Make no mistake: Having a conversation around a topic we’ve been conditioned not to talk about is very much a skill. It’s coachable, and if you work at it, you’ll get better over time.
But to develop that skill, it can help to have a place to start. Here are eight practices you can borrow to make your next difficult conversation more successful. Use them often, and you’ll find your skills improving, too.
1. Know what kind of conversation you want
It’s important to know whether you’re trying to have a dialogue or a monologue. Are you seeking an agreement, a compromise, a collaborative solution — or are you simply presenting someone with an uncomfortable decision you’ve already made unilaterally?
In other words, what is your goal? For instance, if you’re breaking up with a partner or firing an employee who’s just not working out, those are difficult actions and involve uncomfortable conversations, but they’re not dialogues. Yes, you’ll listen politely to what the other person has to say, but the goal of this conversation is to make a clean break, not to have deep, two-way communication aimed at solving a problem.
2. Don’t surprise people — make an appointment
One of the worst things you can do is ambush someone with a hard conversation. I’ve seen people try to sneak these in at the breakfast table (during the morning rush), on the way to the airport, or — God help us — over text. Randomly phoning someone or dropping into a colleague’s office unannounced to have a conversation about a controversial or long-buried topic suggests the discussion is casual and unimportant — the opposite of what you should convey here.
Similarly, even when distance separates the people involved, I try to convince them not to have these conversations via videoconference. If an issue is important enough to require this kind of thought, it’s worth the logistical hassles to do it in person. That’s also why I suggest setting an appointment for the conversation, ideally at least a day in advance. Tell the other person what you want to talk about without getting too deep into the specifics.
While you can arrange the appointment in a conversation, often I advise my students and colleagues to do it by email. There are advantages to this: In email you have complete control over what you’re going to say. You don’t need to worry about your on-the-spot response to how the person reacts. Setting an appointment also holds another advantage: It forces you to follow through and have the conversation.
3. Practice and role-play
Chances are you’ve been ruminating about the conversation for a long time. You are probably frustrated, and you might even be angry. Most likely you’ve practiced your parts of the discussion in your head over and over. Maybe you’ve even practiced saying it out loud in front of a mirror. That’s a good thing, but only up to a point.
The problem with solo practice is you can make assumptions about how the other person is going to respond, and those assumptions may be totally wrong. You have a script in your head, and the moment the real-life conversation deviates from your script (as is inevitable), it’s likely to knock you off balance. The advantage of role-playing and rehearsing the conversation with someone you trust is that it allows you to practice responding to different scenarios and reactions. It also gives you a chance to experience and prepare for the emotions you may feel based on the other party’s responses.
When I role-play with students or colleagues, I try to behave in ways they might not expect. I’ll typically begin by reacting defensively, aggressively, or even combatively. My goal isn’t to be a jerk but to demonstrate for them how the conversation may play out in ways they don’t expect. This encourages them to try different approaches and to invest more time in preparing.
When role-playing these conversations multiple times, I love watching how someone shifts their strategy. In the first round, most people tend to focus on persuasion: They’re marshaling the evidence and listing facts. Often they sound like an attorney making a closing argument in a trial. But over time their approach typically shifts. Most of them become softer spoken. They ask more questions. They learn that if they approach the conversation from a place of curiosity, with the goal of understanding the other party’s perspective, they’re more likely to achieve a good outcome.
This fact-finding, empathetic approach is what negotiation theorists advise people to do when trying to find agreement, and it’s often the right tactic for a taboo-busting conversation, too.
4. Set norms for behavior
As soon as we sit down, I try to establish some ground rules. I turn off my phone and ask the colleague or family member I’m meeting to do the same. “I’m going to give you my full attention,” I say. “I’m not going to interrupt you, and I ask you to do the same. I’m going to talk, and I hope you’ll really listen without getting defensive. When I’m finished, and it’s your turn, I promise I’m going to listen carefully to every word you say for as long as you need to speak.”
One important norm to set is around time. This will not be a 15-minute conversation. You might say, “I’ve set aside an hour for this conversation, and if we don’t cover everything in that time, we can set up another meeting. Are you able to spend an hour with me on this?” In most cases, time-bounding the conversation (and not letting it go on for too many hours) is in everyone’s best interest.
5. Establish a common goal
The key to a successful discussion is to define the goal at the outset and collaborate toward it together. For a goal to be common, it can’t be seen as being about one side winning and the other side losing. It doesn’t even have to involve a solution or a compromise. Very often the root problem you’re going to discuss involves a lack of understanding or things that aren’t being talked about. In those cases, simply getting facts, intentions, and feelings out in the open can be a common goal.
6. Control your behavior
While preparing for these discussions, most people focus exclusively on the words they plan to say. You should also prepare your body language, which conveys more than most people think. Sitting through these conversations without interrupting, getting defensive, expressing sarcasm, rolling your eyes, or pointing a finger is sometimes difficult. I get it. Do it anyway. Lean forward to show attentiveness. Don’t cross your arms. Don’t fidget. When the other person is talking, focus not only on listening intently but also on observing body language. When the other person finishes speaking, pause before you begin.
Avoid using a tone that sounds like you’re a litigator. Instead, speak in a way that suggests you’re looking for a compromise. Be vulnerable and acknowledge your emotions. Remember, the goal is to share your perspective and be receptive to theirs. The goal isn’t to win, and it probably isn’t to solve the problem with any finality. If a conversation is about something truly difficult, it’s not going to be solved in a single conversation.
7. Summarize and agree on next steps
As the conversation winds down, pull out a pen and paper. Using bullet points, try to capture the main points each party has made. Ask the other person, “What do you see as constructive next steps?”
I don’t want to minimize the value of having a single tough talk: Oftentimes it brings new facts and perspectives into the open, and that can result in an epiphany, new understanding, and a rush of emotions. (Some of my clients describe it as a dam finally breaking.) But knotty problems aren’t solved overnight, so before you get up from the table, you both need to agree on the next step, even if it’s as simple as putting time on the calendar the next week to talk again.
You might be surprised by how frequently participants disagree afterward about what exactly they agreed to. Partly it’s because of the emotions that can come up in these conversations. That’s why it’s important to put something in writing that summarizes, sets out areas of agreement, and makes clear what work remains to be done.
8. Follow up
The hours and days after the conversation are an opportunity to reflect. Did the discussion go differently than you imagined? If things went off the rails, why did that happen? Were you surprised by the emotions you felt or those the other person expressed? Can you empathize with the concerns that were raised? What can you do to reframe your approach to address these concerns?
As you do this work, thank the other person for the first conversation. This is not a moment to be silent. If it didn’t unfold the way you’d hoped, acknowledge that. In the spirit of common goals, focus on the parts of the conversation you felt went well and thank the person for taking the time to listen.
Finally, set up another time to talk. Make another appointment and be clear about the specifics of what you want to address in a second meeting. Continue to express your hope of solving the problem at hand, and let the other person know how much you want to continue understanding their side of the story.
It’s great to understand in theory why we should talk more openly, but unless someone actually says something, nothing changes. So, say something. Start with the simple words, “Can we talk?”
And then keep going.
This article 8 rules for navigating a difficult conversation is featured on Big Think.