Welcome to issue 82! Did someone forward this to you? If so, Subscribe here!
⚡ Today’s Skill In A Sentence ⚡
A pilot without structure isn't a pilot and it can make the whole point of it backfire.
Today’s Skill: Structuring a Pilot the Right Way
I’ve had my fair share of pilot discussions with clients in the last few months so I’m imagining you might be pondering the same thing they are.
How should I set up a pilot for potential buyers?
But, that shouldn’t be your first question.
We must ask a few others before we venture down that road.
Let’s start there.
3 Questions To Know If You Need A Pilot
Did they ask for a pilot or is this something you surfaced?
Often, founders early into their business lack the confidence to ask for the full value of what they are worth.
So instead of being confident in discussing a full partnership they start small with a pilot.
While starting smaller could be helpful in some cases it also adds other complexities to the sales process if not mapped out correctly.
Why do you need to offer a pilot?
In close relation to #1, if you are thinking you need a pilot, why? Is it what you’ve heard from the market? Have many buyers brought it up? Do other vendors do this?
Clearly state: I am doing a pilot because ________________.
Could a trial accomplish your goal?
Based on your answer to #2, could a short trial get you where you need to go? Or better yet, get the client to see the value to enter into a partnership?
That distinction matters, and most people blur the two together.
If someone just wants to try your software for free, quickly, on their own, that's a trial.
→ And my advice there hasn't changed: Do a Guided Tour instead of just throwing your software at them and letting them play around in it.
There's a lot of reasons that trials go sideways. I've written about it before so go check that issue if you haven't. (ICYMI: Issue 14 “Stop Offering This One Thing.)
But, let’s say you’ve answered the 3 questions above and it does make sense to have a pilot for your business.
Here’s where most founders get stuck after that.
They have no clue on what the pilot entails, what steps are included and how to know if it works.
If you don't know the details, how can you expect the client to know them or buy into them?
Let’s walk away today knowing exactly how to lock in your pilot.
Here's the order of operations
I’ll share 5 specific steps to help you think through your pilot program so that you can effectively communicate this to the buyer and have a plan of action to stick to throughout the engagement.
1. What timeframe is the pilot?
Like how long does the pilot run for? It can’t be indefinite.
Is it 14 days or 30 days or something else?
Only you can accurately choose this timeframe and it should be based on how long your buyer might need to hit 1-2 outcome goals or see the main value.
→ Nail down the structure from a time standpoint first.
2. What's the outcome goal?
What are the success metrics that tell you the pilot worked?
This could be something you develop and stick to for every pilot or it could be customized per client.
This needs to be defined before the pilot starts, not after.
→ You and the buyer should know clearly if it was a success.
3. What are the exact steps?
We’ve created boundaries with the time allotted and success metrics.
Now, what are the steps from start to finish?
Let’s say you decided on a 14-day pilot…
Is there an onboarding call?
A check-in call?
Are you doing the work for the client?
Are they in the product working toward something specific?
→ Define the exact steps so you can clearly discuss (and even visually show) here's how we do a pilot, here's what we work through, here's the success metric.
4. Is there a price for it?
A lot of people assume a pilot has to be free. There's no reason it should be.
Pilots are typically a sample size of the full engagement annd even having a smaller amount makes the buyer have to commit and have skin in the game.
They have to be invested in it and show up accordingly.
→ You must be crystal clear, one way or another, as this sets the tone for how the pilot is structured and the expectations you have of your buyers.
5. What does the partnership look like after the pilot ends?
Here's where you can run into trouble:: The pilot ends, it went well, and now you have to resell. Even if the pilot was a success, the structure of the full partnership might cause challenges and negotiations may get delayed.
So talk through it up front.
Be confident you're going to be successful. If you are, why not already know what the contract looks like: length, pricing, parameters? If you can get a full contract signed with the pilot language included that is the best outcome.
Depending on the size of the organization, this may not be feasible or it might slow down the pilot start but get enough of the contracting done that when the pilot ends and they're good to go, it's just a formality.
→ If they're doing a pilot, they're probably already committed to doing something full-time after so get ahead of all of that beforehand.
Final Thoughts
You don’t have to lead with the pilot. This could be a fallback if your original proposal didn’t land well or if the buyer is being indecisive. At that point, a pilot might make the most sense to give them a taste of what the full partnership looks like.
Think of the pilot like the sample at an ice cream shop. It's a small taste of the bigger two-scoop cone they're about to get. So, you offer the sample for the buyers who don’t know what they want.
However, this isn’t always the case. Many buyers know what they want and feel you can deliver on it. Offering a pilot slows the sales process and causes undo friction.
Make sure you bake out all of the steps to do the pilot effectively.
Then, keep it in your back-pocket until you actually need to use it.
Action Item
Before you agree to your next pilot, sketch these five things out first:
Timeframe
Success metrics
Exact steps, call by call
Paid or free
What the agreement looks like the moment it's successful
Figure it out on paper before you're on the call agreeing to anything.
As always, feel free to send it over to me for a quick once-over. I read every reply.
Need more help? Here’s how I can step in to assist.
Need to get a quick W? Let me roast one of your sales calls so you can get immediate & actionable feedback to use on your very next call → Get Roasted Now
Want to build a repeatable sales foundation? Let’s see if the 90-day Sales Accelerator is right for you → Grab time to chat here

That’s all for today! If you wanted to say hello, reply to this email or catch me over on Linkedin
The best way you can support me is by passing this newsletter to a fellow founder or shout it from the rooftops on your socials!
until next week!
just get started,
Brian


