The Conversation You Keep Having Is Probably About Something Else

Most of us are really good at talking about the surface. The best leaders learn to go deeper.

My five-year-old had a meltdown recently because we missed our flight to New York. There was no flight. There was no trip planned. She had decided the night before at bedtime that we were going, drew herself a paper ticket, went to sleep excited, and woke up ready to board. The devastation when reality set in was real - and lasted 45 minutes.

Around the 40-minute mark, I looked at my husband Jason and said: "This has nothing to do with a trip."

She wasn't upset about New York. She’s literally never even been there. She was upset about something else entirely, something neither of us could name in that moment but was clearly very real to her. The trip was just the surface.

I keep coming back to that, because I've noticed the same pattern in most of the hard conversations I have as a leader and as a partner. The ones that keep circling and never quite resolve are rarely about what they appear to be about.

The Spreadsheet That Wasn't About Money

A few weeks ago, Jason and I sat down with Jeff Greenberg, a former Wall Street analyst who now coaches at Clay and runs money psychology workshops. In 75 minutes, something cracked open.

Jason and I would both say we're good communicators. With finances, we do what we're supposed to: pull up the spreadsheet, review spending, talk about goals. We thought we were having the right conversations. Turns out we were looking at the same data and seeing completely different things, because we each brought different stories to the table. Stories about what money means, what it signals about safety, control, and worth. Those stories came from childhood, from formative experiences, from roles we'd each quietly settled into over years.

We were always talking about money. We were never actually talking about money.

Jason said it plainly afterward: "I have a much better understanding of how you think about things now." And I finally have a name for the thing that happens to me in an uncomfortable financial situation, the way my body and mind just go offline. I can see it now. I can work with it instead of being owned by it.

That is the kind of change that makes you a better leader, a better partner and, a better person.

Why This Matters

If you've been in leadership for any amount of time, you've had the conversation that won't resolve. The recurring tension with a peer. The team dynamic that feels fine on the surface and isn't. These conversations have surface topics, but the surface topic is rarely the real one.

Most professional development skips this layer entirely. It gives you frameworks and tactics. It makes you better at surface conversation. But it doesn't help you recognize when the surface conversation is a decoy.

The leaders who grow most are the ones willing to look at the layer beneath the spreadsheet, beneath the performance review, beneath the 45-minute argument about a flight that was never booked. And ask: what is this actually about?

If something in this post landed, that question is a good place to start.

Jeff is joining the Arcadia Constellation to talk through all of this with our members - join us here.

Arcadia creates community and events for technology leaders focused on multi-dimensional growth through professional coaching, personal wellness, and accountability. Learn more at BeArcadia.com