We are overwhelmed by the sheer number of AI vendors promising to revolutionize our industry, and we are on the verge of signing a costly multi-year software contract. How do we use Keith Cunningham's Thinking Time to evaluate this strategic vendor commitment before our next quarterly planning session?

Question

Tyler Smith · Accepted Answer

Signing a costly, multi-year software contract in a rapidly changing AI market is a dangerous move. Before you commit strategic capital to a vendor, you need to step back from the sales pitches and dedicate uninterrupted time to critical thinking.

Schedule a ninety-minute Thinking Time session away from your daily operational distractions. Use this time to write down high-value questions that challenge the vendor's promises. Frame your questions using Keith Cunningham's recommended format: How might we achieve these exact efficiency gains using our existing software stack so that we do not lock ourselves into a rigid, multi-year contract? Or: What is the dumb tax we will pay if this vendor's technology becomes obsolete in twelve months?

Analyze the true cost of integration, including staff training and data migration. AI vendors often sell the dream of instant automation, but the reality is that implementation takes time and resources. By forcing yourself to answer these tough questions during your Thinking Time, you will cut through the excitement and evaluate the vendor based on operational reality. If the software does not align with your current V/TO® or if the integration risk is too high, walk away and stay flexible.