Free · 7-page PDF · 2026 edition

Choosing AI Software for Your Small Business

A calm, jargon-free playbook for owners who want the right tools — not the loudest ones. Written from real client engagements, not vendor demos.

Inside the guide

• The five questions to answer before you shop
• A simple 5-dimension scoring rubric (fit, cost, learning curve, lock-in, ROI)
• The six AI categories most small businesses actually need
• A 30-day pilot plan that limits your risk
• Red flags, honest trade-offs, and a printable checklist

Written by Robb Pleasant, founder of Pleasant Oak Solutions.