top of page

Challenging Conversations – Realise the Reason

Stuart looked at his diary.

He had Dave’s performance review at 11am and here he was at 8.30am sitting here dreading it. The last few meetings with Ian had not gone well and Stuart knew he had to speak to him about his regular grumpiness in the office and the 2 complaints he had on his desk from his colleagues and he knew she couldn’t put it off any longer. Dave needed to receive a challenging conversation. But Stuart so hated this part of his job. It gave him anxiety just thinking about it, especially as previous conversations had not gone down well with Dave.  


It’s bewildering for many. How did I get to this position in leadership and yet find having a challenging conversation so hard. Everyone thinks it is just them, but in my coaching with people it is the thing that comes up time and time again. In my work as a coach and a trainer in leadership and communication, the biggest issue we come across time and again is having confidence to have a challenging conversation. So, over the next 4 weeks we are going to cover the basics of how to develop confidence in this area. 


  • Realise the Reason 

  • Recognise the issues 

  • Reaction awareness 

  • Raise with 4P’s 


So, let’s explore how we ‘Realise the Reason’ to give us confidence in the conversation. 


What is the purpose of the conversation? 

Stuart knows what. He needs to speak to Dave about, it is the fact that he is grumpy. This though is the ‘what’ of the conversation and Stuart needs to get clear on the ‘why’, the reason things need to change. This is the first of 3 steps in a conversation with someone.

1.      Are you clear on the reason and purpose for the conversation? 

2.      Do you have the facts available? 

3.      Do you have the skills and structure for holding challenging conversations? 


Before any conversation takes place, we need to know the reason why we are having the conversation. In the situation with Stuart. He knows the ‘what’ of the issue. Derek is grumpy in the office and with his colleagues. But what she needs to be clear on is ‘why’ he is having it. To do that, he needs to think about the impact Dave’s behaviour is having and what impact he is looking for.


Take the ‘what’ of ‘grumpy in the office and with his colleagues’ and ask what is important about the impact of this? Grumpiness is harming relationships, impacting on colleagues wanting to communicate with him. Again ask, what is important about Dave understanding this? We want Dave to understand the impact and take ownership if it.


Dave is clearly unhappy and it is affecting his relationships. So, the reason behind this conversation is to

a) shine a light on what is causing Dave’s unhappiness,

b) help Dave understand that it is affecting his relationships at work and therefore the team performance,

c) help Dave understand what is needed in the office and in his manner

d) help Dave know where he can get support if he is struggling.


Ask yourself what underpins all of these? Each of these is about helping gain clarity and illuminate the situation.


So, Stuart’s purpose in this is to ‘Illuminate for clarity and ownership’. This now gives Stuart clarity on what his role is.   


Values driven in a VUCA situation. 

Difficult conversations can get tricky and uncertain, maybe even volatile. Some items can be complex and maybe ambiguous. So, when you are in these Volatile, Uncertain, Complex and Ambiguous (VUCA) conversations, we need to know our values and operate within those. These become our guiding lights when there is not necessarily a play book to follow. Before you start any conversation, remind yourself what your core values are (see a previous blog on how to do this ) When you are clear on these, they become a guide to you when the conversation takes an unforeseen turn. I know for example that my values are ‘Curiosity, Authenticity and Integrity’. When I hold a conversation, I aim to help empower participants to see things then didn’t know. I approach it with curiosity and questions, and I hold honest, authentic conversation and do the right thing, with integrity. However they respond, I respond with those four elements as my guide. Stuart’s core values of compassion and growth mean that he builds relationship and understanding to help Dave grow through this situation.  



It only takes a few minutes to gather your thoughts around your purpose for the conversation. It is answering the question before you start of

What impact am I hoping for? What is important about that?

This becomes like an anchor for you, a foundation on which you return to when the conversation gets tough.


Your values act as your guiding principles and your security. To know these for this conversation it is about asking yourself, who do I want to be in these moments?


So often we feel uncertain in challenging conversations because we have a weak foundation for the conversation. Get your foundation right and you have a much more stable base to build upon. 




Further Everyday Leader events on this

If you would like to know more we have a LinkedIn Live event on Thursday 18th January 2024 at 4pm and the Leadership Lounge podcast on Challenging Conversations coming out on Friday 26th January 2024


Live LinkedIn webinar

Thursday 18th January 4pm


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.  



Featured Posts
Recent Posts
Search By Tags
Follow Us
  • Facebook Basic Square
  • Twitter Basic Square
  • Google+ Basic Square
bottom of page