Lease Lessons From A Dental Lawyer

Who represents you in a dental lease? Why the listing broker works for the landlord

Picture the moment: you’re driving home from the practice where you associate, you pass a building with great visibility and a “space available” sign, and your future flashes in front of you. You pull over. You photograph the sign. And then most dentists do the natural thing — they call the number.

Rob Montgomery has spent 15 years lawyering almost exclusively for dentists, and he makes rooms full of startup doctors pledge out loud: I promise not to call the name on the sign. He also warns that three in twenty will do it anyway. When he joined us on the Dentelligentsia podcast, he explained what that phone call actually costs — and it’s much more than a worse rent number.

The name on the sign works for the landlord

The broker on the sign has a fiduciary duty — to the landlord. Their legal and financial job is to fill the space on terms that favor the building’s owner. When an unrepresented dentist calls, they haven’t found a helpful guide to the property; they’ve announced themselves to the other team’s negotiator.

Montgomery’s observation from thousands of deals: “There are two deals the landlord puts out there: the deal for the represented party and the deal for the unrepresented party. They do not look the same.” The difference shows up in rent, in tenant improvement money, in free rent — and most expensively, in the clauses nobody prices until years later.

The clause that decides what your practice sells for

Ask Montgomery for the number one deal killer in practice transitions and he doesn’t hesitate: “an uncooperative landlord.” The practice sale needs the space; the space transfer runs through the lease’s assignment language; and the assignment language got written back when you had all the negotiating power and, if you were unrepresented, never used it. His prescription: “We want to take advantage of being in at the ground floor and get assignment language that limits or eliminates the landlord’s seat at the table when you sell.”

His cautionary tale still stings: a specialist forced by disability to sell, whose deal died over a landlord’s $60,000 security-deposit demand at assignment. And his warning about the comforting phrase in every first draft — consent “not to be unreasonably withheld”: “‘The landlord will be reasonable’ — that’s punting. What Remy thinks is reasonable, what Rob thinks is reasonable, what a judge thinks is reasonable, and what a landlord thinks is reasonable could be five different things.” Specific, objective standards beat adjectives.

There’s also a fairness argument for pushing back, and Montgomery’s version is our favorite: “A dentist with $350,000 of student debt and negative net worth — that’s who buys dental practices. The bank has no problem with them. Why should you, landlord?”

Win it in the LOI, not the lease

The order of operations matters more than most tenants know. The letter of intent feels informal — non-binding, just a framework — so hard topics get deferred to “the lease negotiation.” Montgomery’s statistics say the opposite: “If it makes it into the LOI, nineteen times out of twenty it makes it into the lease. If the LOI says ‘to be determined,’ we’re lucky to get it one time in five.”

The LOI is where the represented tenant’s team earns its keep: assignment terms, guarantee limits, TI, delivery condition — negotiated while landlords are still competing for you. By lease drafting, the alternatives have gone home and the moving truck is booked. As he reminds every client: “You’ve signed apartment leases and a lease for your Subaru — contracts with consumer protection baked in. These are grown-up contracts now. There’s no such thing as a standard agreement.”

Build the team like the transaction can’t be undone — because it can’t

“You can’t undo these transactions. You can’t give back a practice, you can’t unsign a lease. It’s the old Fram oil filter commercial — pay me now or pay me later.” That’s the case for representation on both sides of the table: a tenant-side broker whose duty runs to you (the listing broker’s fee structure means your representation typically costs you nothing — the commission is split, not added), and a dental-specific attorney who isn’t quoting the lowball flat fee. On that last point, Montgomery is blunt: the cheapest lawyer is “just not putting in the time,” and those are the deals where problems surface after closing, when nothing can be fixed.

Hear the full conversation with Rob Montgomery, Your Dental Lawyer, on the Dentelligentsia podcast — non-compete reality (banks treat them as enforceable even when judges might not), zoning and title diligence, and more from 30 years of dental deals.

Next time a building stops you mid-drive: take the photo, skip the call, and text us the address instead. Tenants and buyers only — talk to us.

For more on our interview with Rob Montgomery, check out our article, “Never Call The Name On The Sign — And Other Lease Lessons From A Dental Lawyer.”

And follow Rob Montgomery on Linked In or check out the Your Dental Lawyer website.