Startup Corner #23: The problem with pilots
Why “getting your foot in the door” can trap you longer than you think
Hey friends,
Let’s talk about pilots.
Not the ones flying planes (deepest apologies for the dad joke).
The ones you say yes to at 11 p.m. because a big-name customer finally replied to your email.
The ones that sound like the beginning of a deal — but slowly morph into a black hole of custom dashboards, shifting expectations, and endless check-in calls with no clear path to revenue.
We’ve all done them. I’ve done them. And when they work, they’re magical: a signal of demand, a story for your deck, maybe even a contract.
But when they don’t? They quietly drain your time, your focus, and your roadmap — without ever saying “no.”
Here’s the problem with most pilots:
They sound like validation.
But they behave like fiction.
The startup hears: “They’re interested!”
The customer thinks: “We’ll test this — maybe.”
There’s a huge difference between trying something new and planning to adopt something new. And if you don’t draw that line early, you end up stuck in what we call the enthusiasm zone — where everyone’s nice, no one’s committing, and your team’s building features for a customer who might never convert.
So how do you know if a pilot is worth it?
Here’s what I’ve started looking for:
A real pilot solves a real problem — with urgency, ownership, and a path to money.
If even one of those is missing, your “pilot” is probably just a prolonged demo.
Urgency means there’s a pain they’re trying to fix right now.
Ownership means someone inside the org is on the hook for making it work.
A path to money means they’ve at least talked about budget — or what success looks like in business terms, not just product terms.
If you’re not hearing those signals, you’re not in a pilot. You’re in a sandbox.
The worst part?
Even bad pilots feel productive.
They create motion. You’re meeting stakeholders. Getting feedback. Tweaking the UI. Shipping fast.
But if the incentive alignment isn’t there — if your champion isn’t influential, if the budget isn’t scoped, if success isn’t defined — then you’re not building traction.
You’re building a case study… for someone else’s resume (shudder!).
So here’s how I think about running pilots now.
1. Scope it small.
I don’t pitch a “pilot” unless I can define a measurable result in 30 days. Not usage. Not sentiment. A result. “Help this team do X faster.” “Cut Y process in half.”
2. Gate it with intent.
Before we start, I ask: What happens if this works?
If the answer is “not sure,” we don’t start. If the answer is “this will unlock budget,” we’re in.
3. Track what’s custom.
If I’m bending the product for a pilot, I write it down. Because every hour spent on a one-off edge case is an hour you’re not spending on the core loop — the one you’re trying to scale.
4. End it clean.
Every pilot gets a stop date. Not a renewal. Not a “let’s see.” A clear end, with one decision: are we rolling forward, or are we walking away?
Final thought:
Pilots aren’t bad.
They’re just not inherently good.
They’re not validation. They’re tests.
And you should run them like tests — fast, focused, falsifiable.
Because at the earliest stages, you don’t just want customers.
You want committed believers. And those don’t come from infinite betas. They come from clarity, tension, and a shared urgency to solve something real.
— RB
Startup Corner