There is a lot of pressure on leaders to do something with AI right now. Boards are asking questions, vendors are selling solutions, competitors are announcing pilots, and nobody wants to be the company that got left behind. 

But moving fast and being ready are not the same thing. 

This workshop asks leaders to take a harder look at the AI initiatives already on their plate and answer a simple question: are we making a smart bet, or are we moving because we feel pressure to keep up? 

Participants will bring two or three real AI use cases into the discussion and run them through a simple Bet or Hedge test. 

Bet is an initiative where the organization is moving largely on conviction, urgency or competitive pressure, without enough clarity around the problem, data, process or measure of success. 

Hedge is grounded in a real business problem, supported by the right data and operating conditions, with a clear way to know whether it is actually working. 

There is no middle column. 

For anything that lands in Bet, the next question is the useful one: What would need to be true before we should move?

Not “more buy in” or “better change management.” Something specific. Better data. A clearer workflow. A measurable business outcome. A defined owner. 

Participants leave with:

• A clearer read on which AI initiatives are genuinely ready and which may be running ahead of the organization 

• One concrete readiness gap to address before investing more time or money 

• A simple Bet or Hedge test they can use the next time someone says, “We should be using AI for this” 

The goal is not to slow AI adoption down. It is to make sure we are accelerating the right things.