Typically, the desire to begin a difficult conversation stems from a personal desire, and so naturally our instinct is to begin with our own side of the story. The problem with a one-sided opening is that it centers our own story and perspective to the exclusion of the other. In doing so it creates a tension between the dialogue partners, and usually pushes the other into a defensive stance: “Our story sends up flares, warning them to defend themselves or to counterattack” (148). The answer to this dilemma is rather to start from the “third story” (149).

Rather than conceiving of the difficult conversation like a battle, it should be imagined as a puzzle to be solved. Instead of beginning with our own story, the issue should be approached from the perspective of a mediator. The “third story” is the story as assessed by a third party, with attempts to be as objective as possible, bringing in both sides of the story. Starting this way removes a foundation of blame, and seeks to find a middle ground from which progress can be made—regardless of who may or may not be in the wrong. This manner of approaching the conversation signals to the other party that one is serious in attempting to understand their perspective, that it’s not all about scoring points and winning the conversation: “A real conversation is an interactive process — one where you are constantly going to be listening, sharing your view, asking questions, and negotiating” (162).

One of the most underrated life skills is the ability to be a good listener; no matter one’s position in life, we all want to have our stories heard and understood. Developing the skills to be a good listener will go a long way toward making this a reality for those with whom we engage in conversation. The problem is that many people listen to determine what they will say next, rather than listening to genuinely understand what the other person is saying and what they want to communicate.

When an individual truly listens, they also make it far more likely that they in turn will be listened to and understood reciprocally. The best way to do this is to cultivate an attitude of curiosity, not just an attitude of problem-solving. People can tell when someone is listening just to use their words as ammo: “The problem is this: you are taught what to say and how to sit, but the heart of good listening is authenticity” (168).

Not everyone has this skill naturally, and so it will need to be developed. To do this, three skills can be employed: inquiry, paraphrasing, and acknowledgment. Ask questions that are genuine attempts at understanding, not leading questions that already assume the correct answer. Repeat what the other person has said back to them to ensure that your dialogue partner is on the same page, and that you are approaching the issue with the same assumptions and background information. Finally, find a way to indicate explicitly that you are working your hardest to understand their perspective, and are attempting to meet them where they are.

This chapter explores The Importance of Effective Communication. One of the pitfalls a skilled conversationalist can fall into when engaged in a difficult conversation is resorting to artful rhetoric. One thinks that the goal is to win the conversation, and that the means to achieving that end will be easier if one resorts to intelligence, wit, a vast vocabulary, or skill in logical persuasion. This is a temptation that needs to be largely avoided. The goal is not to demonstrate one’s power as an orator, but to demonstrate one’s desire to engage in meaningful dialogue and mutual understanding. One must not turn a difficult conversation into a debate or a lecture.

The opposite side of the coin is the temptation to feel as though one is not worthy of being heard and understood; the result would be an inability to speak up for oneself: “Sometimes we can feel trapped between the belief that we should stand up for ourselves and a hidden feeling that we don’t deserve to be heard, that we’re not entitled” (187). The best way to approach any difficult conversation is to speak clearly and explicitly about the issue at hand. A third mistake is to think that by bringing up a problem obliquely, or in a way that requires reading between the lines or using subtext, the problem will be broached in a moderate way. This is a mistake—“You end up triggering all of the problems you worried you’d create by bringing it up, without getting the benefit of clearly saying what you want to say” (191).

There are three guidelines to follow to ensure clarity in these conversations. First, do not resort to couching what you have to say in terms of the hard truth, as if you already have everything figured out 100%; this will destroy any chance of meaningful, reciprocal dialogue. Second, be clear about how you came to your conclusions. Third, never use extreme or exaggerated language; it will leave you open to criticism, destroying any goodwill that can be garnered by a calm, clear, and open discussion.

Unless a difficult conversation comes up naturally, someone will need to initiate it. When a conversation is initiated, one needs to take the lead in a constructive way, leading the conversation and guiding it toward a hoped-for goal without being dictatorial about the particular steps along the way.

One way to do this constructively is avoid couching things in terms of “either/to” and instead consistently resorting to the language of “and” (205). This will help to prevent false dichotomies and give you the ability to reframe the conversation in terms that will be beneficial to both parties. There are many ways to help move the conversation forward in this way. One of these is to come up with a mutually agreed upon test, where both individual’s assumptions and claims can be tested in some way, and then see what the outcome is. Another important aspect is to make sure that the principles in play are agreeable to both parties and make sure they are being consistently employed: “If you can’t find a creative way to solve the problem, ask what standards of fairness should apply, and why” (214).

At the end of the day, however, it is important to remember that difficult conversations take time, and that they will often be a series of conversations rather than a single event.

It’s important to prepare for difficult conversations. You wouldn’t approach other difficult tasks without a plan of attack, and difficult conversations are no different. Prepare for them by reviewing the three conversations, the three aspects of any interaction that are involved in dialogue. Next, examine your intention in initiating the conversation; while your motives don’t have to be purely altruistic, they do need to genuinely have the common good in mind, and not be purely utilitarian.

Next, remember to begin with the third story; an objective perspective is going to do double-duty in giving credence to your interlocutor’s position, while also presenting your own position in the most powerful way. In the end, you’re not looking to make any enemies or crush anyone in the process of achieving your desired result. The goal is to problem solve, and come out the other side of a difficult conversation knowing that the best result possible has been achieved, regardless of the specific outcome.