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How To Have A Difficult Conversation

Updated: Nov 10, 2020

Are you avoiding having a difficult conversation which might result in confrontation? Maybe it is just going to be too tough and you are thinking about emailing or even messaging the person rather than talking to them?

In a recent webinar with Richard Branson and Simon Sinek, Simon suggested that we should be looking at how we communicate and relate to each other. Simon states that we are losing the capacity to have those challenging conversations. We text, we email. Things are lost in translation and sometimes misunderstood. We are losing the ability to have a verbal conversation effectively. Especially when there is something difficult to be said.

Conflict in the workplace can cause mental health issues, reduce productivity and increase employee turnover. A study here showed that training and coaching in verbal conflict resolution can increase teamwork and resolve many issues more rapidly.

Here are some ideas you can use for conflict resolution and having those difficult conversations.

Be self aware

Ensure that you are looking towards the best possible outcome and result for all involved rather than becoming emotionally attached to the conversation or situation. Stay calm and focused on ensuring this great outcome. It is ok to talk about emotions and how someone may feel, or how you may feel, but how this is delivered is important.

Break it down into 2 parts

Holly Weeks’ a lecturer in Public Policy and expert in difficult conversations suggests this. Discuss the issues non-emotionally and factually in the first part. Then take a break. In the second part discuss solutions. This gives you both time to think about what has happened and come up with solutions.


This can be with a non biased friend. Video yourself or use the perceptual positioning tool described here. Listen to language patterns you are using and imagine how they will be interpreted. Remember what you are saying may not be how you are heard.

Be direct and specific

But not confrontational. Again this goes back to your language patterns. Rehearse what you want to say.

Be empathetic

Let them know that you are genuine. That you care about the outcome and how the other person feels, or what might be happening with them at the moment, which might be acting as a block for their resolution.

Ask more questions

“What will happen if this continues? What will happen when it stops?”

Allow them to reflect. This will take them to the middle part of the brain which is responsible for creativity and long term memory.

Suggest solutions as questions

Allow the person to take ownership for the solution and make a choice. For example:

“ I am hearing you. How about doing ……..? How do you think this would work out?”

This further empowers them to make a choice about potential resolution. Think about brainstorming together to come up with solutions and make the choice about the actions to move a step forward as a team.

These are just some suggestions relating to how you can work with these conversations. Having future focus with an outcome stated in the positive for people to work towards is essential. Coaching your leaders to have these conversations can help ensure conflict resolution is swift, effective and facilitates maximum output of performance, employee happiness and wellbeing.

Caroline Langston is the Founder of Successful Consultants Ltd, an Executive, Personal and Career Development Coaching company in Hong Kong and New York. She is also the Founder of a nonprofit providing free information and coaching to people who are unemployed. Caroline is dedicated to coaching people for success and happiness in their careers and lives. She is degree qualified with a Certificate in Professional Coaching from the ICF, Certificate in Team Coaching from the EMCC. Also further certifications in Neuro Linguistic Programming at Master Practitioner and Coach level.


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