The Questions You're Not Asking

Customer discovery is one of the most lied-about activities in startups. Not because founders are dishonest. Because they’re human. And humans are really good at hearing what they want to hear.

I’m speaking on a MassChallenge panel this Wednesday on the topic, and in the process of jotting down some notes, I realized I’ve seen the same failure modes play out across hundreds of founders I’ve worked with through various accelerators and my own deal flow. These patterns are so consistent that they’re worth writing down.

The common thread? Founders treat discovery as a box to check rather than a discipline to practice. That difference explains a lot about why some companies stall.

You’re Selling Features to People Who Buy Outcomes

I’ve sat through more pitches than I can count where a founder opens with a wall of technical specs. What their platform does, what technology it uses, how their system processes data. And every time, I’m sitting there thinking… okay, but what does this actually do for me? The better version is always simpler. Instead of telling me about your proprietary algorithm, tell me “we cut the time your team spends on invoicing from four hours a week to twenty minutes.” One tells me how smart you are. The other tells me why I should care.

But here’s the thing… this isn’t just a pitch deck problem. Founders who think in specs also ask questions in specs. They walk into a discovery interview and say “would you use a tool that does X?” instead of “walk me through how you handle invoicing today and where it breaks.” The spec mindset doesn’t just contaminate how you present. It contaminates how you listen.

Fifty Interviews and Still Wrong

Most founders think they’re doing discovery. They’re not. They’re asking leading questions to friendly audiences and interpreting polite interest as demand.

I’ve mentored founders who completed fifty customer interviews and still built the wrong thing. Every single question was structured to get a yes. The problem wasn’t the volume. It was that every conversation was designed to confirm what the founder already believed.

Here’s a simple exercise: before your next discovery interview, write down the answer you’re hoping to hear. Then redesign the question to make that answer impossible to give. If you’re asking “would you use X?”, the desired answer is yes, and that’s exactly what you’ll get. If instead you ask “walk me through the last time this problem cost you money,” you can’t pre-script the response. The discipline is in making yourself unable to hear confirmation.

The founders who tend to get this right are the ones who were the customer not long ago. They sat in that seat, felt the pain firsthand, and said “I need this, why doesn’t it exist?” Their discovery interviews sound different because they’re not fishing for validation… they’re pressure-testing whether their own experience is shared widely enough to build a business around. They already know what breaks. They know what’s expensive. That kind of founder empathy is really hard to fake, and it’s one of the first things I look for.

Follow the Pain

From an investment standpoint, I screen for one thing before anything else… is the problem painful enough that someone will pay to solve it? That question is its own discovery framework.

If you can’t find people who are actively spending money, time, or duct-tape workarounds on the problem you’re solving, you don’t have a market. The most underrated discovery question is deceptively simple: what are you doing about this today, and how much does it cost you in dollars or hours?

The answers tell you everything. If a prospect says “oh, we have an intern who handles that in a spreadsheet every Friday,” that’s a workaround. That’s money being spent. That’s time being burned. You can quantify it, and more importantly, you can sell against it. “Right now you’re paying someone to do this manually for ten hours a week. We make that go away.” That’s a conversation that leads to a purchase order.

But if you ask that question and get a blank stare… if they shrug and move on… that tells you everything you need to know. The problem might be real, but it’s not painful enough to trigger a buying decision. No workaround means no urgency. No urgency means no sale. Doesn’t matter how elegant your solution is.

Who Writes the Check

This one’s especially relevant in healthcare, which is where I spend a lot of my time. The user and the buyer are often completely different people with completely different priorities.

I’ve seen founders nail the clinical discovery. They talk to doctors, nurses, technicians. They understand the workflow pain. But they never talk to the person who actually controls the budget. The clinician cares about diagnostic accuracy and patient outcomes. The health system cares about reimbursement codes and workflow integration. Discovery that only covers one side is half-done.

In healthcare specifically, reimbursement isn’t an afterthought… it’s a product requirement. If you can’t answer “how does this get paid for?” with the same confidence you answer “how does this work?”, you’ve got a gap that no amount of clinical validation will fill.

Ask Better Questions

Every failure mode in this piece comes back to the same root cause. Founders who pitch specs instead of outcomes are answering questions nobody asked. Founders who run fifty interviews and learn nothing are asking questions designed to confirm what they already believe. Founders who miss the workaround signal aren’t asking what the customer does today. Founders who talk to the user but not the buyer aren’t asking who writes the check.

Discovery doesn’t fail because founders skip it. It fails because they ask the wrong questions to the wrong people and then mistake the answers for validation. The discipline isn’t in doing more interviews. It’s in getting comfortable with questions that might give you answers you don’t want to hear.