The hardest conversation you'll have this year is one you should have had months ago

I had two coaching sessions last week where the entire hour was spent on issues with a co-founder. I also had a hard conversation of my own. Side note: Mercury was in retrograde until late Thursday afternoon. Related? Perhaps, but I digress.

It's kind of ironic that this week we're launching season one of our podcast, and our very first episode is on navigating difficult conversations. Here's the thing. This is hard work, but it is the work. Given the new pod and given the coaching conversations from last week, I wanted to share some thoughts from my own experience, and my own fear of hard conversations.

Two coaching sessions, two different companies, same root issue. That's rarely a coincidence.

I know the conversation I'm talking about, because I've had it, and I've sat across from enough founders and leaders to know they have too. It's the one that's been sitting on your calendar in your head for weeks, even if it's never made it onto the actual calendar. I rehearse mine in the shower. I rehearse them in the car. Some version plays right before I fall asleep, and it's still playing when I wake up.

The night before, it feels enormous. I run through what I'll say, then what they might say back, then what I'll say to that. I draft opening lines I'll never use. I wonder if I'm overreacting, and then I remember the thing that happened last Tuesday, and I know I'm not.

Here's what I've come to believe about that dread, after coaching people through it and living through it myself. It's rarely about the conversation itself. It's about everything that came before it.

Where it actually started

Almost every difficult conversation I've coached someone through traces back to the same place. An expectation that was never spelled out, or one that was set once, a long time ago, and never revisited.

Think about how most working relationships start. There's a big, shared vision at the beginning, and expectations get set in the first week, maybe the first month, while everyone is still new to each other and trying to get it right. Then time does what time does. The role changes. The stakes change. The people around you change. Nobody goes back and says the quiet part out loud again. The expectation quietly ages. The other person never gets the memo that it did.

Before I coach anyone through a hard conversation, I ask two questions, and I ask them of myself too.

1. Does this person actually know what's expected of them? Not what you assume you told them once. What they could say back to you, in their own words, right now, if you asked.
2. And do they know they're not meeting it? Those are two different facts, and in almost every coaching conversation I've had, the leader has only confirmed one of them. Usually the first. Often not even that.

If I can't answer both with a clear yes, I've learned I'm not ready for the conversation I think I'm ready to have. I'm ready for a different one.

The pile-on doesn't work, and here's why

I've watched plenty of leaders, myself included, arrive at the hard conversation with a case already built. Months of frustration, documented in the head if not on paper. Every missed deadline, every short email, every meeting where something felt off. We walk in with the full file, because it feels like fairness. If you're going to say something this hard, surely you should back it up.

It backfires almost every time.

A pile-on doesn't read as thorough to the person on the receiving end. It reads as an attack. They stop hearing feedback and start doing math, trying to figure out how long you've been keeping a list and what else might be on it. Whatever trust was left in the room goes first, and it goes fast.

I've learned that two or three facts, max, do more work than twenty. Not because the other seventeen didn't happen. They did. But specificity builds trust, and volume erodes it. The work is picking the two or three that are true, recent, and clear enough that there's no argument about whether they happened. That's the conversation. Not the case file.

What "not current" actually costs

There's a phrase I keep coming back to in coaching, one that tends to land harder than I expect it to: not being current in that relationship.

It's what happens when the gap between what's true and what's been said grows for too long. The leader knows things aren't working. The other person may or may not know. Everyone else on the team can usually tell something's off, even if they couldn't say what. Being out of date with someone you manage isn't neutral. It has a cost, and like most unpaid things, the cost compounds.

We're here now

Here's what I keep having to remind myself. I cannot fix the backlog. The conversation that should have happened three months ago still won't have happened three months ago, no matter how well I handle the one I'm about to have. That was never going to be the goal.

The goal is simpler, and more achievable. Stop adding to the pile. Say the two or three true things. Ask the two questions first, so you actually know what you're walking into. Then have the conversation you've been dreading, not the one you've been rehearsing.

It won't undo the months. But it will stop them from becoming more months.

Episode one of The Intentional Organization Podcast asks the question this post has been circling: are difficult conversations as scary as we make them out to be? Give it a listen.