Owners ask me this every week. Prices and plan features change every few months, so I do not list them here. Check each vendor's current plan page. What follows are the questions that decide it.
What matters most when picking an AI plan?
Whether the plan trains on your data by default. Business and team plans from the major vendors generally do not; free and personal plans often do. Read the vendor's current terms for the exact plan you are buying, and get the answer in writing before anyone pastes in a customer's information.
Do I already pay for one?
Maybe. If your company runs on Microsoft 365, your plan may already include Copilot or offer it as an add-on. If you run on Google Workspace, Gemini may already be in Gmail and Docs. Check what you have before you buy anything new. The cheapest AI plan is the one sitting unused in a subscription you already pay for.
What should a business plan give me that a personal one does not?
- Admin controls. One person adds and removes users, so when someone leaves, their access and their chat history leave the company account, not with them.
- Shared workspaces. The team shares prompts, files, and projects instead of each person rebuilding the same thing.
- Data terms you can show a client. A written statement that your data is not used for training.
- Single sign-on and billing on the company card, not ten personal cards on ten expense reports.
Can my team use their personal accounts for client data?
No. Client data goes only into a plan the business has approved in writing. If you handle patient, legal, or financial information, your compliance person reads the vendor's terms and decides, and some data needs a signed agreement with the vendor before it goes in at all. A one-page AI policy lists which plan is approved and what never goes in. It is $750 if you want me to write it with you.
Staff using personal accounts for business data is the mistake I see most. It happens in nearly every company before the owner decides anything, because people use what they have at home. A personal account means your customer list sits in an account you do not control, possibly training a model, and walks out the door when the employee does. Buying a business plan and telling the team "use this one, not your own" fixes most of it.
How do I choose between ChatGPT, Claude, and Copilot?
Let the team try two for a month on real work and keep the one they use. They are all capable, and the differences that matter show up in your own tasks: writing, spreadsheets, research, the inbox. Pick a small group, give them one plan each for a month, and ask them which one they opened every day. Then buy that one for everyone.
What does it cost to get help?
"The AI you already pay for" is a 90-minute on-site session for $450. We switch on what is in your current subscriptions and set up the first few uses with your team. A half-day workshop is $1,500. If you want help getting the whole team using it month after month, AI adoption runs from $3,500 a month. Start with where to begin with AI if you have not picked the first task yet.
Answered by Jared Lukes, Minneapolis. Twenty-five years in brand, UX, and technology, currently holding fractional AI and technology seats at three companies. About Jared.