In the previous post, I talked about the inevitability of difficult conversations, the things that make them difficult (like the risk of being candid or the risk of harming a relationship), and the steps you can take to prepare for them to maximize the chance it will be worth the effort.

If you’ve done everything possible to set yourself up for success, it’s time to broach the difficult conversation.

How to Have a Difficult Conversation

Here are some strategies and techniques to make your difficult conversation more likely to lead to a good outcome rather than spiraling into an unhealthy and unpleasant fight.

Begin with Context

If you’re framing the conversation as difficult, you might feel considerable anxiety at the outset. That might make you a little more direct, or even blunt, than is helpful. When broaching an uncomfortable topic, don’t go straight to the heart of it, “Bob, I need to tell you that you offended me in this morning’s meeting!” That will feel like an ambush and trigger a response from Bob that’s not likely to be pleasant.

Instead of going straight to the heart of it, provide a little context. You might say, “Bob, I’ve been thinking about our meeting this morning, and something you said isn’t sitting well. I don’t want to stew over it without talking to you… .” Your context statement can include things like the situation you’re talking about, your motives in raising the issue, the value you place on your relationship, etc.

Lest you get carried away with describing the entire historical context for your conversation ‘since the beginning of time,’ it’s important to say that too much context can be as troublesome as too little. Suppose your version of anxiety is to become woefully indirect, use too many words, and nervously beat around the bush. In that case, your discomfort will likely transfer to the other person, and you’ll both be squirming before you even get to the point. So, give some context, but keep it tight.

Share Your Perspective

Now that you’ve set the stage for the conversation, you can raise the specific issue you want to address. Again, taking care in how you position your point or request will make a significant difference in how it lands and what happens as a result. Here are the most important things to remember:

Avoid absolutes. You might be feeling that the person “always” or “never” does something or that “everyone” or “no one” agrees. Still, absolutes are triggering and make the conversation more extreme than necessary. Use “often,” “most,” or “frequently,” or better yet, be specific, “in the previous three meetings” or “of the six customers I spoke with.”

Soften assertions. Rather than boldly stating what “must” be done or what “has to happen,” use language that promotes a two-way dialogue. For example, you can say, “I’m wondering” instead of “I believe” or “How would” in place of “You should.”

Start with the issue, not the solution. Another way I see difficult conversations devolving into fights is when you go straight to proposing a solution without first aligning on the problem. This is a significant issue in cross-functional teams where people often over-step by telling someone in another department how to solve a problem without the background or expertise to get it right. Instead, frame the problem. “I’m worried we’re going to annoy our suppliers. How could we minimize that risk?”

Be objective about them and subjective about you. When describing another person, keep it sterile and as fact-based as possible. Don’t talk about others being “unresponsive” or “in the weeds.” Instead, say, “I haven’t heard back from them since I left a message on Tuesday,” or “They are giving me grammar corrections while I’m still building the outline.”

Do the opposite when it comes to sharing your take. Expose your feelings, perceptions, and interpretations so the other person has a window into your thinking. For example, it can be helpful to say, “I’m feeling ignored,” or “I’m frustrated that we’re focusing on the wrong thing.” A little vulnerability goes a long way in making a difficult conversation more valuable.

How you serve up your contentious comments will make a world of difference in how easy they are to swallow.

Ask Open Ended Questions

100 Productive Conflict QuestionsAnother hallmark of a great conversation is that you’re listening as much as you’re talking. When the subject matter is contentious, they might not show their cards without the correct prompt. You’ll need to be good at forming questions that create an entrée for them to share their perspective.

The basics of good questions apply. The first rule is that they should be open-ended to broaden the conversation and deepen the connection (I’ll talk in a moment about the place for closed-ended questions). The second tip is to avoid questions that start with ‘why’ because they tend to make people defensive rather than curious. And no, smart a$s, WTF doesn’t count as a great question even though it meets both criteria.

Beyond the basics, good questions are like projective tests that allow the other person to tell the story that is relevant to them. Avoid leading questions that are basically a version of “This is what I think; you agree with me…right?” Try examples like, “How do you see this playing out,” “What would have to be true for you,” or “Where should we be focusing our attention?”

This downloadable resource has 100 questions you can deliver as is or use as inspiration to come up with your own open-ended questions. (Click the image to download.)

Listen for Treasure

Dial showing the subcomponents of the three levels of listeningAfter you’ve served up a great open-ended question, zip it!! Listen. And not just for the information they share with you. Listen beneath that for what emotions are emerging. You’ll hear what they’re feeling in their word choice and tone, pitch, and volume. And listen for what’s not said, too. What do they value that’s making the conversation difficult? What hypotheses can you form? What’s the treasure they are protecting? Here’s a deep dive into what I call Level III Listening–it’s the kind you want to employ in a Difficult Conversation.

Validate Their Perspective

We’ve talked about the importance of open-ended questions and good listening. There’s one other move you’ll see often in a productive conversation—validation. As the person shares their perspective, concerns, and proposed actions, stop and paraphrase what you’re learning before adding anything new. For example, “If I understand correctly, you believe the proposal is getting too expensive, and we won’t win.”

If you get it right, you’ll lock in some progress—ratcheting toward better understanding and potential resolutions. If you get it wrong, the fact that you tried will provide enough goodwill for them to clarify and for you to get another chance. With some luck, they’ll even return the favor and start validating your points.

Test a Proposal

If you get close to a potential resolution, don’t go for the close too quickly. Tossing off a “Great, so we’ll do x, y, and z” before you’re good and sure that’s what they have in mind could make things worse instead of better. Instead, when you see a path forward, treat it as a possibility rather than a certainty. Ask, “It seems like if we did x, y, and z, that would address the key issues. Would that work for you?”

You’ll notice that this is a closed-ended question. This is the point at which you want to switch from open- to closed-ended because you’re trying to converge on a path forward. If, instead of “Would that work,” you ask, “How does that work,” they might give you a long, meandering answer that leaves it unclear whether you have an agreement or not. Stick to questions that require a yes or no response.

As with validation, it’s less about getting it exactly right and more about the signal you send by trying to move forward together rather than imposing your view too definitively. If the proposed solution doesn’t work for them, you’ll probably get a chance to modify it and try a new version.

Stick the Landing

One last step before you run off to exhale and treat yourself to a libation: state the resolution clearly. “I am going to do A. You are going to do B.” If there’s more to it, get it all out. The point here is to ensure you both have the same picture in your heads of what will happen next. Otherwise, you’re likely to go off in different directions, fail to meet each other’s expectations, and set up an even more difficult conversation in the future.

Difficult conversations expend a lot of energy and emotional capital. These few approaches can make them more effective at resolving an issue and more efficient in getting to that resolution with as little pain and suffering as possible.

In the next post, we’ll talk about how to follow up on a difficult conversation in a way that strengthens the trust between you and the other person. Stay tuned.

Additional Resources

How to Have an Uncomfortable Conversation Remotely

How to Broach an Uncomfortable Topic

Pay Off One Conflict Debt in Your Life