Ask Better Questions: The Trusted Advisor Series, Blog #2

  • 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.


Coming Up Next in the Series…

The next post will explore why honesty—even when it’s uncomfortable—is one of your most valuable assets as a Sales Engineer.

Spoiler: It’s okay to say, “No, we can’t do that.” The key is what comes after.