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Questions to ask an employer in the first meeting

Daniel Luna
Daniel Luna
Founder, DPC Bookkeeper · November 2026 · 2 min read

The first meeting with an employer is for listening. You want to learn who works there, what they offer today, who makes the decision and how they pay their vendors. Bring this list, take notes, and don't quote a price until you have the answers.

About the workforce

About current benefits

About the decision

About paying

The payment questions matter as much as the others. A contract that pays 60 days late costs you cash every month. Here's how to handle late employer invoices.

After the meeting

Write up your notes the same day. Estimate how many members the group might add and what care they're likely to use. Then check the numbers against your capacity and your floor price before you send a proposal.

What I'd do this week

Common questions

Should I bring pricing to the first meeting?
I'd bring a range at most. A firm price before you know the group's size and needs is easy to regret.

What if they won't share their health plan details?
That's fine for a first meeting. The plan year and who decides matter most early on.

Should the broker be in the meeting?
If the employer has one, it helps. The broker may know the plan details and the timing.

Want your numbers ready before the next meeting?

We reconcile every account every month and send your P&L and Balance Sheet by the 15th, so decisions like this start from real numbers. If that's what you need, apply to work with us.