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Challenging Conversations - Recognise the issues

“Ah Dave, do come in to the office. Thank you for coming for the chat.”

“Sorry Stuart, I know I said today would be ok for the chat but I’m a bit snowed under at the moment. Perhaps it could wait until next week.”

In the moment of pause, as Stuart wrestled with how he was going to deal with Dave’s stalling, Dave had thanked him and headed off back to his office. If Stuart was honest with himself, he knew he was not quite ready for this meeting. He was concerned about how it was going to go and what Dave’s reaction was going to be.


In my work as a coach and a trainer in leadership and communication, I’ve run a lot of training on developing a confident conversation and in so many cases people worry about how it will go. This results in putting off the inevitable, but with a little thought and preparation it can be different.


In this series of blogs, we are going to cover the basics of how to develop confidence through four key steps.


  • Realise the Reason 

  • Recognise the issues 

  • Reaction awareness 

  • Raise with 4P’s 


This week, we explore how we ‘Recognise the issues’ to give us clarity of emotions in the conversation.


Story you tell yourself

On the surface of it, it is a simple job for Stuart. He needs to speak to Dave about his performance and his treatment of his colleagues. It’s important for him to do this, for the sake of his colleagues and for the sake of Dave. And yet, something holds him back. What holds him back and so many of us, is the story that you tell yourself about how the conversation is going to go. Your emotional centre, your Amygdala, has played the movie forward and processed the potential threat. This could go wrong. In fact, they are likely to be cross/cry/sulk and it will break down the working relationship. Now the pressure is on to make the conversation successful or even better, maybe circumvent even having the conversation to avoid the potential of it going wrong. So, the first ‘Recognise’ is all about recognising the issues, the worries and the emotions you have.


Reservation Reasons

In my training, we explore the reasons we have reservations and hold back from speaking to people about issues. Here are just some of the reasons we hold back.


Fear of rejection

Don’t want to spoil a relationship

Don’t want to hurt someone’s feelings

Doubt your skills to handle it well

Past negative experiences of a challenging conversation

Makes you feel uncomfortable


Underpinning these is we often don’t want to damage a person or a relationship. We tell ourselves this confrontation will be detrimental. But, if handled well, it could in fact enhance a relationship. Think about those you have a deeper relationship with, it is those who have been prepared to step into the messy middle with you and help you raise your game through a spirit of lifting them up to better things.


Risk Reduction

At the root of these issues is we think there is a bigger risk to having the conversation. But it is often the exact opposite. The trick is to analyse the risk by asking these two simple questions:


What do I risk if I confront this issue?

What do I risk if I don’t confront the issue?


When we do this, we often find that the impact of us holding off is greater than us having the conversation. Of course, there is a chance the person might react but hold this on the balance scales with the impact it is having on the team and indeed the impact on the person whilst they continued to behave like this.


Recognise our Reaction

We are emotional creatures. Our emotional centre of our brain has a key part to play in how we respond to things. Steve Peters, in his book Chimp Paradox, talks about important aspects to help our emotional centre, that he calls our ‘chimp’. When we get an emotional reaction, he says that we need to a) recognise the emotions and b) review the concerns and address them. So, when we find ourselves tempted to hold off a conversation, ask ourselves


  • What emotion am I feeling?

  • What is contributing to this emotion?


This then helps us recognise that sometimes those emotions are the chimp just over reacting and being over concerned.


Reflective Recognition

Once we have considered ourselves, we then need to re-consider the person.


Alain, also known as Emile Auguste Chartier, was a philosopher who recognised that we sometimes find people really hard to get on with. He understood that we would then often portray them as the bad guy and maybe even the evil one there to cause trouble. He encouraged us to reframe the story and to understand it better. He said, ‘find the pin’. By that he meant that living their life must be so painful to make them so grumpy/rude/horrible that it must be like having a pin constantly pressing in them to make it painful and result in their behaviour. When we ‘find the pin’ and seek to understand what might be making their life so sad/bad and realise how horrid it must be living like them, we turn our ‘pain into pity’. This enables us to approach them with compassion rather than fear or anger.


Trying to understand the reasons behind someone’s behaviour enables you to choose a way to approach a conversation. Maslow’s hierarchy of needs is also helpful here. He explains that in order for people to engage in ‘self-actualisation’ at the top of the triangle, the person needs to feel safe, loved and have esteem. Consider the person we are going to speak to. What might be affecting them and therefore contributing to their behaviour? If they may have a relationship issue and are feeling like they don’t belong, then emphasising how they belong to the team might be really important. If you recognise that they may have had some knocks, then emphasising how the improvement might help their esteem could be helpful. This step is about putting on their metaphorical bodycam and looking at where they might be coming from. Recognising their issues and how it is affecting them.


Recognising the issues

Recognising the issues starts by recognising that we may be telling ourselves a false narrative about how this is going to go. We may need to recognise our emotions and how they are affecting us. We may also need to recognise the other person’s position. These key questions can help you to gain clarity:


What story am I telling myself is going to happen if I have this conversation?

How realistic is any reaction I might get? What can I do to reduce the risk of this happening?

What are my emotions and what is contributing to this?

What story am I telling myself about the person and their reaction?

What might the person be dealing with?

As a result of this, what do I need to weave into the conversation I have with them?





Further Everyday Leader events on this

If you would like to know more we have the Leadership Lounge podcast on Challenging Conversations coming out on Friday 26th January 2024


Leadership Lounge

This is on all podcast providers. The next one comes out on Friday 26th January.

The podcast show links are below




Can we help you? 

We hope this blog has been helpful and if you would like some more targeted support to explore having difficult conversations and gain better insight then Everyday Leader is here to help you. Our clients find their coaching empowering, as we help them gain a full perspective and find a way forward. We equally run group training on ‘Holding a challenging Conversation’ which we can run online or in person.  If you have a challenge and you would like our support, then do get in contact with us. Give us a call on 01449 710438 or email if you would like us to help you explore this and empower you.  



If you would like help to raise a conversation with someone, contact us at Everyday Leader. We can empower you to gain clarity with some simple questions to help you understand and manage it better. Give us a call at 01449 710438 or email if you would like us to help you explore this and empower you.




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