Trusted Advisor, Blog #2: Ask Better Questions

  • April 16, 2025

Turning Curiosity Into Credibility as a Sales Engineer

When I was starting out in sales engineering, I thought being valuable meant having all the answers. The faster I could solve a problem or point to a product feature, the more confident I felt in the role. But the deeper I got into the work, the more I realized something important:

The best SEs aren’t the ones with the best answers—they’re the ones who ask the best questions.

That might sound counterintuitive, especially in a world where clients expect technical clarity and quick solutions. But over time, I saw that the most impactful moments in conversations didn’t come from rapid-fire demos or pitch-perfect technical walk-throughs.

They came from pauses.

From curiosity.

From slowing down long enough to ask the kind of questions that made people stop and think.

Stop Treating Discovery Like a Checkbox

Let’s be real—discovery can get mechanical if we’re not careful. We show up with a list of pre-approved questions, try to match them to product capabilities, and check off boxes before jumping into the demo.

But if the only goal is to capture requirements, you’re acting like a questionnaire, not a consultant.

Instead, I’ve learned to treat discovery as the first step in a conversation, not the setup for a pitch. I come in with a plan, but I follow the breadcrumbs. I listen for pain, gaps, and contradictions—and I use those to ask better, deeper questions.

Good Questions Build Trust

The right question, asked at the right time, can do more than surface a use case—it can shift how your client sees their own environment.

Here are some questions I come back to often:

  • “What’s driving this initiative now?”
  • “What happens if this problem doesn’t get solved?”
  • “Who else is impacted by this challenge?”
  • “What does success actually look like for you?”
  • “What have you tried already—and how did it go?”

These aren’t earth-shattering questions, but they get people talking. They build trust because they show I’m not just there to pitch—I’m trying to understand.

And when a client feels understood, they let their guard down. They share more. And that’s when you start uncovering the real priorities.

Ask Like a Peer, Not Like a Vendor

There’s a tone shift that happens when you move from order-taker to advisor. It’s subtle, but clients feel it.

When I show up with thoughtful questions—especially ones that challenge assumptions—it signals that I’m here to collaborate, not just transact. I’ve had clients stop mid-call and say, “No one else asked us that,” and that moment becomes a turning point.

Being willing to ask hard questions (politely, respectfully) is a sign of confidence. It says, “I’m not just trying to win the deal—I’m here to help you make the right decision.”

Get Comfortable with Silence

One of the simplest but most powerful tools in my toolkit? Silence.

It used to make me uncomfortable. I’d ask a question and rush to rephrase it or fill the space. But now I give people time to think. I sit in the pause. And more often than not, that pause leads to something deeper—something I wouldn’t have heard if I’d kept talking.

If you’re always filling the silence, you might be missing the signal.

Questions Are How We Earn the Right to Advise

You can’t be a trusted advisor without trust. And you can’t build trust if you’re only talking. Questions are how we earn the right to offer insight. They’re how we demonstrate value long before the product does.

So next time you’re on a call, resist the urge to solve too soon. Stay curious.
Ask better questions.


Bonus Tip: Build Your Own “Power Questions” Notebook

One of the best habits I developed early in my career was keeping a personal “Power Questions” notebook.
Whenever I had a discovery call, a demo, or even an internal brainstorming session, I paid attention to the questions that really unlocked new insights—the ones that shifted conversations, uncovered hidden needs, or built immediate rapport.

I started jotting those questions down in a simple list, adding notes about when and how they worked best.
Over time, it became my secret weapon.

When a conversation started to stall, when I felt a client holding back, or when I needed to move a discussion deeper without being aggressive—I could pull from my own curated library of powerful, thoughtful questions.

You don’t need anything fancy.
A notes app, a journal, a dedicated page in your CRM—whatever works for you.

The key is to treat questions like a skillset you actively build, not just something you “figure out” during calls.

Because asking the right question at the right time isn’t just about discovery—it’s about showing that you listen, you care, and you think strategically about their success.

📋 Quick Starter Ideas for Your Notebook:

  • What happens if this challenge isn’t solved?
  • Who else feels the pain of this issue inside your org?
  • What other projects are competing for your attention right now?
  • What would success look like six months from now?

Coming Up Next in the Series…

Asking better questions opens doors—but honesty is what keeps them open.
In the next post, we’ll explore why telling the truth (even when it’s uncomfortable) is one of the greatest trust builders you have as a Sales Engineer.

Next up: Blog #3 — Don’t Oversell: Why Honesty Builds Deeper Client Trust.