Necessary Confusion and the Bootstrap Heuristic

I’m testing a test tool at the moment. I’m investigating it for a talk. The producers of the tool claim to have hundreds of thousands of users. A few positive remarks appear in a scrolling widget on the product’s web site from people purported to be users.

Me, I can’t make head or tail of the product. It doesn’t seem to do what it’s supposed to do. It looks like a chaotic mess. It’s baffling; it’s exasperating. I don’t know where to start in analysing it and preparing a report. I’m confused. But I’m okay with that.

Any worthwhile testing starts with some degree of necessary confusion.

Why? Because worthwhile testing is primarily about learning something about a product and learning about how to test it in a complex and uncertain space. That’s by nature confusing, and that’s normal.

If the test space is neither complex nor uncertain, and if there’s little risk, you may not need to test at all, and a simple demonstration might do the trick. Knowing that the product can work might be enough, for the moment.

That’s why, for developers, performing checks and automating them at the unit level can make a lot of sense. Those checks tend to address specific, atomic conditions; they’re simple to develop and perform and encode; and they provide quick feedback without slowing down development.

A product gets built from small, discrete components. Through small, gradual changes, it turns into something much bigger and more complex, with interacting components and emergent behaviours that are non-trivial.

An encounter with anything non-trivial that you’re not familiar with tends to be messy and confusing at first. At the same time, as a working tester, you’re probably under pressure to “get things right the first time” or “get everything sorted from the beginning”. But having everything sorted really means that we’re at the end of something that was unsorted, and we’re at the beginning of the next unsorted thing!

In Rapid Software Testing, we refer to the Bootstrap Conjecture:

Any process we care about that is done both well and efficiently began by being done poorly and inefficiently.

Therefore, having “done something right the first time” probably means that it wasn’t really right, or it wasn’t really the first time, or that it was trivial, or that you got lucky.

In learning about something complex and in learning how to test it, there are frequent periods of confusion. In fact, if we’re dealing with something complex and we feel we’re sure about how to test it, that should prompt us to pause and reflect: why are we so sure?

Necessary confusion is confusion for which we do not have an algorithmic resolution. To resolve necessary confusion, we must explore a complex solution space using heuristics (that is, means of solving problems that could work but that might fail) and bounded rationality (that is, reasoning in a space where there are limits on what we know and what we can know).

To overcome confusion, we have to play, puzzle, make conjectures, perform experiments, miss stuff, ask questions, make mistakes, and be patient. Necessary confusion always occurs during deep learning and innovation.

We’re often trained in our cultures, in our social groups, and in our schooling to deny that we’re confused. That gets ramped up as soon as we get into the software business: appearing not to know something is socially awkward—almost seen as a sin in some circles of knowledge work. Confusion can make us uncomfortable.

As a tester, you could just write (or worse, run) a bunch of automated scripts that check a new product or feature for specific, anticipated errors. If you do that without exploring the product and preparing your mind your testing will be blind to important bugs that could be there.

No set of instructions can teach you everything you need to learn about a product, and about the ways in which diverse people will try to use it. No formal procedure can anticipate how you or other people will experience the product. No testing framework will handle surprising behaviour without you learning how to deal with that framework. No tool, no “AI”, can determine whether the product is operating correctly, or whether a product manager will regard a red bar as something that amounts to an important bug. Complete and correct knowledge about those things isn’t available in advance.

You can learn how to test in advance. That will avoid some unnecessary confusion during testing. You can learn about the technology and domain of your product in advance, and that will avoid more unnecessary confusion during testing. You can learn to use particular tools in advance, and that might spare you some unnecessary confusion during testing too.

But you can’t deeply learn a new product or feature before encountering and interacting with it. The confusion you experience when learning a product is necessary, temporary, and healthy.

The key is to accept the confusion; to recognize that it’s okay to be confused. As we interact with the product and the people around it; as we gain experience; as we practice new skills and apply new tools, some of the confusion lifts.

Start with a survey of the product. Take a tour of the interfaces — the GUI, the command line, the API. Play with it. List out its key features. Create an outline of what is there to be tested. Consider who might use it, and for what. Build on your ideas of how they might value it, and how their value might be threatened. Think about data that gets taken in, processed, stored, retrieved, rendered, displayed, and deleted. How could any of that get messed up? How could the data be mishandled, misrepresented, excessively constrained, insufficiently constrained, or Just Plain Wrong?

And then iterate. Go through the same process with each function and feature, getting progressively deeper as you go. Maybe write little snippets of code to generate some data, or to analyze the output. (Have you been working with a product for a long time? This cycle is fractal; it applies to new functions or features, or to repairs in a product you know well.)

As we learn about the product domain; as we go about the business of sensemaking; as we develop our mental models; as we talk about the product and the problems we observe… more of the confusion dissipates. This can all happen remarkably quickly if we allow ourselves just a little time for experiencing, exploring, and experimenting with the product. Ironically, we must deliberately require and allow ourselves room for spontaneity. We need to be brave and open enough to help our managers understand how necessary that kind of work is — and how powerful it can be.

When we embrace the confusion and lean in, things begin to get clearer, our code and maps and lists get tidier, our notions of risk get sharper, and we’re better prepared to search for problems. And then we’re more likely to find the deep, dangerous problems that matter—the ones that everyone has missed so far. At the beginning, though, that process starts as we pull ourselves up by our own bootstraps.

The Bootstrap Heuristic is: begin in confusion; end in precision.

Oh… and that test tool that I’m testing? There’s a reason that I’m confused: I’ve got a confusing product in front of me. The product is inconsistent with claims that its producers make about it. The product’s behaviour is inconsistent with its purpose. It seems incapable of keeping track of its state. It provides misleading results. For outsiders, it seems designed to provide the impression that testing is happening, without any real testing going on. From the inside perspective of a tester, it’s baffling, and that’s largely because it doesn’t work.

So there’s another heuristic: persistent confusion about a product—confusion that doesn’t go away—is often a pointer to serious problems in it. If you, as a tester, can’t make sense of a product, how will the product’s customers make sense of it?

After working with this product for a little more than an hour, much of the confusion I referred to above has evaporated, and I can prepare a report with confidence.

I’m only left with one thing that I find confusing:

How can anybody be fooled by a tool like this?

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