When I look at a launch plan, there is usually plenty of attention given to what needs to go right. The milestones are mapped, owners are assigned, communications are scheduled, and somebody has probably created a spreadsheet with enough colors to qualify as modern art. 🖼️

But why do we not talk about what could go wrong? Wouldn’t that be a good exercise?

Teams naturally build plans around success because everyone is trying to move the work forward. Once people have invested time, budget, reputation, and political capital into a project, challenging the plan can become uncomfortable. Nobody wants to sound like the person trying to kill a good idea.

That is where a Pre-Mortem becomes useful.

A Pre-Mortem is a strategic simulation where you move yourself into the future and assume the project has already failed. Then you work backward to identify the conditions, decisions, assumptions, and warning signs that could have caused the failure. It sounds counter-intuitive, but it actually works!

AI makes this exercise much easier because it can examine the plan from several perspectives without worrying about who is involved and the typical office politics.

Suppose you're launching a new HR technology platform. You could ask AI to imagine that six months after launch, adoption is poor, managers are frustrated, employees are confused, and leadership is questioning the investment. Then have it identify plausible reasons the rollout failed.

It might flag weak manager training, unclear ownership, poor integration with existing workflows, privacy concerns, unrealistic adoption assumptions, or communication that explained the software without explaining why employees should care.

Some risks will be obvious, while others may make you say, "We haven't talked about that."

And that is EXACTLY what you want to capture up front.

Your role remains essential because AI can generate possible failure scenarios, but it cannot decide which ones deserve attention in your organization. You know the people, politics, history, customers, constraints, and consequences.

Use AI to expand the field of risks you consider, then apply human judgment to decide which risks require action.

A launch plan tells you how you expect to succeed. A Pre-Mortem gives you a structured way to look for the conditions that could interfere with that success before they become expensive.

Let's go raise your AIQ.

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