Managing difficult conversations


A step-by-step process to make difficult conversations easier

No one likes having difficult conversations. They’re not easy. If they were they wouldn’t be difficult. Follow this recipe to help make the conversation fruitful. 


These suggestions are for any conversations you need to have but don’t want to have. No one likes having these kind of conversations. No one ever actively looks forward to having them either. 

Resist thinking of the impending conversation as some kind of battle where one person is right and the other is wrong. 

There’s no right way and no wrong way to have them. 

Remember that the only thing that’s in your control is you.

You will need

A strategy
Listening skills


1. Know what your shit is and what their shit is

Take a moment to reflect on what is causing discomfort about this impending conversation. Recognise that the discomfort is about predicting what is going to happen in the future. 

That thinking is in a large part down to your needs or preferences as an individual. The thinking is also an illustration of how you perceive your personal values are being or will be contravened. Ultimately the discomfort about the conversation is a statement on how you think things won’t go the way you want them to (because we’re all disposed to negative thinking). 

That’s your shit to deal with. Anything else is theirs. 

2. Thoughts, feelings, actions

Know that what you think about yourself, the situation, or the other person will influence the feelings you hold about yourself, the situation or the other person, and that will influence your actions or behaviours towards them. Those behaviours (in the form of conversation) will influence their subsequent reaction.

So, if you’re looking to bring about a different reaction from the one you’ve been catastrophising about up until this point, then identify a different feeling to hold about the situation/person/thing, and then work out what thought you need to adopt in order to maintain that feeling. 

2. Adopt a strategy for the conversation

What would you most like to get out of the conversation? Importantly, what can you expect to see or hear by the end of the conversation that will help you conclude that it has been valuable? Are those signs realistic? Is what you’re really hoping for something that can only really happen in the mid-long term? 

Are you, for example, hoping that a 20 minute conversation will transform a relationship? If so, might you need to adopt a longer-range strategy beyond the conversation? Once you know what your goal for the conversation is, you have an anchor.

One challenging question h: what’s the one thing you’re frightened of saying. Write down the answer and read it back to yourself. That statement might reveal what you really think and feel about the situation or person. How does that thought or feeling serve you in this situation? How might you change it in order to reach the goal you have in mind? 

3. De-personalise the issue 

There are two people in the conversation and then there’s the thing between you. It’s easy to link the ‘thing’ between you to a particular individual. Blame usually arises at this point along with a whole host of other unhelpful bits and pieces. So, think of the issue as a fairly banal object like a toilet roll, or a bright yellow rubber glove. This will help reduce its power over both of you in the conversation, and help maintain a neutral and respectful language throughout. 

4. Speak clearly and listen carefully

Open questions with specific outcomes are key. General statements phrased as questions are going to lead to ambiguity. 

Speak about the impact of events on yourself — this is the information you ‘own’. Avoid accusations (you’re not the prosecution in a murder trial) or presuming to know what the other person thinks or feels. 

Be clear on the reason for having the conversation at the outset. Strive to have the conversation move forward at all times. 

Match the tone and pace of the other person in the conversation — this helps establish a commonality between you. 

Be curious and supportive. Does the other party need to get something off their chest? Might you be able to give them that space for this conversation? What difference might that make to how things progress? 

5. Respond with statements are aligned to the strategy 

Resist the temptation to ‘rescue’ in a difficult conversation, especially if the mood is heated. Remember point one: you’re responsible for your shit; they’re responsible for theirs. Anything you do say should serve you (or ideally both of you) in pursuit of the stated goal for the conversation. 

6. Reflect back

The most respectful way to engage in a conversation is to show the other party that you’re listening to what they’re saying. Do this whenever they explain something to do by reflecting back (either verbatim or in summary) what you’ve heard. It may turn out to be what they’ve wanted or needed all along. 

7. Be courteous 

This isn’t a battle or a fight to the death. Why make the conversation any more difficult than it actually needs to be? Your perceptions, assumptions and predictions have already made it a source of anxiety. Maintain courtesy throughout.

9. Be authentic

Don’t create a performance act in readiness. Assuming you’re not a psychopath (you might be, I don’t know), speak to the other party with the spirit and warmth you would greet any dog with a wide smile and a wagging tail. Be your natural self not a projection of the kind of person your negative thinking self thinks you need to be. 

11. Opinion is different from fact

Stick to the facts in the conversation. Avoid opinion. Resist responding to their opinion. Opinion brings emotion. Facts feed rational thinking. Take care you don’t misinterpret opinion as fact — its very easily done. 

13. Show empathy

Think of the other person and how the experience is for them. Acknowledge their contribution to the conversation. Recognise them in the moment. 

14. Appreciate the opportunity in the moment

Before concluding the conversation, complete the following statement making sure that the concluding statement is about the other party and is holding them in positive regard. 

15. Be brave

A successful ‘difficult’ conversation is never going to be easy. At least it shouldn’t be otherwise its not really a difficult conversation (or you’re a cold-hearted bastard). 

But it might be possible to have it go better than you anticipated. And to achieve that you’re going to have to do something you wouldn’t normally do. So you’re going to have to be a bit brave on some level.

16. Reflect on the conversation afterwards

This is more than giving yourself a pat on the back as you walk away from the meeting room by the way. 

Answer a few questions in a notebook. Note down your answers as objectively as you can. 

What did the other party bring to the conversation? What did you do well? What challenged you? What surprised you? What would you like to have been better? What would you differently if you ran the conversation again? 

Now repeat the conversation from the perspective of the other person. 

Thoroughly Good Coaching is a personal and professional development service lead by Jon Jacob — a BBC-trained, International Coach Federation-accredited Executive, Management and Life Coach with over six years professional experience. To work with him, email

Discover more about the people who seek out Thoroughly Good Coaching to help develop their thinking, build their motivation and increase their confidence on the Thoroughly Good Coaching Case Studies page.