We’ve all been there—knowing we need to have a tough conversation but dreading every moment leading up to it. Whether it’s addressing a conflict with a coworker, discussing relationship issues, or confronting someone about their behavior, difficult conversations are an inevitable part of life.
The good news is that these challenging discussions don’t have to end in disaster. With the right preparation and mindset, you can navigate even the most sensitive topics constructively. Keep reading to discover how to prepare for a difficult conversation with expert strategies from the books Difficult Conversations, Crucial Accountability, and The Next Conversation.
Table of Contents
- Tip #1: Determine Whether a Conversation Is Worth Having
- Tip #2: Schedule a Time & Place to Talk
- Tip #3: Identify the Key Issue
- Tip #4: Identify the Conversation’s Purpose & Scope
- Tip #5: Identify Your Own Goals
- Tip #6: Identify Your Own Values
- Tip #7: Consider the Other Person’s Perspective
- Preparing for Difficult Conversations That Others Initiate
- Learn More
Tip #1: Determine Whether a Conversation Is Worth Having
The first step is to figure out whether having a conversation is even the best course of action. In Difficult Conversations, Douglas Stone, Bruce Patton, and Sheila Heen explain that you can’t address every conflict in life—there are simply too many. The authors identify a few situations where conversations won’t improve things:
- The conflict is internal. If the problem exists mainly in your own head rather than between you and another person, you need more internal reflection before involving someone else.
- Actions work better than words. Sometimes changing your behavior might solve the problem more effectively than hashing it out with another person.
- You don’t have time to prepare. Rushing into a complex discussion without preparation usually makes things worse.
If you determine that a conversation is the right choice, and you have time to prepare, the remaining strategies will help you be ready to talk constructively.
Tip #2: Schedule a Time & Place to Talk
In his book The Next Conversation, Jefferson Fisher recommends that you ask the other person when they’re available and choose a private space free of distractions. Don’t ambush them or try to squeeze a serious talk between other activities. When both parties have time to mentally prepare, you’ll have a more productive conversation.
Tip #3: Identify the Key Issue
The authors of Crucial Accountability (Kerry Patterson, Joseph Grenny, Ron McMillan, Al Switzler, and David Maxfield) write that grievances usually come in bundles; instead of just one problem, a whole host of issues make up the grievance. However, there’s usually one key issue at the root of the grievance—the underlying problem causing all the other issues. When the key issue is identified and resolved, the other issues will likely be resolved.
If you don’t pinpoint the underlying problem, you could end up addressing the wrong issue or addressing too many issues at once, neither of which will solve the problem.
| Avoid Gunnysacking Sometimes, when trying to identify the key issue, you’ll end up with more than one fundamental issue that’s bothering you. This could be because you’re actually dealing with several key issues that are independent of each other, rather than linked to a single grievance—in other words, an older set of issues that you’ve harbored over time. Harboring small resentments over time is called gunnysacking and can severely damage or even end your relationship. To address this kind of problem, you’ll need to have multiple conversations so that each individual key issue can be discussed and addressed. |
Tip #4: Identify the Conversation’s Purpose & Scope
The authors of Difficult Conversations argue that, if you can’t articulate a realistic reason for having the conversation, you’re not ready to talk. Jefferson Fisher agrees. In The Next Conversation, he recommends that you determine the purpose and scope of your conversations in advance to keep them on track. This way, everyone understands why they’re talking, what they’re discussing, and how the conversation should end. Without direction, conversations wander off topic and fail to achieve their purpose. They also last too long and cause people to become confused and frustrated.
To keep your conversation focused:
- Tell the other person exactly what you want to talk about, and address only one main issue per conversation, as this allows you to discuss that issue fully.
- Explain what you hope to achieve or how you want both parties to feel afterward.
- Ask if they’re willing to have a conversation under these terms.
(If conversations drift off topic, Fisher suggests you gently redirect people back by using key words from your original topic. Acknowledge the other person’s points while firmly but politely steering the conversation back, offering to address their concern afterward.)
| Use a Basic Framework for Your Conversations While Fisher provides tips on how to prepare for individual conversations, there are basic frameworks you can use in all conversations. In Think Faster, Talk Smarter, Matt Abrahams suggests using a what, why, and how framework to organize any conversation. First, introduce what you’re discussing to give everyone a clear starting point. Then, explain why this topic matters to your listener so they’ll understand its relevance and stay engaged. Finally, provide the how—the details or actions that bring your point to life. This structure mirrors how our brains naturally process information: We need to know what something is before we can understand why it matters and how to use it. Therefore, when you know where you’re starting, where you’re going, and how to get there, you can focus on what you’re saying rather than worrying about how to say it. |
Tip #5: Identify Your Own Goals
Fisher suggests you think in advance about how you want to conduct yourself during the conversation. You can do this by determining your personal values and realistic goals for the conversation.
Fisher explains that realistic goals focus on what you can actually achieve. You might set goals such as staying calm throughout the discussion and trying to understand the other person’s point of view. Avoid unrealistic goals, which expect the other person to do exactly what you want; they probably won’t, and you’ll end up disappointed.
(Shortform note: In The Let Them Theory, Mel Robbins explains that, when we attempt to manage others’ opinions and reactions, we activate our brain’s stress response, leaving us frustrated and exhausted. So she suggests that you separate what others do from what you can influence by using two phrases: “Let Them” and “Let Me.” When someone responds defensively or refuses to see your point, you can think “Let Them” to detach from their reaction, and then follow with “Let Me” to refocus on your own behavior and values.)
Tip #6: Identify Your Own Values
As you prepare for a tough conversation, Fisher suggests you identify your values and let them guide how you communicate. Values affect how you listen, respond, and engage with people. They can also simplify decision-making during difficult conversations. When you know what your values are, you don’t need to overthink your responses because your values will guide your behavior and your words. For example, if you decide that kindness is your core value, you’ll naturally choose gentler words even when you feel frustrated.
To discover your values, ask trusted friends and family to describe your character traits. You can also think back to times when you felt proud of how you handled a conversation or situation and what values guided your words and actions then.
| Create Your Value Hierarchy To identify values to guide your conversations, consider ranking them in order of importance. In Awaken the Giant Within, Tony Robbins says you operate within a hierarchy of values—some matter more to you than others, and this ranking determines every decision you make. When you understand which values sit at the top of your hierarchy, you gain clarity about why you make certain choices. According to Robbins, you actually have two hierarchies working simultaneously: values you move toward (such as love, freedom, and adventure) and values you move away from (such as rejection, failure, and loneliness). Your brain constantly weighs both hierarchies when making decisions. For example, if your fear of confrontation ranks higher than your desire for honesty, you might avoid difficult conversations even when speaking up would serve you better. Robbins suggests you start creating your hierarchy by ranking common values such as love, success, freedom, and security in order of importance. Then, rearrange them by evaluating which values serve your goals and which might be holding you back. Repeat the process for your moving-away values. By reorganizing your values, you can make decisions in your conversations that align with who you want to be. |
Tip #7: Consider the Other Person’s Perspective
When preparing for difficult conversations, seeing the issue from the other person’s point of view avoids entering the conversation with negative assumptions. It’s human nature to make negative assumptions about why the other person did what they did and to not consider outside factors that might have impacted their decision. The authors of Crucial Accountability explain that this is called the fundamental attribution error. It holds that, when we’re the ones who make a mistake, we justify our actions in some way; but, when another person messes up, we attribute the mistake to a flaw in their character.
(Shortform note: In A New Earth, Eckhart Tolle explains that the fundamental attribution error is a result of our ego. The ego constantly seeks to inflate our self image by deflating the image of others. When other people make mistakes and we automatically assume it’s because they are flawed, the assumption inflates our ego by making us feel better than them. By understanding why the fundamental attribution error happens, we can better avoid falling into its trap and more effectively see both sides of an issue.)
Listen First
The authors of Crucial Accountability assert that we need to listen to the other point of view in order to make accurate judgments and solutions. If the issue is about the other person, they’re the ones who’ll have the most information about what went wrong and why. This is arguably the most important step in preparing for tough conversations.
Without hearing the other person’s perspective, you might be seeing the issue incorrectly or incompletely. For example, after hearing the other person’s side of the story, you might realize that their reaction was correct in that particular situation, even if they failed to meet expectations. Ultimately, you need to speak to the other person to get the full picture and identify all the possible barriers. Then you can develop solutions.
(Shortform note: Experts second the authors’ argument here, explaining that, when we enter a conversation with the belief that we fully understand the problem and how to solve it, it becomes difficult to truly listen to the other person and sends them the message that we don’t think they’re capable or valuable in solving the issue.)
Preparing for Difficult Conversations That Others Initiate
Sometimes, other people will approach you first to talk about a challenging topic. In these cases, Jefferson Fisher suggests that you express your appreciation that they came to you and listen to them without immediately sharing your own experiences. You can also ask thoughtful questions to understand their perspective better. How you receive other people’s difficult messages affects whether they’ll trust you with sensitive information in the future.
Learn More
To understand how to prepare for difficult conversations in the broader context of constructive discourse, take a look at our guides to these books:
- Crucial Accountability by Kerry Patterson, et al.
- Difficult Conversations by Douglas Stone, et al.
- The Next Conversation by Jefferson Fisher
