As you go about your working day, you have many conversations. Most are casual, not particularly significant or impactful. And then in a split second a casual conversation can turn into something else – a tricky conversation that can have a material impact on your life. 

And just when you need to be on your best form the opposite happens. You say things you later regret, you behave in a way you are not particular proud of and you make matters worse for yourself, the other person and our relationship. 

The adverse effects of a poor conversation can ripple out far and wide.  

So why do you so often do your worst in the critical moment?

Three reasons. Ok four reasons. We like things in 3 but I couldn’t leave out the fourth!

Firstly, you are wired for fight, flight or freeze. Your emotions often take charge as you react to the social threat triggered by what someone has said. Your brain and body get you ready to deal with the mammoth piercing you with its long, curved tusks when all it actually needs to do is prepare you for a challenging conversation.

Secondly, you are caught out by surprise. So many of these critical conversations come out of the blue and you’re compelled to handle a complex interaction in the moment.

Thirdly, you don’t always have the skills to handle a difficult conversation even when you have time to prepare for it. You’ve probably never seen someone else model it for you – you’re more likely to have experienced how not to deal with a tricky conversation.

Fourthly, you may have lost touch with the art of conversation. You see it as an opportunity to share information, to prove you are right or win a discussion rather than listen, consider new possibilities and to think together.

5 ways to ensure you make the most of crucial conversations

1. Be mindful of the importance of conversations 

I believe that some work conversations – maybe 50 or 100 in a year – have a disproportionate impact on your lives. The same can be said about those conversations you’re not having. Silence is just as harmful as making a hash of a crucial conversation.

There are many reasons why it’s worth getting the crucial conversations right. This quote from William Isaacs in his book Dialogue describes one of those reasons:

“It is a way of taking the energy of our differences and channelling it toward something that has never been created before.”

2. First start with yourself and make sure you stick to your purpose

You can’t change others however much you think you can but you can work on yourself. You can learn to become better at dialogue. Your heart needs to be in the right place, ready to listen and learn not tell and judge.

Before you start a difficult conversation or when you notice you are in the midst of one, remind yourself continually what you want for yourself, for others and for the relationship. Ask yourself the following 4 questions:

  • What do I want?
  • What do I want from this conversation?
  • What do I want for this relationship?
  • How should I behave if I want these results?

By sticking to your purpose, it encourages you to find a creative solution and keeps you from falling into the various traps like trying to win the argument or inadvertently hurt the other.

3. Create a pool of meaning

The roots of the word dialogue come from the Greek words dia and logosDia means ‘through’ and logos translates as ‘meaning.’ Basically, a dialogue is a flow of meaning.

The goal is to create a pool of meaning between the two of you where you each pour in your opinions, viewpoints, feelings, theories and experiences. The fuller the pool the more accurate and relevant the information leading to better conversations and choices. The pool of meaning is the birthplace of synergy. 

The more time you spend filling the pool, the more likely you’ll arrive at unified and committed action later. 

4. Don’t confuse impact with intention

Separating impact from intention require you to be aware of the difference between “I’m angry” and “You made me angry on purpose”. Often when you feel aggrieved by what somebody said or did, you assume their intention was to annoy you. You guess their intentions; and most of the time they are not what we think.

Three questions (and this time I will stick to 3) to ask yourself to help you distinguish impact from intention:

  • What did the other person actually say or do?
  • What was the impact on me?
  • What assumption am I making about the other person’s intention?

Then remind yourself this assumption is just a hypothesis. It is ok to share the hypothesis but make sure you are very clear about it being an assumption and that your purpose is to see if it makes sense to the other person.

5. Understand and talk about feelings

In any conversation, difficult or not, feelings will arise – they are at the core of a tricky conversation. 

Feelings can be confusing, a conversation can evoke a bunch of different emotions and your instinct might be to bury them. 

If you don’t talk about feelings, it is like putting on a theatre production with no actors.

Feelings show you what you are interested in, what you care about. Feelings are signals, sometimes relating to the situation you are facing right now and sometimes carried over from previous events or experiences. Either way it’s critical we pay attention to them.

You can name your emotions in a conversation without being emotional. 

Create the right environment to turn those tricky conversations around

Instead of trying to win the argument, to be ‘right’, to punish or change the other person, next time you have a tricky conversation with your colleague think about creating an environment where the two of you can do your best thinking and fully harness your “collective intelligence”.

Use these 5 things to help you do that:

  • Remind yourself to show your best self for that crucial conversation you’ll have this week
  • Before you have a critical conversation or when you realise you are having one, continually remind yourself of your purpose during the dialogue
  • Fill up the pool of meaning with your stories as well as theirs
  • Don’t confuse impact with intention
  • Share feelings thoughtfully in the conversation


Let’s see how George Clooney deals with a difficult conversation.

In this video, Anna Kendrick uses a logical and rational approach to support and console Bob who has just been told he is being laid off. It doesn’t work. George Clooney is more curious, seeking to learn about Bob by reading his CV and listening to what he says in the conversation. He uses a more heart-led approach, appealing to Bob’s values, passion and emotions and opening his eyes to what makes him happy. 

George’s character understands how important feelings are in a difficult conversation. 


What information do they see that I missed or don’t have access to?


“To get to the next level of greatness depends on the quality of our culture, which depends on the quality of our relationships, which depends on the quality of our conversations. Everything happens through conversations.”

Judith E. Glaser in Conversational Intelligence – How Great Leaders Build Trust and Get Extraordinary Result


If you need help with those tricky conversations, reach out and let’s discuss it.


Mark Farrer-Brown
Founder and CEO Coach, Entrepreneur, Business Builder and Angel Investor

Mark Farrer-Brown

Mark is known for his scale up expertise having been part of multiple successful exits over the last 25 years as a founder, business builder, coach, mentor and investor.

Follow Mark on LinkedIn.

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