Firing My First Nightmare Client

There is nothing like winning your seven-figure dream client. You pursued them over time, you competed against the best, and you won. Then you delivered the results that you promised.

It’s perfect.

Until you find out that you dream client is really a nightmare client. Over time, you discover that your big new client is very low on the business relationships maturity continuum. They are adversarial, and sometimes a lot worse.

Dreams Turn to Nightmares

I had been selling for a good number of years before I ran into my first real nightmare client.

I had called on and won major accounts, all of who had been very demanding and very high on the business relationships maturity continuum. My major accounts had always treated me as a valued partner. I was invited into their internal strategy and planning meetings. For more than half of these clients, I had an employee badge and I could walk right into the building whenever I needed to with full access. I was treated like a crucial part of the team.

I was spoiled. When we had business challenges or issues, we discussed them. No issue was taboo, and there were no sacred cows. When either of us needed something we talked about it. No matter what the issue.

Enter the nightmare.

We had been working with the new dream client for months. We had delivered on every promise. We were doing good work.

But we weren’t being paid, among other issues.

As the sales manager, I was responsible for the client. I was responsible for discussing the payment issues. As it happened, I was at their facility when I ran into the person responsible for paying our bills. I asked her when we would receive payment. She told me that she didn’t know. I told her how much we were owed, that we had spent hundreds of thousands of dollars serving them, and we needed a little help getting paid. I thanked her for her help, and I left, thinking nothing more of it.

A few hours later, the main contact at the new nightmare client calls my cellular phone. He said, almost hyperventilating: “Who the [profanity deleted] do you think you are? You don’t ask my people for payment! We’ll pay you when we pay you!”

Fortunately, I was calm and centered. I replied: “I am afraid that’s a bit of a problem for us. We’ve already spent a lot of money, and we need you to pay within terms so we can continue to provide you services. How about we get together and see what we can work out?”

That wasn’t the answer he was looking for. He was looking for me to be a subservient and intimidated invertebrate. He was looking for someone he could bully. He literally screamed: “Do you know how much [profanity deleted] money we are spending with you? I’ll take my [profanity deleted] business and give it someone else!”

Surprisingly, I was still calm. I said: “I understand your decision.” There was an uncomfortably long silence. Incredulous, he said: “You would really fire a three-and-half-million client?” I answered: “Yes, I would.”

And I did.

Leadership and Money

It wasn’t only the money. That was simply the straw that broke the camel’s back. He was adversarial. His whole staff was adversarial. They were unnecessarily rough on my staff. Some of his male employees made improper and crude remarks in front of my female employees. Their whole culture was misaligned with our culture. If we couldn’t work together through the issues we had, we were never going to be able to work well together over the long term. It was going to end badly one way or another, and I could think of no reason to postpone it.

I have found the real tests of leadership in business often have something to do with doing what is right when it conflicts with making money. That’s when who you are as a leader is really tested.

I called the principals of my company to report that I had just fired our relatively new major account. There were no questions asked. They said: “Good call. We support the decision.”

Money isn’t everything. There are a lot of things that are far more important. Sales can and should be meaningful work. You can and should make a difference for your company and your clients. There is no reason on earth to spend time with hateful, mean, adversarial people that drain the life, the love, and the meaning from your work—money is especially not a reason.

A few years later, the nightmare client was sent to prison for embezzling money from a group of investors.


What are the signs that your client is a nightmare client?

What does it cost you in emotional energy to serve that client?

Why is it dangerous to serve nightmare clients?

What makes your work meaningful to you? Is what you do rewarding in ways outside of monetary rewards?

Do you have a story about firing a nightmare client?

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  • Mark Johnson

    FANTASTIC post AI! I will be linking this to all my reps.

    I think many of us get so enamored by the sales numbers and euphoria of winning the “dream client” that we often forget about the value of philosophical alignment and bilateral respect. And clearly, in some cases, so does the “dream client”.

    • S. Anthony Iannarino

      Thanks, Mark! Alignment and respect. Sounds right to me. 

  • Jeannie Walters

    Great post! It’s painful when the cultures are misaligned. It’s not worth it. Life is so much better when you have clients who respect your team and vice versa. 

    • S. Anthony Iannarino

      More on respect. I agree, Jeannie! Thanks for sharing your comments here. 


  • Scott Thompson

    Outstanding post. This one is must-reading.

    It’s important to have a framework of standards for our work. This framework should be adaptive and supple–like bamboo. But there should always be a line that won’t be crossed. Well written.

    • S. Anthony Iannarino

      Thanks, Scott. I appreciate it!


  • Anonymous

    Great article, I remember one client that I should have fired but did not. This experience actually changed the way my firm does business. It was an unending nightmare.  I have gone on to fire several clients. My advice to all fledgling consultants is to have the courage to do what might seem like the unthinkable.Letting some clients go may be the best way to move forward, it certainly was in my case. Thanks again for the article.

    • S. Anthony Iannarino

      Thanks you for sharing your experience. It will valuable to others, I am certain. 


  • Lawrence Fox

    Yes, I have fired clients before, and I’ll probably fire some more in the future.

    There is nothing worse than a relationship (of any kind) that pulls you down, puts you off work and makes it difficult for you to deliver your best. If you find that you dread going to that client, reading her emails, or even just thinking about the next step in the process, it’s time to move on. Life is too short to put yourself through that kind of pain and aggravation.

    Yes, it’s a very difficult decision to make, especially for new consultants or anyone who has to do it for the first time. But I’ve always found it a liberating experience, even when my cash flow has been affected.

    One of the best things about working for yourself is that you get to choose WHO to work with. Sometimes, you find you’ve made a bad choice. Firing a client is the outcome of either event.

    OTOH, there are some clients that you never want to stop doing business with, like the ones that made you welcome and a part of the family.

    • S. Anthony Iannarino

      I agree, Lawrence. One of the most important decisions we can make as salespeople, businesspeople, and entrepreneurs is who we work with. 


  • Jerry E Durant

    I wonder how many clients are reading this and looking in the mirror?

    • S. Anthony Iannarino

      I would suggest that the answer is not many. This is a sales blog, after all. But, it’s an interesting question. Many of our clients have their own nightmare clients, and lots of my clients have shared similar experiences with me. 

  • Terry Del Percio

    Great story. Great sense of self. Great lesson. I hope many people who behave like this nightmare client recognize themselves and go to bully counseling. For sure people who behave like this, behave similarly in other circumstances. There is enough stress in the world without that.

    • S. Anthony Iannarino

      Thanks, Terry. I didn’t write this post as advice for those that behave badly. I wrote it for salespeople who believe they have to live with a nightmare client. As it turns out, lots of our clients have nightmare clients of their own and are suffering through some of the same challenges we face.