The Conversations You're Avoiding Are Simpler Than You Think

"I need to talk to my business partner about stepping back, but I don't even know where to start."

"I have to tell one of my team members that we're bringing in AI and their role is changing, but I'm terrified they'll quit on the spot."

"My fiancé and I need to discuss how we're going to align our two different businesses after the wedding, but every time we try, it turns into a fight."

I hear this every week. Different situations, same paralysis.

The hard conversation you know you need to have. The one you keep postponing because it feels too big, too risky, too complicated.

Here's what I've learned after twenty years of navigating high-stakes conversations, first as a Chief of Staff of the medical practice where I worked clinically, then building businesses with my husband, now advising family business leaders:

The conversation isn't complex. It's just loaded with emotion. And that makes it FEEL impossible.

Why Hard Conversations Feel Complex

When a conversation carries emotional weight - fear of hurting someone, guilt about changing things, anxiety about their reaction - your brain treats it like it's complicated.

But usually, the actual conversation is simple. It's just one or two sentences:

The complexity isn't in WHAT you need to say. It's in all the emotion wrapped around it.

The fear: What if they get angry? The guilt: What if I'm ruining their life? The anxiety: What if this damages our relationship?

So you avoid it. Or you over-complicate it. Or you have the conversation badly because you're trying to manage their emotions instead of just being clear.

The Telescope Approach

When clients come to me avoiding a hard conversation, I help them telescope out and see what the conversation is actually about.

Not the emotion around it. Not the worst-case scenario. Not all the "what ifs."

Just: What does this person actually need to know?

I worked with a staffing agency owner who was terrified to tell one of her placement coordinators that they were implementing AI and the role would change significantly. She'd been avoiding it for four months. Every time she thought about it, she'd convince herself to wait another week.

"What if she quits on the spot? What if she gets angry? What if she tells the whole team and everyone panics?"

When we telescoped out, here's what she actually needed to say:

"We're implementing new technology that will automate some of the administrative parts of your role. I want to work with you over the next six months to transition your focus to client relationship building and strategic account management; the stuff you're really good at. I'm investing in training you for this. But I need to know, are you willing to make this transition with me?"

That's it. That's the conversation.

Everything else - the guilt about changing things, the fear of her reaction, the anxiety about whether she'd quit - that was emotion. Valid emotion. But not the conversation.

Once my client could see that clearly, she had the conversation. It went better than she expected. And two months later, the coordinator told her: "I was so worried you were going to let me go. I'm actually excited about this new direction."

The Anatomy of a Clear Conversation

Here's the framework I use with clients for hard conversations:

1. Telescope out: What does this person actually need to know?

Strip away the emotion, the guilt, the fear. What's the core information?

2. Separate your emotion from their emotion.

You're responsible for delivering the message clearly and kindly. You're not responsible for managing how they feel about it.

3. Be direct, not dramatic.

Don't soften it so much they miss the message. Don't dramatize it so much they panic. Just say it clearly.

4. Offer what you can, acknowledge what you can't.

If you can offer support, training, time, flexibility; say that. If you can't change the outcome; acknowledge that too.

5. Give them space to process.

They might need time. That's okay. The conversation doesn't have to resolve everything in one sitting.

Why This Matters

The conversations you're avoiding don't get easier with time. They get harder.

The longer you wait:

And here's the thing: most people KNOW something needs to be said. They're waiting for you to say it. The avoidance creates more anxiety than the actual conversation would.

Real Examples

I worked with a construction business owner who needed to tell his 30-year-old son that he wasn't ready to take over the company yet. He'd been avoiding it for over a year, watching his son get frustrated and resentful because he kept getting passed over for leadership decisions.

When we telescoped out, the conversation was simple:

"I see how hard you're working. And I see your potential. But you're not ready to lead operations yet, and I need to be honest about that. You're incredible with clients and vision, but the operational side: managing budgets, holding the team accountable, making the tough calls; that's where you need more development. Here's what readiness looks like to me, and here's how we can get you there together."

Hard? Yes. Complex? No.

I also worked with newlyweds who were both entrepreneurs; she's a financial advisor, he runs a different business, and they kept fighting about how to align their two ventures after getting married. Every conversation about business turned into a fight about values and priorities.

The conversation wasn't complex. It was:

"We're building two businesses and one marriage. Right now, the businesses are competing with each other and with us. We need to decide: Are we running two separate businesses that happen to be married to each other, or are we building one combined vision? Because what we're doing now isn't working for either so let’s align our mutual vision and better align forces."

Emotional? Absolutely. But not complicated.

The Question

What's the hard conversation you're avoiding right now?

If you telescope out and strip away the emotion, what does the other person actually need to know?

That's probably simpler than you think.

And having it clearly, kindly, and directly is almost always better than continuing to avoid it.

If this resonated, share it with another leader who's been postponing a conversation they know needs to happen.

Onward and Upward,

Kasey

P.S. If you're avoiding a hard conversation and can't see it clearly because you're too emotionally close to it, this is exactly what I help leaders navigate. I help you telescope out, see what the conversation is actually about, and have it in a way that's clear and kind. Reply to this email.