Hard Conversations Pt. 2

Part 2: How to Actually Have the Conversation (Without It Going Off the Rails)

In Part 1, we talked about

• Why hard conversations matter
• Why avoidance costs more than we think
• Why conflict isn’t the enemy
• Why being kind and being nice are two very different things.

Now comes the hard part of hard conversations: sitting down and doing it.

Perfect?

I read recently that the national average for hard work conversations, including but not limited to terminations, is about 10-15 minutes. I was preparing for a hard conversation, I reminded myself, I just needed to get the conversation started – say the hard thing. Once it was out in the open, the proverbial band-aid was removed, and we could move forward.

The thing is, there isn’t a “perfect moment” or an “ideal situation”. At the time, progress is better than perfection. When I wait for the perfect moment… if I’m honest, I’m really just delaying.

Are there better times and worse times? Absolutely. Are there environments and settings that matter? Of course. But the perfect moment. The one where you feel ready, where the conditions are ideal, where you know exactly how it will land. That moment doesn’t exist.

Sometimes you have to do it scared. Sometimes nervous. Sometimes uneasy.

Stop waiting for the perfect you… the one that has all the answers, the perfect response, and has no fear. Start with the real you. Genuineness and authenticity can’t be overstated.

That’s part of the work.

Start Before You Sit Down: Setting Expectations

The single biggest cause of defensiveness in a hard conversation isn’t the content of what’s being said. It’s the surprise.

When someone is blindsided…called into an office with no warning, no context, no idea what’s coming, the brain’s threat response activates before you’ve said a single word. And once someone is in that state, they’re not hearing you. They’re surviving you.

Think about a colleague of mine who received an email invitation to a meeting from the CEO and the Director of HR. It was a minute or two of mentally packing up his desk and considering how he was going to tell his wife he’d been let go, before he realized that the invite also included one of our partners. Not only was it not what he imagined, but it was also actually a great opportunity. To hear him tell the story now is funny. But in retrospect, there was a moment when his prevailing emotion was fear. That’s a reminder of the power of our words and how we prepare folks for conversations… the pre-work.

The antidote is clarity before the conversation begins. Let people know a conversation is coming. Give them a general sense of the topic. This isn’t about softening the blow. It’s about giving them the opportunity to show up as their best selves rather than their most defensive ones.

And further back than that: ask yourself honestly whether you’ve been clear about your expectations in the first place. The gap between what you expect and what someone delivers is often not a performance problem. It’s a communication problem.

If the standard was never truly clear, the conversation you’re about to have isn’t about their failure… It’s about yours. That’s uncomfortable, but it’s worth sitting with.

As the cool kids would say, “I’m just gonna let that cook for a minute.”

Check yourself…before you wreck yourself
(and the conversation)

Before you say a word, you have to manage what’s happening inside you.

Hard conversations are physically activating. I have this amazing voice inside my head that can tell me all kinds of stories, narratives, and versions of how a hard conversation is going to go and why it would be easier to delay the message, or better, just ignore it altogether. My heart rate goes up. Breathing faster, shallower. My body can go into full fight-or-flight response as my brain doesn’t know the difference between a difficult meeting and a physical threat. And here’s the thing: whatever you’re carrying into that room is contagious. All emotions transfer. Walk in anxious, and anxiety fills the space. Walk in calm, and calm becomes possible.

Check Yourself Tip: Calm is contagious.

So before the conversation starts, breathe. Literally. Let your first word be your breath. Whatever was going to be your first word, replace it with a breath. A slow, intentional breath. Once done, you can start to speak with greater control.

Slow your tempo down. When I’m nervous or excited, which feels similar from the outside… I talk fast. A lot of words, rapid-fire. That energy doesn’t communicate confidence. It communicates chaos and fear. However, slowing down and speaking with intention is one of the most powerful ways you can set the tone for what follows. But when I breathe, slow, deep, intentional breaths, rather than the rapid, shallow breathing like I just sprinted up 10 flights of stairs, I start to tell my body it’s ok. I start increasing the amount of oxygen reaching my brain, which I need to think and function.

Check Yourself Tip: Breath. Slow.

As Jefferson Fisher writes in his book The Next Conversation, walk in with three words in mind: control, clarity, and connection. Say what you need to say with control over your emotions. Say it with clarity so there’s no ambiguity. Clear is kind. And say it in a way that connects you with the person so that it makes the other person feel, even in a hard moment, that this is happening for them, not to them. This doesn’t mean it’s a Kum ba yah moment. It means you want to be respectful… just as you’d want to be respected if you were in their position.

Tip: Say it with control, with clarity, and connect.

A Simple Framework That Actually Works

A friend shared a structure for hard conversations and feedback with me. It was so simple and straightforward, I’ve tried to use it ever since. Sometimes, the person doesn’t even realize I’m doing it. I didn’t invent this, but I’m happy to pass it along. It goes like this:

Situation. Behavior. Impact. Redirect.

Here’s what it sounds like in practice: “In yesterday’s meeting [situation], you interrupted several people before they could finish their thoughts [behavior]. Consequently, others couldn’t contribute, and the decision we made was less informed than it could have been [impact]. Going forward, I’d like to see you let people finish before responding [redirect].”

That’s it. That’s the whole conversation, in some cases. It can be a ten-second exchange walking down the hallway, or it can be the skeleton of a much longer, more formal discussion. The beauty is the same either way: it’s grounded in observable facts, not feelings; it connects behavior to real consequences; and it points forward.

No ambiguity. No character assassination. No spiral into emotion or interpretation.

Remember – clear is kind, and sometimes, clear is simple.

Listen Like You Mean It

Active listening is not waiting for a pause so you can say the thing you came to say. That’s not listening. That’s monologuing.

Real listening in a hard conversation means staying curious. It means watching for emotion. It’s noticing when someone gets quiet, or tense, or disconnected. It means asking questions not to interrogate but to understand, because sometimes what looks like defiance or indifference has a root cause you haven’t heard yet.

In addition to noticing the emotions, I’ve found great value in naming them. My own emotions and theirs.

• “It seems to me that you’re frustrated…”
• “My perception is that you feel hurt…”
• “It appears that…”

Each of these demonstrates curiosity and creates an opportunity for you to learn (connect) more about the person and the situation.

I’ve heard Active Listening compared to the card game Uno: you can’t decide what card to play until you’ve seen what the person before you just put down. You have to actually wait. You have to actually receive.

This doesn’t mean being passive or giving ground you shouldn’t give. You can be both curious and clear. But when someone feels genuinely heard in a hard conversation, the conversation changes. Defensiveness drops. Possibility opens up.

When They Push Back

“But,” you might ask, “If I do all this, won’t they still get upset?”

Probably…at least a little. Here’s something to remember (and this is a big one): you are not responsible for their emotional reaction. You’re responsible for the words you use. You’re responsible for providing clarity in the way the information is delivered to them. You’re responsible for the care and empathy behind the message. But you’re not responsible for their reaction. This has been and remains a challenge for me. But, with practice and intentionality, I’m getting better.

You are not responsible for their emotional reaction.

When defensiveness comes, return to the ground you’ve already prepared: the expectation, the behavior, the impact, the redirect. You’re not arguing. You’re anchoring. The facts don’t move because the feelings got louder.

One final reminder on this:  Conflict is not failure. If the conversation gets hard, that doesn’t mean it went wrong. It might mean it went exactly where it needed to go.

Close It with Intention

When you’ve said what needed to be said, don’t let the conversation dissolve into awkward silence or trail off into small talk. Put a period at the end of the sentence.

Summarize what was discussed. Name what was agreed to. Clarify who owns what, the next step, and when you’ll check back in. And then, genuinely, not as a script, affirm the person. I’m for you. I believe you can do this.

Not a “compliment sandwich.” Not a technique. An expression of what’s actually true: that the reason you had this conversation at all is that you believe in what’s possible for them. The importance of genuineness and authenticity can not be overstated. That’s what Servant Leadership looks like.

Being “for someone” and correcting them are not mutually exclusive ideas. Often, they are complementary.

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Next in the series: Part 3 .What Comes After (And Why the Follow-Through Is Where Leadership Actually Happens)

This series was drawn from a live presentation delivered by Tim in February 2026 on hard conversations. Tim recommends The Next Conversation by Jefferson Fisher as a companion read and The Next Conversation Workbook. You can purchase these using his affiliate links.