Case Study 1 — Jordan: The City Planner's Insight

Background

Jordan has been Strategic Director for eight months. By conventional measures the team is performing well: methodology depth has improved, psychological safety is measurably better, Priya is being groomed for a senior role, the Customer Journey Council proposal has just been submitted to Rivera. But getting to the Council proposal — the resolution of a coordination failure that had resisted every analytical approach Jordan had brought to it — is itself a story about creativity.

This is that story.

The Problem That Wouldn't Move

The enterprise CX onboarding problem predated Jordan by at least two years.

The structural situation: when a new enterprise client onboarded, their experience touched four teams in sequence — Sales, Product, Customer Success, and Marketing Analytics. Each team's internal metrics looked acceptable. Retention numbers were fine. NPS by segment was fine. But thirty-day churn for enterprise accounts was running at 14%, nearly double mid-market, and the degradation was happening in the handoffs — the transitions between teams where no one had visibility into what the previous team had or hadn't done.

Jordan inherited the problem and applied his analytical toolkit to it. Over six months he tried:

Attempt 1 — Correlation analysis: Jordan's team documented that churn risk spiked within the first 72 hours after each handoff transition. He presented this to Rivera and the functional directors. Everyone acknowledged the finding. The meeting ended with a commitment to "keep exploring."

Attempt 2 — Cross-functional working group: Jordan proposed and was approved to convene a working group with representatives from each team. The working group met twice. By the third scheduled meeting, two members hadn't attended the first two and the coordination cost of rescheduling exceeded the apparent motivation to solve the problem. The group quietly dissolved.

Attempt 3 — Shared KPI proposal: Jordan proposed a cross-functional onboarding KPI — enterprise activation rate at day 30 — that would appear in every team's quarterly report. The proposal was received politely and tabled. Each team's VP believed their own onboarding metrics adequately captured their contribution.

Attempt 4 — Revenue attribution: Jordan built a revenue attribution model showing the compounding cost of 14% enterprise churn — the lifetime value difference between the enterprise accounts that churned in year one versus those retained through year three was substantial. He presented this to the leadership team. Rivera called it "the best case I've seen for fixing this." Nothing changed.

Jordan was stuck. And he knew he was stuck in a specific way.

Diagnosing the Stuck

It was not an information problem. Everyone in the room during Attempt 4 knew the problem was real, the cost was significant, and the status quo was untenable. The revenue model hadn't introduced new information so much as confirmed what was already understood.

It was not a relationship problem. Jordan had good working relationships with the functional directors. He trusted Rivera. There was no interpersonal friction blocking the solution.

He wrote in his decision journal — a practice he'd started in Chapter 24 — a question that he couldn't answer: If everyone agrees this is a problem and agrees it costs money and agrees it should be fixed, what is actually stopping it from being fixed?

He sat with that question. He didn't resolve it. He moved on to other work.

The Running Group

Jordan, Leon, and Chen ran together Tuesday mornings — a ritual established after Jordan joined the running group in Chapter 20. Leon was a city planner, around forty, who worked in urban infrastructure. Chen was the software engineer from Jordan's team who had flagged a flawed methodology assumption in a team meeting — the moment that had confirmed the psychological safety work was taking hold.

The runs were not work conversations. That was part of why Jordan valued them. Leon talked about zoning variances and neighborhood coalitions. Chen talked about distributed systems architecture. Jordan talked about his team, sometimes, and sometimes said nothing useful and ran.

On a Tuesday in late spring, Leon mentioned the Caltrain extension — a regional rail project in the Bay Area that had been stalled for more than two decades before finally moving forward. Jordan knew the name but not the story.

Leon explained: Five agencies had overlapping jurisdiction over the relevant right-of-way. Each agency had its own board, its own budget cycle, its own political priorities. The coordination problem had been real for twenty years. The typical solution — get one agency to lead — had been tried and had collapsed three times. The agency that took leadership absorbed disproportionate political cost when anything went wrong, and there was always something that went wrong.

What finally worked: the formation of a new entity. Not a working group — an entity with its own charter, cross-agency representation on its board, and crucially, a governance structure that distributed accountability. No single agency was the lead agency. Each agency contributed resources and representation. Each shared the risk. The coordination cost was distributed rather than concentrated.

Jordan stopped running.

"Wait," he said. "Say that again."

Leon repeated the governance structure.

"The problem wasn't that no one wanted to solve it," Jordan said slowly. "The problem was that whoever led it would absorb the cost of everything that went wrong. So no one led it."

"Right. Twenty years of that."

"And the solution was to create something new where no one had to absorb it alone."

"A shared entity. Yeah."

Jordan stood on the path. Chen had looped back.

"You just solved something, didn't you?" Leon said.

"Maybe," Jordan said. "Yeah. I think I did."

The Analogical Leap

What had happened — though Jordan didn't use this vocabulary until he read about it later — was an analogical leap: the recognition of a structural pattern across domains.

The enterprise CX onboarding problem and the Caltrain coordination problem had completely different content. One was rail infrastructure; the other was enterprise software onboarding. But they had the same structure:

Multiple parties with partial jurisdiction over a shared outcome. No party has enough jurisdiction to force a solution. Each party would absorb disproportionate cost if they led. So no party leads, even when everyone agrees the problem needs solving.

Jordan had been trying to solve the content problem — get these specific teams to collaborate on this specific onboarding issue. What Leon's story revealed was the structural problem: his approaches (working group, shared KPI, revenue attribution) had all implicitly asked one team or the overall leadership team to absorb the coordination cost. None of them changed the cost structure.

The solution wasn't a better analysis. It was a structural reframe.

From Insight to Prototype

Jordan spent two days after the run not acting on the insight. He had learned something from the deliberate practice work in Chapter 26 and the decision journal work in Chapter 24: the first version of an insight is often a skeleton of a solution, not the solution itself. He let it develop.

Then he applied what he'd been learning about design thinking.

Empathize (re-done): Jordan had conducted stakeholder interviews when building the revenue attribution model — asking about priorities and capacity. This time he reframed his question. He went back to the functional directors and asked: What would need to be true for you to feel genuine ownership of the handoff outcome — not just accountability for your team's piece, but for the customer's experience across the whole sequence?

The answers were different from the previous round. Three themes emerged: (1) they didn't want to lead something that would be blamed on them when it failed; (2) they didn't have visibility into what other teams were doing, which made coordination feel like being held responsible for variables they couldn't see; (3) they actually cared about the customer experience — this wasn't apathy, it was structural helplessness.

Reframe: Jordan rewrote his How Might We question. The old version: How might we get the four teams to coordinate on enterprise onboarding? The new version: How might we create a structure where no single team absorbs the full coordination cost but every team shares genuine accountability for the outcome?

These were not the same question.

Ideate: Jordan ran a brainwriting session with Rivera and three functional directors. He explained the rule: write ideas independently for ten minutes, then pass the paper to the right and add ideas to what you received. No evaluation. Twenty ideas minimum.

The session produced forty-three ideas. Most were variations on themes he'd already tried. But at the bottom of the fourth paper, someone had written: customer journey council — cross-functional, rotating chair, shared dashboard, no single owner.

Jordan didn't know who had written it. It didn't matter.

Prototype: Jordan spent an evening writing a one-page charter. The Customer Journey Council would have cross-functional membership, a rotating chair (so no single team bore the leadership cost indefinitely), a shared dashboard visible to all teams (so the handoff metrics were everyone's problem to see), and a quarterly accountability structure that distributed rather than concentrated responsibility. No team "owned" enterprise onboarding. All teams did.

The charter was intentionally simple. One page. He had learned, somewhere in the design thinking material, that the most important characteristic of a prototype was that it was the simplest possible representation of the idea that allowed someone else to react to it honestly.

Test: Jordan showed the charter to Rivera first. Then to each of the functional directors individually. He asked for reactions, not approval.

The first reaction was from the VP of Customer Success: "This actually solves the thing I couldn't say out loud. Nobody wanted to lead it because whoever led it would get blamed."

Rivera took the charter to the CEO the following week. The CEO's response: "Why didn't we do this three years ago?"

What Jordan Learned About Creativity

The CX coordination problem had taught Jordan something that the analytical work of the previous eight months hadn't: there are problems that more analysis won't solve, because they're not information problems.

He had assumed, for six months, that if he could build a compelling enough data case, the coordination would follow. But the block was structural, not informational. Everyone already understood the cost. The problem was the incentive architecture — the way the cost of coordination was distributed. No amount of attribution modeling would change that. Only a structural change would.

The insight had come from outside his domain, from a city planner talking about rail infrastructure on a Tuesday morning run. Jordan hadn't been thinking about CX onboarding. He had been letting the question sit. The analogical pattern had surfaced in a low-demand context where his mind was diffuse and receptive, not focused and analytical.

He also noticed something about the design thinking process: the empathize-reframe-ideate sequence had been more productive the second time not because the tools were new, but because the question had changed. The "How Might We?" reframe had done most of the work. The brainwriting had filled in the rest.

He wrote in his journal: I'd been trying to convince people when I should have been trying to change the structure. Those require different solutions.

The Conversation with Dev

At dinner the night after Rivera reported the CEO's response, Jordan told Dev the full story — the six months of failed analysis, Leon's Caltrain story, the running stop, the charter.

Dev listened. Dev had been in a period of working through something privately — a decision Jordan didn't fully understand yet but had learned not to push on. They were both, in different ways, sitting with a question they weren't ready to answer yet.

Dev said: "So the obstacle was the container, not the people in it."

Jordan looked up. "Yeah. Exactly."

Dev said: "That's a useful way to think about a lot of things."

Jordan heard something in the way Dev said it. He didn't press. He filed it away.

What Creativity Research Explains

The Einstellung effect: Jordan's six months of repeated analytical approaches is a textbook example. Each new attempt applied a variation of the same frame — how do I get teams to coordinate — rather than questioning the frame itself. The unsuccessful approach was entrenched by repetition and incremental investment.

Analogical reasoning and incubation: The insight required two conditions that deliberate analytical work hadn't provided: (1) a question held in background awareness without being actively worked, and (2) an external input from a structurally similar problem in a different domain. The running group provided both — regular low-demand context for mind-wandering, and access to a person who worked in a different domain with structurally analogous problems.

Design thinking as creative structure: The empathize-define-ideate-prototype-test sequence didn't generate Jordan's insight — the analogical leap did. But the design thinking framework gave the insight a route to implementation. Without the framework, the insight might have remained a vague hunch. The framework gave it legs.

Constraints in ideation: The brainwriting session's time constraint — ten minutes, twenty ideas — produced output that the open-ended working group had not. The constraint forced volume, which forced lateral movement past the obvious.

Problem reframing: The "How Might We?" reframe was itself a creative act — transforming a problem statement that had embedded assumptions (someone must lead, someone must own it) into a question that opened the structural alternative.

Discussion Questions

1. Jordan's six months of analysis was not wasted — it built the shared understanding of the problem's cost and created the relationships that made the Council viable. What does this suggest about the relationship between analytical and creative work in complex problem-solving?

2. The analogical leap came from an unplanned conversation in a non-work context. What does this imply about how Jordan should structure his time and relationships going forward?

3. Jordan reframed the "How Might We?" question from "how do we get teams to coordinate" to "how do we create a structure where no team absorbs full coordination cost." What made the second frame more generative? What cognitive shift does that represent?

4. The design thinking framework gave the insight a path to implementation. What is the difference between having a creative insight and implementing a creative solution? What does each require?

5. The Customer Journey Council is a structural solution to a coordination problem. Is this a creative solution in the psychological sense — novel and appropriate — or an adaptive application of a known pattern? Does the distinction matter?