AI Strategy for Small Business: A 90-Day Plan

Walk through a typical week. Where do you or your team spend more than 5 hours/week on something repetitive? Quoting, invoicing, scheduling, summarizing emails, drafting proposals, answering the same customer questions, transcribing meetings, reconciling spreadsheets?

Pick the single most expensive one. Not the most interesting. The most expensive. Write it down on one line: 'We spend 12 hours/week on X and it costs us $Y in payroll.'

That's your strategy. Everything else waits.

Pick two people who'll try it. Not the whole team. Pick the most patient person and the most skeptical person — if both end up using it, it'll work for everyone.

Use off-the-shelf tools only. ChatGPT Team ($25/user), Microsoft Copilot ($30/user), Claude ($20/user), or a no-code automation tool like Make or Zapier. Do not let anyone talk you into building custom software.

Time-box it: 30 days, then a decision.

Ask the two pilot users three questions: Did it actually save time? Would you be annoyed if I took it away? What broke?

If both say yes to the first two, roll it out to the rest of the team and pick the next workflow. If either says no, kill it. No sunk-cost fallacy. Try a different tool or a different workflow.

Repeat this cycle quarterly. Two workflows per year, fixed properly, will compound into a meaningful operational advantage in three years.