particularly when the individuals who are having to engage in this sort of discussion are so used to being the person in control. Training programmes, such as those we provide, equip managers with a toolbox of strategies and guidelines on putting these strategies into practice.

Preparation is key

Many would say that they do prepare for a difficult conversation by making a few notes or going through the likely (and perhaps ideal) conversation threads in their head, but I would say that this is not enough, particularly for people who don’t do this often.  It takes time and most of all practice to have a successful difficult conversation.  When we work with individuals and teams we suggest that they should consider:

  • how they will manage their own emotion as well as that of the other person
  • when to have the conversation – is the weekend or Monday morning likely to be a better time?
  • where to have the conversation – this can be tricky in an open-plan environment
  • what assumptions we, and the other person, might be holding – could and should you enter the conversation with curiosity rather than certainty?
  • your own contribution to the particular issue or problem (yes – you might also be part of the identified difficulty)
  • reflecting on the other conversations that you have had, and their frequency and content. If you’ve avoided having any sort of conversation with the person, imagine how this approach might be taken
  • finally, whether you have a clearly articulated purpose which is achievable.

The main reason why people avoid having the conversation is that they don’t know what to say, so talk to somebody (preferably someone who you can trust) and practise, practise, practise! The first few times you will not say what you mean, and there will be too much talking and not enough listening – but don’t feel disheartened or put off. Having the tough or difficult conversation is not easy, but dealing with the consequences of conversations that have been avoided is even harder.

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By Ranse Howell


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Ranse Howell
Ranse Howell is the Mediator and Consultant for The Centre for Effective Dispute Resolution (CEDR).

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