Startup Advisory: The Questions I Ask Every Founder

The Questions I Ask Every Founder Before I Say Anything Else

After thirty years of working across Wall Street trading floors, law firms, enterprise SaaS boardrooms, and AI startups, I've developed a discipline that looks simple on the surface but cuts to the bone every time: before I offer a single recommendation, I ask questions. Not the polished, investor-deck kind of questions. The ones that make founders uncomfortable — because discomfort, in my experience, is where clarity lives.

Whether I'm advising on legal structuring, go-to-market strategy, fundraising mechanics, or organizational design, the first forty-five minutes of any engagement look nearly identical. I'm not there to impress anyone with frameworks. I'm there to find the gap between what the founder believes to be true and what is actually true. That gap — when it exists — is usually where the company will break.

The Three Questions That Change Everything

Over time, I've distilled my diagnostic process down to three foundational questions. They sound deceptively simple. They are not.

1. What Has to Be True for This Business to Work?

This is not a question about your TAM slide or your unit economics model. This is a question about assumptions — specifically, the load-bearing ones you've never written down because they feel too obvious to challenge.

Every business is built on a stack of assumptions. Some are trivial. Some, if wrong, will kill the company in eighteen months regardless of how much capital you raise. I want to know which are which. When I ask this question, I'm listening for how deep the founder can actually go. Can they name the three or four things that absolutely must be true — about buyer behavior, market timing, technology capability, regulatory environment, or competitive dynamics — for their model to hold? Or do they pivot immediately to traction metrics and logos?

The best founders I've worked with can answer this question with surgical precision. They've stress-tested their own thesis. They know which assumptions they've validated and which ones they're still operating on faith. The dangerous founders — the ones who will spend eighteen months building the wrong thing — can't distinguish between the two.

"The right questions surface problems long before they show up in the numbers."

2. Who Is Your Actual Buyer — and Have You Talked to Twenty of Them This Month?

I've sat on enough sales calls, reviewed enough CRM data, and built enough GTM motions to know that "we know our customer" is one of the most dangerous phrases in early-stage company building. Knowing about your customer is not the same as knowing your customer.

When I ask this question, I'm not looking for a persona slide. I want to know who, specifically, signs the contract. Not who champions the product internally. Not who uses it. Who authorizes the spend, and what are they actually optimizing for when they make that decision? Is it risk reduction? Efficiency? Career protection? Competitive pressure from their board?

The second part of the question — have you talked to twenty of them this month — is where founders usually flinch. In a given thirty-day window, most early-stage founders are talking to investors, refining their pitch, managing their team, and firefighting product issues. Direct, unstructured, candid conversations with actual buyers often fall to the bottom of the list. That's exactly backwards. At the stage where GTM strategy is still being formed, there is no higher-leverage use of a founder's time than direct buyer discovery. Not demos. Not sales calls with a preloaded deck. Real conversations where you ask open-ended questions and then shut up.

If you can't tell me the last ten substantive objections you heard from prospects — verbatim, not paraphrased — you don't know your buyer well enough to build a repeatable go-to-market motion.

3. What Would Kill This Company in the Next Six Months If Nothing Changes?

This is the question founders hate most. And it's the one I care about most.

It's not a pessimistic question. It's a risk-mapping exercise. Every company, at every stage, has a specific set of failure modes that are most likely given its current trajectory. Some are financial — runway, burn, CAC payback. Some are organizational — a key hire that hasn't been made, a co-founder relationship under strain. Some are market-based — a competitor moving faster than expected, a regulatory shift that changes the sales cycle. Some are product — a technical debt problem that's quietly metastasizing.

I ask this question because most founders are, by psychological necessity, optimists. That's a feature, not a bug — you need extraordinary optimism to build something from nothing. But optimism unchecked by honest risk assessment is how you arrive at a board meeting with three months of runway and no plan.

The founders who can answer this question clearly — who can map their top three existential risks and tell me what they're actively doing about each one — are the ones I want to work with. Not because they're pessimists, but because they've done the hard cognitive work of holding both realities simultaneously: this company can win and here's exactly how it could fail.

Why Polished Answers Are a Warning Sign

Founders who have been through multiple fundraising rounds often arrive at advisory conversations with extremely polished answers. They know the narrative. They've practiced it in front of partners at Andreessen and Sequoia. The deck is clean. The metrics story is tight.

I've learned to treat that polish with respect — and suspicion. Because the questions investors ask are designed to evaluate fundability, not operational health. They're different filters. A company can have a compelling investor narrative and a deeply broken go-to-market motion simultaneously. I've seen it dozens of times.

My job as an advisor isn't to help founders get better at answering investor questions. It's to make sure they've answered the harder, messier, internal questions first. Because if you raise $5 million on a thesis that hasn't been stress-tested, you haven't solved the problem — you've just made it more expensive.

The Role of the Advisor Is Not to Have Answers

I want to be direct about something: the value I bring to an advisory engagement is not my opinion. It's my pattern recognition, and my willingness to ask questions that feel uncomfortable in the room. The founder knows their business, their market, and their team better than I ever will. What I can offer is a structured external lens — one shaped by thirty years of watching companies succeed and fail across industries, capital structures, and market cycles.

My role is to make sure the founder is asking themselves the right questions before I ever weigh in. Because the right questions, asked early enough and answered honestly enough, surface problems before they show up in the numbers — before the pipeline dries up, before the churn spike hits the dashboard, before the board starts asking uncomfortable questions of their own.

The founders who build durable companies aren't the ones who had all the answers at the start. They're the ones who were rigorous about knowing what they didn't know — and relentless about closing that gap before it closed them.

• What has to be true for this business to work? Name the load-bearing assumptions, not the obvious ones.
• Who is your actual buyer, and have you talked to twenty of them this month? Not demos — real discovery conversations.
• What would kill this company in the next six months if nothing changes? Map the risks before they map you.

If you're a founder and you can answer all three of these questions with specificity, honesty, and evidence — you're in better shape than most. If you're struggling with any of them, that's exactly where the work begins.