Week 1: pick and prepare
Choose one process: frequent, repetitive, low-risk, measurable. Classic first picks: proposal drafting, support reply drafting, meeting notes, invoice processing. Define the single success metric and measure the current baseline for one week. Select the tool (start with what you already license), set up business accounts, and pick two or three motivated users. Not the skeptics; not yet.
Week 2: train on real work
A two-hour hands-on session using the pilot users’ actual tasks, not demos. Build the first prompts or a custom assistant together, write down what works, and agree the review rule: humans check everything that leaves the building. End the week with each user running the new workflow daily.
Week 3: run and fix
Full-speed usage with a daily five-minute check-in: what worked, what broke, what is missing. Fix prompts, add missing documents, adjust the workflow. This is the week the pilot either becomes a habit or quietly dies; the check-ins are what keep it alive.
Week 4: measure and decide
Compare against the baseline: time per task, output volume, quality indicators. Collect user verdicts in one honest paragraph each. Then decide explicitly: scale to the team, extend the pilot, or stop. Present the numbers either way; a clean negative result builds more credibility than a vague positive one.
FAQ
What budget does a pilot need?
A few business-tier subscriptions and roughly a day of total coordination time. If a vendor says a pilot needs a contract, pick a different first use case.
What success rate should we expect?
Well-scoped pilots on text-heavy processes succeed far more often than not. Most failures trace to scope (too broad) or adoption (no check-ins), both preventable.
What comes after a successful pilot?
Scale the same use case to everyone who does that work, then repeat the playbook on the next process. Momentum comes from stacking small wins.