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I Don't Know Your Business. That's Why I'm Curious.

Oct 10, 2026

This is a story about marketing a real estate business. At least, that's what I thought it was going to be.

On the drive home from vacation this week, a friend of mine and I spent a good part of the ride talking about how she might market her business. She's been in real estate for more than thirty years. In that time she's represented buyers and sellers, worked new construction and existing homes, sold raw land, and helped people buy their first house as well as people buying at the high end. She works across Burnet, Williamson and Travis counties. Since 1992, I've been in the business of developing tennis players. Nobody is going to confuse my résumé with hers.

We were supposed to be talking about marketing, but before we got anywhere near what to put on a website or what kind of video to make, I kept asking questions, and the questions kept pulling us back toward the business itself. Who does she most enjoy working with? Are those the same people who get the most out of thirty years of experience? How would someone who's never met her know what that experience is worth? Are three counties one market or several? Would she be better off being very relevant to a smaller group of people than somewhat relevant to everybody?

I want to be clear about what I was doing, because it'd be easy to read those questions and assume I was running a consultation in disguise, sitting on the answers and waiting for the right moment to reveal them. I wasn't. My friend knows things about her industry I don't even know enough to ask about yet, and that's a big part of why the conversation held my attention. I asked because I wanted to know.

I'm overtly inquisitive by nature. It isn't a technique I picked up along the way, although I've spent most of my life finding professional uses for it. I was asking questions long before I had a tennis academy, a consulting practice or anything resembling a framework. The subject has never been much of a boundary, either. Sit me down with someone who runs a restaurant, builds houses, manages a school or repairs engines, and I'll have more questions than they have time to answer. I don't think I can do their job. I know I can't, and that's exactly what makes me want to understand how they do it.

Something tends to happen in those conversations. A person with thirty years in a field can answer most questions almost automatically, right up until one shows up that takes a little more thought. Sometimes they finally put words to something they've understood for years but never had to explain. Sometimes they hear their own answer and decide they don't agree with it anymore. And sometimes I just learn something, which is the whole payoff as far as I'm concerned. I don't need every conversation to end in a breakthrough, and I'd be suspicious of anyone who promised one.

Here's where tennis comes back in, though maybe not the way you'd expect. Questions have sat at the center of my work with young players for a very long time, and the useful ones usually aren't the ones steering a player toward the answer I already had in mind. They're the ones showing me what the player actually understands, including the places where I'd gotten it wrong. Lately I've been writing about adults who talk so much they leave no room for the young people in front of them to think. It'd be a little hard to argue for curiosity in a classroom and then drop it the moment the conversation turns to somebody's business.

I do have tools, and some of them are good ones. Years of building programs and telling the stories behind them means I can help a person figure out what makes their work different and how to say it, then produce the writing, photography or video to carry it. But tools are the wrong place to start. If we haven't figured out who we're trying to reach and why they should care, a beautifully produced video just delivers the wrong message more effectively. I'd rather ask a few more questions before anybody turns on a camera.

I also have to keep an eye on myself. Hand me an interesting problem and I'll see connections multiplying faster than any reasonable person could act on them. When my own kids were playing, I'd send messages back to the tennis center after their matches, and I redesigned my entire program every time one of them played. None of it ever got implemented. Seeing a problem doesn't make it the one that needs attention first.

That's a big part of why I push for a written roadmap with a young player's team. If something you notice today is already on it for nine months from now, you can let it go. It's sitting there because somebody already decided other things matter more, and that order holds until real evidence says it shouldn't. A business owner doesn't need an elaborate architecture simply because I can picture one. Sometimes the real value of asking twenty questions is finding out only one of the answers needs attention right now.

I don't know yet where the work with my friend will lead. We've got some ideas worth testing, and we'll learn a lot more once those ideas meet the people they're meant to reach. What the drive reminded me of is the part of this work I enjoy most, and it was never really about tennis or marketing. It's getting close enough to someone else's expertise to ask questions neither of us knew we'd be asking when we started.

So here's my Saturday invitation. If you own a business, lead an organization or are chewing on something you haven't quite figured out, I'd enjoy hearing about it. I won't pretend to know your field better than you do, and I won't promise to find the thing holding you back. I'll be interested, I'll ask a lot of questions, and I'll bring what decades of thinking about people, development and systems have taught me. Maybe we find something worth changing. Maybe we find out something you've been second-guessing is working just fine. At the very least, I expect I'll learn something.

If that sounds like a conversation worth having, reach out. You can email me at [email protected] or call or text 469.955.DUEY (3839).

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