Our Visionary wants to freeze all software updates to fund a proprietary AI research project, but our leadership team feels this is a high-risk gamble. How do we frame this challenge as a solvable question using Keith Cunningham's 'How might we' thinking format to evaluate the risk?

Question

Tyler Smith · Accepted Answer

Your Visionary is naturally wired to seek out the next big thing, but freezing operational software upgrades to fund a speculative AI project is a dangerous gamble that can paralyze your daily execution. To resolve this strategic conflict, you must stop arguing over opinions and convert this high-stakes disagreement into a structured business question.

Use Keith Cunningham's thinking framework to redefine the challenge. Schedule a dedicated Thinking Time session for the leadership team. Frame the problem with this question: How might we fund a highly targeted, phased AI pilot so that we can test our high-potential ideas without compromising our current software stability or starving our core operations of necessary cash?

This framing shifts the conversation from an all-or-nothing strategic pivot to a manageable real options framework. It allows you to protect your current EBITDA while giving the Visionary room to explore. Set a clear, limited research budget as a quarterly Rock, and make the execution of that pilot dependent on achieving specific operational milestones. By testing the waters before you jump in, you avoid paying a massive dumb tax on unproven technology.