This post was originally published on October 19, 2015 and has been updated with additional insights on July 29, 2019.

Every client-facing entrepreneur knows the type: demanding, micromanaging, overly critical, and sometimes just downright rude. We might refer to them as our “most challenging” clients or our clients with the “greatest opportunity for improvement.” No matter what we call them, though, one thing is certain: These are the customers that take up the majority of our time and contribute heavily to workplace stress.

At Acuity, we have so many incredible customers, but, like any business, we also have some challenging ones. Every week, we have a team meeting to review our active customer base and talk through the wins and roadblocks that our team is encountering with clients. And guess what? There are certain clients who have roadblocks every. single. week.

One of the natural responses to pain is avoidance, and dealing with the same issues week after week is certainly painful in its own right. Instead of throwing in the towel, we’ve decided to take a different approach during our weekly team meetings: embrace the challenge, or at the very least, candidly and openly discuss it. We do this not because we’re stubborn or foolhardy, but because we’ve learned a massive amount about how to be a better organization through facing these challenges.

If you’re ready to face the challenge, too, here are a few things we’ve learned from working with difficult clients and how you can manage them more effectively:

1. Put yourself in their shoes and try to feel their pain.

Emails written in all caps. Unreasonable demands or impossible deadlines. Constant arguing over invoices. Sometimes people can be rude, and it’s easy to assume that this behavior is just their normal state of being. But in our experience, when people act this way, it’s often because they are dealing with an unrelated problem. That might sound like pop-psychology, but we’ve seen it often enough to believe it’s true. Are they arguing over bills because they just lost a large customer and revenue took a big hit this month?  Are they asking us to deliver full financial statements to them by the first of the month because they finally landed a meeting on the second with the investor they’ve been chasing for over a year?

The pressures of running a business are numerous and heavy. We get that. So when we at Acuity are able to empathize with our clients, we can better understand and even mitigate their actions. And when that entrepreneur understands that we genuinely do care about their business and are trying to help them succeed, they in turn see us as a member of their team and ultimately treat us with respect.

2. On a similar note, think of them as people — not just clients.

It’s easy to view clients as just another task to handle and it’s also easy for them to see you as just a means to get a task completed. But we’re not items on a to-do list, we’re humans, and building rapport can help both teams get to know and care about each other in a way that builds empathy.

Consider things like video calls rather than phone calls — face-to-face interaction can increase engagement and reinforce the relationship when they can see that an actual person is involved. We’ve also learned to spend time on those calls having conversations about their lives instead of jumping straight into work. In fact, we think that it’s so important to know who you are working with that we’ve put together a blog and video series called Behind the Books. Through these posts, you can meet our hardworking team members and put a face to their names.  It’s these little nuances that help nurture the relationship and aid both sides in developing an appreciation for one another.

3. Find flexibility and create new solutions.

Accounting and bookkeeping are extremely process-based functions, which means working in a consistent and orderly manner is critical. Here’s the problem: What entrepreneurial business do you know that operates in a consistent and orderly fashion? Unfortunately, not many (if any).

Entrepreneurs and accountants are often very much at odds in the way that they work, so there’s a natural tension when accountants are trying to build repeatable processes and entrepreneurs keep pushing for change. In our weekly team meeting, it’s not uncommon to hear a team member say, “I’m having a roadblock with client X because they just completely changed how they want to bill their customers” or “they asked me to threaten one of their slow-paying clients with legal action if they don’t pay this week.”

There are times when we wish our clients could just stand still for a minute — but then they wouldn’t be the entrepreneurs that they are. So our job becomes listening to those client demands and creating solutions that keep pace with their ever-changing environment.

In fact, we figured out the right tools and methodologies to use to account for Stripe and PayPal transactions. We launched our packaged Controller Solutions to manage more sophisticated investor reporting around capital raises. We rolled out a Collections Solution to help customers manage their accounts receivable. All of these were born out of challenges that clients threw at us.

4. Care about what they care about.

Sometimes, it’s not just about being innovative and task oriented — it’s about truly and honestly caring for the client and what they are trying to achieve. Often, difficulties can arise if they believe that you’re not genuinely “in it to win it.”

So, what do we do? Align with their goals. Congratulate them on their wins. Celebrate their milestones. We make it a priority for our team members to follow and engage with our clients on social media. We also like to highlight their business and their journey through our customer stories. Something else that has been helpful has been for our client success team to turn on Google alerts for our clients. That way we get notified when they make headlines, and we can proactively reach out to them to give them kudos on the big news! Taking these steps can mean the difference between a challenging client and a grateful one.

5. Kill ’em with kindness.

Remember that old saying, “you can catch more flies with honey?” Well, it certainly holds true when dealing with the difficult behavior of demanding clients. When a person is under pressure, losing their temper, or lashing out, sometimes the best way to diffuse the situation is with kindness and compassion. By no means are we suggesting that you be a “pushover” or put up with unacceptable behavior — we’ve just learned that being warm and friendly in the face of fire can help loosen things up without sabotaging your working relationship.

6. When all else fails, find the courage to fire them.

If you’ve pulled out all the stops and there’s just no possibility of finding common ground, it’s time to seriously consider parting ways. When someone repeatedly disrespects our team members, there is a simple economic equation that we like to consider. If one of our people is working with 15 clients, and one really bad client has the ability to hurt those 14 great clients by continually making that team member’s life miserable, it becomes a relatively simple financial tradeoff: Get rid of the one bad apple to protect the 14 good ones.

At our core, we strongly believe in our people, and the client’s value will never be worth the price of protecting our team members. That’s because we’ve seen our team walk through walls for clients and go above and beyond what we’ve agreed to do for them. When asked why, we always get the same response: “Because client X is awesome!” or “They’re good people that treat me kindly and fairly.” This simple reasoning that explains why we go above and beyond for great clients should also give us the courage to fire the bad ones. If you think it’s time to fire a client, here’s what you need to know.

In the end, we’ve learned many valuable lessons from working with difficult clients.

There is an enormous opportunity for growth when a company can focus on the clients that they’re struggling with. If you can find ways to combine this focus with an optimistic mindset, the hope is that you’ll develop a deeper understanding of what’s going on in your clients’ lives, where there are opportunities to create solutions for their needs, and where you can show loyalty to your team by protecting and prioritizing them. What have you learned from working with difficult clients?