Look, we’re all human. And we can hack that, yet we don’t. Human’s FOMO. We project our desires onto vague promises. We underestimate both the value of a tool and the work it takes after we have the tool.
The root of almost all disappointment with the product is a mismatch of expectations. We go into so many of our purchasing decisions with an expectation that everything will be better. It’s a bit of sales magic. It’s necessary to get people to put their name on the dotted line, but as post-sale product-people, you really need to shift your strategy. Unless you’re building a bad product, you’re almost always gonna get a honeymoon period after the original purchase where genuinely everything is better. The sharp edges are still safely padded. The productivity and use gains are real.
But like the law of large numbers, it will be increasingly hard to generate the same degree of excitement after they’ve been long term customers. You’re playing on a new field. How do you survive?
You fake it.
Under Promise
Let’s start by what I didn’t say. What I didn’t say here is don’t solve the problem. What I didn’t say is don’t show where you’re going. But you can build trust by opening the container on the black box of product progression and explain how you’re planning to take many-more-smaller-steps to get there.
This creates the perception of progress at the same time it resets expectations way lower than if you focused on going to 100%. The trick here is that you convert them from leaving the call unrealistically optimistic or disappointed. They need to leave the call knowing one thing: somebody that cares is working on their problem.
This is the setup but it’s not enough. To really turn your customers into your evangelists, you need to follow up.
Consistently Deliver
So now your customer’s sitting there, they understand you’ve heard their problem and they’re maybe a little disappointed you didn’t promise them the world. How do you turn this seemingly negative situation into one that’ll generate you more loyalty than the Big Bang feature release? Consistently. Deliver. Improvement.
The best part about this, though, is it’s really not that hard. It takes an engineer. A few extra meetings. Maybe a face to face demo of an early preview. It’s no accident that all of these things actually align with product and engineering best practice. It’s certainly hard to fuck up a release when your customers have already had input into the demos and MVPs.
And then the trick is to build to a steady rhythm. That rhythm can change depending on how demanding your customer is and how frequently your touch points are; but month over month, quarter over quarter you need a continuous, steady stream of improvements towards their goal.
Onwards
If this feels like manipulating customers: it isn’t. It’s building trust that compounds over time into a huge moat. It’s teaching people you care about their problems, that you move deliberately.
It can even be quite fun. Every once in a while you will still deliver magic! But you won’t have to deliver magic because the baseline has been clear, high, and predictable for the entire relationship.

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