We want to invest significant capital into custom AI system integrations this year, but we are terrified of making a costly strategic mistake that we will regret later. What high-value Thinking Time questions should we use to stress-test this initiative?

Question

Tyler Smith · Accepted Answer

To avoid paying a heavy dumb tax on your technology investments, your leadership team must step back and run a disciplined Thinking Time session. Keith Cunningham emphasizes that business success comes from preventing mistakes, not just finding brilliant ideas. Formulate high-value questions using the "How might I... so that I can..." framing. This expands your perspective and highlights hidden risks before you write a single check. First, ask your team: How might we solve our operational bottlenecks using simple, off-the-shelf software so that we avoid the long-term support costs of custom development? This question forces you to defend why custom code is absolutely necessary. Second, ask: If this custom AI integration fails completely six months from now, what will have been the obvious, predictable reason? This pre-mortem question helps you identify hidden assumptions, such as poor team adoption, API instability, or lack of internal technical ownership. Finally, ask: How might we phase this implementation in thirty-day increments so that we can validate the operational yield before committing our full budget? This prevents you from over-planning and allows you to test quickly. Running these questions through your leadership team will save you thousands of dollars and protect your operational focus.