← InsightsBuyingOct 7, 2026Chris Cohen

What I'd ask a wellness vendor before signing anything

Eleven questions I would want answered if I were the one signing the contract, written from the other side of the table.

I have sat on the vendor side of enough evaluation calls to know how they usually go. The buyer asks about services, features and price. The vendor answers in the same language. Everyone leaves with a good feeling and no idea what week nine will look like.

So here is the list I would want asked of me, written by the person who would have to answer it. If a vendor can't answer these plainly, that is the answer.

1. Who is actually in the room?

Not the company, the person. Ask for the coach's name and credentials, and ask whether that same person will be there every week. A program staffed by whoever is available is a program that restarts every month.

2. What days and hours, and who owns the room?

Fixed days and hours are the whole ballgame. Then ask who books the space, you or the vendor. A coach with no guaranteed room becomes a coach in the lobby, and the third time that happens people stop coming.

3. How does somebody get a slot?

If the answer involves downloading something or creating an account, ask how many people actually did that in their last engagement. Booking should be a calendar invite, not a registration flow.

4. What happens when someone cancels, and what happens when they disappear?

Everyone misses a session. The question is whether anyone notices. I would expect a vendor to say they chase no-shows and flag the person who has missed three weeks, because that is the actual work.

5. How do you define participation?

This is where most numbers get soft. "Participants" often means anyone who attended once, ever. Ask for the definition in writing.

6. What is your 30, 60 and 90-day active rate?

Not sign-ups. Active. If the answer is a single lifetime number, the program has been counted rather than measured. And ask what active means in their data, because one session in 90 days is not participation.

7. What will I actually receive, and is it written?

Ask for last quarter's report with client details removed. You are looking for a document a CFO can read in ten minutes: what was delivered, what changed, what the vendor is changing next. A dashboard of logins is not a report.

8. What do you do in month four, when the newness is gone?

Every program gets a spike at launch. Ask what the plan is for the quarter after it. The good answers are boring: a new group session format, a block of coaching aimed at one team, a push on new hires.

9. What can't you do?

I would rather hear "we don't treat mental health conditions, we refer out" than a menu that includes everything. A vendor who names their limits has usually thought about where they end.

10. What happens to our data?

Who holds the body-composition results, who can see them, and does the individual see them before the employer does? My answer, and the only one I would accept: the employee sees their own numbers first, and the employer sees aggregate trends, never a person's scan.

11. What does exit look like?

Ask what the team keeps if the engagement ends: plans, habits, a written handover. If everything lives inside the vendor's platform, you are renting participation rather than building anything.

12. What does the first month look like, week by week?

Ask for the sequence, not the promise. A good answer sounds like a schedule: week one walkthrough and sign-ups, week two baseline sessions, week three first group session, week four review with the HR contact. A vague answer about "driving engagement" means the launch will be improvised.

13. Can I talk to two clients you have run for more than a year?

Not the references a vendor picks for being happy. Ask for clients who renewed twice, then ask those clients the question the vendor cannot answer for them: what changed in month seven?

How to read the answers

Specific answers arrive fast. If a vendor needs a follow-up email to tell you the coach's name, that is information about how the engagement will run.

Why I wrote this down

Because I would rather lose a deal at question five than run a program that quietly dies in month five. The pattern in almost every engagement that failed is not a bad coach. It is a program that was never specific enough to be delivered: no fixed days, no named person, no working definition of participation, no report that could be argued with.

Ask for names, days, rooms and definitions. The vendors who can send them to you in one email are the ones who will still be there when the novelty wears off.

If you want to compare answers, that is a fine reason to get on a call. Bring the list.