I freelance as a kind of corporate communications troubleshooter, taking on projects for corporates who need specialist help.  I've been working on a program which is six months late, part of which entails a new logo design and associated collateral. After just a few weeks I can see why the project is so late, as the logo design alone goes back and forth with no clear direction and continued last-minute changes from the client. 

Me: Here are the final-final logo designs as discussed. 

Client: Great! By the way, I want them to be editable so I can make changes in future. 

Me: That's...  not very usual. The logo should be consistent so that we build up recognition and people value it and the program. 

Client: But it may not work in all contexts. 

Me: Well if it needs updating later, we can ask the agency to do a refresh. 

Client: They charge too much. I just want to be able to do it myself. 

Me: They're the specialists. Design work should be handled properly so the results are fully-realized and high-quality.  And they have the specialist software to edit the files. 

Client: Don't worry... I'm getting Photoshop installed on my laptop.  Just be sure to get the original files from the designers.  

Me: Errmmmm...

I have a media consultancy and have worked on many small and medium-sized projects. Clients give me their objectives, budget, etc., and I create an entire go-to-market strategy including media strategy, budgets, etc. 

I was contacted by this guy who had spent a dozen years in private aviation, then decided to "build an airline" to compete regionally. He complained that he had approached several big shops in NY but that they wanted too much money upfront just to talk. We agreed to meet for an hour in my office to see if there was a future there.

My first red flag went up when the guy shows up in shorts and told me he had walked from his hotel (a good 20 blocks away). So, OK, I decided, maybe a bit unusual, but OK.

We spoke for about 90 minutes, and everything he said sounded normal. So I relaxed my red-flag radar a bit. After all, Florida is full of unusual people with money.

He asked for a second meeting, but we could not communicate via email.

Client: My friends at the NSA told me that all my emails were being read by American and Delta.

Second red flag. Still, despite myself, we arranged the second meeting. When we did meet he started questioning me more aggressively.

Client: What's going on the website? What influencer platform will you use? Who do I hire to create an in-house agency? 

Me: Great questions, but everything you're asking is exactly what you'd pay me to deliver. I don't have answers yet because that will take a bit of research, and even if I did have them I would need a contract before I give you those answers.

When I said this he looked at me for a second, stood up, turned around and left without saying a word.

My only contribution to this site: if your red flag radar turns on, listen to it. Don't do anything out of desperation.

Not a client from hell, but certainly a contractor from hell.

We received a lighting plan for a restaurant we were designing, and it was based on a six-month old plan that didn't match any of the other drawings, details, or renderings. As we were preparing to start construction, we were understandably concerned. It's important to note that in order to keep track of the design process we place the date at the end of all our file names.

Me: It looks like this plan is very out of date. What date is on the plan?

Contractor: This is the plan we were given.

Me: Understood, but this design doesn't align with anything we've discussed. What is the date on the plan?

Contractor: March 15th.

Me: ...it's October now. The updated plan has been available since September and is noted in the file with the date.

Contractor: We can't be expected to keep track of what plans are the most current.

Internal screaming forever.

Client: Hi, how much does a brochure cost to print?

Me: Before I answer, I just need a bit more information, such as size, pages and how many...

Client: Well, if you want to be that difficult I'll just find someone else...

I was hired by a large "megachurch" to come on staff and design and maintain a new website. I was instructed on my job duties and "to only work on the website" even though I had many other skills as an illustrator and designer.

Client: Focusing on this one area would allow me to excel in that task. We've found that giving too many other roles to people stretches them to thin.

So I designed and built the site in record time, and once it was up running well, I organized several ways to maintain and upkeep, as well as expanding some of the functions of the site, Everyone was very happy.

A few months later, I was visited by my supervisor and given my two weeks notice. They liked my work, but they'd recently hired a video production guy who promised he could "do it all": video, audio, web design, graphic design, stage lighting... he was even certified in IT.

In all they ended up getting rid of me, the audio engineer, the video director, the other graphic designer and even canceled their contract with an IT maintenance company, replacing them all with this one guy!

They stopped updating the site I built- the new guy promised to build a great one from scratch, when he could find the time. They finally got a new website... 8 months later... and they ended up firing the guy a little later on because he was "stretched too thin to get any of the tasks done at a high level."

I worked for a local screen printer for a total of 5 years. In the first 2 years, they were a start up and it was just the owners who were a husband and wife team, myself and a screen printer. The screen printer was in another warehouse 1/2 a mile away, so he had to use his car to get films from me and his cell phone to call if there were issues. 

I did the graphics but was also expected to do sales even though I was clear that my math skills were severely lacking, not to mention that the constant interruptions make doing graphics very difficult. The owners showed up until after noon, but would act like we should feel sorry for them because they had to "work late" to 8 PM. In other words, a regular 8 hour day. 

The owner once got P.O.'ed about the time it was taking me to do a complex custom project and insisted he could do it in 30 minutes because he took a Community College Course in Illustrator. I invited him to educate me, as in my  20 plus years as a designer, I hadn't learned that trick yet. Thirty minutes later he threw the mouse and stomped out, going home for the day to nurse his bruised ego.

They made promises of raises as the company grew and benefits, none of which I ever got. After year two, I finally asked for a raise from $12 per hour. With my experience, I felt I deserved better as the company had "grown." Instead, I was fired because the screen printer and his wife (who started working for the company the previous year) walked out the day before and started their own printshop. We were friends, so I got fired.

Gotta love a Right-To-Work state.

Two years later they came back to me trying to hire me again. 

I was recently discussing a digital marketing project with a prospective client. We were scheduled for about a 30-minute meeting. He came across as very defensive and hostile, which raised some red flags for me. However, I didn't want to get up and walk away.

The client's website was very basic. He had very little digital marketing done for his brand, even though his business had many locations. 

Client: Now, I've heard a number of proposals from you marketing people, so just let me know what you have to offer.

He was already very negative. I described some of my knowledge and services in a friendly and informative manner.

Client: Well, would you be able to update the website? Provide content? Partner with others? I'm not naive to this you know. 

He hissed that last part.

I briefly explained more about my skills and experience, and how I could help or partner with others. This included website updates, writing articles, and more.

Client: (sneering)I had a small agency working on my website, but they have other clients, so they couldn't help me as much as I would have liked. Well, how would you create videos, how would you get people's permission? What about e-mail campaigns? How would that work? 

I was starting to grow weary of explaining the entire realm of digital marketing to this client in a span of 30 minutes.

Client: What about content? How would you write that? If I were to build out a team, who should I hire for the team? How about photos? What about partnerships? What's PPC? How about SEO? You know, our competitors, they're all about the money. We actually care. What would your budget be for working on various projects?

I also remembered that I saw on some reviews of his business that some people commented that management was all about the money, which I thought was interesting given his criticism of his competitors.

The guy's face became more and more red with tension and anger as he asked more and more questions. I tried to keep things basic and let him know some options. Red face; red flag.

Working with this guy would be a nightmare. The client was having a very hard time grasping everything I was talking about and was ready to take that frustration out on me.  That told me everything I needed to know.

I work in a Help Desk center for a university, we typically get calls from students, but sometimes we get calls from Faculty and Staff. Today, the same person had called over a dozen times, and it was only noon.

I came in, and then they called. I gave my usual introduction.

Client: I can't access my voicemail on my office phone!

Me: Okay, are you getting any error message?

Client: Yeah, I'm entering the default passcode, but it's saying I need to use my ID and hit pound.

Me: ...And have you tried that?

Client: No, why would I?

Me: Give it a try!

After this, she just hangs up then calls back about an hour later.

Client: Now the phone is locked up! What the hell did you do?!

Me: I can't access the phone in any way, ma'am, did you enter your ID and hit pound?

Client: No, I entered the default passcode and then it locked up!

Me: Okay, I'll send a tech out, but I'll need to verify some information first.

I ask her for the usual, DoB, ID number, Room number, etc.

Client: Why the hell do you need that? Just fix my phone, asshole, I'm not telling some asshole my personal information.

I could see all her information already, I just had to ask to verify. After a bit of a difficult back and forth, she gave me her office number and hung up angrily. The technician went to the room and she wasn't even there, having gone home early. He checked, though - her phone wasn't locked.

Later, her husband, another faculty member, called, furious that someone had called his wife "a bitch" on the phone. I hadn't. 

Luckily, we keep a transcript of all support calls, so my boss informed him that we could sit down and listen to the conversation if he was concerned.

He never came in. 

I was talking with a potential client about her wanting to hire a marketer. I asked her questions about why she was hiring.

Me:  So you want to hire a marketer. Great. Why now? What are you trying to achieve?

Client: I'm the General Manager of this luxury events facility. There have already been millions of dollars invested in it, but I need help marketing it. 

Me: Wow! Congratulations. That's exciting.

Client: Yeah! I've been involved in some previous projects that failed, so I'm so glad this one is working out.  

She proceeded to interrogate me in the interview and she came across as quite arrogant and condescending. The pay wasn't great, and she needed a lot of help understanding what she wanted.

Client: I have had some trouble with freelancers before, but I'm finally at a point where I'm ready to hire someone to manage my marketing plans.

Me: ...Ok.

Client: If I were to call your references, what would they say about you? What kinds of criticisms?

Me: Well, I don't know about criticisms. I think they would say that they enjoyed working with me and wished I had stayed longer with them.

Client: What else? 

Me: Uh... 

Afterward, I re-visited the website for her business, and it looked like it was created on a shoestring budget. It looked very haphazard. Remember, there were "millions" invested in the facility, but very little money in the website. Red flag. 

I didn't want to have to be the one to tell her that she would need to overhaul her website, and I certainly didn't want to be in charge of holding her hand through it.