How to start a difficult conversation. Never dodge a conversation again!

Think of the conversations that you hate to have. The conversations that you’ll put off, discuss with other people, but never actually start. They are also the conversations that matter most at work. Learning how to start a difficult conversation is an essential skill.

Here’s why difficult conversations are so important

In the Crucial Conversations training program, these conversations are described as ‘the crossroads of productivity’.

You can either hold the conversation, and hold it well, in which case you’ll build the relationship and move forward with the work. Or you can avoid the conversation, or hold it badly, in which case you’ll damage the relationship and delay the work.

Learning how to successfully start a difficult conversation is critical to your success. Difficult conversations are the crossroads of your productivity.

How to succeed before you start the conversation

The success of your difficult conversation is going to be decided long before the conversation starts. To be successful, get laser focused on what you want, for the relationship.

Yes, there are business outcomes that you need from the conversation, but this is not the right focus. What do you want for the relationship?

Be honest with yourself.

Do you want a successful collaboration? Or, are you nursing past grudges and want to get even? Perhaps you want to win, and leave them fatally wounded? If it’s either of those last two, you have some reflection to do before the conversation!

The point is this: you’re not going to have a successful conversation until you focus honestly on what you want for the relationship. Why is this so important? Because during the conversation you’re going to be tested. Emotions will swell. You’ll be tempted to respond ‘in the moment’, with potentially destructive consequences. At that moment, you need to remember what you really want for the relationship, take a breath, and act in a way that will build the relationship and move the work forward.

Don’t let your motives and behaviors change during the conversation. Get clear up front about what you want for the relationship and keep your behavior aligned as you’re in the conversation.

How to start a difficult conversation

There are three simple points to remember:

1. Ask permission

Use a simple phrase such as “I’d like to catch up, do you have a moment?”, or if the conversation is likely to be longer and a meeting would be better, “I’d like to schedule some time next week to discuss ____, is that OK?”.

Asking permission creates buy-in and commitment on the part of the other person. You’re starting with a mutual commitment to the conversation, which is exactly where you want to be.

And if the person says no? that’s fine. It’s their right to do so. Be patient and ask them when would be a good time to talk.

2. Keep it short

When you launch into the conversation you many feel nervous, it’s tempting to ramble. Also, it feels safe to talk, you’re in control. But the longer you are talking the more the emotions are rising, and the more likely it is that the other person is shifting negative.

People would rather hear that they’re not cutting it for 2 minutes rather than 20. Shari Harley.

Plan your opening and keep it short.

3. Keep your tone light, let the message speak for itself

It’s a difficult conversation. It’s not going to get any easier if you plaster anguish all over your face and weigh down your tone with too much gravity. Keep it conversational, keep an easy expression on your face.

Remember to keep positive, keep focused on what you want for the relationship and the work.

Use the ‘3Fs’ model to guide you

This 3Fs model will help you structure the start of the conversation:

  1. Facts
  2. Feelings
  3. Finish with an open, neutral question

Sharing the facts is a great place to start because it establishes context, facts are relatively uncontroversial, and they provide a platform for sharing your feelings. Make sure you express the facts as facts, with no ambiguity or doubt. And make sure they are facts that the other person cannot dispute… the last thing you want is the conversation veering off towards a debate about what happened.

Expressing your feelings helps the other person to understand what’s at stake.

Finishing with an open, neutral question invites the other person into the conversation without trying to control or direct their contribution. It’s neutral and non-threatening. More on asking questions.

Examples of how to start a difficult conversation with your team member

Over the past months I’ve asked you several times to get to our meetings promptly, but the last two occasions you’ve still been late. I’m starting to think you are not interested in improving your performance. What are your thoughts on this?

The company is going through a lot of change, and we need everyone committed to the journey we’re on. However, I see you’re still using the old processes. I’m starting to think you’re not really committed to making the change a success. What are your thoughts on this?

Examples of how to start a difficult conversation with your manager

Do you have a moment to discuss something? Over the past couple of months, you’ve assigned all the new projects to Sally, I’m starting to feel a bit left out. Could you help me understand what’s going on?

Can I have a moment of your time? The last 3 times we had a 1-1 scheduled you cancelled at the last minute. I know you’re very busy but it meant that I couldn’t get your time to discuss some critical tasks. And it left me feeling that my work is not important.

Examples of how to start a difficult conversation with your coworkers

Can we talk? This past week you’ve come to me with three requests, all of which required an immediate response. I want to help you, but these last-minute requests make it hard for me to hit my own deadlines. What are your thoughts on this?

Do you have a moment? In the meeting yesterday you were congratulating the team. You used the phrase “well done guys” several times. There are several women on the team, and “well done guys” made me feel a bit uncomfortable. Maybe I’m over-reacting, what are your thoughts?

Points to note on all the above:

  • Sometimes its appropriate to ask for permission to talk, but not always. If you’re talking with a team member (perhaps in a 1-1 meeting), it’s not necessary.
  • You’ll see some consistency through all the examples. “I’m starting to think…” (or “I’m starting to feel”) and “what are your thoughts on this?” are useful phrases.
  • Aim to keep negative emotions out of the language that you use. In the first example I could have said “I’m starting to think that you don’t care…” but I used “I’m starting to think that you are not interested” instead. It still gets the message across, but it’s less likely to create a negative or defensive reaction.
  • Sometimes it’s not necessary to even ask the question. Say what you have to say, and then simply close your mouth, wait, and leave the space for the other person to talk.
  • Always express your feelings as your own, don’t try and represent others. In the final example, you could have said “I’m sure it made them uncomfortable” – but then you’re representing someone else and potentially opening up a debate about how other people feel. That’s a rabbit hole, avoid it.
  • I’ve mentioned keep it short already, all these examples are very quick!

For even more difficult conversations, watch this video (it’s 14 mins, but worth it).

Shari Harley explores how to say anything to anyone. There’s a medical context to the video (she’s talking at a medical conference), but the skills she describes are relevant to anyone in any situation. Grab a coffee and enjoy.

If you don’t have time to watch the video, I want to highlight just one point.

Expect a response.

It doesn’t matter how well you start a difficult conversation, you’ll likely get a response (that’s why it’s difficult!). It might be shock, anger, self-justification, it might even be tears. Be prepared and stay calm. Let the other person express themselves.

Listen to what they have to say. And be ready to ask questions or make a recommendation. Acknowledge that the conversation is difficult, thank the person (if appropriate).

How to start a difficult conversation: in summary

Difficult conversations are the crossroads of productivity. Being able to hold them well is critical to your success!

Get clear up front about what you want for the relationship, it will help you keep your behavior aligned as you’re in the conversation.


  1. Ask permission
  2. Keep it short
  3. Keep your tone light

Use the ‘3Fs’ model to guide you:

  1. Facts
  2. Feelings
  3. Finish with an open, neutral question

Expect a response.

More on how to handle difficult career conversations with your team.