Guiding Questions > Leading Questions

Marketing & Writing

Sometimes, we forget how easy it is to fall into psychological manipulation. Especially those of us who do “sales and marketing” on the Internet.

It even creeps into the way we talk about things. We’re going to “close” a sale? Why not, “Open an opportunity” instead?

The way we talk says a lot about the way we think. Changing the way we think will lead to a change in the way we talk.

The reverse is also true. By intentionally changing the way we talk, we can change the way we think. And if we change the way we think, we change the way we show up for people.

Enter the concept of “leading questions.” It’s a common phrase in the worlds of sales, marketing, and coaching—worlds where I spent the majority of my time.

I don’t think this concept is inherently wrong. But if we’re not careful, we can allow a concept like this to cloud our motives.

Rather than asking leading questions, I prefer to ask guiding questions. If leading questions are what you ask to lead people to a destination of your choosing, guiding questions are what you to ask to lead people to a destination of their choosing.

It’s easy to spot the difference.

For example, have you ever watched someone ask a question clearly meant to lead in a particular direction, and the other person fumble the answer over and over, until the questioner finally gets frustrated enough to tell the other person the real answer?

That’s a leading question. The person being asked didn’t go there because it wasn’t the answer they needed. It was the answer the questioner thought they needed.

Leading questions are confusing. Guiding questions are clarifying.

Leading questions have a hidden motive. Guiding questions have a visible motive: true discovery.

Leading questions are disingenuous. Guiding questions make meaningful distinctions in a person’s thinking.

Two archetypal examples from my worlds:

Why do you think a recurring revenue model makes the most sense for your business? (Leading)
If you had to choose between a recurring revenue model or a one-time payment model to structure your business, which most resonates with you? Why? (Guiding)
Mr. Client, If we don’t perform this audit on your website, I can’t guarantee it will be secure. Don’t you worry about security issues on your website? (Leading)
Mr. Client, I’m sorry to hear you’re not interested. Curious, if we don’t perform this audit on your website, what do you think could happen? (Guiding)

Sure, these examples are a little forced and the distinction is usually more subtle than that. Fact remains: Leading questions cause hesitation, guiding questions create trust.

In your conversations aimed to persuade people, slow down, and consider the questions you’re really asking. Do they guide towards the right answer for the person, or do they lead towards the right answer for you?

Feb 14, 2025

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Hey, I'm Steve — a Christian, entrepreneur, thinker, and creator. Thanks for stopping by!

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