The questions that actually matter are the ones that reveal how someone thinks. How they make decisions. How deeply they understand what they’ve done and why it worked.
I’ve screened hundreds of AE candidates for early-stage startups. These are the three questions I always ask, and what I’m actually listening for when they answer.
Question One: Talk Me Through a Specific Deal
This is the most important question you can ask a salesperson. And most founders don’t go deep enough on it.
Here’s how I frame it:
“Pick a deal you closed that you’re proud of. Walk me through it from the beginning. How did it get into your funnel? How did you move it forward? Where did it almost go wrong? Where did it go right? Why did they ultimately buy? What hurdles did you have to clear along the way?”
Then I shut up and let them talk.
What I’m listening for:
I want to see if they actually understand their own sales cycle. Not the version they rehearsed for interviews—the real thing.
Can they articulate how the opportunity originated? Did they source it themselves, or did it come from marketing? Do they know the difference, and does it matter to how they approached it?
Can they walk me through the middle of the deal? This is where most candidates get vague. They’ll tell you about the first meeting and the close, but the middle—the part where deals actually get won or lost—is fuzzy. If they can’t explain what happened between the first call and the signature, that’s a red flag.
Can they explain the objections and how they handled them? Every deal has friction. If they say the deal “just kind of came together,” they either got lucky or they don’t understand why they won.
Can they tell me why the customer actually bought? Not the features they pitched. The real reason. The pain that was acute enough to get someone to sign a contract and cut a check. The best salespeople understand buyer psychology at a deep level. They know it wasn’t the product—it was the problem the product solved and the moment the buyer believed it would work.
Why this matters for a founding AE:
Technical founders especially tend to stop at “150% to quota” and assume that’s enough. It’s not.
Quota attainment tells you someone can sell. It doesn’t tell you whether they understand how they sell. And for a founding AE, understanding the how is everything.
They’re not going to have a playbook. They’re going to have to build one. If they can’t reverse-engineer their own success—if they can’t articulate the mechanics of why deals close—they won’t be able to replicate it in a new environment.
The best candidates can narrate a deal like they’re giving a masterclass. They remember the details because they were paying attention. They know what worked because they were being intentional about it.
That’s who you want.
Question Two: Talk Me Through This Career Move
Every resume has transitions. Company A to Company B. Big company to startup. Startup back to big company. These moves tell a story—but only if you dig into them.
I’ll pick a specific transition and ask:
“Why did you leave? What were you looking for? What were the risks you were weighing? How did you decide this was the right move?”
What I’m listening for:
I want to understand the depth of thought behind the decision.
Career moves are big decisions. They affect your income, your trajectory, your learning, your lifestyle. A thoughtful person treats them seriously. An unthoughtful person just… jumps.
Some candidates will say things like “I wanted a new challenge” or “It felt like the right time.” That’s not an answer. That’s a placeholder for an answer.
The candidates I get excited about can put me in their headspace at the moment of decision. They can articulate what they were optimizing for. They knew what they were trading away and what they were gaining. They had a thesis about their own career.
Red flags:
If every move was about escaping something—bad manager, bad culture, bad product—that’s a pattern. Sometimes you do need to leave a bad situation. But if someone’s entire career is a series of escapes, they might be the common denominator.
If they can’t explain the risk they were taking, they probably weren’t being intentional. Every career move has risk. If they didn’t see it at the time, they weren’t thinking clearly.
If their reasons are all external—“I got recruited” or “They offered more money”—that’s fine, but it doesn’t tell me much. I want to know what they wanted, not just what was offered to them.
What great answers sound like:
“I was two years into that role and I’d learned what I was going to learn. The product was mature, the motion was established, and I was running the same play over and over. I wanted to get closer to zero-to-one. I knew I was giving up stability and a clear path to a management role, but I wanted to test myself in an earlier stage environment. The risk was that I might not be good at it. But I figured I’d rather find out at 28 than wonder about it at 40.”
That’s someone who’s being intentional about their career. That’s someone who’s going to be intentional about their work.
Question Three: What Do You Consider Yourself World Class At?
This one catches people off guard. And that’s the point.
I ask it exactly like this:
“What do you consider yourself world class at? It doesn’t have to be professional. Could be anything. And how did you get to be that way?”
What I’m listening for:
I’m looking for spikes.
The best founding AEs aren’t generalists who are pretty good at everything. They’re people who have demonstrated the capacity to become exceptional at something. The specific thing matters less than the fact that they’ve done it.
Maybe they were a competitive athlete. Maybe they’re an incredible cook. Maybe they built a following doing something weird on the internet. Maybe they taught themselves to code or learned a language or became the best at some niche thing nobody else cared about.
What I want to see is evidence that this person knows how to get great at something. That they’ve put in the reps. That they understand what deliberate practice looks like. That they have the drive to reach a level most people don’t reach.
Why this matters:
Founding AE is a hard job. Harder than most people think. You’re building the plane while flying it. You’re going to fail constantly. You’re going to have to figure things out that nobody can teach you.
The people who succeed are the ones who’ve already proven—somewhere, somehow—that they can push through the plateau where most people quit. That they can get to world class.
If they’ve never been world class at anything, that doesn’t mean they can’t do the job. But it’s a risk. You’re betting they’ll develop that capacity for the first time, in this role, at your company.
I’d rather bet on someone who’s already done it.
What great answers sound like:
“I’m a competitive poker player. Not professionally, but I’ve won a few regional tournaments and I’ve been studying the game seriously for about eight years. What got me there was treating it like a skill, not a hobby. I track every session, I review hands, I work with a coach twice a month. Most people play poker to have fun. I play to get better.”
The content doesn’t matter. The disposition does. You’re looking for someone who knows what it means to be great at something and has done the work to get there.
How to Use These Questions
These three questions won’t tell you everything. You still need to assess culture fit, communication skills, and all the basics.
But they’ll tell you things the resume can’t.
The deal walkthrough tells you if they understand how they sell—not just that they can.
The career move question tells you if they’re intentional about their decisions—or just reactive.
The world class question tells you if they have the capacity for excellence—or if they’ve never pushed themselves that far.
A founding AE is going to face ambiguity every day. They’re going to have to make decisions without enough information. They’re going to have to learn faster than they’ve ever learned before.
These questions help you find the people who are built for that.
—Ryan