How to Have Hard (and Worthwhile) Conversations

Is there a conversation you’re avoiding right now?

One you know you should have, but it feels uncomfortable, too high-stakes, or unclear where to even begin?

In this edition of Shed Some Light we build upon our last episode on giving feedback with the brilliant

Liane Davey

and explore how to initiate and lead through those tricky moments. Not conversations to check a box. The type that get us to a better place with clarity, courage, and care.

Here’s an example to make it real…

My co-host

David Nebinski

was mid-wrestle in a work situation where he was struggling. He didn’t know if he should speak up, what to say if he did, how to say it, or if it would even be worth it. So he reached out to me. We talked it through. And what unfolded was the anatomy of a hard, and, what turned out to be, a worthwhile conversation.

Here’s the thing: these conversations aren’t just about confrontation. They’re about connection, the kind that moves relationships, teams, and decisions forward.

There’s a rhythm I’ve noticed in crucial conversations that go well; those that feel both vulnerable and productive. I call it the anatomy of a hard conversation, and it looks like this:

1. Should I do this? → Consider this: Is it safe enough to speak up? Is it worth it? More on this dynamic in my book, Speak-Up Culture.
2. Preparation → Write it down, talk to a trusted friend or resource, clarify your intentions.
3. Invitation → Don’t blindside. Ask: “Can we talk about something important?”
4. The Dip → It will feel messy. Imperfect. Vulnerable. That’s normal. That’s kind of the point and the cost of progress.
5. The Transcend Up → A good conversation (or conversations) leaves both people clearer and better.
6. Follow-through → Act upon your agreements. Without it, you’ll have to repeat the conversation. With it, you grow.

Sometimes, one of the tricky places is where and how to start. One of the most powerful conversation openers we’ve learned is from

🌀 david spinks

. Check it out in his Substack post here: “Can I say something imperfectly?” 🤌

This approach lowers defenses, signals humility, and invites dialog, not monolog. It makes for progress. 

What conversation are you avoiding that, if done well, could leave you and another in a better place?

Reach out to a friend. Write it down. Start small. But most of all, start.

Keep making it safe and worth it for the people around you to speak up. 🗣️🆙 And when the moment comes, may you lead, speak, and listen with courage, humility, and curiosity.