If you own rental properties long enough, you’re going to end up working with an attorney. Maybe it’s an eviction. Maybe it’s a zoning issue with a neighbor. Maybe a tenant is taking legal action against you. Whatever the reason, at my property management company, we engage with attorneys pretty regularly — probably several on any given month.
https://www.youtube.com/watch?v=4efIEp09buc
And after all these years, I’ve learned there are good attorneys and there are bad attorneys. There’s one specific thing I look for to tell the difference, and I want to share it with you because it can save you a fortune in legal bills and headaches.
The One Sign You Have a Bad Attorney
Here it is: an attorney who never asks the other side for anything is a bad attorney.
That’s it. That’s the tell.
It’s very common for us to deal with attorneys — either on our side or on the opposing side — who come in acting like a bully. They’re aggressive, they’re unreasonable, and they never actually ask for something specific. They never say, “Hey, we’re trying to resolve this. What would resolve this is if the property management company did X, Y, and Z.”
That’s step one of any negotiation, and a legal action is basically a negotiation. You’re trying to advantage your side. If your attorney isn’t reaching out and asking for something, you have a problem.
Why This Matters: They’re Running Up the Bill
When an attorney doesn’t ask for anything, one of two things is happening. Either they’re trying to run up their billable hours by perpetuating the conflict, or they’re addicted to the drama. Neither one is serving you.
A conversation that could be resolved in five minutes can get dragged out into a legal action that lasts years. Years. The longer they prolong the conflict, the higher their billing goes, and the longer you’re kept from a resolution. That’s the opposite of what you hired them to do.
What a Good Attorney Actually Looks Like
The good attorneys I work with are relaxed and friendly in the way they talk. They have a certain security about them. They ask with confidence.
That doesn’t mean they shy away from hard questions or hard asks. They don’t. They’ll say, “Hey, this is what we want” — but they say it in a reasonable tone, and they say it early. That’s the key. Almost immediately, they’ll come out with something like, “We want to fix this, and here’s how we fix it. Mr. Property Management Company Owner, this is how this goes away.”
In your case as a landlord, it would be, “Mr. Rental Property Owner, this is how this goes away.” They just ask. Early, reasonably, and directly.
What to Do If Your Attorney Isn’t Doing This
If your attorney hasn’t asked the other side for anything yet, give them a directive. Tell them:
- “I want you to make an offer to the other side.”
- “I want you to ask the other side what it is they actually want.”
If your attorney isn’t willing to do that, or if you’re sensing they’re escalating things rather than resolving them, it’s imperative that you walk away and find a new attorney. I mean it. This isn’t a small thing. I see it happen over and over again.
An attorney who’s addicted to drama, who finds it empowering to intimidate people, who’s addicted to conflict — that person is not meeting your objectives. They’re doing the opposite. They’re going to keep escalating, and every escalation costs you money and time.
It’s Just Business
Here’s the mindset shift a lot of landlords struggle with. When you’re in a legal fight, you often feel wronged by the other party. And you might be right. We feel that way sometimes at our property management company too.
But this is an investment. You have to make investment decisions, not emotional ones. Like the Godfather said, it’s just business. Your job as a rental property investor is to put more money in your pocket, and a huge part of that is reducing liability quickly, not dragging it out.
A good attorney understands that. A bad attorney sees your file as a revenue stream.
Bottom Line
Next time you’re working with an attorney — whether it’s for an eviction, a tenant lawsuit, a zoning issue, or anything else — pay attention to one thing: Are they asking the other side for something specific, early, and reasonably?
If yes, you probably have a good attorney. If no, give them a directive. If they still won’t do it, walk away.
That one habit alone will save you thousands of dollars and years of unnecessary conflict.
Just a humble Philadelphia property management company owner, doing my best to answer your rental property investing questions. As always, happy rental property investing.
