How to Start a Difficult Conversation (Video)

Elinor Whitmore provides advice and guidance on how to start a challenging conversation with a difficult person, on a difficult issue, or both.

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How to Start a Difficult Conversation

Here’s the video link of the transcript below: https://www.youtube.com/watch?v=dwZCPHoCrl8

{Transcript}

We’re going to be looking today at how to start a difficult conversation. I was teaching a difficult conversation workshop a couple of years ago, and I had a pilot in the class. At the end of the class, he came up to me and said that some of the training had reminded him of the training he’d received as a pilot. He said, “When I was being trained as a pilot, we were taught there are two ways you can get a plane on the ground: you can land it or you can crash it—and it’s all in the approach.”

He said, “I sort of feel that that’s true of these difficult conversations.” And there is a certain truth in that—we can land a difficult conversation, or we can crash a difficult conversation, and a lot of it is in how we approach the conversation.

A lot of clients come to me and say, “I don’t know how to start. I don’t know what to say to begin the conversation.” So what we’re going to be doing today is looking at some templates. They’re almost like checklists that we can use to start a difficult conversation. We’re going to look at a few of them.

Of course, having a few templates isn’t going to cover every possible difficult conversation that you could possibly have, and yet I think these templates will cover a lot of the conversations that you might want to have. Also, the underlying concepts can be used in lots of different conversations. So, the templates are there to provide you with a kind of focus and a way to get started.

But I, of course, would leave it up to you to decide how you breathe life into it—sort of based on your personality, based on the person you’re speaking with, based on the situation.

So the first one we’re going…

Three Toone problem solve

To talk about is one that they call “Three-to-One Problem-Solve,” and it was developed by a man named Doug Stone at Harvard. It was designed to try to deal with some of the typical mistakes that people can make when starting a conversation. I’m going to give you an example.

Let’s say my colleague Paul and I have been charged with the task of upgrading the technology in our organization. Now, let’s just be clear—I’m not going to be upgrading the technology; we’re supervising the project. So we’ve been charged with that task, and we’ve talked about how to do it. He thinks that we should use external IT consultants, and I think that we should use our internal staff.

A mistake that I could make in starting the conversation with Paul would be to go to him and say, “You know, Paul, I’d like to talk with you about why I think we should use our internal staff.” The reason that that’s a mistake is that I’m starting the conversation at precisely the point of disagreement. That’s exactly what we disagree about, and I’m putting forward my perspective—which is the one he does not share. So I’m starting the conversation in a way that increases the likelihood of us having a difficult conversation.

If I were to follow the template “Three-to-One Problem-Solve,” the first thing I would do is try to think about: how would a third party—a neutral third party—describe what’s going on here? What’s the goal of the conversation? So they might say, “Well, the goal of the conversation—the reason why we’re upgrading the technology—is to improve productivity and improve efficiency, and we want to do it on budget. We have a difference of opinion about how to do that.” So that would be the third-party perspective.

Then the second-party perspective—in this case, because I’m the person starting the conversation—would be Paul. So they would say Paul’s perspective first, so that he knows it’s out there, it’s on the table. Then describe your perspective, then extend an invitation to problem-solve.

So what that might look like would be me going to Paul and saying, “Hi Paul. You know, I was hoping that we could find some time to talk about this project for upgrading the technology. I know we both want to make sure we improve productivity, we increase efficiency within the office, and that we do this project within budget. So we share those goals. Now, one way of achieving that would be to use external consultants. Another way would be to use our internal staff. There may even be other options that we haven’t talked about. I’m wondering if we could sit down and talk about those options—and maybe some other options—maybe look at the pros and cons of these approaches. And hopefully, at the end, we’ll be able to identify what we think might be the best approach.”

Fierce Conversations

Not saying that’s a perfect way to start a conversation, but you can see it’s going to have a very different impact. I’ve identified the shared goals and named his perspective first, and then mine—rather than starting with mine. So that’s “Three-to-One Problem Solve.”

The next template we’re going to look at is for beginning the conversation, and this would be one that we’d use more likely in a situation where we find somebody’s behavior to be unacceptable in some way. This particular template was developed by a woman named Susan Scott, and it’s set out in a book she wrote called Fierce Conversations.

The first thing she invites us to do is to name the issue. So let’s say you’ve got a colleague who’s coming in late for meetings. The issue might be punctuality. You might think, “I need to speak with them about punctuality.” Or, when you think about it, you might realize, “Well, they come to the meetings late, they’re dressed inappropriately, they make a bunch of personal calls, and they use inappropriate language in front of the clients.” Suddenly, there’s a very different issue on the table. When you pull all of those things together, you might think, “You know what? We’re no longer talking about punctuality—we’re talking about professional conduct.” So the issue I need to speak with this person about is professional conduct in the workplace.

The first thing you need to do is identify what’s the issue. Then the second step is to provide an example. Because if I just say to this person, “You know, you’re really unprofessional and I’d like you to be more professional,” well, they have no idea—perhaps—what they’ve been doing that’s unprofessional. Particularly if it’s just based on them coming late in the morning, they might say, “Well, at my old place of business, people showed up when they needed to, and they worked through lunch if they had to. Sometimes we stayed late, sometimes we came late—we just managed our time as long as we got the work done.” So to just say to somebody they’re unprofessional, you need to provide an example as to what’s giving you that impression.

But notice that the second step is “provide an example”—it’s not “provide the 598 examples that you’ve been storing up in your cheeks like a little squirrel storing nuts,” and the minute you have a chance to say them, they’re going to come flying out at the person. So it’s one example—maybe you’ll give two, maybe three—but you have to stop. You know, the idea is you just want to give them a sense of why you’re having the conversation.

The third piece is to describe the impact or the emotion that this behavior is creating. So in a workplace, the impact might be: if they’re coming late to meetings, it’s hard to stick to the agenda, or it’s having a negative impact on their colleagues in terms of morale, or it’s interfering with teamwork. You can use the same template at home, and at home or in your personal life, you might be more comfortable naming some emotions. So maybe somebody has done something and it hurt your feelings or it embarrassed you—and this would be the point in the conversation where you’d want to name that.

The fourth step is to name your contribution—how you might have contributed to the situation arising. Now, I think a lot of people would say, “How could I possibly have contributed to my colleague coming late for work?” And you’re right—you haven’t. You’re not responsible for them coming late to work. But you may have contributed to them coming late for work. And the way you may have contributed is: maybe somebody else came in late and you never said anything to that person, and they started to think it was okay. Or maybe you don’t always punch the clock and come in on time, and they looked at you and thought, “Well, it seems like this is the workplace where things are a little more easygoing around time.”

Or a classic one is—very rarely do we talk to somebody the very first time they do something that bothers us. So they come in late once and we think, “Well, I hope that doesn’t happen again.” And they come in late a second time and we think, “Well, I hope this isn’t going to become a pattern.” And then the third time, we go to speak with them. Well, if you’re going to speak with somebody the third time, your contribution may have been that you didn’t bring it to their attention earlier—that them coming late to meetings is a problem. And by not doing that, they started to think it was okay.

The last two steps are fairly quick…

Resolving Conversations

So the fifth step is just to indicate that you wish to resolve the issue, and the last step is to invite the partner to respond. Remember, this isn’t the whole conversation—this is just how you’re getting started.

So here’s how we might start a conversation with somebody who’s coming late to meetings. You could say: “Hi John, I just wanted to speak with you about an issue. I need to speak with you about the issue of punctuality. I noticed that you came late this morning to the meeting, and that’s the third time that you’ve come late. As I think you can appreciate, when you’re late for meetings, it means we don’t get started on the agenda, and I think it also has an impact on the other people who have come on time. I may have contributed to the situation by not bringing it to your attention earlier when you were late for the other meetings and not letting you know that my expectation is—when we set a meeting for 9:00—that people are going to come a few minutes in advance and get ready, and we’re going to be ready to go at 9:00. So I’d really like to try to resolve this to ensure it doesn’t happen again. Is there anything you want to add, or is there anything we need to discuss about this issue?”

There—you’re done. Sixty seconds. Six steps. You’ve been very clear, you’re very concise, and you’re done.

Now, there is a slight variation on that, which we call confronting. Confronting would be when you need to speak with somebody maybe for the third or fourth time about something that they’ve done, and you need to up the ante because you’ve already talked with them about it a couple of times and it continues to be an issue. Or, the thing that they’ve done right out of the gate is so unacceptable that you’re not going to have one, two, or three conversations in the hope that they change it. You need to confront them right out of the gate and say it’s not okay.

So in those situations, you insert a step after naming your contribution, which is to identify what’s at stake if they don’t change their behavior—and we’re even encouraged to use that language of “what’s at stake.”

Let me give you an example. I had a friend who called me up one day and her son had taken the family car without her permission. When I’m speaking with her, she’s all up in arms about it. She said, “He’s taken the car!” Then she’s really upset and said, “I’m going to confront him,” and she knew about these steps.

So we’re walking through the steps, and I’m trying to be mindful of her emotional tenor. We get to the part about what’s at stake, and I said, “What’s at stake here? What’s the consequence if he does this again?” And she said, “If he does this again, I will be so mad!” I said, “Okay, let’s take a look at the situation,” because I knew he’d already done it a few times. I said, “When he did it those times, were you mad then?” And she said, “Yeah, but I’ll be really mad now!”

And the thing about “what’s at stake” is—it has to be something that matters to the person you’re speaking to. I think we could see that her son had already done a cost-benefit analysis. He said, “I could be out with my friends in my mum’s car having a fun time with a mad mother at home, or I could be at home with my boring little sister watching the television while all my friends are having a good time, and have a happy mom. Hmm… which one do I choose?” Well, we’ve seen which one he chose—he’s busily driving downtown in her car. So her being mad isn’t enough at stake for him.

I reminded her that “at stake” needs to be for the person you’re speaking with. Then she said, “Well, the only thing he seems to care about is girls. So maybe if I said to him, ‘If you take that car again, you will never have a girlfriend’—that would get his attention.”

Again, I’m trying to be careful because I understand she’s upset. I said, “I’m sure it would get his attention. Now—is that something that’s within your power?” Because of course, what’s at stake needs to be something you have control over—a consequence you’re going to impose. Of course, him not having a girlfriend is not a consequence she can impose.

So what she said in the end was: “I need to speak with you about the use of the family car. You took it last night without my permission and I’m very angry. I may have contributed to the situation by not letting you know the last time that this could never happen again. What’s at stake for you here is: if you do this again, you will never be allowed to use the family car under any circumstances. I’d like to try to resolve this with you. Is there anything you need to say?”

So I think the last part came out a little sharp. I think she may have been a bit pinched by the end, but you can see how you name what’s at stake—and we can certainly do that in workplace contexts as well. It just has to be something that’s within your control—a consequence that you’re prepared to impose. Whether it’s you’re going to speak to the person’s manager, or—if you are the manager—you’re going to put a letter in the file, there’s going to be some consequence if they do the action again. And then you leave it to them to decide how they want to behave.

I started by saying that we want to land our difficult conversations—and not crash them. I hope you’ll find these ways of starting a difficult conversation give you a way to land your difficult conversations. So good luck.