Difficult Conversations: How to Discuss What Matters Most

There are 10 questions that readers most frequently asked the authors in the years following the book’s initial publication. These were about the book’s style, method, content, and the authors’ suggestions about how to make difficult conversations as fruitful as possible.

First: “It sounds like you’re saying everything is relative. Aren’t some things just true, and can’t someone simply be wrong?” (238). The truth of the matter is that the truth is slippery, it can be hard to determine, and while objective truth does exist, it takes a conversation to determine what that is and how it affects the people involved in the discussion.

Second: “What if the other person really does have bad intentions—lying, bullying, or intentionally derailing the conversation to get what they want?” (244). The best thing to do is assume good intentions and good faith; however, it takes a conversation to really determine if that is the case. If the conversation is continually derailed no matter how hard you work, however, then eventually the conversation will need to be dropped for the sake of both parties.

Third: “What if the other person is genuinely difficult, perhaps even mentally ill?” (249). Some people are genuinely difficult to deal with, and some people are that way because they can’t help it due to some kind of health issue. You might not be able to force someone to change, but it just may be possible you can help them identify some flaws in their own perspective. By engaging in conversation, you can be assured that you have done your absolute best to solve the problem.

Fourth: “How does this work with someone who has all the power—like my boss?” (258). This goes back to remembering that not every conversation is going to end with your desired result. Sometimes you can only give the other person a chance to hear your perspective, and even that is sometimes a big win. At times, things may be so difficult or imbalanced that the most you can hope for is to find a workaround for the problem; this too should be considered success if you are able to do your best and take control of everything in your own power.

Fifth: “If I’m the boss / parent, why can’t I just tell my subordinates / children what to do?” (264). Sometimes a parent simply needs to tell a small child not to do something if the child doesn’t understand the reasons for the command. In most cases, however, a difficult conversation is based on influencing someone’s behavior based on the truth and that we want them to change beyond the simple reason of achieving a result. Giving reasons for why someone should change is always going to be more effective than simply attempting to issue a command.

Sixth: “Isn’t this a very American approach? How does it work in other cultures?” (268). While the mode of speech presented in the book may be more typically American, the underlying structure of most difficult conversations is fundamentally the same; this is why the authors argue that the book and method have been so successful in a wide range of contexts and situations.

Seventh: “What about conversations that aren’t face-to-face? What should I do differently if I’m on the phone or e-mail?” (273). On the one hand, electronic communication has made exchanging information extremely efficient and timely; it also allows for a written record that can prove extremely useful in sensitive situations. On the other hand, it is also highly impersonal since it fails to convey facial expressions, tone, attitude, and body language, which all assist in getting across our meaning and intentions.

Eighth: “Why do you advise people to ‘bring feelings into the workplace’? I’m not a therapist, and shouldn’t business decisions be made on the merits?” (278). The typical line of thinking assumes that emotions and opinions should be left at home, not brought into the more objective and impersonal place of business. This ignores how human beings are emotional creatures. While the exchange and expression of emotions and a person’s interiority can be risky, it’s usually riskier to hide them, as it creates a highly impersonal environment.

Ninth: “Who has time for all this in the real world?” (283). In fact, the opposite assumption is more damaging: Who doesn’t have the time to make sure they’re communicating effectively? As the authors write: “Given that we’re already dwelling on the problem, we might as well use that time and energy in ways that will help rather than hurt” (285). A small amount of time dedicated to resolving conflict upfront can save exponentially more time down the road when issues become more complex and tense.

Tenth: “My identity conversation keeps getting stuck in either-or: I’m perfect or I’m horrible. I can’t seem to get past that. What can I do?” (287). A person’s identity consists of their nature, nurture, and mode of interpreting their interplay. While the first two can’t typically be changed, the third can. You can always be reinterpreting and recreating your perspective on life and who you are in the world. Putting yourself in the proper context in relation to the world around you ensures that you are maintaining an accurate picture of yourself.