How to Have Difficult Conversations at Work

There’s a particular sentence that can make even the most confident person develop an urgent interest in reorganising their inbox: “Can we have a quick chat?”

Four innocent words, but depending on who says them and how they say them, your brain can start trying to work out what you’ve done, whether this is about yesterday and, at the more dramatic end of the scale, whether you’re about to get fired.

Most of us find difficult conversations at work uncomfortable. Whether you need to challenge someone’s behaviour, give feedback, address poor performance or tell a colleague they’ve upset you, there’s always the temptation to put it off and hope the problem sorts itself out.

Sometimes it does. Quite often, it doesn’t.

When nobody says the thing that needs saying

We were working with a team where communication had become a problem. There wasn’t one huge falling-out or dramatic event we could point to. Instead, there had been a series of small communication breakdowns. Things hadn’t been said, assumptions had been made and messages had been interpreted differently from how they were intended.

Over time, those small things had started to change the way people felt about each other. People were having conversations about what was going wrong, but often with the wrong person. Instead of saying to a colleague, “When you did that, I found it frustrating,” they might discuss it with somebody else over coffee. Instead of asking, “What did you mean by that?”, they filled in the gaps themselves.

We all do this. The trouble is, we’re not always generous when filling in those gaps. “She doesn’t value my opinion.” “He doesn’t care.” “They’ve deliberately left me out of this.”

Before long, something that started as a communication problem has become a relationship problem.

One of the reasons this happens is that many of us associate being kind with avoiding conflict. We don’t want to upset someone or make the relationship awkward, so we say nothing.

Kim Scott has a brilliant name for this in Radical Candor: Ruinous Empathy. It happens when we care about somebody, but our desire to protect their feelings stops us from telling them something they would benefit from knowing.

I see this a lot when we work with teams. Someone will say, “I didn’t want to make a big thing of it” or “I didn’t want them to feel bad.” The intention is good, but the problem hasn’t disappeared. The person may carry on doing the same thing because nobody has told them there’s an issue, while everyone around them becomes more frustrated.

There’s a useful question to ask yourself when you notice you’re avoiding a conversation: Am I protecting their feelings, or am I protecting myself from an uncomfortable conversation?

Sometimes it’s a bit of both.

Start with what happened

Imagine you have a colleague who keeps talking over you in meetings. You could start the conversation by saying, “You’re disrespectful in meetings.”

The problem is that you’ve given them something to disagree with. They don’t think they’re disrespectful, so now you’re having an argument about their personality rather than talking about what happened.

Compare that with: “In the meeting this morning, I was halfway through explaining the figures when you started speaking.”

When we teach feedback at Body Talk, we encourage people to separate an observation from an interpretation. An observation is something a camera could have recorded. “You interrupted me three times” is an observation. “You don’t respect me” is your interpretation of why they did it.

Your interpretation might turn out to be right, but it’s worth finding out before you build the whole conversation around it.

Mind the gap between intention and impact

There’s another idea I love from Douglas Stone and Sheila Heen’s Thanks for the Feedback. They use something called the Gap Map to explain why we can have such different versions of the same interaction.

The problem is that you have access to information about yourself that the other person doesn’t. You know what you were thinking and feeling, and you know what you intended. The other person can’t see any of that. They see your behaviour and experience the impact it has on them.

Imagine you’re under pressure and someone asks you a question while you’re trying to finish something. You give them a short answer and go back to your laptop.

In your version of events, you were busy. You might even think you were being helpful because you stopped what you were doing and answered their question.

Their version might be different. They saw you barely look up, heard your clipped tone and walked away thinking, “Well, I won’t ask her again.”

Neither person has the complete picture.

This also explains why we all have blind spots. We experience ourselves from the inside, complete with all the context that explains our behaviour. Other people experience us from the outside. They see our face, hear our tone and notice things we may have no idea we’re doing.

This is useful in difficult conversations because we often get stuck arguing about intention.

“I didn’t mean it like that.”

“I was only trying to help.”

“That wasn’t what I intended.”

All of those things may be true. They don’t erase the other person’s experience.

Equally, if you’re the person raising the issue, it’s worth remembering that you know the impact something had on you, but you don’t know what motivated the other person.

That’s why curiosity matters.

Be curious about the bit you don’t know

Imagine your manager has cancelled your one-to-one for the third time. It’s easy to start thinking, “They don’t value my time.”

Once you believe that, you’re likely to enter the conversation differently. Your tone changes, your body language changes and the words you choose may be sharper than you intended.

Now compare, “You keep cancelling our meetings and I’m getting fed up with it,” with, “I’ve noticed our last three one-to-ones have been cancelled. Is everything OK?”

You’re raising the same issue. The second version leaves room for information you might not have.

Perhaps they don’t value your time. Perhaps they’re dealing with something you know nothing about. Perhaps they hadn’t realised how often they’d done it.

You won’t know until you ask.

Explain the impact

Once you’ve described what happened, it helps to explain why you’re raising it. You might say, “When decisions change without the team knowing, we end up duplicating work,” or, “When I’m interrupted halfway through explaining something, I find it harder to contribute.”

This is where the Gap Map becomes useful. The person might say, “I was only jumping in because I thought I was helping.”

Great. Now you know their intention.

You can acknowledge that and still talk about the impact: “I understand that, and I appreciate you were trying to help. From my side, it meant I didn’t get the chance to finish my point.”

Both things can be true at the same time. That idea has rescued more than a few conversations.

Try not to save up six months of evidence

I think we’ve all either done this or had it done to us. You decide to talk to someone about something that happened on Tuesday, and while you’re there you remember the thing they did in March.

Then another example comes to mind. Before you know it, you’ve reached the Christmas party.

Nobody enjoys discovering that the person sitting opposite them has been maintaining a secret spreadsheet of their misdemeanours.

This is another danger of Ruinous Empathy. We tell ourselves we’re being nice by letting things go, but we don’t always let them go. Sometimes we store them.

If something matters enough to discuss, try to discuss it close to when it happens. You’ll both have a better chance of remembering the situation accurately, and you’re less likely to have spent several months becoming more irritated by someone who may have no idea there’s a problem.

Be careful with “always” and “never”

There are two little words that have an extraordinary ability to make difficult conversations even more difficult: “always” and “never”.

“You always do this.”

“You never listen.”

The problem is that these phrases are almost never true. As soon as you say “You never listen”, the other person starts searching their memory for evidence that they do. If they can find one occasion when they listened brilliantly, you’re debating whether your statement was factually accurate.

The conversation you wanted to have has disappeared.

Being specific makes it easier for the other person to understand what you want them to think about. Instead of “You never listen to me”, you can talk about the meeting that morning when you were interrupted three times.

Now you have something concrete to work with.

Remember there are two people in the conversation

Sometimes we prepare so carefully for a difficult conversation that we forget the other person is going to speak.

We rehearse our opening, work out the points we want to make and anticipate what they might say in response. Then we deliver our prepared speech and wait for them to realise that we are entirely correct.

Annoyingly, they may have a different version of events.

It’s worth hearing it.

You could ask, “What was happening from your perspective?” or “How did you see it?” If you’re trying to move things forward, you might ask, “What do you think we could do differently next time?”

Then comes the harder part, which is listening to the answer rather than listening while preparing your next argument.

This is the Gap Map in action. There will be things on their side of the map that you couldn’t see from yours.

What if they get defensive? And what if you do?

They might. Even carefully delivered feedback can sting, particularly if the person wasn’t expecting it.

If someone becomes defensive, try not to match their energy. You can acknowledge what they’re saying without abandoning the point you wanted to raise. Something as simple as, “I can hear that you saw it differently” or “I understand that wasn’t your intention” can help you keep the conversation open.

But there’s another possibility worth considering. What happens if they tell you something about your behaviour that you weren’t expecting?

This takes us back to those blind spots. There are things other people can see about us that are difficult for us to see ourselves. We hear our words alongside our thoughts and intentions. Everyone else gets the version of us that shows up in the room.

You might think you’re being efficient; somebody else experiences you as impatient. You think you’re asking challenging questions because you’re interested; they experience it as interrogation. You think you’re being calm and measured; apparently you have a facial expression that suggests otherwise.

This is where our own defensiveness can kick in. If somebody tells us something that clashes with how we see ourselves, the instinct is often to explain it away. “That’s not what I meant.” “I was under a lot of pressure.” “You’ve misunderstood me.”

Those things might be true, but before you reach for them, get curious.

Ask, “Can you give me an example?” or “What did you notice me doing?” You could even ask, “Is that something you’ve noticed before?”

You don’t have to accept every piece of feedback you receive as an unquestionable truth. Sometimes feedback tells you as much about the person giving it as it does about you. But if you hear the same thing from several people, or somebody points out a pattern you hadn’t noticed, it’s worth paying attention.

This is where difficult conversations become more interesting. You might go into one thinking you’re there to tell somebody else what they need to change and discover there’s something useful for you to hear too.

That requires humility, but it can change the tone of the conversation. Instead of two people defending their version of events, you have two people trying to understand what they might be missing.

This is also where Radical Candour is useful. Challenging someone directly doesn’t require you to become cold or aggressive, and caring personally doesn’t mean agreeing with everything they say. You can be clear about the impact their behaviour has had on you while remaining curious about the impact yours may have had on them.

Sometimes the most useful question in a difficult conversation is: “What am I not seeing here?”

Make sure they hear what you need

One of the other things I see with difficult conversations is people being so worried about creating conflict that they soften the message to the point where the other person has no idea what they’re being asked to change.

There’s an interesting cultural dimension to this too.

In The Culture Map, Erin Meyer looks at the different ways cultures communicate and give negative feedback. Some cultures are more comfortable being direct, while others rely more on context, subtlety and what Meyer calls “downgraders”, those little words and phrases we use to soften what we’re saying.

And we Brits are rather good at them.

“I just wondered if perhaps…”

“It might be worth thinking about…”

“I’m a little concerned…”

Anyone who has worked in a British office will recognise these. “I’m a little concerned” can cover an impressive range of emotions.

Meyer tells a great story about a German manager whose British boss “suggested” that he might think about doing something differently. He did exactly that. He thought about it and decided not to do it. He later discovered, to his surprise, that his boss had been giving him a clear message that his behaviour needed to change.

Neither of them thought they were being unclear. They were speaking different cultural languages.

This becomes interesting in global teams. A message that feels clear to someone accustomed to indirect feedback may sound like a gentle suggestion to somebody used to more direct communication. Equally, a direct communicator may believe they are being clear while the person on the receiving end experiences them as blunt.

Of course, these are cultural tendencies rather than rules about individuals. There can be enormous variation within any country, and personality, company culture and the relationship itself all play a part.

But it’s a useful reminder that your version of “clear” may not be the same as mine.

So before you finish a difficult conversation, it’s worth checking that the message hasn’t disappeared underneath all the diplomacy.

If you need something to change, say what that change looks like. You might say, “I’d like us to agree any changes before communicating them to the wider team,” or, “If the deadline is going to move, could you tell me as soon as you know?”

You can say it warmly. You can explain why it matters and invite the other person’s perspective. If you’re working across cultures, think about how your message is likely to land with that person.

Because there’s nothing more frustrating than walking away from a difficult conversation relieved that you’ve said what needed to be said, while the other person walks away thinking you’ve had a nice chat.

The conversation you’re avoiding isn’t getting any easier

Going back to the team I mentioned earlier, what they needed wasn’t a clever communication trick. They needed to start talking to each other.

Once people were able to explain what they had experienced, hear somebody else’s perspective and talk about what needed to change, the atmosphere began to shift. It didn’t mean everyone agreed with each other, and that wasn’t the aim. People started replacing assumptions with conversations.

I think that’s worth remembering when we worry about getting difficult conversations exactly right.

You might stumble over your words. The other person might need some time to think about what you’ve said. You may walk away and think of a better way you could have phrased something. That’s normal.

Some conversations are uncomfortable because the subject matters. We can approach them with curiosity, be clear about what we’ve observed and give the other person the chance to tell us what we might not know.

We can also resist the temptation to be so nice that we never say what needs to be said.

If there’s a conversation you’ve been putting off for a while, there’s a fair chance the other person already knows something isn’t right anyway.

You may as well have the chat.