The One Question NEVER to Ask in Sales 

It’s the one question never to ask in sales. Not that it’s a bad question. In its day I’m sure it was quite serviceable. Perhaps, even, insightful.

But not any more. 

Ask this question and you’ll get rolled eyes and blank stares. You’ll look like every other sales leach prowling the planet, and you won’t get an honest answer anyway. 

What’s the question?

Here it is: What’s keeping you up at night?

If you’re still asking that question in sales, stop it. Now. 

Use this alternative instead: Here’s what should be keeping you up at night …

Note the pivot from supplicant to advisor, from dependent to consultant. 

Not that you don’t ask questions any more in sales. That’s far, far from the truth. You must earn the right to ask them, however, by providing value first, by proving yourself as a business person with substance worthy of the investment thoughtful answers will take.

In short, selling with insight. 

Two Truths and A Lie

You’ve played the party game two truths and a lie, yes? Everyone writes three things about themselves on a piece of paper. Two of them are true and one of them is not. Each person reads their statements and the group tries to guess the lie. 

Here’s my sales version of this game:


In today’s crazy-busy, chaotic business marketplace, prospects don’t have time to build a relationship with a salesperson. They want—and need—immediate help solving their pressing problems.

This is true.

There was a time when life was less hectic and business less hurried. People would be willing to sit and chat with a salesperson, perhaps even demand it, before getting down to business. Those days are gone. Long gone.

Every person you call on, every one of them, wants help solving their business problems. The faster, the better.


Selling with insight involves leading with valuable information about a pressing problem within a prospect’s business, inviting them to engage in an ongoing discussion on resolving that problem.

This is true as well.

You gotta give before you get in sales. In many ways that’s always been true, but it’s even more true today. In specific, you’ve gotta give helpful, valuable, and insightful information to earn the right to even schedule a meeting. You’ve gotta prove your chops as a thought leader and not another empty suit.


Relationships don’t matter in sales anymore.

This, of course, is the lie.

Relationships have never been more important in sales, but a different kind of relationship. Not the schmoozing of a two martini lunch or the good ol’ boys club of a round of golf. No one has time for that any more. 

Relationships that work in sales today are in-depth professional relationships where each party is working for the best interests of the company, the customer, and the community. Selling with insight puts you on par with these priorities.

Selling with Insight Formula

How do you actually sell with insight? Here’s the formula with an example:

Step One: State the Issue

Present a revealing piece of information about a pressing business problem in your prospect’s industry from a reliable source.

Step Two: List the Implications 

Provide a succinct summary of the impact the issue could have on your prospect’s business in both a negative and positive way.

Step Three: Make an Ask

Make a request to take the next immediate step in your sales process that makes sense right now.

Selling with Insight Example

Here’s an example from my business.

I specialize in helping heads of sales and their teams successfully execute a complex sales process. When I introduce myself to a prospect, one of the things I share with them is the average amount of decision makers who are actually involved in a complex sale, making the sale even more complex. Here’s how I do it:

The Issue

In every business-to-business buy there’s an average of 5.4 decision makers, according to the research of CEB in The Challenger Customer.

The Implications

A failure to identify all of these decision makers, their role in the process, their buying motives, and who can block your efforts completely, leads to deals mysterious collapsing in close and a pipeline full of fluff.

The Ask

I’m inviting you to attend my webinar next week, Mastering the Decision Maker Matrix. In it you will discover how to map the political landscape for every deal and build an internal champion to sell on your behalf.

In less that 100 words, I have a talk track for a phone conversation, the text for an email, the script for a voice mail, or the outline for a networking meeting. With these words I establish credibility by providing valuable information and using that information to open an opportunity.

Are You Missing the Mark?

The question, “What’s keeping you up at night?” and others like it misses the mark miserably in sales. It doesn’t provide value or establish you as a thought leader who can help people solve their problems. Sell at a higher level by identifying the critical issues affecting your prospects, the implications of those issues, and the next logical step to take with you to address them. 

Getting that right is what should be keeping you up night. 

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