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Challenging Conversations - Realise the Reason

Otama reviewed the data again. There was no avoiding it. She had to have a conversation with Derek. This was the third month in a row that Derek’s performance scores were down. Mix that with his regular grumpiness in the office and the 3 complaints she had on her desk from his colleagues and she knew she couldn’t put it off any longer. Derek needed to have a challenging conversation. But Otama so hated this part of her job. It gave her anxiety just thinking about it, especially as previous conversations had not gone down well with Derek.

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 6 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

  • Respond with 4P’s

  • Review for growth

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

What is the purpose of the conversation?

Otama came to me with this problem. How can I confidently hold Derek to account in a way that I feel comfortable with, that values Derek and ensures that he takes responsibility? When considering how to have those difficult conversations with people, it will come down to 3 key areas.

  • Are you clear on the reason and purpose for the conversation?

  • Do you have the facts available?

  • 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. When this reason aligns with our passionate purpose then we gain confidence in having the conversation. Take the situation with Otama. She knows the ‘what’ of the issue. Derek is grumpy in the office and his performance is down. But what she needs to be clear on is ‘why’ she is having it. To do that, she needs to think about the impact his behaviour is having and what impact she is looking for. Derek is clearly unhappy and it is affecting his performance. So, the purpose of this conversation is to a) shine a light on what is causing Derek’s unhappiness, b) help Derek understand that it is affecting his relationships at work and his performance, c) help Derek understand what is needed in the office and in his performance and d) help Derek 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, Otama’s purpose in this is to ‘Illuminate for clarity’. This now gives her a clarity on what her role is. This becomes even more powerful when it aligns with her personal purpose. In the case of Otama, her personal purpose is to ‘equip people for success’, so this synchronicity means she will now be holding this conversation in synchronicity with her personal purpose. When you plan your conversation, ask yourself

  • What this the current impact?

  • What impact do I want?

  • What underpins or is a common thread to these impacts?

What is my purpose? What are my values?

Difficult conversations can get tricky and uncertain, maybe even volatile. What do we need in volatile and uncertain times? We need to know our purpose and 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 passionate purpose is. If you are not clear on this some of our previous blogs touch on this. The basic trick for finding this is asking yourself what you are doing on your best day and then asking yourself three times, ‘what about this is important?’ Then hone this down to a word or short phrase that describes what you love doing in any context. Remind yourself too of your core values (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 purpose is to ‘Empower’ and my values are ‘Curiosity, Authenticity and Integrity’. When I hold a conversation, I aim to help empower participants to see things that they 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. Otama’s purpose of ‘equip people for success’ guides her to help Derek. Her core values of compassion and growth mean that she builds relationship and understanding to help Derek grow through this situation. When you plan your conversation, ask yourself

  • What is my passionate purpose?

  • What are my core values?


It only takes a few minutes to gather your thoughts around your purpose and purpose for the conversation. This becomes the foundation for you to build upon. 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.

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.


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