Coaching a leader through a high-stakes decision
This is for you when a client is about to make a big bet. They can name ten reasons it will land, then go quiet when you ask what could go wrong. You want them to see the risks their excitement hides, without cooling the call.
A big bet is rarely lost on the numbers. It's lost because a leader who has decided can no longer see how it might fail. Ask "what could go wrong?" and you get a thin, loyal answer.
So don't ask it that way. Start with their report.
First, open their Career Discovery report to How Your Mind Works and read Making Decisions. It tells you how they reach a call: how fast, how much they trust gut over data, whether they decide alone or bring others in. Keep it close for step three.
Then run the pre-mortem. About thirty minutes.
- Jump to the failure. Set the scene out loud: "It's a year from now. We made this decision, and it clearly failed. Not a wobble, a real, visible failure." Have them say the date. Treat the failure as a fact, not a maybe.
- Write the story of how. Give them a few minutes to write why it failed, in the past tense: here is what happened, here is what we missed. The past tense is the trick: it's easier to explain a failure than to predict one.
- Read the story against how they decide. Bring back their Making Decisions read. Where does the failure line up with how they naturally decide? A leader who trusts a fast read tends to fail by moving too soon; one who waits for full agreement, too late. Name the one or two failure modes that shadow how they decide well.
- Guard the top reasons. For each big reason, pick one guard: a move that prevents it now, or an early signal they'll watch for to catch it while it's small. Write each one down next to its reason.
Somewhere in here your client flinches, naming a way this could fail they'd been talking past. That flash is the work. Stop and stay with it; the questions below are for that moment.
They walk out holding a one-page pre-mortem: the failure story, the few reasons that felt most real, and one guard against each. Just the risks their confidence had hidden, now on paper.
The leader owns the call. You own the structure that let them look straight at failure without losing their nerve.
Coaching questions
This isn't a worksheet to run in order. Once your client has seen a failure mode they'd been skating past, pull whatever fits the room:
Sitting with it
- Reading that story back, which part felt the most possible?
- What did you already half-know and keep setting aside?
- Where does this failure line up with the way you like to decide?
Widening it
- Where else has a call gone like this, sure going in, surprised coming out?
- Whose read did you not go looking for this time?
- What kind of risk do you tend to wave off, and what kind do you over-weight?
Moving toward change
- Which reason is cheapest to guard against right now?
- What's the earliest signal it's starting to go wrong?
- Who could you hand one of those signals to, so it isn't only you watching?
