Why Pilots Don't Close

Title: Why pilots don’t close


Read Time: 2.5 min

Happy New Year! Hope everyone had a great holiday season.

Today, I am breaking down why pilots stall, drag, and end up in pilot purgatory. One of the biggest misses we see is skipping the scoping call, so no one is clear on what is being tested, how it will be judged, who owns it, or what happens if you actually deliver what the customer says they want.

Once that is locked, the pilot's objective is to demonstrate alignment with the customer's stated needs to validate. If you have no visibility into their expectations, how could you possibly hit the mark? You can’t. That blind spot is where pilots get smoked.

When we look under the hood, we see the same pattern among many founders. Deals look alive, but are barely moving. The team is grinding on setups and support for teams that have not really committed to anything. We have not identified a real problem, a clear metric, or a date by which the customer will reach greenlight, so it feels busy, but it is not really going anywhere.

When nothing is clearly defined, no one takes ownership. The customer says they’re evaluating. We say we are in a pilot. Nobody has agreed on what success is or what happens if we hit it, and that is how you end up in pilot purgatory.

There are old pilots, and there are bold pilots. However, there are no old, bold pilots.

~ E. Hamilton Lee

We had a client come on board in late October. One of their biggest issues was a bunch of deals that were stuck at the bottom of the funnel. One deal in particular had been running a $40k pilot since early April.

Several people were logging in, but no one was actively engaged. Light activity, no depth. The deal came in through an investor intro; there was never a real scoping call, no success criteria, and no clear owner on their side or ours.

So we reset it. We reached out to the team multiple times to schedule a call and clarify our status. On that call, we treated it like the scoping they should have done on day one. We drilled down into the specifics of the success criteria. If we were able to check all the boxes, were they ready to pull the trigger and commit? Then we set a simple plan: milestones, owners, review dates, and the next step for each box once it is checked.

We ran the pilot using specific criteria and validated it over 45 days. We are now nearing the end, and we’re almost 100% sure they will close.

Ultimately, the purpose of the scoping call is simple is to get painfully clear on what they want, what validation means to them, and then reverse-engineer the pilot around that. Once you know the target, you can design the pilot to lead them directly to that outcome rather than hoping they see the value on their own.

Let’s break down what this looks like.

3 Tactical steps you can use right now

Here’s how you want to think about running scoping calls to ensure success on the pilot.

1. Set the agenda and replay their pain

Open the call with a brief preamble and set the agenda.

For example, you can say the goal for today is to define what success looks like for this pilot, map how you will get there, and lock in next steps if it hits.

Then reiterate what you already know from your previous conversations in a couple of lines, so they hear their own story back.

You might say that last time they shared the main issues and what they are hoping you can help with…

Ask whether that is still accurate and whether anything has changed since you last spoke. This shows you actually listened and gives them a chance to update the picture before you begin discussing the pilot.
 


2. Get clear on success, ownership, and risk

Now, zoom in on the success criteria. Think in buckets. Make sure you nail these.

• Success metric:
  Ask what has to change or improve for them to call this pilot a win.
  

• What they are really validating:
  Ask what they want to prove first, whether that is performance, reliability, workflow, cost, or something else.
  

• Who owns it:
  Ask who owns this pilot on their side and who is on the hook for the result.
  

• How you will run it:
  Ask who is using it, how many people are using it, and what active usage looks like for them.
  

• Check-ins and friction:
  Ask when you should check in and if there is anything that could slow things down, like security, data, approvals, or integration work.

You want to leave this part with a real scoreboard, a real owner, and a short list of possible blockers. If you do not have those, you are not done scoping.

3. Turn it into a simple plan with dates and a decision point

Once success is defined, turn it into a plan they can see and feel.

Restate what you are committing to, both what you are doing on your side and what they are doing on theirs. Agree on the pilot window, with a clear start date, end date, and one or two key milestones in between.

Book two things while you still have them: the kickoff and the decision review at the end of the pilot. Tell them you will send a short mutual action plan that recaps success metrics, owners, dates, and how you will communicate, whether that is Slack, email, or something else they use every day.

When you hang up, nobody should be guessing what happens next or what happens if the pilot works. The path from try it to signed should already be on paper.

Key Takeaways

• Scoping calls exist for one reason: to define what a win actually looks like before anyone touches the product.

• If you don’t drill down on success, it’s very difficult to understand what will move the needle for them.

• You need a clear metric, a clear owner, and a clear timeline before you start a pilot.

• Every pilot should have a start date, an end date, and a decision meeting scheduled before it begins.

• If you cannot identify the boxes that need to be checked before the pilot begins, it’s not ready to kick off.

  
  

The pilots that turn into revenue are the ones where both sides agree up front what a win looks like, who owns it, and what happens when you hit it.

That’s it for today!

See you all next week.


Darren

P.S. If finding PMF and scaling to $1M in ARR through founder-led sales is on your radar, book a call with me here.

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