Case Study 1 — Chapter 24: Decision-Making Under Uncertainty

Jordan: The Database Decision and the Harder One

Background

Two decisions in the first quarter of the Strategic Director role. One is a straightforward business problem with genuine complexity. The other is personal, with much higher stakes, and Jordan does not realize it is the more important one until he is already in it.

Decision One: The Database

The customer research database situation is the decision Jordan was navigating at the chapter's opening. By the time he applies the chapter's framework, he is two weeks past the initial briefing from Sandra and has more information than he knows how to use.

He applies the toolkit:

Pre-mortem: He asks his team to participate in a brief pre-mortem exercise. They imagine it's Q3, a year from now, and the database decision went badly. What happened?

The team generates five failure modes: 1. They retained the old database and it became a single point of failure for a major campaign 2. They retired it and lost institutional knowledge that wasn't documented elsewhere 3. They built new infrastructure but underestimated the migration cost 4. Vendor 2 won the proposal and failed to deliver on scope 5. The team spent so much time on the transition that the core CX strategy work was delayed

Jordan reviews these. The one that concerns him most: institutional knowledge loss. He hadn't adequately investigated whether the existing database contained non-migratable client insight. He makes a call: spend three days documenting what exists and whether it can be transferred. This is new information that changes the cost-benefit structure.

Disconfirmation: What's the strongest argument for keeping the old database? He forces himself to engage with it seriously. The answer: the team knows it, the quirks are understood, there's no learning curve. The transition cost is real and the improvement is not guaranteed.

He steelmans the retention argument and finds it substantive — not decisive, but not trivially dismissable. He records it.

Decision: He retires the database and builds new infrastructure, with a structured documentation phase. He documents his reasoning explicitly.

He does not feel certain. He notes that certainty was never available. He makes the best bet with the available information.

Decision Two: The Children Question

Buried in Chapter 18's narrative was a disclosure Jordan made to Dev during a Sunday morning update conversation: he doesn't know what he wants about children. He had disclosed it as a fear; he had not followed it up.

Twelve weeks later, Dev brings it back.

It is a Thursday evening — protected time. Dev makes tea. They have been talking about something else when Dev says: "I've been thinking about what you said a few months ago. About not knowing what you wanted. Are you still in that place?"

Jordan is aware that this is a different kind of conversation from the ones they usually have. He says: "Yes. Mostly."

Dev says: "I think I'm closer to knowing than you are. I want to know if that's a problem."

This is a values conflict decision with no additional information that would resolve it. Jordan recognizes the structure. He cannot gather his way to certainty. He cannot pre-mortem his way to the right answer. The uncertainty is not epistemic (answerable with more data) but aleatory — the decision involves values that are genuinely in tension, a future that is genuinely unknowable, and a person he loves whose answer is different from his current answer.

He does not try to resolve it that evening. But he does something he has not done before: he says, out loud, what the decision's actual difficulty is.

"I think I'm afraid that if I decide I don't want children, something in me will be closing. And I'm afraid that if I decide I do, I'm not sure I'm the person who can do that well. Both of those fears are doing the deciding instead of me."

Dev is quiet for a moment. Then: "Those are both fears about yourself, not about us."

Jordan says: "Yes."

Dev: "So the question that's actually pending is whether you want to figure out what you want — not just what you're afraid of."

Jordan: "I think so."

The Framework Applied to the Hard Decision

Jordan applies the chapter's framework to the children question in the next three weeks — not to make the decision quickly, but to understand its structure.

Source of difficulty: This is not primarily an information problem. He has read extensively; he has talked to parents and non-parents; he knows the data on life satisfaction. More information is not the missing element. This is primarily a values conflict (between different versions of his future self, different conceptions of what matters, different relationships to continuity and family) with a fear dimension layered on top (the fear of closing, the fear of being inadequate).

Values clarification: Jordan writes, in his decision journal: - Value A: Freedom and continued self-directedness — the life I've built, the pace of growth, the ability to choose - Value B: Connection and continuity — the thing my father and I never had, that I might be able to give and receive differently - Value C: Dev — the relationship, the future, the shared life

He notices that Value C is not in conflict with A or B — it depends on what Dev wants, and Dev has already begun to say. He cannot hold the children decision separate from the relationship decision much longer.

10-10-10: At 10 minutes: he doesn't want to have this decision pending. At 10 months: if he decides against, and Dev wants children, this is the beginning of a different kind of conversation about the relationship. At 10 years: which version of this life would he regret not having tried?

He does not complete the decision in this quarter. But he arrives at something he hadn't had before: a clear statement of the structure. The decision is not "children yes or no." The decision is "am I willing to do the work of finding out what I actually want, rather than what I'm afraid of?"

He brings this to his therapist. His therapist says: "That's a significant reframe."

Jordan: "I think Dev helped me find it."

Analysis Questions

Jordan applies the pre-mortem to the database decision and discovers a failure mode (institutional knowledge loss) he hadn't adequately considered. The pre-mortem is a disconfirmation exercise. Why is it psychologically easier to identify failure modes in a pre-mortem format than in direct analysis of the decision before commitment?
Jordan's steelman of the database retention argument finds it "substantive — not decisive, but not trivially dismissable." He records it and still makes the opposite decision. What is the purpose of steelmanning when you end up not being persuaded? What does the exercise accomplish even when the conclusion doesn't change?
Jordan diagnoses the children question as primarily a values conflict with a fear dimension, not primarily an information problem. The chapter distinguishes these three sources of decision difficulty and argues they require different interventions. Why would applying an information-gathering intervention to a values conflict not resolve it?
Dev's observation — "those are both fears about yourself, not about us" — reframes the decision's structure. Jordan had framed it as a question about what he wants; Dev identifies that he is asking about his capacity rather than his desire. How does this reframe change what the decision actually requires?
Jordan does not complete the children decision in this chapter. He arrives instead at a prior question: "am I willing to do the work of finding out what I actually want?" How does this illustrate the chapter's observation that many difficult decisions are not primarily about choosing between options but about clarifying what is actually in conflict?