A Guide to Managing Difficult Conversations

Managing Difficult Conversations

Catherine Brown practised as a barrister for 15 years at Kings Chambers in Manchester, and brings all of that experience with her into her coaching and training business, www.skilfulconversation.com.  The subject of her flagship workshop, and a consistent theme in her professional coaching is Managing Difficult Conversations.

Since leaving the bar, Catherine has worked globally as a trainer and coach, founding a limited company in 2018.  Through this work, she has come to realise that it is frequently people’s inability to communicate effectively that prevents them from achieving their full potential in their career.  Similarly, companies, including law firms, may find that their senior leaders, including Equity Partners in the legal world, cling onto ineffective and hierarchical methods of communication which can cause problems with the recruitment and retention of staff and, in turn, hold back the firm itself.

Ahead of the Women in Law Summit in London, in this article she shares some of her top tips for managing difficult conversations.

Find the motivation to have the conversation

The most common problem I see is people, often but not always women, avoiding conversations that they would like to have because they fear confrontation.  There is a widely held perception – which I actually view as a myth – that if you speak up for yourself, it will end in a row, or at the very least, discomfort.  It doesn’t have to be this way.  And, it is important to recognise that inaction also has consequences, and can lead to even greater discomfort.

Most people will benefit from focusing on the positive impact of having the conversation.  Try asking yourself:

  • What are ALL of the potential benefits of having this conversation?
  • If it all, or even only 50% of it goes well, how will your life/business/team/relationship improve?
  • What learning will you be able to walk away with?
  • What would happen if you were REQUIRED to act?
  • What could you do if you got out of your own way?

Some people are motivated by moving away from the situation – if that’s you, the following questions might be more helpful:

  • What is putting off this conversation stopping you from doing?
  • What are you tolerating and how is that making you feel?
  • Where will you be in 3 months/6 months/12 months if you keep avoiding this conversation?
  • What’s the worst that can happen?

Once you’re motivated to have the conversation, you will need clarity around what you want.

People Sitting Talking

Be clear about your aims.  Or, beware “the principle”.

As barristers we are taught to “write our closing speech first”.  It reminds us that we need to know where we want to end up before we start.  Too often, people gear themselves up to have a conversation and come away disappointed because they haven’t been clear enough at the outset (in their own mind) about what it is that they want.

As a coach, I often come across people who feel that they need to “tackle” or “confront” someone because:

  • They’ve been hurt by them
  • They feel slighted by them
  • “It’s the principle” – if life as a lawyer teaches you anything, it’s that it’s almost never the principle…

The risks of going into a conversation without a clear idea of what you want out of it are many.  For one thing, how will you know when the conversation is over?  So, your time is well spent in working out what you want to achieve in this conversation.

For example, if you have decided that what you really need to do is ask your line manager for a pay rise, then you may think you’ve tackled this bit already.  Your identified outcome is an increase in the amount paid into your account each month.  But, how big do you want that increase to be?  Is it really the money you want, or do you just think you are undervalued for what you do?  Would you happy with the same pay but reduced hours or responsibilities?

Some questions to ask yourself here are:

  • What is it that I want?
  • How will I know when I’ve got it?
  • Can I simplify this even further?

Then, you can think about how best to get what you want.


Communicate your message effectively

For most people, the key here is preparation.  Think about what it is you want to say, based on what it is you want to achieve.  Spend some time working on strengthening your message and anticipating objections but keep most of that in reserve.  When it comes to actually starting the conversation, simplicity is the key.

Another tip we are given as barristers is, “Tell them what you want and tell them why they should give it to you”.  You can keep it to that in probably 90% of the conversations you have.  Chances are you’re dealing with busy people.  If they want to see your working out, they’ll ask.  Be clear about the message and then be ready to keep quiet and listen to the other person.

As a final piece of courtroom wisdom that you can apply to everyday life, remember that bad points don’t improve with repetition.  Nor do good points.

Be clear and keep it simple.

Next steps

Catherine will be attending the Women in Law Summit at the London Olympia on 17th May.  Please come and speak to her about in-house workshops and coaching packages.  

You can also contact her on cathbrown@skilfulconversation.com, or sign up to her mailing list here https://skilfulconversation.com/contact/ so that you will be first in line to receive a free copy of her ebook on Managing Difficult Conversations, which is coming soon.