We've all had conversations we weren't looking forward to. Maybe you need to address an employee's performance, have an uncomfortable discussion with a customer, disagree with a colleague, or talk to someone close to you about something that's been bothering you.
You know the conversation needs to happen, but you keep thinking about how it might go. What if they get defensive? What if they don't agree? What if they get upset or the conversation makes things worse?
Before you've even spoken to the other person, you've already imagined several ways it could go badly. And that's often where we make a difficult conversation even harder.
The Conversation We're Having in Our Own Heads
There's nothing wrong with preparing for a difficult conversation. In fact, I encourage it. But there's a difference between preparing for what might happen and convincing ourselves we already know how the other person will respond.
We make assumptions about what they're thinking, what they'll say and how they'll react. Sometimes those assumptions come from previous experiences. Other times, they come from our own fears or frustrations. Either way, we can walk into the conversation expecting the worst.
That affects how we show up. We may already feel anxious, frustrated or defensive. We might focus so much on getting our point across that we stop listening. A question can sound like a challenge, or a different perspective can feel like an argument. We might even soften what we really need to say because we're worried about upsetting the other person.
I've worked with leaders who spend a lot of time preparing what they'll say but give much less thought to what they're bringing into the conversation themselves. And that's worth paying attention to, because emotions are contagious. The frustration or defensiveness we bring into a conversation can influence how the other person responds, sometimes making an already difficult conversation even harder.
Think about a team member who's missed a few deadlines. Their work is holding other people up, and understandably, you're frustrated. You may start wondering whether they take their responsibilities seriously or prioritize the work.
But what do you actually know? You know the deadlines were missed and the impact they've had. What you don't necessarily know is why. Perhaps expectations aren't clear, they're juggling competing priorities, or they need more support. Or it could genuinely be an accountability issue.
The point isn't to excuse poor performance. It's to recognize the difference between what we know and what we're assuming. When we enter a conversation believing we've already figured out someone's motives, we leave very little room to learn anything different.
Prepare for the Outcome You Want
One tool I use when coaching clients through challenging conversations is the Feel–Know–Do Framework. It helps us focus on what we want from the conversation instead of everything we worry might happen.
Before the conversation, consider three questions:
FEEL: How do I want the other person to feel?
You can't control someone's emotions, but you can choose how to approach them. Do you want them to feel respected, heard and supported, even if the message is difficult? Just as importantly, how do you want to feel and show up? Calm, confident and open to listening?
KNOW: What do I want them to know or understand?
Think about the information that needs to be shared and any expectations that need to be clarified. It's equally important to consider what you need to understand from their perspective. Sometimes we focus so much on getting our message across that we forget there may be something important we need to learn.
DO: What do I want to happen as a result?
Think about what you're hoping will change. Maybe you need to agree on next steps, address a behaviour, resolve a misunderstanding, or better understand each other's perspectives.
The framework doesn't guarantee that the conversation will go the way you hope. But it does help you clarify what matters before you walk into the conversation.
You Can't Control Their Response, but You Can Influence the Conversation
Even with thoughtful preparation, some conversations will still be uncomfortable. The other person may disagree, get upset, or say something you weren't expecting.
You might still feel frustrated, anxious or uncomfortable. The important thing is recognizing those feelings before they take over the conversation. That gives you a better chance to listen instead of immediately defending your position, ask questions when something surprises you, and stay curious instead of jumping to conclusions.
And I don't think these things necessarily get easier just because we've been leading people for years. They can be especially challenging when the relationship matters, or emotions run high.
Before your next difficult conversation, consider what you assume about the other person, what you know to be true, and what you're most concerned might happen. Clarify what you want to accomplish and how you want to show up, regardless of how the other person responds.
We can't predict or control every outcome. And sometimes a difficult conversation really will be difficult. But we can take responsibility for the mindset we bring.
So here's a question worth considering: Are you preparing for the conversation that's actually going to happen, or the one you've already imagined?
Originally published on the Noomii Coach Blog on October 23, 2026
