The Conversations No One Wants to Have

We’ve all been there.

That moment when your stomach flips, your brain races, and you suddenly have an urgent need to alphabetize your spice rack instead of talking to your colleague about... that thing.

Difficult conversations at work? No one’s lining up to have them. But here’s the truth: they’re unavoidable and they’re also a sign of strong leadership and personal growth.

The most effective leaders (and teammates, and humans) don’t shy away from tough talks. They lean in, with empathy, courage, and a little bit of prep.

Let’s break it down.

Three Conversations You’re Probably Avoiding (And Why They Matter)

Here are the big three I see most often in coaching:

1. Giving Feedback

You want to be honest, but you’re worried they’ll get defensive or worse, upset. So, you either sugarcoat it until it’s unrecognizable or say nothing and stew quietly.
Why it matters: Clear feedback helps people grow. Without it, confusion or resentment often takes root.

2. Setting Boundaries

You’re saying “yes” way too often, working late again, or feeling overextended and it’s starting to show.
Why it matters: Boundaries aren’t walls. They’re clarity. And they protect your energy, time, and focus.

3. Raising Concerns

You notice something isn’t working, a process, a dynamic, a pattern, but don’t want to rock the boat.
Why it matters: Speaking up (constructively) can spark necessary change and strengthen trust on your team.

What Not to Do in a Difficult Conversation

Let’s start with what won’t help:

• Avoid it and hope it magically fixes itself. (It won’t)

• Sugarcoat the issue so much that the real point gets lost.

• Go in hot—emotional, reactive, or unprepared. That’s a fast track to defensiveness.

What To Do Instead

Here’s the better path forward:

1. Prepare: Think through what you want to say and more importantly, how you want the other person to feel walking away. Ground yourself in facts, not feelings.

2. Be Clear, Not Cruel: Say what you mean with kindness and directness. “I care enough to be honest with you” is a powerful mindset shift.

3. Stay Curious: You’re not delivering a monologue; you’re inviting a dialogue. Ask open questions. Listen. Adjust.

A Simple Framework to Help: SBI

Try the SBI model (Situation – Behavior – Impact) next time you’re stuck:

“In yesterday’s meeting (Situation), you interrupted me several times (Behavior), and I felt like my ideas weren’t being heard (Impact). Can we talk about how we collaborate going forward?”

It’s clear, specific, and anchored in your experience, not assumptions.

Are You Ready for This Conversation?

Here’s a quick checklist:

• Have I identified the core issue, not just my frustration?

• Am I grounded and emotionally regulated?

• Do I know what I want the outcome of the conversation to be?

• Am I willing to listen, not just talk?

• Can I approach this with empathy, not just efficiency?

If you answered yes to most, you’re ready. And if not? That’s okay too—this is the perfect time to pause and get support.

Let’s Make This Easier (And More Effective)

You don’t have to white-knuckle your way through these moments. I’ve got tools to help.

Download my free Difficult Conversation Prep Worksheet to get organized and confident before your next big talk.

Or…

💬 Book a free Discovery Call and let’s talk through what’s on your mind. You don’t have to do it alone.

The bottom line?

Difficult conversations may be uncomfortable, but they’re also powerful. They build trust, drive clarity, and deepen connection when done well.

And the more you practice, the easier it becomes.

Let’s start today.