The Bootstrapping Phase

I think I have a slightly better way of describing a particular moment in a product’s life that I alluded to in Rock tumbler teams, Chances to get it right,  and later, Build a thing to build the thing. I call this moment the “bootstrapping phase.” It very much applies to consumer-oriented products as well, but is especially pronounced – and viscerally felt – in the developer experience spaces.

I use the term “bootstrapping phase” to point at the period of time when our aspiring developer product is facing a tension of two forces. On one hand, we must start having actual users to provide the essential feedback loop that will guide us. On the other hand, the product itself isn’t yet good enough to actually help users.

The bootstrapping phase is all about navigating this tension in the most effective way. Move a little too much away from having the feedback loop, and we run the danger of building something that nobody wants. Go a little too hard on growing the user base, and we might prematurely conclude the story of the product entirely.

The trick about this phase is that all assumptions we might have made about the final shape of what we’re building are up in the air. They could be entirely wrong, based on our misunderstanding of the problem space, or overfit to our particular way of thinking. These assumptions must face the contact with reality, be tested – and necessarily, change.

The word “bootstrapping” in the name refers to this iterative process of evolving our assumptions in collaboration with a small group of users who are able and eager to engage.

Those of you hanging out in the Breadboard project heard me use the expression “unbaked cookies”: we would like to have you try the stuff we made, and we’re pretty sure it’s not yet cooked. Our cookies might have bits of crushed glass in them, and we don’t yet know if that cool new ingredient we added last night is actually edible. Yum.

At the bootstrapping phase of the project, the eagerness to eat unbaked cookies is a precious gift. I am in awe of the folks I know who have this mindset. For them, it’s a chance to play with something new and influence – often deeply – what the next iteration of the product will look like. On the receiving end, we get a wealth of insights they generate by trying – and gleefully failing – to use the product as intended.

For this process to work, we must show a complementary eagerness to change our assumptions. It is often disheartening to see our cool ideas be dismantled with a single click or a confused stare. Instead of falling prey to the temptation of filtering out these moments, we must use them as guiding signals – these are the bits that take us toward a better product.

The relationship between the bakers of unbaked cookies and cookie testers requires a lot of trust – and this can only be built over time. Both parties need to develop a sense of collaborative relationship that allows them to take risks, challenging each other. As disconcerting it may be, some insights generated might point at fundamental problems with the product – things that aren’t fixable without rethinking everything. While definitely a last resort, such rethinking must always be on the table. Bits of technology can be changed with some work. The mental models behind the product, once it ships to the broader audience are much, much more difficult to change.

Because of that, the typical UX studies aren’t a great fit for the bootstrapping phase of the project. We’re not looking for folks to react to the validity of mental models we imbued the nascent product with. We fully realize that some of them – likely many – are wrong. Instead, we need a collaborative, tight-feedback loop relationship with the potential users, who feel entrusted with steering the product direction through them chewing on not-yet baked cookies. They aren’t just trusted testers of the product. They aren’t just evaluators of it. They are full participants in its development, representing the users.

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