Which Rules Should You Break?

I follow lots of rules. I stay inside my lane on the highway. I wear my socks inside in—or, if you will, outside out. I always take my medication and I always take it the way I am supposed to. I even floss at night, the way my dentist tells me to do so.

But sometimes, I break the rules. I don’t color inside the lines. I break some “standard” rules more often than not, because breaking them works better.

When agile was new to many people, I started suggesting that people change one of their three questions at their standup. Instead of “what did you work on today?” I suggested that they ask, “What did you finish today?” You can see that there is an emphasis on smaller chunks of work and finishing that way.

I adapted my advice to what my clients needed. They needed smaller stories. They needed a way to self-prompt to looking at the work in progress, and seeing how to complete work “faster.” My advice was helpful to them.

Some people thought I was nuts. Now, my advice seems normal. At the time, I was a rule-breaker.

Last week, when I was at a client, I was supposed to only take taxis wherever I went. No rental car. No car service. No airport “limo.” Just taxis. I checked this with my contacts, and explained that a car service to/from the airport was often cheaper than a taxi because it was fixed price. Nope. “Just taxis,” I was told.

After being stuck in traffic three times, and one memorable occasion where all my stuff was in the back of a locked taxi with the keys in the ignition, with the driver and me outside the locked taxi, I decided to break the rules. I ordered a car service to drive back to the airport. It was faster and cheaper than the taxi that left the airport, which wasn’t in rush hour.

We’ll see if my rule-breaking fits my client or not.

Rule-breaking is about seeing the reality, generating other options, taking a step, measuring that step or getting feedback, and seeing the reality again. It’s a problem solving loop.

If you break the rules without generating options, you’re not considering the context enough. You might not understand the problem well enough. Maybe you don’t or can’t see your reality that well. If we’re in chaos, sometimes it’s difficult to see our reality well enough to generate options. Or, we don’t know the subject matter well enough.

Once you’ve generated options, can you take a small step and measure it and get feedback? Will that help you see another reality?

This is not so far off from Boyd’s OODA loop: Observe, Orient, Decide, Act. Notice how he built feedback into his loop. His loop was specifically created for fighter pilots. I’m not a fighter pilot, so I’ve adapted his loop (broken the rules?) to something that fits me better.

That’s what the best of rule-breakers do. They adapt the rules to the new reality.

If you never color inside the lines, why? Does everything require adaptation? If you always color inside the lines, why? Does nothing require adaptation?

That is the question this week, my dear adaptable problem solving friends: Which rules should you break? You may not find this question easy to answer.