Over the last 9 plus years, hundreds of founders have come to me for coaching on their sales and go-to-market challenges. And I’ve done my best to help. In the next few months, in the form of weekly episodes, we’ll be looking at the top startup sales misconceptions folks possess. And how I get them to think instead. Reading this series will make you smarter and more aware than most startup operators, as you’ll already know how to think about go-to-market and sales, and avoid some of the biggest pitfalls. Consider this your cheat sheet in shaving months off your revenue growth journey. Here’s your sixth installment. Read on.

“We plan on asking our customers what they’d like to accomplish in the free trial or pilot period.”

I know I’m an oddball, but go ahead and do it.

You’ll find a few surprises, I’d be willing to bet. I’ve always been dumbfounded by some of the reviews I land on.

“This omakase was not worth the money and I was still hungry leaving the restaurant.”

“The waiter we had was snooty and the pasta lacked flavor.”

My experiences at those restaurants couldn’t have been more different. The reviewed sushi spot was one of the best I’d ever been to. And the described Italian restaurant delivered an elaborate pasta tasting menu at their chef’s counter.

What I’ve come to realize is that people’s opinion of the same product or service can vary greatly. Based on numerous factors. The lens through which they look at life. Their relationship to money. Their current mood. The quality of their day leading up to the experience.

What some interpret as pretense. Others consider elegant. What some view as refined. Others see as finnicky. What some experience as delicate. Others perceive as dull.

The point here is: when we rely on people’s feelings, it’s hard to get to a singular view on the same experience.

So if you allow folks to tell you what they’d like to accomplish during a free trial or pilot, you run the huge risk of getting many different answers. And find yourself running around trying to satisfy very different expectations.

Not a role you want to play.

Flash back to my time at Whitetruffle. When tasked with figuring out our sales model, I initially didn’t know what to do with our credit-card activated free trial.

‘How was I to make sure that we converted a large chunk of our trials into paid customers? Was there anything I could do to set the right expectations? Expectations we’d clear often and that also felt valuable to our customers?’ I asked myself.

I desperately wanted to find a way to control the sale. Folks would convert automatically through the magic of credit card processing, if they felt satisfied. And thus, I felt we should set a narrative for success that would lead to customer satisfaction.

The first place I turned to was our analytics dashboard. If ARR/MRR was our number one company metric. A close second was introductions. Quick refresher: Whitetruffle was a tech talent sourcing platform. We called ourselves a “dating site for tech talent”. Leveraging an algorithm that took in fifty plus core signals, the platform would match tech candidates – software engineers, product managers, UI/UX folks and designers – with companies looking to hire them. Employers – who were our paying customers – would get daily matches. Any match they would say ‘Yes’ to would receive a message, asking “Yelp is interested in chatting with you. Do you want to get connected to them?” If the candidate responded, ‘Yes”, an intro was made through the website.

Classic double opt-in. Introductions were a critical metric because they were an indicator of the marketplace’s liquidity. The more introductions we’d deliver, the more value candidates and companies were getting from Whitetruffle.

I started taking a look at the number of intros we were delivering in the 14-day free trial. I noted that the average was 4-5 intros for that time period.

So I decided to deflate that number a bit when it came to setting expectations. On our trial onboarding call – coined “Account Optimization Call” – I’d tell our new trial customers, “You can expect to get 2-3 intros during your fourteen day free trial with us.”

You might ask, “Paul, what about this success narrative made it so potent?”

Great question.

A few elements are at play here. The first? Our success narrative was anchored to an objective metric that’s tied to value derivation from our product. There’s no arguing with a metric. As a matter of fact, when folks would reach out mid-trial complaining about their lack of intros, I’d check their account. When they’d been doing well objectively, I’d respond, “You guys are seven days into your trial and already have 3 intros. That’s a lot more than most. You’ve gotten the number of intros we’d expect for the entire trial! Candidates are responding super well to you guys. You’re a sexy company.” This helpful reframe would most often get the trial customer to calm down and rethink how they’d initially perceived their experience.

The second attribute of our narrative that made it potent? Folks were conditioned pre-trial to expect these “aha” moments of value. Just like Pavlov’s dog. There was an understanding that they were supposed to look for these intros. And once one was offered up, they’d think, ‘I’m getting to meet with this candidate I’d been interested in. This is cool. I wouldn’t have been able to do that were it not for Whitetruffle.’ Value that was promised was delivered. Nothing like meeting expectations to build trust.

The third dimension of our narrative that made it powerful: we deflated our numbers a bit to make sure we cleared our bar more often than not. It was a layup for us to get there. As opposed to a three pointer. Or a stretch goal. By artificially picking a smaller number, we gave ourselves a greater chance at success. And nobody budged. Because they knew they were still getting three distinct moments of value.

So next time you’re constructing a free trial or pilot, control the sale by setting the narrative for success for your customer. Don’t ask them to formulate one. If you can make it based on objective metrics that are tied to value derivation for your product, that’s even better. Plant the seed in your customer’s heads that they’ll be getting value every time this event happens. And lastly, deflate your numbers a bit, so they’re attainable most often. I don’t know about you, but I’d rather bet on a layup than on a three pointer.

Do all those things and you’ll not only set your customers up for success. But also yourself. And if you ever want me to take a look at what you’ve concocted narrative-wise, just reach out to me at paul@gassee.com. Good luck.

Next week, we’ll discuss how startup operators put too much pressure on themselves when personalizing their outbound.