Finding Your Way Into a Hard Conversation

The Conversation I Almost Avoided

A few weeks ago, I had a conversation I had been avoiding, dreading even. I knew what I needed to say. I had rehearsed it in the shower, on bike rides, lying awake at night. I kept thinking, maybe tomorrow I'll feel more ready.

When I finally stopped to think about it (and be coached on it), I noticed something. I wasn't afraid of finding the right words. I was afraid of everything that might happen after I said them.

What if the other person got upset? What if the conversation didn't go the way I hoped?

Most of us don't avoid difficult conversations because we don't know what to say. We avoid them because we don't think we are ready, and we can't control what happens next.

After years of having hard conversations in medicine, leading teams in healthcare technology, and now coaching physicians and healthcare leaders, I've come to believe that feeling ready isn't something that magically shows up one morning.

It's something we build.

The Insight: Preparation Isn't About Having All the Answers

I used to think preparing for a difficult conversation meant rehearsing every possible scenario. If I could just think through enough "what ifs," I'd be ready.

I've learned that's not how it works.

Preparation is not about predicting every response, because that is impossible and out of our control. It is about getting clear on what matters most before we walk into the conversation.

"Preparedness is not about eliminating uncertainty. It is about knowing our own mind well enough that uncertainty does not run the show."

A Tool: Preparing for the Conversation That Matters

Before your next important conversation, try walking through these questions. Not to script it, but to ground yourself.

Why am I having this conversation? Clarify purpose. Are you sharing information, or working toward a decision? Naming this keeps you from getting pulled into rabbit holes or trying to solve everything at once.

What story am I already telling myself? Check your assumptions. What are you assuming about how this will go, or how the other person will react? Which of those assumptions are facts (circumstances), and which are stories (thoughts), that your anxious brain is telling you?

What tends to throw me off? Notice triggers. Is there a phrase, a tone, or a topic that tends to pull you off center? For me, it is criticism and someone raising their voice. Naming it in advance gives you a better chance of staying present when it shows up.

Can I stay present instead of trying to be perfect? Manage the moment, not just the message. Take a breath, pause if you need to. Take a sip of water. You don't have to respond immediately to every comment. Sometimes the most grounded thing you can do is allow a little silence.

Can I speak from my own experience? Try shifting from "this is how it is" to "I think" and "I feel." It invites the other person in rather than putting them on the defensive.

Can I stay curious? Leave room to listen and ask questions. When we get anxious, we stop listening. We start planning our next sentence. Curiosity changes the conversation. Instead of assuming you know what the other person is thinking, ask. I am often surprised by the response.

Finally, close with intention. Summarize what was accomplished. If the meeting time is over and it feels unfinished, don't rush to wrap things up in the next five minutes. Instead, name that and set a time to continue. Ending on a note of progress, even a small one, changes how both people carry the conversation forward

A Question to Sit With

Before your next hard conversation, ask yourself: What am I actually afraid will happen?

And then ask one more. Is that fear based on what's happening now, or on something that feels familiar from the past? Because I have found that those are often two very different things.

One Last Thought

That conversation I'd been avoiding? It wasn't perfect.

There were awkward moments. Things I wish I'd said a little differently. A few long pauses.

And you know what? It was still worth having.

I've stopped waiting to feel completely ready before saying or doing something that matters. These days, I aim for something different. I try to show up grounded, honest, and willing to stay present, even when I don't know exactly how the conversation will unfold.

Because in the end, that's really all any of us can do.

"There is no conversation more boring than the one where everybody agrees.”
-Michel de Montaigne