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By Stephaine Burns

Ever taken on a new client and then quickly regretted it?

You’re not alone. Whether you really needed the money and were overlooking negative signs or you genuinely thought it would be a good business move, every entrepreneur has suffered the indignity of signing on with badly behaved clients. Perhaps they keep “forgetting” to pay you or treat you like their personal therapist when they’re in the midst of a meltdown. Or maybe they demanded work outside the scope of your agreement or started calling your phone at 3:00 a.m.—and then treating you like a pariah when you didn’t answer. Whatever your experience, the battle scars they’ve left behind are real.

“The problem isn’t just their outlandish behavior, it’s the fact that they have serious boundary issues,” says licensed psychotherapist Terri Cole, author of Boundary Boss: The Essential Guide to Talk True, Be Seen, and (Finally) Live Free. “While you can institute policies to protect yourself, it’s vital to know what to look out for before you climb into professional bed with someone who doesn’t respect and value your limits.” Even if it feels momentarily uncomfortable, better to cut and run rather than get stuck with a needy or inappropriate client. Keep an eye out for the following red flags in your discovery calls, and you’ll be able to save yourself a bad testimonial, lost wages, and sleepless nights.

Wendy Yalom
You put your best foot forward with potential new clients, and that effort should be reciprocated. “If someone hops on a scheduled call 15 minutes late or reschedules with you multiple times, they are giving you a preview of how they’ll behave when you’re officially working together,” says Cole.

It is perfectly acceptable to call out this behavior and let them know you don’t think you two should move forward. Cole suggests saying something like, “In my experience, when a client reschedules the intro call multiple times, that means they’re not ready to dive in at the level I require. I don’t think we’re a fit.”

“One of my pals had a first meeting with a client who had to reschedule in the midst of the appointment due to severe neck pain,” recalls Cole. “Later, when she got a two-minute voicemail from him detailing how he was managing his pain—with Vicodin and vodka—that was the end of the possibility of them working together.”

Ask them about their prior experience working with professionals in your field or other people who offer comparable services. “If they lead with a woe-is-me story about someone who took advantage of them or spill personal details about that person’s life, you are officially on notice,” says Cole. “How they speak about their prior relationships is how they might be talking about you a year from now.”

Cole warns that a special type of problematic client might understand that it’s not cool to trash talk and pepper in diplomatic-sounding phrases like, “She was a lovely person but she really didn’t get me like you do” or “She was often late but I cut her slack because she was going through some things that I really shouldn’t mention.” Read between the lines and you’ll have all the info you need.

If you know colleagues who have worked with this client in the past, give them a call. “They could alert you to potential trouble spots, like, the person never answers calls before noon, that help you plan accordingly,” says Cole. If you don’t know any of the contacts your potential client mentions, Cole suggests doing due diligence by looking them up on LinkedIn and reaching out to see if they have any valuable intel. The more you know, the better equipped you’ll be to make a wise decision.

Vibes don’t lie, as the saying goes. Trust your gut if something feels off. “The beauty of feelings-as-messengers is that you don’t have to have a bullet-pointed analysis of what, exactly, is off,” assured Cole. “Let your discomfort be enough—because it is.”

Your body might flash visceral sensations to communicate with you. Cole says to be on the lookout for a queasy stomach, a headache or a heaviness in your chest. If you have a moment to reflect after the call, imagine what it would be like to work with this person. Does the prospect make you feel light and excited? Or are you full of anxiety and dread? There’s your answer.

You should also listen carefully to your thoughts. “Does the prospective client remind you of, say, your entitled ex? Or your punitive parent? That could be your instincts telling you this may not end well,” says Cole, who notes that personal relationships can give us insight into professional ones. “Or maybe you’re doing mental gymnastics to justify saying yes—like, ‘This is going to be hell but I’ll suck it up and worry about my sanity later.’ If that’s where your head goes, just say no.”

If you are 50-50, sleep on it, suggests Cole. You may even want to set an intention before bed to wake up with crystalline clarity around whether or not this will be a productive partnership. Once you get your answer, don’t ignore it or talk yourself out of it. It’s a lesson in knowing what works (or doesn’t) for you will ensure that your partnerships are always healthy, successful, and hopefully fulfilling, too.