How to Have Difficult Conversations

To maintain good relationships, we sometimes have to have difficult conversations. Here we’ll explore the delicate art of handling difficult conversations, both in our personal lives and professionally, and how to succeed in achieving a favourable outcome for all parties.

1.    Consider why the conversation is needed

Managing difficult conversations isn’t a task many people relish, so the chances are there’s an important reason for your impending chat. You might need to:

·         break some bad news

·         bring up a criticism or complaint

·         ask for something you want

·         sit down and talk to someone about an emotional issue

These are all examples of tough conversations that require careful handling.

Before approaching the person, think carefully about what you want to achieve. Are you looking for a way to get their co-operation or agreement? Do you want them to modify their behaviour in future? What is your ideal outcome, moving forward?

Be awae of your own prejudices, which might colour your approach. Does the issue ‘press your buttons’ in a way that’s unrelated to the other person? Do your best to stay impartial and not let unrelated issues get in the way of your goal.

2.    Bring it up promptly and directly

Confrontation isn’t pleasant, so it can be very tempting to put off critical conversations. However, in the long run, avoidance is likely to make things worse. By not speaking up about a crucial issue, you could give the impression that everything is fine – so that when you finally do broach the subject, things are likely to have got worse. Meanwhile, the person you’re speaking to may justifiably feel deceived, because they weren’t aware of a problem.

As soon as the issue raises its head, ask the person for a chat. Be upfront and clear about what you want to talk about, so that there’s no ambiguity, and they can spend some time thinking things through from their own point of view.Difficult conversation in the offiice

3.    Choose the right time and place

The location you choose for a difficult conversation can affect the way it plays out. Confronting someone in front of their colleagues is likely to humiliate them, for example, whereas talking in private could help you achieve a more favourable outcome.

·         Have your conversation somewhere neutral: if you’re the boss, go to a café rather than inviting someone to your office.

·         Give them privacy. If they are likely to react with tears or other strong emotions, ensure that there’s somewhere they can go to calm down.

4.    Listen and learn

Sometimes our preconceptions don’t reflect the reality of the situation. When having difficult conversations, it’s important to go in open-minded, with a spirit of inquiry.

·         Give the other person space to say their piece without interrupting.

·         When they’ve finished, repeat back what you have understood from their words, acknowledging their point of view and showing that it matters to you that you see things their way.

·         Avoid trying to ‘win’ an argument. Instead, approach the conversation constructively with the aim of arriving at a solution together.

·         Sometimes, there’s no solution to arrive at. If your conversation is more about feelings and emotions, it may be enough for the person to simply feel that they have been heard.

·         Acknowledge feelings expressed. Don’t try to ignore tears or other signs of emotion – stay matter-of-fact rather than pretending it’s not happening.

5.    Use language and body language mindfully

The way we conduct ourselves during a conversation can convey non-verbal cues about our true feelings and attitudes. With that in mind, try to be mindful of the way you express yourself when handling difficult conversations.

·         Maintain eye contact with the other person – let them feel they’re being heard.

·         Make sure you’re both on the same level physically – rather than one person standing over the other, for example – to avoid the feeling that you’re talking down to someone. 

·         Stay on-topic: keep your conversation about one particular situation and don’t use it as an opportunity to vent other frustrations.

·         Don’t use generalisations such as, “You always do this”, but do use clear and specific examples about the situations you’re talking about.

·         Be wary of the language you use to describe what’s happened. “You hurt her feelings” is much more direct and accusatory than “When you did this, she felt hurt.”

Women listening during difficult conversation

6. Manage the conversation assertively

During your conversation, it’s important to strike the right balance between assertiveness and aggression, and to be direct and matter-of-fact.


·         If you find it hard to be assertive, remember that being likeable is not always the main goal. Don’t be apologetic or take things back if you’re not sorry. Stand your ground but do it calmly with self-belief.

·         Remember that success here isn’t about winning or losing – it’s about listening and working together.

·         Be prepared to have a break from the conversation and come back later – but don’t storm off. Space to think is important and helps you avoid kneejerk reactions to being challenged.

7.    Know what success looks like

The secret of how to have difficult conversations is to keep in mind what you want to get out of them. With your ideal outcome firmly in your mind, you’re more likely to arrive at a way to move forward together. If necessary, reframe your attitude. Difficult conversations should not be about winners and losers – you need to work together to decide on a way forward.

·         If necessary, reframe your attitude. Difficult conversations should not be about winners and losers – you need to work together to decide on a way forward.

·         You’re both here because you need to solve a problem, so keep sight of your goal and explain it to the other person.

·         Ask them for their own views on how to move on, and agree on next steps for everyone involved.

·         Before concluding the meeting, arrange a follow-up chat to monitor progress and discuss any further issues.


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