Every fall I get the same call. A resident or a new grad has two job offers, both from nice people, both with numbers that look fine, and no way to tell them apart. So they pick the higher base salary, or the one closer to family, and three years later they call again, because the job that looked fine turned out to be a job with no next step.

Here's my best advice on how to pick a good first job as a dentist. Pick the one where you'll build clinical confidence, learn how the business actually runs, and work for people who have time to teach. That job gets you to ownership fastest because of the confidence you’ll build, either at that practice or somewhere else.

The problem is that "good mentorship" and "we're open to a path" sound the same in every interview. So here are the eight questions I'd ask before signing. They fit in one conversation, none of them is rude, and the answers are at least as important as the amount of money you’ll make.

1. What would my schedule and clinical work actually look like in the first three months?

Patient flow, procedures, appointment length, who assists you, and how that changes once you've proven yourself. What you do in years one through three is what you'll be good at in year four, and it's what a bank looks at when you eventually try to buy.

2. Who do I go to with a hard case, and when do we review my work?

Ask for a recent example. "Great mentorship" means nothing until someone describes steps. The specific answer, or the absence of one, tells you what your first six months will feel like.

3. How will my pay actually be calculated? Can I see my production numbers?

Base versus percentage matters less than the real number. Ask what happens when the guarantee ends, how production is calculated, and which costs come out of your paycheck. A generous percentage on production you never get to produce is worth less than a modest percentage in a practice that keeps your schedule full.

4. Will I get to see the numbers and learn how the practice runs?

Some owners won't show an associate the numbers. Ask anyway; the answer tells you a lot about culture. A practice that plans to bring you in as an eventual partner will show you. Then ask about scheduling, staffing, collections, and overhead, because that's the education you're really there for.

5. Could I speak with a current or former associate about working here?

When you’re the one hiring, you’ll ask for references. This is the same thing. What support did prior associates actually get, what surprised them, how problems got handled. A yes to this question is a good sign on its own. A no is an answer too.

6. If ownership here is a possibility, what do you have in mind, and on what timeline?

This is the one people are most afraid to ask and the one owners are usually most willing to answer. Who decides, whether the owner has an exit plan, and what the next real conversation would be. If there's no plan to sell, judge the job on its own. It might still be the right one. Just don't take it for a future that was never on the table.

7. What would have to happen for us to seriously discuss a purchase or partnership?

Experience, production, timing, and how a price would be set. It's not a commitment; it's a thought experiment, and it forces a specific answer. If the owner has never considered the question, you just learned that too. Get any ownership terms or purchase rights in front of a dental attorney before you sign anything.

8. Any objection to my dental attorney reviewing the contract?

This is the time to get good at paying for legal help with major career and financial decisions. The contract will explain time off, how duties can change, and what happens if you leave. Have a dental attorney explain the agreement. All of it. If the future boss hesitates, that’s more useful information.

Then write it down

Show how much you care by writing the answers down in front of the person you’re talking to. In almost every case, they’ll be impressed and perhaps a bit flattered. Best practice here is to write the answers down while they're fresh, in the owner's own words. A specific example beats a general promise every time, and "we'll figure that out" is an answer too.

One more thing: a good first job is where you start meeting the people who'll tell you about a practice before it's ever listed. The CPA, the banker, the supply rep, the retiring dentist two towns over. That network is the other thing a first job is for.

I've put these eight questions, with follow-ups and a page to compare two offers side by side, into a free two-page worksheet. It's not contract advice; for that, get a dental attorney. It's the conversation to have before you need one.

Get the worksheet: https://www.dentalbuyeradvocates.com/wp-content/uploads/2026/09/Before_You_Say_Yes_Associate_Job_Worksheet_DBA-1.pdf

Brian Hanks, MBA, CFP®, is the founder of Dental Buyer Advocates and the author of How to Buy a Dental Practice and Taxes for Dentists. He has advised on more than 1,500 practice acquisitions in 49 states.