Seven questions to ask an AI consultant before you sign
Ben McDermott · September 2, 2026 · 3 min read
Every marketing agency in the Twin Cities added "AI" to its services page last year. So did every freelance developer. Here's how to tell, in one call, whether the person across the table will leave you with working tools or a deck.
1. Who will actually be on the screen share?
The person selling you is often not the person doing the work. Ask directly. If the answer is "our team," ask for a name and how long they've been building with these tools. At 1771 the answer is Ben or Dan, every session, because there isn't anyone else.
2. Where does the result live, and what do I keep if I stop?
This is the question that matters most and gets asked least. Many agencies build on their own platform. The automation works, but it's theirs. Change it, and you're back in their queue; stop paying, and it's gone. The right answer is that it runs in your accounts, in tools you already pay for, and you keep everything.
3. What will be working after the first session?
"We'll start with discovery" is fine for a 400-person company. For an owner-led business, six weeks of discovery is six weeks of paying for nothing. A good consultant can look at your inbox for twenty minutes and build something useful in the same hour. Ask what that something will be.
4. What's the price, before the call?
If the price isn't on the website, ask why. "Every engagement is different" is sometimes true and often a way to price you by what you look like you can pay. Ours is $1,999 a month for the retainer and $1,500 for a team session, and it's the same for everyone.
5. What happens when it breaks at 9 p.m.?
Automations break. The tool updates, the form changes, a login expires. Ask what the response time is and whether you can turn it off yourself. If you can't switch off your own automation without a support ticket, you don't own it.
6. What will you refuse to automate?
This one tells you whether they've done this before. Anyone who has will have a list: moving money, regulated communications, decisions that need a human to own them, a voice agent in front of customers on day one. Our partner Dan Roseman spent twelve years building compliance programs at Coinbase, Circle, Square, and Robinhood, and that list is why we keep a person pressing send on anything that matters.
7. Show me something you built that's still running.
Not a demo. Something in a real client's business, running today, and what it replaced. If they can't, they're new at this, which isn't disqualifying, but you should be paying a new-at-this price. We'll show you a weekly SEO digest, an after-hours responder, and a call-to-proposal pipeline, and tell you which client each came from where we're allowed to.
Answers that should end the call
- "We'll need to do a full assessment before we can say what we'd build."
- "It runs on our platform, so you don't have to worry about it."
- "Pricing depends on the engagement." (After you've described the engagement.)
- "We can automate anything."
- "Our AI receptionist handles that." (Before they've asked what "that" is.)
More insights
- What an AI consultant costs in Minneapolis, with our actual price
- Ten workflows we'd automate first in an owner-led business, and three we wouldn't
- One in five Minnesota businesses now uses AI. Here's what the other four are missing.
- Claude or ChatGPT for a five-person company: what we actually use and why