How to Manage Difficult Conversations

There are many times in life when difficult conversations come up. Many of the most challenging chats happen with family or friends, but most people – and especially leaders – seek guidance for uncomfortable discussions that come up in a work context.

What is the most difficult conversation you have ever had?

One of the most difficult conversations I have ever had at work was having to tell my line manager that I did not think they were the right person for promotion.

I was working for a fast-growing start-up. We had started as a small team, all good friends, with quite a flat structure, but as we grew there were different demands on the team and evolving approaches needed from us leaders. My line manager was highly talented but some of the things that made this person so good at being a leader at the early stages of the organisation could start to become a problem as the team grew. Other members of the team asked me to share my thoughts and opinions with the leader concerned.

I still remember that talk vividly. Sitting down for coffee, the feeling in the pit of my stomach, the look of hurt and betrayal in their eyes as I was speaking. It was tough, but we had a conversation.

The result? He did not get the promotion.

But do you know the amazing thing? Although it was painful, and that later on, we both ended up moving on to other organisations and roles, we are both better off, and even more amazingly, we are both still friends.

I cannot guarantee that you will always have such a happy ending to a difficult conversation but here are some tips, gained from my experience and others, can really help in those tough exchanges.

What is a difficult conversation?

Here are a few issues that you are likely to face in the workplace, particularly if you are in a position of leadership: What’s the best way to challenge poor performance? How do you let someone go from a position? When do you say no to a superior? How do you stand up for a value, idea, or project when you face opposition? What should you remember when you answer challenging questions in times of crisis or failure?

Fortunately there are some approaches and tips that can help you deal with all these circumstances.

How do you prepare for difficult conversations?


The first thing to do is to mentally and emotionally prepare. You don’t want to be overly emotional in the moment, you want to remain as neutral as possible, and envisioning the difficult conversation can help this. Running through the conversation in your mind, imagining any questions and objections that might arise, can help you both mentally and emotionally before an interaction.

Pick your ground

In the military I was taught to ‘praise in public, criticise in private.’ You may not always have the choice but if you can, think about the environment you are going to have the difficult conversation in. A private space, a neutral one away from the office, is often a good choice.

Getting the balance right

There is a balance to preparing for a challenging exchange as over planning can make things feel rehearsed.  Too much preparation and you can lose the authenticity of the message or diminish your empathy and compassion for the other person. If you establish calm and know your main message then have the courage to take the initiative and have the conversation.

How do you stay calm?

If you have followed the preparation steps above these will aid you in starting and maintaining calm through your meeting. Here are a few more tips:


Something that will also help is remaining mindful and centred. Start with your breathing. Ensure you are breathing slowly and deeply. If you feel yourself losing your calm, take a pause and breathe again.

Be mindful of your environment. This is where a neutral space can help be a calming influence and give a broader perspective to your conversation, rather than the intense magnifying glass effect of a busy office.

Pay attention to the other person. Pay attention to their body language and truly listen to what they have to say. Giving someone real attention demonstrates your respect for that person and their views, even if you disagree on something.

Be aware of your body, particularly of any tension building up. Being mindful of your body will help you with your non-verbal communication too.

Posture and Body Language

Try to keep a relatively neutral expression and an open posture. Mirroring other people’s body language is a good way to build rapport but if the other person is starting to display negative body language – angry expressions and displays, crossing arms defensively or slumping in defeat – then don’t copy them. 

Maintain a relaxed (but not casual) openness. This will also help you maintain an even tone of voice and the right volume. If you tense up then tone and volume rise; if you slump and look down the opposite tends to happen. A lot of difficult conversations happen face to face, for example over a table in a coffee shop. This can be quite confrontational. You could consider going for a walk, and there are some big advantages to this (as you can read here), although bear in mind they might just walk away if you don’t gauge things correctly!

How do you start difficult conversations?

Start with something positive, then state the facts.  This is good advice for any conversation but particularly a tricky conversation. Here is an approach that can help:

Sandwich technique 

People best remember the beginning and end of any communication. Therefore structure your response with the most difficult message in the middle and keep the start and end positively:

  • Opening–a positive statement at the start with thanks and appreciation
  • Middle–state the difficult facts, acknowledge the problem
  • Finish–give the positive steps being taken, highlight what has been achieved and give more appreciation and thanks

How do you answer a challenging question?

It could be during the course of a difficult conversation with an employee, during a job interview, or a time of crisis but sooner or later you will face a really robust question.

Whether you have time to prepare for a hard question or not the best thing to do is remember your key message. Take a pause, however small, then answer the question and make sure that point is put across. 

Here is a technique to help you do this clearly, succinctly but strongly:

Remember ‘SEX’

When delivering the difficult part of the message, the acronym ‘SEX’ can provide a useful structure:

  • S (Statement) – Be direct, state honestly what the challenge or problem is, without making it personal. Communicate your main point.
  • E (Explain) – Explain the context, why it is a problem or how the challenge came about.
  • X (Example) – Give specific examples of what the problem is (particularly if its behaviour) and also specific examples of solutions and what can be done.

Here is an example of Steve Jobs answering a difficult question and following this framework:

In this clip he gets his most important point across in his statement, that security is important to Apple. He then explains why security is important, giving context, and then provides a specific example to prove his point; in this case how Apple ensures security regarding location and GPS on phones.

How can I improve my question and answer technique?


One way to get good at having difficult conversations or answering challenging questions is to use role-play. Have someone ask you a scripted or improvised set of tough questions. The more you answer, the better you will become in answering coherently and concisely while maintaining your key message.


If you want to go a little deeper into the subject and particularly the psychology behind difficult conversations I can recommend these:

How to build and re-build trust

This is a great TED talk highlighting the importance of empathy, authenticity and logic.

Games People Play by Eric Berne

Berne developed the idea of transactional analysis; psychological insight that is useful particularly in difficult conversations. You can purchase the book on Amazon through this link:

Games People Play by Eric Berne.


Finally, as with so much in life and leadership, take time to reflect on the conversations you have had and what you could do better in the future. Whether that is through journaling, discussing with a friend, mentor or coach, or just taking some time out to think and analyse. 

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