There’s a lot of content out there about how to have difficult conversations. These often focus on tools and techniques to plan and prepare and how to be during the conversation.

Whilst these guides can be useful, framing these conversations as being difficult is one of the reasons that these conversations simply don’t happen.  By seeing these conversations as difficult, people avoid them. 

It can’t be denied that some conversations can be uncomfortable but….

Is discomfort a bad thing? 

After all, often the experiences that lead to our greatest learning and growth are the most uncomfortable.

Jean-François Manzoni from INSEAD suggests reframing such conversations as an opportunity for learning on both sides. By doing so, a more honest conversation will take place as both parties will approach the conversation with an open mind and a growth mindset. Manzoni argues that by framing the conversation as being difficult, a manager might over prepare which will narrow the discussion and reduce the chance of openness and dialogue.

My research into organisations undergoing change led me to conclude that real conversations are sadly lacking in organisations. This is something that I have observed as being at the root of many issues in organisations for some time (see my very first blog post way back in 2015). So, what needs to be done to have more and better conversations in organisations?

More real conversations and less talking

I recently discussed conversations at work with my long time colleague and friend Ann Knights of Talik & Co and Hult Ashridge, as we recorded an episode of my upcoming ChangeStories podcast. We discussed how there is a lot of talk in organisations but not much conversation. This talk takes up a lot of our time but actually adds very little value to either us as individuals or to the organisation as a whole.

In contrast, a real conversation is founded in awareness: of self, of the other, of being present in the moment and of how both parties can be changed in and by the conversation. Ann has written a great article summarising how a leader can bring these behaviours to bear in coaching but this is also relevant to all conversations in organisations.

Part of this awareness then, is to be aware of how uncomfortable we feel about the conversation and to consider why this is? Going back to feeling uncomfortable and learning again, part of having more real conversations is to sit with that uncomfortable feeling. This is part of what Peter Bregman calls “emotional courage”.

Maybe this uncomfortableness is a fear of emotions?

Of how the other party might react?

A fear of getting it wrong?

Of upsetting people?

Whatever the reason for the fear, instead of avoiding the conversation, emotional courage requires us to go ahead and have the conversation as best we can, acknowledging mistakes that we might make as we go along.

Instead of framing conversations as difficult, we in the consulting /HR/ coaching community have a responsibility I believe to frame all conversations as important and to help people to develop their confidence in having real conversations, warts and all. This means developing these skills and behaviours:

Think about how you are framing the conversation:

Do think that you are in the right and the other person is wrong? Could you frame this differently as “I have my own point of view but also might be missing something” ?

Do you think the other person is to blame? Could you frame this differently as “both us of may have contributed in ways that we can’t fully see at the moment”?

Do you want to avoid saying things that might upset or anger the other person? Could you reframe this as seeing a negative reaction as uncomfortable but maybe necessary for progress to be made?

Do you want to get the other person to see things your way or do you feel that you need to defer to the other person? Could you reframe this as a conversation to create common understandings and a path forward?

When I am asked for advice about having a difficult conversation, I always say “imagine that you were having to hear this news – how would you like to hear it?”. Use this as a means to think about what you might want to say and how you might like to say it.


Whilst it’s good to prepare for a potentially uncomfortable situation, you must also be ready to be responsive to the situation as it unfolds.

Notice what is going on in the meeting.

How is the other person reacting?

How are you reacting?

What is interesting about that?

Plan tight, hang loose

Much of my work is rooted in appreciative inquiry and the great Jane Magruder Watkins used the mantra “plan tight, hang loose” to describe how to prepare for an appreciative inquiry session. This is a useful reminder here too. Do some planning if that makes you feel more comfortable about the conversation, but don’t stick to it no matter what. Be guided by the other person in the conversation with you.

Above all, remember that this is not all about you. There are two of you in this conversation. Keep your focus on the other person more than yourself. How can the conversation help both of you to develop and grow? And if it doesn’t go right first time, pause, reflect, get help and try again. As Brené Brown says:

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Real conversations are at the heart of organisation change and of individual development. Be brave and get out there and start having rather than avoiding ‘difficult’ conversations.

Let me know how you get on.