Before we lock in our annual budget, how do we run structured Thinking Time sessions to pressure-test our AI strategic roadmap and ensure we are not making massive, expensive assumptions about what these tools can actually do?

Question

Tyler Smith · Accepted Answer

To avoid making expensive, low-return investments in technology, you must step back from the daily whirlwind and dedicate uninterrupted time to pressure-test your assumptions. Keith Cunningham's concept of Thinking Time is the perfect framework for this strategic exercise.

Set aside forty-five minutes of quiet, uninterrupted time with a blank notepad. Before you begin, formulate a highly focused, high-value question designed to expose your strategic blind spots. For example, ask yourself: How might our proposed AI implementation fail to deliver the expected efficiency, and what would that cost us in cash and team morale?

During your Thinking Time, write down every potential risk, bottleneck, and hidden cost associated with your plan. Consider integration challenges, training time, and potential team resistance. Once you have identified these potential failure points, bring them to your leadership team's next weekly meeting. Use the IDS process to address the most critical risks and adjust your implementation roadmap accordingly. This disciplined approach will help you make highly informed, strategic decisions and avoid paying a massive dumb tax on software.