Change that Sticks

Change that Sticks

You Have to Earn "It Depends"

How contextual judgment develops.

Marian Heather Hartman's avatar
Marian Heather Hartman
Jul 22, 2026
∙ Paid

The phrase “it depends” is a signal that tells us that individual has so much contextual awareness of your situation that they can’t simply give you a ‘pat answer’. They need more clarifying information to narrow down the context before they are comfortable giving a direction.

In this sense, the Green Path functions as a sequence of expanding awareness. I call it a path for skill acquisition, but with true skill acquisition comes contextual awareness. As contextual awareness builds, “it depends” comes more and more into play.

This contextual awareness moves from something unavailable to the practitioner, to something understood within solutions, and finally to something understood within the definition of the problem itself.

The Green Path with context building at each practice level.

Simple Robot

At this stage the practitioner has not yet accumulated the context that judgment requires. This absence of judgment is not a low discernment skill, but as a genuine lack of any basis for discernment. Each repetition of the Simple Robot level skill accumulates experience through grounded practice to where contextual awareness will become possible.

“It depends” remains unavailable at this stage. The practitioner has not yet come to know the behavior well enough to know on what it might depend.

Solo

By this stage, context has accumulated sufficiently that the practitioner begins to value variation. Some cases call for the standard solution, others call for an adjustment. Each solution can also be implemented using different combinations of behaviors they learned in Simple Robot, and the right combination depends on the context. “It depends” becomes operative here, but it’s limited to the solution space. The problem itself is still taken as given. The only judgment is about which solution to apply to that problem, and how to go about accomplishing that solution in this specific situation.

This first layer of contextual awareness can look like flexibility from the outside, but it is better understood as pattern recognition, built through the accumulated repetition of the preceding stage.

Planner

At this stage “it depends” expands its reach from solutions to problems themselves. The practitioner no longer accepts the named problem as given. They recognize that the identified problem is sometimes several problems, or that the problem worth solving isn’t the originally described problem. The question itself becomes subject to judgment, not only the answer.

This represents a different order of skill. Where novices focus on surface issues, practitioners at this stage focus on structure. They ask what kind of system would produce a given problem, and what solving it here would leave unsolved elsewhere.

Layering the Skill Learning

The recipes in Simple Robot may look like rigidity from the outside, but its purpose is to build the raw material from which judgment is formed. The keystones within Solo then activates that judgment within known space. The practices with Planner extends it to the problem itself.

The result, ultimately, is a practitioner who has internalized the method deeply enough to see past it, rather than one who simply continues to follow it.

Free posts help you see the system. Paid subscribers get access to my 15-minute coaching calendar, as well as my gratitude for supporting my coffee shop writing!

Happy to writing this in a London coffee shop where I’m also facilitating “Design Change that Holds in Real Work” for delivery managers!

No article can think out loud with you about your specific situation. As a thank-you for paid subscriptions, I continuously offer 15 minutes to brainstorm, consult, or just explore whatever’s on your mind. No agenda, no upsell.


User's avatar

Continue reading this post for free, courtesy of Marian Heather Hartman.

Or purchase a paid subscription.
© 2026 Marian Heather Hartman · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture