I had dinner this past Monday night with my old college friend, Rob.

Rob lives in Vancouver and I live in Boston, so it doesn’t happen very often. In fact, it’s been 15 years since we’d last seen each other.

Fortunately, and as is often the case with people who’ve seen you drunk, high, naked and stupid (usually not all at once), it didn’t take long to get reacquainted.

Rob had asked me to pick a restaurant downtown and I settled on The Black Rose, a spot so quintessentially Boston Irish that they list a “Pint of Guinness” as an appetizer on the menu.

Other enticing heart-stoppers include Shepherd’s Pie ($15), Bangers and Mash ($16) and Buttermilk Fried Chicken (6 months off your estimated life expectancy).

We weren’t there long before the waiter came by, introduced himself and took our order. A few minutes later, we were happily eating and drinking.


Now as it turns out, I had visited my doctor that very morning. All went well (I had not yet eaten the fried chicken), and she recommended some follow-up tests and actions.

It struck me later that a visit to a restaurant and a visit to a doctor share several things in common.

In both situations, you arrive with a problem in hand – “I’m hungry” or “My leg hurts” – and the professional who’s waiting on you presents a solution, whether that’s Guinness Beef Stew or an MRI.

There is, however, one critical difference between your interaction with your waiter and your interaction with your doctor:

Your waiter gives you a list of possibilities and asks you to choose one. He may guide you a bit, but he’s essentially an order-taker, bringing whatever you request.

Your doctor, on the other hand, doesn’t ask what you want (“Today’s special is an angioplasty. Would you like an X-Ray with that?”).

Rather, she asks broad questions regarding things that affect your overall health: How are you feeling? How much alcohol do you consume? Why are you here today?

As you respond, she follows up with ever more specific questions, always with an eye towards narrowing down what’s wrong and offering solutions regarding how it might be fixed or improved.

So now here’s the key question for you as a solo professional: When you interact with prospective clients, are you a waiter or a doctor?

If you’re a waiter, when asked to talk about your services, you rattle off a list of programs and prices, inviting the listener to choose one.

If you’re a doctor, on the other hand, you never go right to solutions. Instead, you say something like, “I’d be happy to tell you more about what I do, but do you mind if I first ask you a few questions about your business?”

Then, as a doctor does, you probe (insert your own inappropriate joke here): What’s not working? How long have you had this problem? How have you tried to fix it yourselves? Why do you think you need help from somebody outside your organization?

And on and on, asking ever more specific questions based on the answers you receive.

Why does it matter which approach you use? Two reasons.

First, because by identifying and clarifying what your prospect needs up front, you’re much more likely to offer an appropriate solution (or walk away entirely if there isn’t a good match).

Second, because the very act of questioning people leads them to see you as expert.

Let me repeat that last sentence, because you might have missed it: The very act of questioning people leads them to see you as expert.

Why? Because only an expert, on a given topic, knows what to ask.

Only an expert – someone with a 30,000 foot view, years of experience and an understanding of how seemingly unrelated pieces fit together – has the ability to pull clarity from confusion.

The more you ask, the more obvious it becomes to the other person that you know what you’re talking about – not to mention how clueless about what’s really going on and in need of help they may be.

When the other person starts saying things like, “Oh, I never thought about that,” or “Hmm, I guess we don’t really know,” you can be sure you’re on the right track.

Here’s the bottom line. Your waiter and your doctor may both be experienced, capable and friendly. But each of their approaches to solving your “problem” is entirely different.

The more you can help frame the situation, by asking questions that help prospective clients narrow in on what really matters, the more you become the obvious solution to the problem.


This article was originally published on Blue Penguin Development.