Startups, Uncertainty, Work You Love and Why Founders Start Fires

It’s a surprise to no one that startups deal with a high degree of uncertainty. What is less intuitive is how to break uncertainty apart in order to take action on it. Here’s where the Cynefin framework comes in handy, he breaks the spectrum of work into different categories with increasing levels of uncertainty: clear, complicated, complex, and chaotic (plus a category called confusion for anything that can’t be categorized, but we’ll set it aside for now).

Each of those categories comes with a prescriptive way to take action on questions or challenges in that category. When work is clear or obvious, it’s simply added to a backlog of work to be done. When work is complicated, it means you might not know how to do it but someone has the answer or the answer can be found. The way to move forward on complicated work is to ask an expert or gather and analyze data. When work is complex, it is by definition part of a complex system. The way to find the answer or to move ahead with complex work is to run experiments to determine which hypothesis is correct. Finally, when work lands in the chaotic category, the way to take action is to do whatever will stabilize the system and do it fast.

To channel Donald Rumsfeld for a minute, another way to think about this framework is to map the categories to known-knowns, known-unknowns, unknown-unknowns and our familiar friend chaos.

I learned this framework from Zach Nies who helps startups relate each of these categories to their daily work lives (he also has an excellent strategy exercise on the topic of entrepreneurs). For example:

• Obvious work is something you know how to do, there may be a checklist for it, something like, “fulfill a customer order”. It’s well understood what that means.
• Complicated work is an answer you have to look for, either from an expert or from data analysis. For example, complicated work could be filing a patent which would require a lawyer, or determining which of your products has the highest margin, which is an answer you can calculate.
• Complex work in contrast is not an answer that is known already. A good indication of complex work is when two competing hypotheses are equally likely. Only by testing will you know which hypothesis is correct. For example, should we launch on the East Coast or the West Coast? Or, on our website, which converts better, a green buy button or a purple one?
• And finally there is the chaotic work. These are the things you don’t see coming. One of my favorite examples because it’s so visceral is a server room literally on fire, but taking action in a global pandemic would be a more recent example. It doesn’t have to be that extreme either. It could be a big customer that doesn’t renew that you planned on. It could be a product defect. The way to move forward in chaotic situation is to take action, whatever is needed, to stabilize the system.

This is a handy framework for figuring out a way to move forward and work or is not clear how to make progress or break down and work into smaller components, but it’s not what I find most interesting about it. Another insight is that people tend to gravitate and feel fulfilled by work in one category more than others, and they’re usually pretty comfortable in the category or categories next to it.

Some people really like doing similar work over and over again. They like checklists and knowing what’s coming next. They like having an operating procedure and following it. Other people like to do research and figure out an answer after a data gathering process. Still others love to run experiments and optimize. And some of us, many of them are founders, like to solve hairy problems, preferably ones where no one knows what to do.

In my work with founders, they tend to be drawn to work in the complex and chaotic categories. And that makes sense. Starting a company from scratch is incredibly chaotic, and it requires someone who is capable of thriving in that environment. The challenge often comes later when the company finds some success and they develop a system for repeating that success. Suddenly, the skill set that the company needs most to grow is not in the wild problem-solving arena, it’s in the data gathering and standard process types of work, the clear and complicated categories.

Founders are known to get bored just as the company is starting to take off unless they can find a way to frame the new challenges the company has due to its growth as a fun problem to solve. When I see founders in this position, I encourage them to think about how the company as a whole could be a fun project to experiment on or to solve problems around. Culture, for example, is part of their job and it’s not an easy task, it’s never done.

Founders who don’t figure out how to get out of the way for the people who are good at process repetition and improvement develop a habit for breaking things just so that they can have the satisfaction of fixing them. It’s not conscious, it usually sounds like pivoting to a new product or launching a new market or anything that sounds new and exciting and shiny and potentially totally wonderful for the company. If it involves a bunch of stuff to figure out, that’s a sign of a founder who is missing that job of solving for chaos and experimentation.

There’s a saying that firefighters also make great arsonists. If you are founder who is drawn to situations where uncertainty is very, very high, be careful, you are probably also drawn to creating exactly those situations. If this is you and you have power in your company to change directions or make new plans, find someone in your life, a cofounder, a partner, a coach, a mentor, someone who can help you check your enthusiasm for whatever new idea you have against this tendency.