We all know them: Conversations that we should have, but keep postponing and avoiding. We just know that they will blow up. We know that they will most likely not end well.

And yet, it keeps bugging us. Why is the operations team blocking our work? Why does my colleague revert my code changes without talking to me? Why does my boss pass off my work as his?

There should be a way to have these difficult conversations without things blowing up and going all wrong. Unfortunately, there is no guarantee. However, if you follow the seven proven techniques and strategies below, you will maximize the probability of success. Let’s dive in.

1. Seek privacy

Jenny approaches Amanda: “Amanda, this was not at all what we agreed on! You just launched the campaign without taking my input! You have not kept your side of the deal!” Amanda’s team mates, sitting close by, interrupt their work and look up. Amanda immediately becomes defensive.

If you accuse somebody in public, you are begging for the conversation to blow up. Even if you provide constructive, critical feedback with others standing by, you are heading down a dangerous path.

The rule of thumb goes: Praise in public, criticize in private. And there is a reason for that.

If you criticize somebody in public, the receiver of the feedback — Amanda, in our example — will immediately be aware that others are watching and listening. Her reputation and the respect others have for her might be affected by how she reacts to the criticism.

Will others think of her as weak if she does not “fight back”?

Will she now be perceived as sneaky, because Jenny accuses her of not sticking to an agreement?

Will others not take her seriously any more?

Does Jenny want to humiliate her in front of her colleagues?

Such questions trigger our “fight or flight” mode. We feel attacked. Many will react by counter-attacking, or becoming defensive.

In contrast, if you deliver feedback in private, behind a closed door, it is a thing between the two of you. Nobody has to save face, because nobody else is watching. The possibility of humiliation is off the table.

Therefore, most people will be more likely to listen first before they respond. Their reaction will be less emotional and more thoughtful. Having the conversation in private is not enough, but it is pretty much a necessary requirement for a successful difficult conversation. A bit like not starting off by yelling at each other.

2. Start with facts

Peter talks over Ben in a meeting. Ben thinks: “He is doing it again! This must be the fifth time this week! He always does this. He thinks that his opinion is more important than mine, or anybody else’s. He is an arrogant idiot who has no respect for other people!”

When we witness annoying behaviour repeatedly, it’s easy for us to jump to conclusions. We jump from specific events — Peter talks over Ben — to generalizations — Peter always does this — to conclusions about character — Peter is an arrogant idiot who has no respect.

This is a classic villain story that makes life very easy for us, or rather: simple. Peter is the villain, he cannot help it, I cannot help it, it’s just how things are.

Villain stories free us from all responsibility to do something about the situation.

The downside is, of course, that nothing will change if all we do is tell villain stories to ourselves. However, it would be even worse to tell the villain story to the “villain”.

Just imagine: “Peter, I know you think your opinion matters more than that of other people, but it’s not actually true.” If Ben starts a conversation with Peter like that, it is unlikely to go well. Peter will feel attacked, and either become defensive, or counter-attack, or deny, or refuse to continue the conversation.

If we have the difficult conversation, we have to take a step back, and start with the facts. The more specific you can be, the better: “Peter, about the meeting just now, you interrupted me twice. Once when I was telling the others about the conference, and once when I was pitching my idea about the search feature.”

These are facts. Peter will have a hard time denying them. Moreover, he does not have to feel attacked. This is a much better start to a productive conversation, one that Ben can build on. Ben can then go on to tell his story.

3. Keep your goal in mind

Dan: “Why are you getting angry? All I did was suggest that we reconsider the user flow.”

Linda: “Because you are changing your mind at the last minute again! You keep doing this! Sometimes, I feel like planning and commitment are not really your thing.”

Dan: “What is that supposed to mean? And, besides, look who’s talking about commitment! Who missed the last three deadlines, me or you?”

Linda: “That’s because we never get the time to clean up this mess! We have accumulated so much technical debt that all we ever do is piling shit on top of shit!”

Dan: “That sounds a lot like an excuse to me. I hear no one else complaining about this but you.”

Let’s pause for a second here. A minute ago, Dan and Linda were talking about the user flow of a feature. Now, they are insulting each other and throwing accusations back and forth.

When a conversation goes awry like that, it is helpful to mentally step back for a second and ask yourself: What is actually my goal here?

Or, to quench your and my thirst for pop-culture references, ask yourself the Spice Girls Question:

“What do you really, really want?”

Dan’s goal for the conversation with Linda is to talk about the user flow. Having that sorted out, a follow-up question is equally important: “How would I behave if that was really my goal?”

If talking about the user flow is really Dan’s goal, why is he now accusing Linda of missing deadlines and making excuses? Is it likely that this will bring him closer to his goal? Certainly not.

Why is he doing it, then?

He wants to win the conversation. He was attacked by Linda, and jumped straight into counter-attack mode. This is understandable, because such behaviour is hard-wired into our brains. At the same time, though, it is horribly unproductive.

If Dan wants to act according to his goal, he should try something like this:

Linda: “You are changing your mind at the last minute again! You keep doing this! Sometimes, I feel like planning and commitment are not really your thing.”

Dan: “I understand that changing the user flow now delays things. I don’t want to make your life harder just for the fun of it. But I truly fear that we are about to make a mistake that will be hard to correct later on. Can I please share my concerns with you?”

Dan does not react to the accusation that planning and commitment are not his thing, and thus reduces the amount of dangerous fuel in the conversation. Instead, he makes his intentions clear, and keeps the discussion on track, straight towards his actual goal: Talking about the user flow.

4. Paraphrase

Patricia: “This project team is not a team. Everybody sits somewhere else, and nobody knows who does what. We need to change the team setup.”

Mary: “We do not have to change the team setup to become faster again. Next week, the new project manager will finally arrive. He will improve the coordination.”

Patricia: “Are you even listening to me? A project manager might mitigate the problem, but by no means solve it!”

When you get strong signals of opposition from the other party, try to show that you are truly listening to them. An excellent way to do that is to paraphrase what they are saying.

Paraphrasing signals that you are trying hard to understand their point of view, and that you are not just trying to win the discussion and dismiss their concerns as irrelevant.

In the above example, Mary can use paraphrase like this, without giving up her position:

Patricia: “This project team is not a team. Everybody sits somewhere else, and nobody knows who does what. We need to change the team setup.”

Mary: “So you are saying that the team is too spread out, and responsibilities are unclear. Right? I understand your concerns, but I am not willing to change it right now. Next week, the new project manager will finally arrive. I am confident that he can improve the coordination.”

Patricia: “I am not really convinced, but let’s see what he can do.”

On the surface, the outcome is not that different. Patricia still has a different opinion. However, she knows that Mary understands what she was trying to tell her, and she is more willing to go along with Mary’s course as a result.

Smart people do not always have to get their way, but they need to know that they have been heard. Paraphrasing is a powerful way to demonstrate exactly that.

5. Watch for warning signs

Jeff: “You said that we would tackle the clean-up in the next sprint. Now, I see so many features in there. If we try to do all of these, we will not have time for much clean-up.”

Marc: (takes a deep breath, exhales audibly, and stares at his screen) “Fine. What do you want me to change?”

You can never predict how well a conversation goes. Therefore, you have to stay alert and observe. When you perceive one or several warning signs, consider acting on them. I will show how in the next section.

In the example, Marc takes a deep breath and avoids looking at Jeff. This is a typical sign of anger and frustration.

Other typical warning signs are:

• Tone: This is a very noticeable one. When somebody raises their voice, or assumes a threatening, sarcastic, or mocking tone, you realize instantly that the conversation is taking a dangerous turn.
• Silence: Some people will withdraw from a discussion when they feel powerless or not heard. Silence is sometimes accompanied by gestures like leaning back in one’s chair and staring at the desk, or staring into empty space.
• Gestures: Some people will gesture aggressively when they get emotional — some start pointing their finger in a threatening way, others even bang the desk or throw objects around. These are warning signs that are hard to miss.
• Conversation off track: In the example with Paul and Linda above, the conversation was suddenly not about the original topic any more — the user flow of a feature —, but about accusations of lacking commitment. If the conversation veers off course like that, this is a warning sign and should be corrected.

I recommend you practice spotting these warning signs very consciously. The earlier you pick them up, the easier it will be for you to course correct. The longer you wait and try to go on as planned, the smaller the chance that you can lead the conversation to a successful outcome.

But what does “course correct” mean exactly? What should you do when you spot these warning signs? This is the topic of the next section.

6. Establish safety

Carol: “Steven, we should send the report now. Can you add the data that you have so far?”

Steven: “It’s not my fault that this is taking so long! Why don’t you try to get data from half a dozen reluctant stakeholders and unify all their stupid different formats?”

Carol: “You don’t have to yell at me like that. All I’m saying is that the deadline is an hour away. We should get going, data complete or not.”

Steven: “You know what? I’m going for a cigarette now, before I start smashing some equipment.”

Steven shows a violent reaction that Carol did not expect. All she said was that they had to send a certain report now. However, Steven takes that as an accusation. He feels attacked, and starts defending himself.

People resort to violence, silence, sarcasm, and mockery when they do not feel safe. They might feel attacked, or belittled, or humiliated, or manipulated. Their reaction makes it difficult to continue the dialogue “as planned”. First, they need to feel safe again.

If you want to be really great at leading conversations, you have to learn how to establish or re-establish safety. In order to do that, you should step out of the dialogue: Forget what you were aiming for so far. Safety has become your new primary goal.

Picture “Step out of dialogue” from presentation

Let’s have a look at what that might look like with Steven and Carol from the example above:

Steven: “It’s not my fault that this is taking so long! Why don’t you try to get data from half a dozen reluctant stakeholders and unify all their stupid different formats?”

Carol: “Steven, I know that it is difficult to aggregate all this data. And I know you worked hard on that. It must be frustrating for you that you did not get as far as you wanted to. I understand that, and nobody is blaming you for anything. Do you believe me?”

Steven: (hesitates, then) “Yes. Sorry I got so angry.”

Carol: “It’s ok. So, will you add the data that you have so far?”

Steven: “Yes. I’ll get right on it.”

Carol re-establishes safety for Steven in several ways:

• She acknowledges his hard work.
• She acknowledges his feeling of frustration, and shows understanding for it.
• She makes it clear that there is no accusation or blaming going on.

The additional “Do you believe me?” at the end prompts Steven to either accept or reject her explanation, and creates clarity. With this clarity established, Carol can step back into the conversation, and pursue her original goal: Get Steven to add his data to the report.

Acknowledging the other’s challenges and negative feelings is an effective way of staying in dialogue. It can prevent the other person from giving up and refusing collaboration.

Let us look at the example of Jeff and Marc again, who were arguing over sprint scope. Marc shows the first warning signs of becoming angry and frustrated. Jeff will now acknowledge these feelings.

Marc: (takes a deep breath, exhales audibly, and stares at his screen) “Fine. What do you want me to change?”

Jeff: “Look, I know this must be frustrating for you, because you were hoping to move faster. I would like to move faster, too. But if we do not stabilize this codebase now, we will be in deep trouble before we know it. “

Marc: “All right, all right. I know. So what are we going to do?”

If you still do not believe that safety is that important, consider this: Good friends usually can tell each other anything — harsh criticism, candid feedback, etc. — without the other person becoming angry or defensive. That is because, with a good friend, we know that they are on our side. We feel safe.

As the authors of Crucial Conversations put it:

“People rarely become defensive simply because of what you’re saying. They only become defensive when they no longer feel safe.”

If you turn this around, that is really good news: Make the other person feel safe, and you can tell them a lot of things they do not want to hear, but must hear.

The message is not the difficult part. Safety is.

7. Emphasize mutual purpose

Let’s look at the dialogue between Carol and Steven one more time:

Carol: “Steven, we should send the report now. Can you add the data that you have so far?”

Steven: “It’s not my fault that this is taking so long! Why don’t you try to get data from half a dozen reluctant stakeholders and unify all their stupid different formats?”

The argument is becoming heated, and people are starting to turn against each other. Previously, Carol defused the situation by establishing safety for Steven. Additionally, she could remind Steven of their mutual purpose:

Carol: “Steven, I know that it is difficult to compile all this data. And I know you worked hard on that. It must be frustrating for you that you did not get as far as you wanted to. I understand that, and nobody is blaming you for anything. However, we have to move on now, because if we don’t, your work and our work will have been in vain. Ok?”

Steven: (hesitates, then) “Yes. I guess you’re right.”

Carol reminds Steven that they are in the same boat, and that they depend on each other. This lets Steven put his frustration with the past aside, and helps him focus on the future instead.

Conclusion

We have looked at seven strategies to master difficult conversations:

1. Seek privacy so that nobody has to save face
2. Start with facts, because they are undeniable
3. Keep your goal in mind. Don’t let it become “Win the argument”.
4. Paraphrase to demonstrate you are truly listening
5. Watch for warning signs so that you can react early when the conversation takes an unsafe turn
6. Establish safety to bring the conversation back on track
7. Emphasize mutual purpose to convince the other party to collaborate

While these strategies do not guarantee a successful outcome, they drastically increase your chances. Also, keep in mind that some of these read simple, but they are hard to implement, and require a lot of practice.

Personally, I find the “establish safety” part the hardest one. When emotions take over and annoying behaviour starts, it goes against our nature to stay calm and acknowledge the other person’s feelings. Our instinctive reflex is to go into fight or flight mode, and it takes some training to get over this. However, establishing safety is also the most important hurdle to take. If you want to dive deeper, I recommend the Crucial Conversations book.

How do you handle difficult conversations? Do you use any of these strategies? I would love to hear your thoughts, so do not hesitate to comment below!

Time investment

This blog post took me about 5h to write and edit.