A free 15-minute Zoom call. No cost, no pressure.Start with whose account it is
This is the first question and the one that matters most. Ask whose name the AI subscription sits under. If the consultant signs up on their own account and resells it to you, you are renting access. If it is set up on your own account with Claude, ChatGPT or Gemini, you keep it no matter what happens next.
Ask directly: "Whose account is this, and who pays the AI company?" A good answer is that it is your account, your billing, your login. That means if you ever part ways, your AI keeps working and your history stays with you.
At RMDW we set AI up on the client's own account and the client pays the AI company directly. We never resell the subscription.
Ask who owns the work and the setup
Once AI is running, things get built. Prompts, saved instructions, document templates, automations, a website. Ask who owns those when the engagement ends.
You want to hear that the work is yours. The prompts and templates live in your account. The website and the automations are handed over. Nothing is held hostage behind a login you do not control.
Also ask what happens to your data if you stop. Can you export it? Is it sitting in a tool only the consultant can reach? Get a plain answer before you start.
Ask if there is a real person to call
AI breaks in small ways. A login stops working. A connection to your email drops. Someone on the team asks "how do I" and nobody knows. Ask what support actually looks like after setup.
Good questions to ask:
- Is there a person I can text or email, or just a ticket form?
- How fast do you normally reply?
- Is there a check-in, or do I only hear from you when I chase?
- If I cancel, do I keep my AI account?
A real person you can reach is the difference between AI that gets used and AI that quietly dies after the first month.
Ask what gets connected, and how
Setup is not just creating a login. Ask what the consultant will connect the AI to. Your email, your shared files, your calendar, the tools your team already uses.
Ask how they do it and what access they need. You want to understand which accounts get linked and who can see what. A careful consultant will walk you through it in plain words, not hand you a wall of permissions.
If you are in law, medical or finance, ask about client files. You want to hear about zero data retention, which means the AI provider does not keep your prompts or files after it answers, or private AI on a machine inside your office so files never leave. Nobody should claim a product is simply compliant. They should tell you to check your own rules and talk through the options.
Ask what the first month looks like
Vague promises are easy. Ask what actually happens in week one and what your team will be doing. You want a clear picture, not a slide.
A normal start looks like this: the account gets created, it gets connected to your email and files, each person on the team gets set up, and there is a first training session. After that, people start using it on real work with someone behind them.
Ask what training looks like and whether it is hands on. Ask what you should bring to it. If the answer is fuzzy, that tells you something.
Ask about levels, pricing and getting out
Ask what the levels are and what each one includes, so you are not pushed into the biggest package on day one. You want to start where it fits and move up or down later.
Ask when you get a price in writing. A fair answer is before anything starts, after a proper look at your business. Ask if there is a free call first and what happens on it. Ask about cancellation and what you keep.
At RMDW every client starts with Setup, can move levels anytime, and gets their price in writing after the free AI game plan call, before anything begins.
Red flags to watch for
A few things are worth a second look, without writing anyone off.
- They cannot tell you whose account it is.
- They talk in tool names and jargon and never in outcomes.
- They promise big results with no look at your business first.
- They cannot name a person you would call.
- They want to hold your logins or the work they build.
- They rush you to sign before you understand the levels.
None of these are deal breakers on their own. But if several show up, keep looking.
What a normal week looks like after
It helps to know what you are buying. Once AI is set up and your team is trained, a normal week is quiet and useful. Someone drafts an email faster. A quote gets written from notes. Meeting notes get cleaned up. A question gets texted to your support person and answered.
The point is not a big launch. It is small daily use that adds up, with a real person to call when something snags. That is the thing to look for in any consultant.
If you want to see how this works, book the free AI game plan. It is a free 15 minute Zoom call, no cost and no pressure. We look at your business, show where AI helps first and say which level fits. Nothing is set up on that call.