How to stop your pilots stalling
The 4 key calls that get you across the finish line
When your pilot stalls before the finish line, its seldom because the product didn’t work. Its usually because you didn’t build a process around the ending.
I see this a lot. A founder runs a pilot and end users love the product but then the trial period ends with no contract signed. Users ask for a trial extension, the founder happily grants it and suddenly finds themselves in no man’s land with no urgency to get a deal done.
You can’t wing the conversion from pilot to annual contract. You have to engineer it from day one.
This post covers:
How to structure the four types of calls that turn a pilot into an annual contract
What to do on each type of call and what to stop doing
Why the ROI call is a readout, not a pitch, and why that framing matters
Book four types of calls before the pilot starts
Before the pilot kicks off, get 4 types of meetings on your buyer’s calendar:
The kick off call
One or more end user onboarding calls
One or more mid-pilot check-ins, depending on how long your pilot is
The ROI decision call
By far and way the simplest and best approach is to set up a weekly recurring meeting and adjust the agenda and attendees based on where you are in the pilot. This matters for three reasons:
It signals that this is a structured evaluation, not a free trial with soft boundaries.
It’s easier to schedule the ROI call when there’s no conversion pressure yet.
If you don’t block the time on your buyer’s calendar you won’t be on their to-do list and your deal will stall.
Use the kick off call to align on goals, success criteria, process and stakeholders
The kickoff call is not a demo. The decision to pilot has already been made. Stop selling and focus on locking in the following:
Goals: Why did they start this pilot? Restate the problems, desired impact and critical event that led your buyer to kick off the pilot.
Success metrics: How will we know 2 weeks from now that the pilot was successful? Be specific. For example, “We want to reduce time spent on X by Y%” is good whereas a vague statement like, “We want to try using with the product for ourselves” is not a success metric. Don’t just pick one metric, pick a handful. The more metrics you pick, the fuller the picture of success will be.