How to have that “Difficult Conversation” that you’ve been putting off

Monday, 21st November 2022

by Cath Brown,

Before coming a coach and trainer I was a barrister for nearly 15 years and one of my passions is bringing the advocacy and negotiations skills I learned at the bar to those outside the profession.

One of the areas in which I do that is in helping people work out how to have and to manage the difficult conversations that they have been avoiding.

For many people, the trickiest part is persuading yourself that you are brave enough to have the conversation. In my experience, people are very good at talking themselves out of being brave. They can produce brilliant “excuses” listing everything that might go wrong it they speak up. Some really creative thinking emerges.

But what they are less good at is working out what might go wrong or carry on being wrong if they don’t speak up. Silence also has a consequence. And, unless you want to go through life tolerating the intolerable, there will be occasions when you need to speak up.

So the next time you find yourself being creative about why not to have a difficult conversation, ask yourself what might happen if you were able to get out of your own way and also what might happen if you don’t.

And here is one more crucial tip from the world of litigation to make your bravery worthwhile.

“Write your closing speech first”

This is what we’re taught as barristers – you should be clear about what you want before you start your planning and preparation.

I paraphrase that advice as “beware the principle”. I work as a coach with lots of people who tell me “it’s the principle” “I need to have it out with him” “it’s not fair I’ve been hard done to” and what I frequently ask them is well where is that going to get you?

Communication, largely, should have a purpose. (Incidentally, this is not advice on how to behave at dinner parties) but, if you are going to approach somebody and ask for more flexible working then it is a good idea to be very clear at the outset what you want before you have that conversation.

If you’re going to have a difficult conversation you want to try and avoid it going round and round in circles. Unless you really know what it is you want it’s quite hard to know when the conversation is finished either successfully or unsuccessfully. So the key is to be very clear about the purpose of your conversation.

Once you have that clarity, you can work on preparation – thinking about the content, the evidence you can use, the objections you might meet as well as when and where to have the conversation.

And if that sounds a bit like hard work – I would agree.

One of the things that most surprises people I work with is that many of the people whose communication skills they admire, are not naturals. They are hard-workers. And they are brave. But all of that increases their chances of getting what it is they want, whether that is for them, or for their team members.

You can find more tips in my Guide to Managing Difficult Conversations which you will get access to if you sign up to my newsletter at