Stop Selling and Start Asking

I’ve sat through hundreds of first calls with prospects and clients. And I can tell you, within the first ninety seconds, I know exactly what kind of call it’s going to be.

The ones where we walk in with curiosity feel different. They breathe. They meander. They surprise us.

The ones where we walk in with a pitch masquerading as a conversation feel like — well, like a pitch masquerading as a conversation.

The Pressure to Be the Answer

Here’s what I think happens, especially for those of us in agency work. We put insane pressure on ourselves to have THE ANSWER. Like if we’re not demonstrating expertise in the first five minutes of the call, we’ve already lost.

So we show up over-prepared. We load the deck with our diagnosis. We lead with our POV, our framework, our solution — before we’ve even asked anything interesting.

The whole posture is wrong from the start. We’re performing expertise instead of actually being useful.

I used to do this constantly. I’d walk into a meeting and immediately start proving how smart I was — how much research I’d done, how quickly I could see the problem, how clear the answer was. I thought that’s what clients were paying for. I thought credentials and confidence and a pre-baked perspective were what earned trust.

It took me a while to realize I had it completely backwards.

What Actually Happens When You Pitch First

When you lead with your answer, something subtle happens to the conversation. The other person stops exploring with you. They start defending.

They push back on your diagnosis because they weren’t part of arriving at it. They question your conclusions because they didn’t help shape them. They leave the meeting with the same opinions they came in with — except now they also think you weren’t listening.

And you leave with less credibility and even fewer useful insights.

Because here’s the thing — you didn’t earn the right to have an opinion yet. You hadn’t asked enough questions. You hadn’t gotten curious about their specific situation, their constraints, their history, their fears, what they’ve already tried.

You just jumped to the answer.

I think about this in the moment now. Every single time I’m about to open my mouth to make a point or share my expertise, I ask myself: have I actually earned this? Do I know enough about this person’s world to say anything worth saying?

Usually the answer is no.

The Discomfort of Not Knowing

There’s an uncomfortable truth about walking into meetings with curiosity as your primary posture — it requires you to be okay with not being the smartest person in the room.

It requires you to sit with questions that don’t have immediate answers.

It requires you to let silence exist for a moment while you actually think about what someone just told you, rather than using that time to formulate your next point.

Most of us aren’t trained for this. We’ve been rewarded our entire careers for being fast, for being smart, for having the answers. We’ve learned to cringe at the idea of saying “I don’t know” or “I hadn’t thought of that” or “tell me more about that.”

We think it makes us look weak.

But the opposite is true. When you show up genuinely curious, when you ask questions you don’t already know the answer to, when you actually listen to what someone is telling you — that’s when trust gets built. That’s when the conversation becomes real.

That’s when you actually learn something that matters.

Curiosity as a Strategy

I’m not talking about fake curiosity. I’m not talking about the kind of listening where you’re already composing your response in your head while the other person is talking.

I’m talking about actual curiosity. The kind where you want to understand how this person thinks. Where you’re genuinely interested in why they made the decisions they made, what they’re optimistic about, what keeps them up at night.

The kind where you might actually change your mind.

When you lead with that — when you show up to a meeting willing to be surprised, willing to learn, willing to adjust your thinking based on what you hear — the conversation changes. The dynamic shifts. You’re no longer performing a role. You’re actually working together.

And here’s what happens next: you earn the credibility to have an opinion. Because your opinion, when you finally offer it, is informed by a real understanding of their situation. It’s specific. It’s connected to something they actually care about. It doesn’t feel like a pitch. It feels like a thought — one that came out of genuine dialogue.

This is something I remind myself of constantly. And I say it to every account person I work with.

We don’t need to be the best strategist. We don’t need to be the smartest person in the room. We don’t need to be the one with all the answers, the perfect framework, the solution that fits everyone.

We just need to be curious.

That’s actually the thing that makes a difference. Not our expertise. Not our years of experience. Not our track record.

Our willingness to care more about understanding the other person’s world than we care about demonstrating how much we know about our own.

The Practice

This isn’t something you get right the first time. I’m still working on it. I still catch myself loading the deck when I should be asking a question. I still feel the pull to perform expertise, to prove my value, to jump to the answer.

But I’ve learned to pause before I do it. To ask myself what I actually need to know before I open my mouth. To sit with the discomfort of not having a point yet.

And every time I choose curiosity over answers — every time I actually put in the work to understand someone’s situation before I start talking about mine — the conversation goes somewhere better.

The insights are richer. The ideas are more useful. The relationship deepens.

So that’s what I’m practicing. That’s what I’m encouraging everyone I work with to practice.

Curiosity over answers — every time.

Because at the end of the day, that’s what actually builds credibility. Not what you know. But that you actually care enough to understand what someone else is dealing with.