Difficult Clients: What to Do and How to Deal With Them

For better or for worse, the freelance lifestyle is filled with twists and turns. Whether it’s the ups and downs of feast or famine or the struggle of handling difficult clients, if there’s one thing the freelance lifestyle lacks, it’s not excitement. 

The constant changes that freelancers deal with are a blessing and a curse. With new clients popping in and out, freelancers get the opportunity to connect with lots of great people and work on a variety of new and interesting projects. 

But the stream of clients presents a unique risk: some of them are bound to be bad apples. Indeed, it can be argued that the key to successful freelancing is simply learning to deal with difficult clients. 

In this article, we’re going to do our best to equip you with the tools, weapons, and tactics you need to resolve disputes, appease unhappy clients, and get out of toxic client relationships alive. Here, you’ll learn the best practices to reduce tensions, facilitate understanding and empathy, and keep things calm. 

Four Types of Difficult Clients

There’s no singular event that makes client relationships become problematic. To build on a phrase by Tolstoy, one could say that “Happy client relationships are all alike; every unhappy relationship is unhappy in its own way.”

Sometimes, a relationship starts out great and becomes problematic over time due to a specific conflict. Other times, it starts out bad and just never gets better. 

Here are a few common types of difficult customers that you may encounter. 

1. The Time Suck 

The time suck is impressively skilled at wasting time. They’ll schedule an hour call to go over something that could be hammered out in a short email. You’ll ask them a quick question, and they’ll embark on an irrelevant philosophical tirade about Adorno’s Negative Dialectics only to tell you that, in short, they’d prefer another font for the logo. When you finally do get them a deliverable, it’s all wrong, and you’ll need to either start over or make endless revisions. 

Sometimes, all it takes to save this client relationship is to set out a clearer contract or to let them know you’ll bill for phone time, additional revisions, etc. Unlike some of the other types of difficult clients, this one isn’t necessarily intentionally problematic, so it’s possible to work with them. 

2. The Cheapskate

Is the going rate for your work $200? How about twenty bucks and the exposure of being a ghostwriter?

The cheapskate is sure to devalue your time and your work throughout your relationship. In fact, they may even try to cheat you out of paying what they owe you, either by referring to some arbitrary and illusory goal you didn’t meet, or simply by saying they don’t feel like paying you at all.  

The one saving grace is that you’ll often be able to tell you’re dealing with one of these clients pretty quickly. 

3. The Toxic Biohazard

Sometimes, you just end up dealing with an unpleasant and angry client. Even if you do all your work perfectly and deliver it just how you were instructed, there are some people who will always find a problem with it. 

In some cases, they’ll exhibit straight-out toxic behavior, such as directly insulting you, but in other cases, it can be more subtle, like being passive aggressive, showing disrespect, or constantly making it clear that they think they know more about your job than you do. 

A telltale sign of this type of client is that they’ll start telling you right away about how terrible all their past contractors’ work has been. If they’ve gone through dozens of freelancers without luck, chances are the problem lies with them.

4. The Late Payer

You submit an invoice due in two weeks, and you receive payment six weeks later. 

The late payer needs no other introduction. If this client is consistently just a few days late with payment, it can be a workable situation, but at a certain point it becomes untenable and can seriously hurt your cash flow. 

Unlike the Cheapskate, the Late Payer isn’t necessarily trying to cheat you out of money. Sometimes, they just run a small business that has cash flow issues of its own, and they’ll be transparent about that. In cases like this, it’ll be up to you to decide whether or not you can continue working for late payment.

Strategies for Handling Difficult Clients

Now that we’ve established some of the barriers to successful client relationships, let’s look at some ways to deal with them. 

1. Set Clear Expectations

No matter what type of client you’re dealing with, difficult or otherwise, setting clear expectations for what you’ll be providing at the outset is essential to avoiding problems down the line. That means making it clear what you’ll be delivering, when you’ll be delivering it, how much you’ll charge, what additional consulting services you’ll offer (phone time, advice, etc.), how many revisions you’ll provide, and anything else that you can think of.

The best way to lay this all out is to send your client a contract that states everything in clear terms. 

2. Maintain Professionalism at All Times

Dealing with angry or unreasonable clients can be a taxing experience. But as difficult as it gets, you need to make sure you don’t give into emotion. Responding to an outburst with an outburst of your own won’t do anything to help your case and will only serve to make it more difficult to come to a resolution. 

One pitfall to be mindful of here is that resorting to excessive professionalism can come across as aggressive in itself. Ideally, you’ll want to try to keep the same general tone and demeanor that you use in your normal communications. For example, if you normally sign your emails “Best, ____,” don’t suddenly switch to “With sincerest regards, _____.” This will likely come across as disingenuous and somewhat passive aggressive. Remember that it is possible to be assertive without being aggressive. 

If you need to go on a rant, make sure you do it in private. It’s normal to need to let off some steam, so if you need to get something off your chest, just make sure you do it somewhere your client won’t find out about it, i.e., not on social media. 

2. Identify the Conflict and Resolution

When you get into a dicey situation, it’s easy to let your feelings get the best of you. But when you do that, you often lose sight of the bigger picture: what do you actually want to achieve? 

For example, if your client isn’t paying you, what does a resolution look like? Are you willing to accept a payment plan? If your client is asking for unreasonable revisions, what is your goal? To completely satisfy the client or to simply be done with the project and receive payment for it?

Without identifying where the heart of conflict lies and what the ideal outcome is, it’s impossible to work towards that goal. So, take some time to focus yourself and set out clear goals. 

3. Listen and Respond Carefully

Everyone, client or otherwise, wants to feel understood. When we feel like we’re not being heard, we naturally become upset and frustrated. 

Social interactions are complex, and people have a strange and indescribable sense of whether or not they’re clicking — that’s what we refer to as “vibe” or “wavelength.” When someone says they don’t vibe with someone else, it often comes down to subtle differences in speech patterns, which can lead to conflicts over time.

For example, if you tend to be the type of person who speaks very casually, but your client is intent on maintaining strict professionalism, failing to meet them where they are and assume their communication style can really push their buttons. 

When a conflict arises, start by listening to your client and see whether you’re responding in kind. Evaluate whether there are any adjustments you can make to show them that you’re listening and understanding what they need. 

The reality is that sometimes you and your client simply won’t gel, and it’s a normal part of freelancing to turn down clients because of personality conflicts. However, if you’re already in one of these situations, start out by listening and seeing if there’s anything you can do on your part to fix it. 

4. Respond Quickly — But Not Too Quickly

You know the saying “time heals all wounds?” That does not apply to freelance clients. Out of all the things that will de-escalate a heated situation, taking your sweet time to reply is not one of them. When you’re dealing with a tough client, do your best to respond promptly to them. 

That said, it’s also important to give yourself enough time to cool off if you’re angry yourself. It’s far better to respond too slowly than it is to send something out of anger that you’ll regret later. 

A good rule of thumb when dealing with a difficult situation is to write out one email that gets all your thoughts out, take a break for a few minutes, and then write a second version. The first version will serve as your cathartic venting session, and the second email will be the one you actually send. 

5. Be Compassionate and Acknowledge Their Concerns

It’s easy to say the other side is being unreasonable when you’re not in their position — for all you know, you’d be acting just the same if you were them. That’s not to forgive poor behavior but to acknowledge that it happens to the best of us. You should make an effort to be empathetic and put yourself in your client’s shoes. 

One way you can do this is by using a variation of the Speaker Listener strategy. Although it was originally developed for marriage and family counseling, it can be useful in business as well. 

In short, the speaker and listener alternate, with one side being the designated speaker, and the other being the designated listener. When the speaker is speaking, the listener doesn’t interrupt. Then the parties swap positions. 

Obviously, in a business situation, you won’t have such a formal designation. But some of the features of this structure can still be applied. 

To start, you can make sure that you don’t interrupt your client when they are speaking. Then, when they’ve finished, you can repeat back what they’ve said to show that you’ve listened. For example, you might say something like, “so, from what I understand, you’re saying that ________. Is that correct?”

If your client confirms, you can then move into the speaker position. Start by laying out your side of the story, and when you’re finished, ask them calmly if they can see where you’re coming from. In this way, you acknowledge their feelings without agreeing or disagreeing, and you open a space for productive conversation. 

6. Be Ready to Let Go of Bad Clients

Sometimes a situation is simply unfixable — at least without spending far more time than it’s worth. The reality of freelancing is that you have to “fire” bad clients from time to time. When that happens, do so politely, and simply explain that it’s not working out between the two of you. Wish them well, and do your best to end on good terms. 

On a similar note, do your best to be discerning when taking on clients in the first place. If you get a bad feeling about a new lead, don’t be afraid to trust your gut. 

7. When Necessary, Seek Legal Help

This should be your absolute last resort, but there are times where it’s necessary. If your client is refusing to pay you for a $20,000 project, for example, you may have no option but to seek legal remedies. 

Key Takeaways: Difficult Client Relationships

Relationships of all kinds are fraught with conflicts. Client relationships are no different. 

While there’s no silver bullet to resolving conflicts with your clients, there are some basic principles you can hold onto as you navigate them: stay polite and professional, listen to what your client has to say, be clear on what a resolution looks like, and try to be compassionate. 

When all else fails, sometimes you’ll just have to throw in the towel, take your losses, and move on. 

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