Dragons, Disney, and Difficult Conversations

Last month, I took my 2.5-year-old son and pregnant wife to Disneyland for three days. Before going, we made one critical decision: everyone naps daily at noon, no exceptions.

It worked. Every day by noon, we were completely cooked. We'd retreat to our hotel room, and everyone (including Mom and Dad) would crash for two hours. Well, most of us. Our son needed occasional reminders that Mater could wait, and that the afternoon's adventures required rest now. Even in a place designed to overstimulate and exhaust, we stayed patient and present because we had a plan.

*(Caption - Two out of three members of our family enjoyed meeting Mickey)*

In between Disney trips, running a business, and growing a family, my other hobby has been playing Baldur's Gate 3. For the non-nerds: it's basically computer Dungeons and Dragons. What sets it apart is that it's turn-based, with no lightning reflexes required. Instead, it rewards careful planning and resource management. Half the game is spent deciding what to bring on each quest: Do I need arrows of ice for the lava monsters? Or the spell scroll of instant recovery for the evil dwarf king? Yes, I'm aware how this sounds.

But here's what Disney and dungeon crawling taught me about leadership: preparation doesn't just prevent disasters. It creates better outcomes.

I see this constantly when working with managers preparing for difficult conversations. The ones who struggle are those who walk in unprepared, essentially marching into battle without thinking about what tools fit the precise challenge ahead.

The 4-Question Feedback Prep

When I teach feedback skills, the single most effective practice is writing down what you want to communicate before the conversation. A quick note covering these four questions changes everything:

  • What was the situation when it occurred?

  • What was the behavior I saw that concerned me?

  • What was the impact of that behavior? Why does it matter?

  • What could they try doing differently next time?

Walking into feedback without this five-minute prep is like walking into a dungeon without checking your inventory. You might survive, but you won't be effective.

You don't need to treat every conversation like a final boss battle. But the interactions that matter (the feedback that will shape someone's growth, the difficult conversation you've been avoiding) deserve your best preparation.

Not because you're trying to win, but because preparation improves outcomes. For you, for them, for the relationship.

Take the time. Write the notes. Pack the right tools.

Just like at Disney: the nap isn't the punishment. It's what makes the rest of the day possible.

Try this week: Before your next challenging conversation, spend five minutes with these four questions. Notice what changes.

What preparation rituals help you show up at your best? Hit reply. I'd love to hear what works for you.