Dealing with “Clients From Hell”? Here’s How to Deal With Them

Clients From Hell

What is the common denominator of a bad day at work as a small business owner or operator? A lot of times it’s your clients.

You see the good, the bad, and the ugly when it comes to clients, but it doesn’t have to be that way, and we’re here to tell you. Read on to learn about how to spot ‘em, avoid ‘em, and circumvent bad relationships! 

How to spot a “client from hell” 

Resources for how to be a better entrepreneur are abundant, but what if you held your clients up to the same standards and learned how to find a good client partner? If you don’t already, you should. 

As a small business owner in a service-oriented industry, you have the power to create strong relationships with clients—and just what you are looking for. The key is to spot a client from hell far in advance, so you avoid headaches down the line. 

So, what patterns of behavior drive us toward the wrong clients? Thinking that you need to take on every client out there. Think about the overall ROI of your new client… And it doesn’t just have to do with money. Your mental wellbeing is equally as important. 

Pay attention to warning signs when you’re in the beginning stages of a working relationship, so you don’t get stuck down the road with a client from hell. If you get that spidey sense that a client is no-good, really listen to it. Your intuition is usually right.

What are examples of “clients from hell?”

Here are some examples of clients from hell. We’ll share the worst client archetypes so you can spot them from afar and save your time, energy, and focus for the clients worthy of you AND willing to pay. Yes, you’ll turn down some work, but your work won’t wear you out AND both your business and mental health will be better in the long run.

1 – “Ticking Tanya” – The unreasonable deadline-setter

A woman with a clock on her head

Sure, a deadline is a deadline. But setting unreasonable deadlines of 24 hours or less, or worse, isn’t fair to you. Avoid clients who demand quick turnaround times, as they will utterly disregard your personal life for their professional gain. 

Rushing never works, anyway. It often requires re-work and could be full of mistakes. A good client will understand the boundaries of a work-life balance. They also inherently “get” that quality work takes time and will plan ahead with realistic timetables. 

Need proof this type of client from hell exists? Here’s an example from

I’m a freelance video editor. The “client” here is a “former” friend.

Client: I need a favor. I need a movie trailer for Sundance.

Me: I’m really busy on another project. I wish I could help you but I don’t have the time.

Client: I can pay you 180 per shift!

Me: … That’s really low.

Client: I need you to finish it in 3 days.

Me: First, that’s not enough time to cut a really high-quality trailer from the raw footage you have, and second, I really, really don’t have the time.

Client: I need you to start on Thursday

Me: I’m on a shoot that day and the following days.

Client: This is a really great chance to impress my DoP. He shoots dozens of movies a year – this could lead to more work.

Me: I really want to help you but I don’t have the time.

Client: I gotta go, I have another call coming in.

Me: OK. Good luck.

A few days later I discovered he unfriended me on social media. I saw him again a month later and he was extremely rude to me for having the gall to actually be doing paid work I guess.

What to do about it: Being a slave to your work is not good for your work-life balance. You shouldn’t have to pull all-nighters when it clearly could be avoided. So, to avoid this situation or client-type, establish a clear list of what you can do, set to a calendar. Time-sensitive checklists can give your clients a holistic picture of what you can do for them and when. If they disagree on this process, don’t work with them.

2 – “Undercutting Urkel” – The missing cheapskate

Man with penny on his head

So many people in the business world try to nickel and dime you for your services. Don’t take any significantly undercut offers. Run for the hills if you have to negotiate with prospective clients who clearly don’t see (and are unwilling for you to pay for) your services. 

If you end up working with an “Undercutting Urkel,” they might screw you over in the future by expecting more work in return for nothing. Or, you might have to continually negotiate pay with them. And, you’ll get the raw end of the deal.

Here’s an example published on via

Conversation between clients

What to do about it: Your price point is a symbol of value to customers, and good ones will pay what you’re worth. Learn more about pricing strategies here.

This client archetype is pretty clear to identify. If you’re finding that during the negotiation stages, the prospective client is trying to nickel and dime you, walk away. Cheapskates don’t change. 

If you truly are desperate for revenue and honestly need to say ‘yes’ even to the bottom-of-the-barrel clients… Here’s how you can handle it.

Create a contract or written agreement to make my case for your payment. Protect yourself with these legally binding documents. There should never be an exception, not even for referrals or friends.

Contracts or agreements should include payment details like:

  • Amount due
  • Payment terms
  • Deliverables 
  • Work expectations 

Your contract could include interest for late payments. If you don’t get a payment, you can use the contract in arbitration. 

“Sometimes, the idea of legal action can get the client to contact you and, at the very least, make an arrangement to pay what they owe,” said freelancer Christina Majaski. 

Worst case, you sue a client and send them to small claims court. But keep in mind this is usually an expensive endeavor.

3 – “Scope-Magnifying Susie” – The project scope-creeper

Woman with binoculars on her head

“Scope-magnifying Susie” is a common client taboo. This is true (especially) in the service industry… Because you don’t have a tangible product, it’s easier for clients to request project add-ons. 

For example, if you’re a coach and your client comes to you requesting a “one-time favor” of adding on to the initial scope, this favor sometimes goes unpaid. 

Or if you’re a marketing consultant who was asked to design a website for a client and all of a sudden they are asking you to create printed marketing collateral for you, that is not OK. 

Scope creep is more common than you think… And it will cost you in the long run. 

Here’s another example from

Client: (two weeks ago) One more little tweak and we’re done!

Client: (one week ago) One more little tweak and we’re done!

Client: (Monday) One more little tweak and we’re done!

Client: (Tuesday) So if we print this 8.5×11 brochure on 11×14 will it look the same?

Client: (today) We’re going in a different direction with content and images. We’ll get back to you.

How to avoid this: While it’s hard to spot this archetype initially, you stop this dead in its tracks. Walk prospective clients through a list of what is within—and outside of your scope. That way, you will be on an equal playing field with them, and they will be less likely to request things that are not on that list.

As a small business owner, it’s important to create documents prior to establishing what you are contracted to do. This helps both you and the clients have equal expectations of what work needs to be performed. 

Unlike full-time workers who can count on a steady paycheck, entrepreneurs’ lifeblood is funded by billable hours. So, after a project is complete, and a client demands additional work, you’re working for free… And that’s not OK. 

4 – “Mike the Micromanager” – The missing micromanager 

Man with microscope on his head

Some clients inherently helicopter over other people’s work. It’s built within them to be overly invested in the work they’ve outsourced to others. Even if they are looking to get less on their plate, they needlessly become over-involved in your own obligations. 

Other clients second-guess your talents and abilities and contact you incessantly. Consider this scenario—you’re a real estate agent who is helping sell a clients’ house. The client becomes obsessed with their ability to sell their own house, that they check in every 30 minutes, require the real estate agent to do specific marketing techniques to promote their listing… While it could help, the stepping on toes is actually counter-productive in most scenarios. 

Here’s another example from

I was transporting some equipment for a client several hundred miles. They insisted on following my truck and were very adamant that I go the exact speed limit. The following took place at the first rest stop.

Client: You were speeding. We had to catch up to you several times.

Me: No. I made sure to set the cruise control at exactly the speed limit.

Client: Yeah. But your engine is bigger than ours.

Me: … Haha … huh? … Ha… Wait. Are you serious?

Try as I might, I could not impress on them that 60 mph is the same no matter how big the engine.

What to do about it: Also, take the time to select the right client. So, research them. Look for referrals. And stalk their web presence

Ask for space to do a good job, and then once the work is performed, request organized and helpful critiques. That way, they feel involved, and you won’t feel overly bombarded or micromanaged. 

5 – “Unorganized Oliver” – The unclear or erratic client

Man with lots of books, papers, and notebooks swirled around his head

Watch out for clients who are disorganized from the initial onset. In order to produce an amenable final product, both the client needs to be organized and able to communicate. If they don’t know what they need, how will you? 

If a project is unclear from the get-go, it’s a tell-tale sign that the entire project will be frustrating.

Here’s an example from

Me: So roughly what size would you like the finished design to be? 

Client: Oh, about the size of a digestive biscuit.

Me: ….

What to do about it: Communication fosters a good final product. There’s nothing more frustrating to a freelancer than client unavailability—especially when they have an essential question about the assignment. Good clients serve as helpful resources—not overstepping boundaries but offering just the right amount of information.

6 – “Sam the Special-Treatment Seeker” – Seeking special treatment

Woman with trophy on her head

Run for the hills if you encounter clients who ask for special treatment. If they ask for special payment terms, reduced fees, or different treatment of any kind, think twice about taking them on as clients. Again, this is a tell-tale sign they won’t respect you down the line. Because they should know that they are not the only client, and should respect your boundaries. 

Here’s an example from

Yesterday, I met with some potential clients to discuss being involved in one of their projects. We discussed and agreed to a weekly rate for a 40-hour workweek when the following took place:

Client: The expectation is that you will donate 5-10 hours of your time per week to the project.

Me: I’m sorry, we just agreed on me being paid for 40 hours.

Client: That’s right, but we want you to work 45 – 50 hours a week, and we’ll pay you for 40.

Me: No, sorry. I will work the 40 hours stipulated but no more unless you pay for the extra.

Client: You see, this is why you millennials are never able to afford to buy property!

I still fail to see the connection between working for free and owning property.

What to do about it: Set up specific conditions for payments, pricing, and timelines in advance. Pre-work with contracts and legally binding documents can help a lot. 

7 – “The Over-promissory Pete” – Promising you a future of more work

Man with hands shacking on his head

Clients are the lifeblood of your small businesses. While the majority can be pretty great, some are terrible. In fact, some clients try to suck you into working with them by promising work in the future. They might lowball you to get you to sign or work with them, and with that low-ball, they promise future work to sweeten the deal. 

Point blank: don’t fall for it! 

Here’s an example from

What to do about it: While it’s great to hold onto this hope of future work, nothing is promised unless you have it in writing. Get any client promise in writing, with a dollar amount and time frame associated with it, and that will help hold them accountable in the future. 

8 – “The Houdini” – The client who goes dark on you

"The Houdini" - The client who goes dark on you

Some clients are overly available, while others disappear for days or weeks on end. Then they resurface again requesting something different or wanting something ASAP. 

This client type is terrible for one reason, and one reason only. Anytime you have a question (which you should), they are unavailable for an answer. This leads to confusion and potentially a project outcome they won’t love. 

Here’s an example from

I have a client who is notorious for “overworking” ideas. A project was coming close to completion, and it required them submitting their final artwork for printing:

Me: Are you certain this is the final version?

Client: Yes, it is

Me: You’re entirely happy with it, then?

Client: Yes – I am. This is it, print away!

Three months later – he calls me on the phone:

Client: DUDE! I’m looking at the prints now! It’s not the final version! I can’t believe you made this mistake!

Me: I’ll forward you the email where you said this was the final version and you were happy with it.

Client: Well, there’s clearly been a miscommunication. It looks like someone has used an old draft and sent it off.

Me: No, there definitely hasn’t been a miscommunication. You agreed right there that this was the final version. Twice.

Client: So, how much will you refund me for this miscommunication?

What to do about it: Hold clients to their end of the deal. At the get-go, tell them you need them responsive to your question. Otherwise, they are responsible for the risk of a different deliverable than they might have in mind.

9 – “Lack-of-Chemistry Cheryl ” – The personality mismatch/jerk

Woman with cancelled sign over her head

Do you have a spidey sense that a prospective client is going to be difficult to work with due to their personality? Is the person abrasive, disrespectful, sexist, racist or rude? Watch out for strong personality differences. 

Here’s an example from via

A conversation with a bad client

What to do about it: Business relationships are a lot like dating, believe it or not. You can’t force chemistry, and personality can’t be changed, so why try to force it?

If you can tell that you’re not going to get along with a specific personality, or worse, you can tell the person is going to be a pill to work with, avoid it. 

Setting Yourself Up For Success

Here are some processes, systems, and beliefs either protect you from poor clients or send you straight into their grasp.

  • Remember your WHY and remember that you (literally) train people how to treat you. Establish clear boundaries of how you want to be treated, and don’t tolerate poor behavior. 
  • Be clear about your expectations from the beginning. This can help to avoid future problems. 
  • Respect yourself and your time, and clients are more likely to do the same.
  • When there’s a problem, don’t be afraid to stand up for yourself. Letting the problem linger doesn’t help anyone!
  • Know when enough is enough. If you’re dealing with real problem clients, sometimes the healthiest thing to do is to let them go.
  • Remember, clients, are not your friends. You are bound to experience some hiccups in any working relationship, and that’s OK. Try to shield your emotions and keep work, just that—work. 

Wondering what to read next?

Here’s what we suggest:

10 Fast + Simple Strategies For Getting Clients

Bad clients are avoidable

With these red-flag clients, you should be able to spot them early—and reduce the chance of hardship and soul-sucking projects. Use your gut, too. If a client seems like a bad fit, they probably are. 

Take your self-worth off the table. If you find yourself compromising in ways you shouldn’t or are feeling unduly triggered by a client situation. Check to see if you’re seeing things clearly. Are you responding to the business event before you? Or reacting out of your ‘self-worth’ feeling threatened?

As you get further in your entrepreneurial journey, the choosier you can get. As you have good retainer clients, you can start saying “no” more. What a freeing feeling! 

Need more guidance when it comes to finding the perfect client? Use our guide to getting clients now.

Have some experience of dealing with downright bad clients? Share your hard-won wisdom in the comments section below. What have you learned? What are you doing differently these days?

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