How We Fail at Difficult Conversations (And One Way to Succeed)

Most difficult conversations fail before they even begin. Not because of what gets said, but because of what we're trying to do when we're saying it.

In any conversation – whether you're an FBI agent conducting a challenging interview, a manager addressing performance issues, or a parent talking to a teenager – you're doing one of three things with what the other person has said to you:

·       You are reacting to it.

·       You are responding to it.

·       Or you are engaging with it.

Only one of these works to establish trust at the beginning and to allow the conversation, difficult as it may be, to progress productively.

The Three Levels

React is emotional reflex. It's what you feel in the moment, unfiltered. "Your life is a mess." "That's ridiculous." "How could you do this?" It's honest, sure, but it communicates only one thing: my assessment of you matters more than my understanding you.

Respond is more sophisticated but still centered on your agenda. You're pushing toward what you need, what you want them to understand, what you think should happen next. It feels productive because you're being cognitive rather than emotional. But you're still talking past them, not with them. You're advancing your frame, not exploring theirs.

Engage means you've set aside your agenda entirely, at least for now. You're genuinely curious about their reality on their terms, not as it relates to what you need. "Tell me about what's going on." "Help me understand why you believe that." "What does this mean to you?"

The distinction isn't about being nice and it is not about agreeing with them. It's about whose reality is driving the conversation and allowing space for their experience to take the forefront.

What This Looks Like in Practice

Years ago, late one evening as part of human trafficking work we were doing, I found myself in a crack house talking to a teenage prostitute. The surroundings were beyond squalid, and she was a mess—angry, terrified, and definitely not wanting to talk to the FBI.

My reactive response would have been to tell her what I saw: her life was a disaster. True, perhaps, but utterly useless, judgmental, and not communicating anything she was not already aware of. The result would be her dismissing everything I had to say after that.

My responsive response would have been the classic righting reflex—to describe her situation and explain how talking to me could help her out of it. This feels helpful. It's certainly better than reacting. But it's still my assessment, my solution, my agenda. And she would just have heard “FBI Agent wants me to do something I probably do not want to do.”

What I actually did, somewhat to my surprise, was engage. I sat down on that wet, stained and thoroughly disgusting floor with her and said something like, "Tell me about what's going on." Then I just let her talk.

Here's what made the difference: sitting on the floor wasn't just a physical act – it was a relinquishing of positional power. I met her where she was, not where I needed her to be. "Tell me about what's going on" had no visible agenda in it. It wasn't "tell me about these guys" or "tell me what I can do." It was open to whatever her reality was in that moment.

That absence of agenda created enough safety for her to talk. It often feels so counterintuitive to do this, but by completely abandoning my agenda, I actually got more of what I needed – information, cooperation, and insight into a challenging situation.

When Responding Is Necessary

This doesn't mean engaging is always the endpoint. Sometimes you do need to drive the conversation forward. Sometimes you need to present evidence, establish facts, or move toward resolution.

Imagine you're interviewing a suspect who says, "I didn't do it but you’ve already decided I have."

You could engage: "Tell me about what you're feeling right now."

Or you could respond: "That's a fair concern, and I haven't decided anything – that's why we're talking. What I have decided is that I need to understand what happened here. You're the only person who can tell me your side. Whatever that is, I'd rather hear it from you."

That response is strategic and it advances your objectives. But notice what it requires to work: the other person has to be in the conversation with you. If you lead with that response before you've engaged, before they believe you've heard them, you're just two people talking past each other.

The same applies with an employee. You could engage: "How is this impacting you?" Or respond: "Here's what I see as the best way forward."

Both might be necessary at different points. But the sequencing matters.

The Timing Principle

You can't effectively respond until they believe you've genuinely engaged. You can't push your agenda until they trust that their reality has been heard and understood.

Engage first to establish shared understanding and trust. Respond later when you need to move toward resolution or action.

The engaging moves create the foundation that makes responding moves able to land. Skip the engagement phase and your carefully crafted responses fall on deaf ears – or worse, they confirm the other person's suspicion that you were never really listening in the first place.

The Question to Ask Yourself

Before you speak in a difficult conversation, ask yourself one question:

Am I about to tell them why I'm right, or am I about to learn why they think they're right?

That's the diagnostic. That's the difference between responding (pushing your frame) and engaging (exploring theirs).

Most of us default to responding because it feels productive. We have things we need to say. We have solutions. We have perspective they don't have. All of that might be true.

But none of it matters if the other person isn't in the conversation with you.

What Engagement Actually Communicates

When you react, you communicate: My assessment of you is what's important here.

When you respond, you communicate: My solution for you is what's important here.

When you engage, you communicate: Your experience is what's important here.

Not forever. Not instead of accountability or action or moving forward. But first.

Because you can't get to effective responding—the kind that actually changes behavior, builds cooperation, or solves problems—without establishing that the other person's reality matters enough to understand on its own terms.

That teenage girl in the crack house taught me something I've used in thousands of interviews since: the most effective way to get what you need is to genuinely care about understanding what they're experiencing, regardless of whether it serves your immediate agenda.

Think about that the next time you are engaging with someone who has a different political perspective than you. Your reflex may be to point out that they are not being rational, your response may be to point out the facts that dispute their belief. But what really matters is that they are experiencing something that feels very real to them. Take the time to explore what they are experiencing and how it has impacted them before you dive into the data.

Engagement isn't a technique to manipulate people into talking. It's a fundamental stance that the other person's reality is worth understanding – not just as it relates to what you need, but on its own terms.

Start there. Always. You can move to responding later if you need to drive action or establish consequences.

But you can't skip the engagement phase without losing the person.