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Difficult Clients in Difficult Times
We’ve all had difficult clients. In the best of times, they can be a challenge but in the times we’re living in right now they can be even more...
5 min read
Mark Bassingthwaighte, Risk Manager
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Updated on August 20, 2026
by Mark Bassingthwaighte
| Posted on April 12, 2017
Sooner or later most lawyers end up taking on a client they wish they hadn’t. This just comes with the territory. That said, if you’re seeing this happen more often than feels normal, the real problem may not be an isolated lapse in judgment, it may be that your screening process isn’t supporting consistently sound decision‑making. For solo and small‑firm lawyers, where time, energy, and cash flow are always front and center, learning to identify the potential clients you should say no to is an essential practice‑management skill that can pay a nice dividend over time.
The hard truth is that even promising matters can come packaged with a client who will make your life miserable. And when they do, the consequences often include stress, financial write‑downs or write-offs, unpaid invoices, and sometimes even a grievance. These clients drain your time, energy, and profitability. You may have bills to pay, but problem clients rarely help you pay them.
To illustrate the point, Phil, a fictional prospective client, walks into your firm one morning for a scheduled consultation clutching a thick stack of papers. He explains that he’s in a dispute with a contractor. The facts are messy, the damages are modest, and the contractor has already hired counsel. But Phil isn’t interested in talking through the timeline or the documents you ask for. He wants to talk about what he has “discovered.”
“I ran everything through ChatGPT,” he announces, tapping the stack like it’s a winning lottery ticket. “It analyzed my case and said I’m entitled to triple damages. It even drafted a demand letter that I want you to use. The AI has already figured out the strategy. I just need you to implement it.”
You try to steer the conversation back to the actual facts, but Phil refuses to engage. He insists you follow the AI‑generated plan, won’t answer basic questions, and becomes irritated when you explain that the AI’s legal analysis is inaccurate. As the conversation continues, more red flags appear. He expects daily updates, immediate responses, and he hints more than once that he doesn’t have the funds for a full retainer but believes you should “trust the process” because the AI has assured him his case is a winner.
By the end of the consultation, your gut should be screaming. Phil isn’t looking for a lawyer; he’s looking for someone to validate the output of a chatbot and do its bidding. This is exactly the kind of client you should decline.
Now consider “Marcy,” another fictional client, but one you decided to accept. She came in seeking representation for her divorce, visibly upset and overwhelmed, convinced she had been wronged at every turn. During intake, a few warning signs surfaced. Marcy had already been turned down by three other divorce attorneys. She insisted her case was “simple.” And she was looking for constant reassurance. Despite all this, you felt sympathetic, and the matter looked manageable enough. So, against your better judgment, you agreed to take her on. That’s when the trouble began.
Marcy started calling three or four times a day “just to check in.” Whenever she grew anxious, she retold the marital history, changing details you had already documented. She demanded that you file aggressive motions and then would panic after every response. She insisted on approving every sentence of every communication. She wanted weekend calls. She wanted late‑night texts. She wanted you to “fight harder,” and then would later accuse you of being too aggressive.
When opposing counsel produced financial records that contradicted Marcy’s version of events, she became defensive and evasive. She blamed you for not “fixing” the problem. She refused to pay her bill because she didn’t like the outcome of a hearing she had been warned she might lose. And when you finally came to your senses and withdrew, Marcy filed a grievance claiming you “didn’t care” and “didn’t fight.”
The red flags were there from the very beginning. You just didn’t want to say no; but this is what can happen when you ignore the warning signs and fail to trust your gut.
As a malpractice risk manager, I’ve heard “I should have listened to my gut” more times than I can count. Your instincts are often your first and best warning sign because clients like Phil and Marcy aren’t rare. They show up with sky‑high expectations, a shaky grasp of how the legal system actually works, and an unshakable confidence in whatever an AI chatbot or late‑night Google search told them. They will often treat you as an obstacle rather than a guide. And once litigation begins, they can become even more demanding, more frustrated, and more likely to blame you for anything and everything that goes wrong in their eyes.
Effective screening starts with taking a realistic look at the person sitting across from you. Some prospective clients reveal themselves immediately. They arrive with expectations completely detached from reality. They may demand justice, expect a large payout despite a modest loss, or assume their matter should outrank every other file in your office.
Others show their true colors through behavior. They interrupt constantly, treat your staff poorly, and/or shift their story every time you ask a clarifying question. If obtaining even basic information feels like pulling teeth, that’s not going to improve once opposing counsel starts picking the case apart.
And then there are the modern red flags: clients who bring AI‑generated legal research, AI‑drafted pleadings, or AI‑created “case valuations” and insist you adopt them. Technology can be helpful, but when a prospective client thinks a chatbot’s output is superior to your professional judgment, you’re already in trouble.
Client screening isn’t just about evaluating the prospective client. It’s also about evaluating you. Do you have the experience the matter requires? The time? The staff support? The emotional bandwidth? Are you equipped to meet the client’s legal needs and their emotional needs? The attorney‑client relationship is a two‑way street, and compatibility matters. If you can’t work effectively with the person in front of you, the representation will suffer, and so will you. Learn to choose wisely.
To bring structure to this process, many lawyers benefit from developing a standard set of intake questions. These don’t need to be complicated. Ask what outcome the client is hoping for and why. Ask how they’ve handled legal matters in the past and what their experience was like. Ask how they prefer to communicate and how quickly they expect responses. Ask how they plan to pay for the work. Ask what concerns them most. And in today’s world, ask whether they’ve already used AI to research their matter and how much weight they’re giving that information. Their answers will tell you a great deal about expectations, flexibility, and whether they’re willing to trust your judgment.
These questions do more than gather information. They reveal honesty, attitude, and whether the relationship is likely to be healthy. They also give you a chance to observe how the client responds when you set boundaries, which can be the most telling part of the entire conversation.
Even with a solid screening process, you may still occasionally find yourself dealing with a problem client. It happens. Just know that the difference between lawyers who keep repeating the same mistakes and those who don’t is what happens after the representation of a problem client ends. The lawyers who don’t repeat the same mistakes take a moment to reflect. They ask themselves what was missed during intake, what red flags were ignored, and what needs to be adjusted going forward. They look at both the client and themselves. Their goal is simple. It’s to prevent an unintended repeat of the situation because life is too short to keep onboarding your own headaches.
In sum, a thoughtful screening process won’t eliminate every problem client, but it will dramatically reduce how often they show up in your practice. And when you’re running a solo or small firm, that’s not just good risk management, it’s also good for your overall wellbeing.
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