The Question Behind the Question

I’ve been asking CEOs the same question for years.

What do you truly want?

Not what’s the right next move. Not what does success look like.

What do you want?

The answers are almost always impressive. Articulate. And almost always not quite true.

Not because they’re lying. They’ve just swapped my question, without knowing, for a more comfortable one.

One they already have an answer to.

Because for most of their careers, the answer has been out there. The next role. The next company. The next challenge. 

That’s where they’ve looked – outside. It works. Until it doesn’t.

Some eventually arrive at the wise conclusion: the answer isn’t out there.

So they turn inward. And that’s right.

But here’s what no one tells you: going inward doesn’t automatically get you to the truth. The instrument you’re using to look has been shaped by the same patterns that got you here. Patterns that are extraordinarily good at generating convincing answers.

The first answer is almost never the real one.

I see this in a few common forms:

Bill — founder and CEO of a commercial general construction firm.

Runs on intensity. Fills a room. Has conquered every challenge put in front of him.

The question he’s asking: “What’s the next challenge?” (unsaid: that is worthy of me?)

What he says: “More scale. Higher stakes. Greater impact” 

The question underneath: “What’s is true success?” “What is true fulfillment?”

What he discovers: “I’ve been chasing scale when what I truly want is real connection. I think I’m lonely. I’ve never said that out loud.”

Priya — founder of a healthcare consulting firm.

The résumé that others admire. Always in motion, packed calendar. Performs to what’s needed at the highest levels.

The question she’s asking: “What’s the next right move?” (unsaid: that would elevate my status)

What she says: “This third board opportunity is a great fit.” 

The question underneath: “What do I truly want when nothing needs to be proven?”

What she discovers: “I have no idea. I’ve been executing for so long I don’t know what I feel anymore. I want to do something that moves me, not just something that looks right.”

Shane — co-founder of a deep tech firm.

Wired for possibility. Infectious. A genius at the start.

The question he’s asking: “What’s possible?” (unsaid: that is interesting, stimulating, and fun to me?)

What he says: “There’s this climate tech angle we’re exploring, I’m advising a friend on his new fund, and I’m doing a number of VC/founder podcast and conferencet interviews”

The question underneath: “What do I want badly enough to stay with when it stops being new or when it gets harder than hard?” “What would I say no to?”

What he discovers: “There’s one thing I’ve been circling for three years. I think I’m scared — if I commit and it doesn’t work. Or worse, if it does and I have to give it all of my attention.”

James — managing partner of a business law firm with a tech platform

Highest standards in the room, including for himself. Built something meaningful, and he did it right. 

The question he’s asking: “Where should we focus our efforts to improve?”  (unsaid: to make it perfect, to make my team perfect)

What he says: “We have a duty to keep improving our platform for our clients even if the team’s burnt.”

The question underneath: What do I really need underneath the duty and perfection?

What’ he discovers: “I sense I need rest but that’s hard to admit. And I need more joy. I want to build something for the joy of it… not because I should or that it’s right.”

Chris — CEO of a third-generation family business.

Makes everyone feel seen. Expresses great leadership through generosity and mentoring.

The question he’s asking: “How do I create more value for the people around me?” (unsaid: so they love me)

What he says: “Culture is everything to me. I want to build something they’ll appreciate and remember.”

The question underneath: What do I need beyond others’ appreciation and approval?

What’s more true: “I’ve always defined myself by what I give. I want to also take care of myself, to be true to myself, maybe for the first time.”

None of these people were being dishonest. The first answer was real — just not deep enough. It was coming from the part of them that’s been in charge for a long time. Competent. Practiced. Convincing.

The second answer came from somewhere more spacious and still.

The questions worth sitting with don’t have ready answers. They’re the ones that produce a pause.

When do I feel most alive, not most effective?

What would I choose if nothing needed to be proven?

What have I been circling without committing?

What do I truly want, not what I’ve been trained to want?

The answers are in there. They just require a different quality of listening than most of us have practiced.

That’s the work.

What question have you been answering — that isn’t quite the real one?