Tips on dealing with challenging clients

“Difficult clients” often become like that because you’ve allowed them to become like that. They may get frustrated because they think you aren’t delivering what was agreed upon. To avoid this, manage expectations from the get-go. This will generally prevent misunderstandings.

If a disagreement does happen, the worst thing to do is to start a conversation when you are upset. Instead, try to deal with it when everyone is calm, preferably with a face-to-face conversation.

—Mendy Jacobs, Managing Director, Jacobs & Co.

Dump them! Too many people are afraid to fire clients and customers. Don’t be. It’s a big, bold step toward growth.

—Michael Greenfield, CEO, Prime Source

Behind every difficulty, there’s a gift to unwrap. Working with difficult people can be very rewarding, as they are the ones who point out where a company can improve. However, working with difficult people is an exercise of stretching your giving muscle. Just like you need to find the right balance at the gym, you need to be careful not to overextend yourself.

In short, embrace difficult people and show empathy, but be sure you don’t lose yourself in the process.

—Michael Rubin, CEO, Anchora

I never argue with a client; I treat them with the same respect that I want to be treated with. If a client is so challenging that he is eating at your time and emotional well-being, it’s time to wave goodbye. He is not family. (If your challenging client is a family member, now that’s a problem.)

—Shmily Treger, Photographer, Shmily Treger Studio

Define expectations and boundaries up front to avoid misunderstandings.

I learned this the hard way. I was working on a project and the client was messaging me at all hours of the day and night, and then got antsy when I didn’t respond quickly enough. I realized that he was under a lot of stress, and I stayed empathetic, making the effort to understand his concerns, but I made a point of only responding during the hours that I set aside for responding. Pretty quickly, his concerns simmered down, he felt more secure, and we were able to work really well together.

Take some time to feel out your boundaries, and stick to them, kindly and empathetically. You’ll find that everything will settle down.

If you find a client is still draining you of the energy and joy from what you do, give clear communication about what you can do — and stick to that boundary. You may lose the client, but you’ll gain a lot more peace of mind. You are allowed to stand up for yourself.

—Dovid Azerad, Founder, NextArc Performance Solutions

The most common client issues are scope creep, missed payments, missed deadlines (projects that never end), and feedback by committee (too many cooks in the kitchen). Ninety percent of the time, these can be avoided with a clear written agreement. It doesn’t need to be a jargony ten-page contract; for smaller projects, a simple email with bullet points works well. But the core terms must be in writing: price, scope, timeline, payment schedule, single point of contact, what happens if feedback isn’t sent back on time.

That said, some people are simply more menschlich than others — and they make fabulous clients! They value your expertise, show up to meetings on time, honor your working hours, and communicate concerns clearly and respectfully. Use your messaging and positioning to attract those kinds of clients — then delight them and hold them close.

—Michal Eisik, founder, CopyTribe & Profitable Freelancer

Never make it personal. While it’s important to maintain a personal relationship with clients, business disagreements should always remain professional.

As an auditor, my role is to ask questions, validate the client’s numbers, and ultimately provide an opinion on their financial statements. This process benefits the client’s company in many ways. However, if a disagreement arises, it’s crucial to remain calm and explain your reasoning clearly. Acknowledge and validate their perspective. Then, in a nonjudgmental and composed manner, explain why you believe their rationale is incorrect, backing it up with clear evidence rather than emotion.

By fostering a mutual understanding and clarifying that the disagreement isn’t personal, you create an environment where discussions remain professional and respectful. This approach helps maintain a positive and collaborative relationship, even when resolving challenging topics.

—Zevie Adler, Audit Supervisor at Roth & Co.

Listen first! Clients are always right. You can give them advice, although make sure not to upset them more. Offer a discount on your next service.

—Esther Walter, CEO, Lifesize Plans

Be patient and listen to the client. It’s important to make the client feel understood.

—David Safdie, Owner, ABC Environmental

Boost Those Referrals!

As a referral-based business, you rely on people to bat for you. Here are some tips on boosting referrals:

Don’t forget your personal network. Ask family and friends if they’re in need of your services. Most referral-based providers get started through their inner circle — even if they don’t need your services now, they’ll be happy to refer you.

Be kind, curious, and interested in other people. Be friendly, personable, and helpful.

Ask for referrals.

Once you get a client, consistently deliver exceptional results and go the extra mile to make sure they get maximum value for their investment.

If you’re having trouble generating traction, there are different strategies you can use, such as creating targeted joint-venture partnerships. Find other service providers who are working with your ideal client from a different angle, and see if they would refer to you. Remember, their name is on the line so you have to understand that and build a foundation of trust with them.

Ask for referrals.

Today’s marketing strategy is personal branding. No matter what service or product you offer, you can stand out by leveraging social and print media as a space for your personality and expertise to shine. Be authentic, helpful, and professional, and it will go a long way. Oh, and ask for referrals!

Dovid Azerad, Founder,  NextArc Performance Solutions 

Your clients are your best sales reps. I boost referrals by paying attention to them. Birthday wishes, for example, are appreciated by all.

Say thank you with more than just words. The minute someone makes a referral I send them a special gift.

Michael Greenfield, CEO, Prime Source

(Originally featured in Mishpacha, Issue 1048)