Difficult Conversations: How to Discuss What Matters Most

by Douglas Stone

accept. If, on the other hand, you say, “Can you help me understand . . . ?” you offer the role of advisor. “Let’s work on how we might . . . .” invites a partnership. “I wonder whether it’s possible to . . . .” throws out a challenge, one which offers the other person the potential role of hero.

“I’d like to explore whether a raise for me might make sense. From the information I have, I think I deserve one. [Here’s my reasoning.] I wonder how you see it?” This seemingly small change in how you begin should not only reduce stress but also get the conversation off on an even keel.

Talk About How to Talk About It.

Explore where each story comes from “My reactions here probably have a lot to do with my experiences in a previous job. . . .” Share the impact on you “I don’t know whether you intended this, but I felt extremely uncomfortable when . . . .” Take responsibility for your contribution “There are a number of things I’ve done that have made this situation harder. . . .” Describe feelings “I’m anxious about bringing this up, but at the same time, it’s important to me that we talk about it. . . .” Reflect on the identity issues “I think the reason this subject hooks me is that I don’t like thinking of myself as someone who . . . .”

On the face of it, these would seem to be good strategies. But they’re not. Why? Because in the great majority of cases, the reason the other person is not listening to you is not because they are stubborn, but because they don’t feel heard.

“Are you going to leave the refrigerator door open like that?” (Instead of “Please close the refrigerator door” or “I feel frustrated when you leave the refrigerator door open.”) “Is it impossible for you to focus on me just once?” (Instead of “I feel ignored” or “I’d like you to pay more attention to me.”) “Do you have to drive so fast?” (Instead of “I’m feeling nervous” or “It’s hard for me to relax when I’m not in control.”)

Open-ended questions are questions that give the other person broad latitude in how to answer. They elicit more information than yes/no questions or offering menus, such as, “Were you trying to do A or B?” Instead ask “What were you trying to do?”

Each of the Three Conversations provides fertile ground for curiosity: • Can you say a little more about how you see things? • What information might you have that I don’t? • How do you see it differently? • What impact have my actions had on you? • Can you say a little more about why you think this is my fault? • Were you reacting to something I did? • How are you feeling about all of this? • Say more about why this is important to you. • What would it mean to you if that happened?

It is a fundamental rule: feelings crave acknowledgment. Like free radicals, feelings wander around the conversation looking for some acknowledgment to hook onto.

A Final Thought: Empathy Is a Journey, Not a Destination

Empathy involves a shift from my observing how you seem on the outside, to my imagining what it feels like to be you on the inside, wrapped in your skin with your set of experiences and background, and looking out at the world through your eyes.

Psychologists have found that we are each more interested in knowing that the other person is trying to emphathize with us – that they are willing to struggle to understand how we feel and see how we see – than we are in believing that they have actually accomplished that goal.

“Always” and “never” also make it harder – rather than easier – for the other person to consider changing their behavior. In fact, “always” and “never” suggest that change will be difficult or impossible.

There are a set of powerful “moves” you can make during the conversation – reframing, listening, and naming the dynamic – that can help keep the conversation on track, whether the other person is being cooperative or not.

Divergent views are often rooted in one or more conflicting assumptions or hypotheses. If these can be identified, then you can discuss what would constitute a fair test of which assumption is empirically valid, or to what extent it is valid.

Naming the dynamic requires you to “put on the table as a topic for discussion what you see happening in the conversation.” Of particular value is making explicit the other side’s implied rule for how to make decisions.

The consultant suggested that the boss feared that his subordinates’ ideas might result in loss of face, embarrassment, and public “failure.”

So you might say to your boss, “I know there are lots of factors you have to take into consideration, and at the end of the day, I’m onboard with whatever you decide. I just want to make sure that as you think about it, you are aware that. . . .” Your boss is now more likely to be open to influence, because they don’t need to push back, defend their turf, or clarify that this is their decision to make.

Use questions when you want to learn and statements when you have something to convey. Ultimately it is the combination of assertiveness and inquiry that helps us pool our insights, learn things we didn’t know, and lay the foundation for creative and effective problem solving.

We emphasize listening here because the far more common mistake in conversation is failure to listen rather than failure to assert.

If an employee is not being promoted, for example, they are likely to feel disappointed and hurt no matter what. But if they can’t talk with you about their reactions, they may also feel betrayed, unappreciated, frustrated, and ignored. Then they’re likely to start making attributions about you — that you’re a difficult person to work for, or that you don’t like them and are playing favorites, perhaps. If, on the other hand, you elicit their feelings and show that you care about their reaction, they’re much more likely to be able to take in your reasoning for not promoting them, and to work with you to improve their performance.