You just got a pilot request from a Fortune 500 company. Big logo, real revenue potential, and an enthusiastic contact who wants to get started right away. Your instinct is to say yes immediately.
That instinct is wrong about half the time.
The pilots that wasted the most of my time were the ones I was most excited about at the start. The bigger the logo, the more I wanted to believe. And every time I got burned, the signs were there from the first conversation — I just didn't ask the right questions.
Luigi Mallardo, a GTM advisor whose thinking on this I keep coming back to, nails the core mistake: most founders diagnose how to run the pilot before diagnosing why the prospect wants one. They jump straight to timelines and success criteria without ever asking whether this prospect can actually buy.
Here are six questions I now ask before agreeing to any pilot. If you can't get good answers to at least four of them, think carefully about whether this deal deserves your team's time.
1. Is there a committed champion — and do they have political capital?
You're looking for someone with a title, a budget line, and a track record of getting things approved internally. What a good answer sounds like: "I've been allocated budget for this initiative, and I've brought in two new tools in the last eighteen months through our standard procurement process."
What a bad answer sounds like: "I love what you're building and I really want to champion this internally." Enthusiasm is great, but enthusiasm without organizational power is Mallardo's "Pet Pilot" — your contact is curious, they're genuinely interested, but they've never pushed anything through procurement and they don't have the standing to start now.
The test isn't whether they like your product. It's whether they can get a purchase order signed.
2. Can they define what success looks like in specific, measurable terms?
Good: "We want to reduce ticket resolution time from 48 hours to 24 hours." Bad: "We'll know it when we see it." Also bad, and more common than you'd think: "We just want to see how the team reacts."
I've written a whole post about why this question matters so much. The short version: if they can't define success before the pilot starts, they won't be able to confirm it after the pilot ends. You'll finish the evaluation with a product that performed well and no way to prove it.
3. Is there a clear path from successful pilot to signed contract?
This is the question most founders forget to ask, and it's the one that saves you the most time when you do. Good: "If we hit these numbers, I'll take it to our VP for budget approval in Q3. She's already aware we're evaluating solutions in this space." Bad: "Let's see how it goes and figure out next steps."
Mallardo's diagnostic question here is simple and powerful: "What happens if the pilot goes well?" If the prospect can't describe a concrete next step — a specific person who approves, a timeline for the decision, a budget process — then there is no path. The pilot isn't an evaluation. It's an activity. And activities don't have conversion rates.
4. Is there committed budget — for the pilot and for the deal?
Good: "We have budget allocated for this category, and our discretionary limit covers the pilot fee." Bad: "We'd need to find budget" or "Let's start with a free trial and I'll build the case from there."
The second answer isn't necessarily disqualifying, but you should know what it means. "We'd need to find budget" means this person hasn't sold the initiative internally yet — and they're hoping your free pilot will do the selling for them. That rarely works.
5. Will they pay for the pilot?
This one is binary, and it ties directly to the core argument in Stop Running Free Pilots — willingness to pay is the single best signal of seriousness. Not the only signal, but the best one.
When a prospect is willing to write a check for a pilot — even a modest one — they've done something important internally. They've gotten someone to approve spending money, which means someone with authority believes this is worth evaluating. When they won't pay, you don't know whether the resistance is financial, political, or a sign that nobody with real power cares.
6. Is there a hard end date with a decision attached?
Good: "We need to have a recommendation to the steering committee by end of Q2." Bad: "No rush — we're just exploring options."
"Just exploring" is fine for the buyer. It's expensive for you. Outreach's data shows that deals closed within 50 days achieve a 47 percent win rate. Beyond 50 days, it drops to 20 percent or below. Open-ended timelines almost always produce open-ended outcomes.
A good follow-up when you hear "no rush": "Is there a business initiative or quarterly review that's driving this evaluation?" If the answer is yes, you have a real timeline even if they didn't frame it that way. If the answer is no — if there's genuinely no time pressure and no triggering event — you're probably dealing with curiosity, not buying intent.
When to say no
If fewer than four of these six questions get good answers, I'd recommend declining the pilot — or at minimum, restructuring the terms before you agree.
I know that's hard to hear, especially if you're early stage and every logo feels like it could be the one that changes your trajectory. I've felt that pull. But here's the math: a pilot takes real resources — engineering time, sales attention, customer success effort. If you're running two pilots and one of them was never going to convert, you've cut your effective capacity in half.
How to decline without burning the relationship: "I think the timing might not be right for a pilot — here's what I'd want to see before we invest in one together." Then tell them specifically what would need to change. Maybe they need to secure budget approval first. Maybe they need to define the problem more clearly. Whatever it is, name it. You're not rejecting them. You're being honest about what a productive engagement looks like — and most good buyers will respect that.
The counterintuitive thing about saying no is that it often makes the prospect take you more seriously. A vendor who's willing to walk away from a deal signals confidence in their product and respect for both sides' time. I've had prospects come back three months later with budget, a defined problem, and a real champion — specifically because I was honest the first time around.
The pilots you decline free up capacity for the ones that convert. That's not gatekeeping. That's choosing where to spend the only resource you can't get more of — your team's time.