Handling Difficult conversations

Handling Difficult Conversations

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Much of my recent coaching conversations have been dominated by the ‘difficult conversation’ and the struggles that my clients have faced. There is no one way or single solution to having a difficult conversation, but there are a few approaches that may be helpful.

Prevention Is Better Than Cure – Handling Difficult Conversations

Firstly, prevention is better than cure. The best way to have a difficult conversation is to agree on how you are going to do it before you need to in a work setting, this can be;

  • at the beginning of a new working relationship
  • at a one-to-one
  • in the terms of reference of a newly created group/board

This enables everyone to agree on how you will challenge or progress conversations that everyone knows will be difficult before emotions are heightened or we feel defensive.

On The Spot – Navigate Difficult Conversations Effectively

But hindsight is unhelpful when you find yourself having to have a difficult conversation, or even worse, find yourself accidentally in one halfway through!

In these cases, the following can be helpful;

  • be prepared for the conversation, and decide what you need to achieve and what the other person may also need. If you don’t know what the other person needs- ask. Do they need a solution? Information? Compassion? To be listened to?
  • Are you sharing bad news- what might the other person need to know from you?
  • Try not to couch the conversation with minimising language, traditional management books advise people to have a “good news-bad news-good news” kind of conversation which often leads to confusion from the other person and no one achieves what they want from the conversation.
  • Check-in with the other person- are they ok? Have they understood your meaning correctly? What do they need from you now?
  • Be clear if you don’t know or don’t have an answer to any queries they may have, and agree on what actions you are both going to take.


A key point is not to avoid the conversation. It is understandable to want to have all of the answers or to execute it flawlessly. But these are unlikely, so making an imperfect start is often the best approach.

Avoiding the conversation altogether can lead to misunderstandings, hurt feelings, and unresolved issues. It’s important to approach it with an open mind and a willingness to listen and understand the other person’s perspective. Remember, the goal of the conversation is to communicate openly and honestly, not to have a perfect performance. It’s okay to acknowledge when you’re unsure of something or when you make a mistake. Being authentic and vulnerable can actually help strengthen the relationship and build trust.

So, don’t let fear of imperfection hold you back from having the conversation. Embrace the opportunity to communicate openly and work through any challenges together. 


When faced with the prospect of a difficult conversation, it’s natural to experience a range of emotions. Identifying where these feelings manifest and recognising them as part of the process is an essential step toward managing them effectively. Each of the aforementioned pointers offers valuable insights and strategies for navigating challenging discussions, and incorporating them into one’s approach can lead to more constructive outcomes.

How do you feel when you know you have to have a difficult conversation? Where do you feel it most? Which of these pointers is a good takeaway for you?

How Can The Conversation Company Support Difficult Conversations

Difficult conversations can arise in any workplace setting, whether it be between colleagues, employees, or supervisors. When tensions run high and conflict lingers, it’s essential to tackle difficult conversations head-on in order to resolve issues and move forward. The Conversation Company can support these challenging conversations by providing the tools and mindset needed to reframe perceptions and try to understand the other person’s intention. By recognising triggers and contributions to the problem, individuals can take the next step towards a constructive dialogue.

Through resources and workshops on difficult conversations or related topics, you can clarify your approach and help you stay focused during emotionally charged exchanges. Conversation becomes easier when you recognise you aren’t going into the discussion to win, but rather to understand and improve the situation.

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