Inquiry-in-Action: Leaving the Harbor

Jonathan Reams

The “Big Idea” Summary

Habits are low-energy expenditure “autopilot” modes that resist change; to rewire them, we must treat new behaviors as “prototypes”—low-stakes experiments where we expect clunkiness, welcome prediction errors, and use “dual awareness” to observe the data without judgment.

In the two previous essays, we stood on the shore. We oriented ourselves with a compass (the goal) and used a sextant to map our coordinates (distinctions). We have a direction and a plan.

But a map is not the territory, and as the saying goes, a plan is only good until our first encounter with reality. To actually learn, we have to leave the safety of the harbor and encounter the weather on the high seas. We have to step into the messy reality of a Tuesday morning meeting and try to do something different.

This is Step 3 of the Learning Loop: Experimentation, or what I like to call inquiry-in-action. We go into the laboratory of our everyday life as a bricoleur, where can see lessons all around us. We get out our lens of curiosity, an attitude that reframes problems as prediction errors we can learn from.

While it all sounds nice to read about, the moment you try out your new skill, you can just as likely hit a brick wall as a home run. You might feel the rush of successfully breaking an old habit or performing a new skill. You might also feel a strong, almost magnetic pull to go back to the way you’ve always done things.

While the feeling of success is nice, we typically feel bad when we fail. However, this isn’t a failure of character.

The Challenge of the New

Remember, your brain’s main job is keeping you alive. To do that, it focuses on energy-conservation. Your old habits—your “automatic autopilot”—are efficient. They run on well-myelinated neural pathways (well paved roads, compared to dirt bush tracks) that require almost zero effort or cognitive load. They are the “system 1” fast thinking that gets you through the day without burning out.

Your new skill, however, is expensive. It requires “system 2” effort. It demands that you override the habits that served you for years.

When you try to introduce a new behavior—say, “pausing for three seconds before answering”—your brain’s prediction engine screams in protest. “This feels weird! This is taking too long! Just give the answer!” It tries to pull you back into the habituated, low-energy expenditure state of your old habit.

In the previous essay we discussed downward assimilation. Here I want to take a moment to see how it contributes to the challenge of trying new things and how it can help explain the ‘knowing doing gap.’

Let’s be clear, we really intend to implement our plan. Our will is strong. However, we often fall prey to a form of self-deception. We confuse our intellectual understanding of a term for the actual capacity to execute it. We mistake our map for the territory. This low-resolution map ends up cutting off all the bits of high-resolution reality we actually don’t know about.

Then we go into action and ‘do’ what we intend and find we are lost in a gap that has suddenly opened up between knowing and doing. We receive a prediction error. Maybe many of them. Our knowing was limited and thus so was our doing.

It is here that maintaining an attitude of curiosity becomes so important. If we receive the inevitable prediction error as a failure of performance, we negatively judge ourselves, others, or the situation. If we receive it with humility and curiosity, we can decode the error signals to fill in the gaps in our knowledge.

We can stop focusing on “performing” and start prototyping.

The Prototyping Mindset

In design thinking, a prototype is not a finished product. It is a rough draft. It is meant to be tested, broken, and refined.

When we treat our attempt at a new leadership behavior as a prototype, we lower the stakes. We aren’t trying to be the perfect leader today; we are running a 5-minute experiment to see what happens if we change one variable.

This shifts us from a “performance mindset” (where errors are humiliating) to an “inquiry mindset” (where errors are data for humble inquiry).

We want to “fail fast”—to catch the prediction error quickly so we don’t waste time on a strategy that doesn’t work. We also want to “learn slow”—to take the time to deeply encode the new neural structure so it becomes robust.

The Clunkiness Factor

Here is a litmus test for a good prototype: It should feel clunky.

Remember the example from a previous essay about learning to tie your shoes? At first it was clunky; slow, awkward and full of mistakes. (I remember creating some knots my mom had to cut with scissors). If your new behavior feels smooth, natural, and easy, be careful. You might be slipping into a form of downward assimilation. You might be giving an old script a new title.

Real learning feels awkward. It feels like writing with your non-dominant hand. It feels like the “fog” we talked about earlier—moments of uncertainty where you aren’t quite sure if it’s working.

Embrace the clunkiness. It is the somatic signal that you are actually rewiring the machine. Tune in to the signals from your body (what is called interoception). Do you feel flush in your face? A tightness in your throat? Tenseness in specific muscles? Learning to decode these signals can be a tremendous asset.

One more thing here. Clunkiness can also be quite subtle. It can be difficult to pinpoint a specific sensation in your body. Sometimes prototyping a new skill can feel clunky because it is touching a deeper nerve and disrupting the coding of your identity. Your stable sense of self becomes more malleable, and this can be disconcerting. Take heart, it’s a good sign that important growth is happening.

Dual Awareness: The Balcony and the Dance Floor

To run these experiments effectively, we need to cultivate dual awareness.

On the Dance Floor: You are in the meeting, asking the question, pausing, interacting. You are the actor.
On the Balcony: Simultaneously, a part of you is observing. You are the “navigator,” watching the interaction from above.

You are asking: “What is happening right now? I feel the urge to interrupt—that’s the old model. I am choosing to wait. What is the impact on the room? Is the other person relaxing? Are they speaking more?”

This split attention is demanding. It burns energy. That is why we keep the experiments small. We don’t try to overhaul our entire leadership style in a week. We use micro-loops that last for one conversation, or even one exchange.

The Anomaly Effect

Be prepared for one other challenge. The people around you are also running predictive models. And their models predict that you will act the way you have previously acted.

If you have acted in a controlling manner for five years, and suddenly you try a collaborating move, they might not even notice the new behavior. Or they might misinterpret it. For example, they might interpret your silence as disapproval rather than opening a space for collaboration.

This is the anomaly effect. Your new behavior is an anomaly in their data set. They are not being difficult just to spite you. Any system tends to maintain itself, and their prediction models are efficiently navigating the situation by using prior experience of the old you to predict what is happening now.

Do not let this discourage you. Treat it as data. “Interesting. I changed my input, but the system hasn’t changed its output yet. My signal wasn’t strong enough. Or maybe I need to be explicit about what I am doing.”

Designing Your Prototype

So, how do we build our prototypes for running experiments? We have a variety of ways to do this. Here is one simple script to design an experiment.

1. Select the Lab (Low Stakes)
Do not try your first experiment in a high stakes meeting. In such an environment your vulnerability factors can be high enough to outweigh your resources. Pick a low-stakes lab: a routine 1-on-1, a weekly stand-up, or even a dinner conversation at home.

2.The Script
Write it down: “I will [apply specific distinction] during [specific context] and notice [specific response].”

Example: “I will count to three (distinction) after asking a question in the weekly team update (context) and notice if more people speak up (response).”

3. The Aikido Check
If the experiment goes “wrong”—if you get interrupted, or if you feel awkward—don’t judge yourself. Use the Aikido move. Remember to stay curious and pivot from “I failed” to “What is this telling me?”

Maybe the distinction was too big. Maybe you were too tired (low resources). Maybe the context was stormier than you realized. This might look something like: “The current is stronger than I predicted; I’m adjusting my heading, not abandoning the voyage.”

This isn’t failure. It is the raw material for the next iteration of the loop.

Turning the Key

We have a compass. We have a map. We are ready to prototype.

Now, let’s turn the key. Let’s step out of the theory and into practice. Let’s be willing to be clunky, to be imperfect, and to be curious.

In the next essay, we will look at Steps 4 & 5: Reflect and Revise. We will explore how to take the messy data from these experiments and use it to update our maps, using each little experiment weave another connection making your new skill more robust.

The Reflection Loop

The Clunkiness Audit: Think about a new skill you tried recently. Did it feel smooth or awkward? If it felt smooth, challenge yourself: Did you really change anything, or did you just rename an old habit?

The Energy Check: Before you start your next experiment, check your “battery.” Do you have the cognitive energy to maintain Dual Awareness? If not, can you pick a smaller, simpler prototype?

The Observer: In your next conversation, try to spend 10% of your attention on the “Balcony.” Watch yourself talking. What do you notice that you usually miss?