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Executive brief

Three questions before you buy the AI

A short, honest filter for executives evaluating their first generative-AI deployment.

Drew Jonsen · Founder, Jonsen LLC September 19, 2025 4 min read
Bottom line
  1. 01If you cannot describe the decision the AI will make, you are buying a demo, not a system.
  2. 02The model is the cheap part. The integration, evaluation, and change management are the expensive parts.
  3. 03Pick a use case where the cost of a wrong answer is measurable and bounded.

Most AI initiatives do not fail because the model was wrong. They fail because the question was wrong. Before you sign a contract, sit with three questions long enough that you can answer each of them in a single sentence.

What decision is the AI making?

Not "what is it doing" — what decision. Drafting a reply is not a decision. Routing a ticket is. Approving an invoice is. Flagging a transaction as suspicious is. If you cannot name the decision, you are buying a productivity demo and calling it strategy.

What does a wrong answer cost?

Pick a domain where the answer is auditable and the downside is bounded. AI is at its most valuable when it is doing the eighty percent of work that is high-volume and low-stakes, freeing humans to handle the twenty percent that is rare and consequential.

Who owns it after the pilot?

A pilot with no operator is a science experiment. Before you start, name the human who will live with the system in production — who will tune the prompts, watch the metrics, take the page when it misbehaves. If that person does not exist yet, hire them first.

DJ
Drew JonsenFounder, Jonsen LLC

Drew leads Jonsen LLC — a Denver technology practice guiding law firms and growing businesses through AI, cybersecurity, and systems that compound over time.