Coaching a leader through a high-stakes decision
This is for you if a client, a leader, is about to make a big bet and the room is full of confidence. They can name ten reasons it will work and go quiet when you ask what could go wrong. You want to help them see the risks their excitement is hiding, without pouring cold water on the call.
A big bet is rarely lost on the numbers. It's lost because a leader who has already decided can no longer see the ways it might fail. Once someone is sold on a plan, "what could go wrong?" gets a thin, loyal answer. Naming risks feels like betraying the call they just made.
So don't ask it that way. This move changes the question, and it starts with their own report.
Before you run it, get a read on how your client decides. Open their Career Discovery report to How Your Mind Works and read the Making Decisions part. It tells you how they reach a call: how fast, how much they trust gut over data, whether they bring others along or decide alone. That read shows where this leader's instincts serve them, and which risks those same instincts skip past. Keep it close; you use it in 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. The point is to 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 whole trick. It is easy to explain something that already happened and hard to predict something that might.
- Read the story against how they decide. Bring back their Making Decisions read. Where does the failure they wrote line up with how they naturally decide? A leader who trusts a fast read tends to write failures about moving too soon; one who waits for full agreement, about moving too late. Name the one or two failure modes that are the shadow of how they decide well.
- Guard the top reasons. For each big reason, pick one guard. Either a move that prevents it now, or an early signal they will watch for, to catch it while it is still small. Write each one down next to its reason.
Somewhere in here your client flinches. They name a way this could fail that they had been talking past. That flash is the work. Stop and stay with it; the questions below are built for that moment.
What they walk out holding is a one-page pre-mortem: the failure story, the few reasons that felt most real, and one guard against each. Not cold feet, and not a longer plan. Just the risks their confidence had kept out of view, now on paper where they can act on them.
The leader owns the call. You own the structure that let them look straight at failure without losing their nerve.
Coaching questions
Remember, this isn't a worksheet to run in order. Once your client has seen a real failure mode they'd been skating past, pull whatever fits the room and follow where it goes. Here are some questions that help.
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 the way this could fail 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
- Of the reasons you wrote, which one is cheapest to guard against right now?
- What is the earliest signal that would tell you it's starting to go wrong?
- Who could you hand one of those signals to, so it isn't only you watching?
