It seems to be the season for toxic personalities to come out of the woodwork and be on full display.

This is happening currently in politics, as some of the most banal, hateful personalities dominate the news cycles and break apart long-standing structures (and relationships) on the national and international stage; it’s happening in families which has lead to massive disruption as certain individuals uplevel their boundaries and understanding of how to deal with, separate from, and process the impact of these types of personalities. And… it is happening in business: across the board it is the season for so many of my clients to uplevel their own leadership (and business boundaries) by dealing with these personalities head on.

Business imitates life.

I’ve always said “business is a numbers game.” And if you are interacting with a fair number of people through your business (whether hiring team, working with contractors, or engaging clients), you are likely to cross paths with one or more humans who can, in some ways, make your life miserable for a time. (Until you learn to deal appropriately with these types).

But how do you deal with problematic personalities?

They can cause really significant issues, legal liabilities, and ultimately costs to your business.

After decades of practicing law, as you might imagine, I’ve learned a thing or two about problematic personalities. They tend to find their way into disputes and often the legal system on a consistent basis.

Just remember: People (and personality) problems, can quickly become legal problems.

Here’s a brief list that may help you in not only avoiding these personalities, but navigating the murky waters of personality problems, once you do encounter them:

9 Steps for Dealing with Toxic Personalities (and the resulting costs) in Business

1. Learn to spot red flags. 

This is easier said than done, but it does get easier especially after you have encountered a few challenging personalities (in business or life). I recommend that you check out my article 8 Business Practices to Minimize Client Confusion and Decrease Disputes. (Especially the section on red flags).

You need to be able to spot red flags in any of your processes involving bringing new people in your business: your client enrollment process, your hiring or vendor selection process, your process for deciding what collaborative projects or partnerships you might put in place, etc.

2. Provide yourself with an “out.” 

This means that when you hire people, put them on a probationary period. Always. Whether working with a contractor or an employee. 

When you take on a new client, make sure you have a way to terminate the contract and relationship if it is not a fit. Thinking through scenarios where you may need to end a relationship well ahead of “schedule” will help you approach solutions proactively and ahead of problems even beginning.

3. Have appropriate contracts. 

So many times, these issues could be avoided or at least minimized with appropriately drafted contracts. Do not sign contracts provided by another party without the assistance of legal support. Just don’t. Over and over and over, I see people signing shitty contracts that are poorly drafted, one-sided, incomplete, or just inaccurate (not adequately addressing the scenario, defining the work, etc.). 

Whether it’s a client services agreement, a joint venture agreement, an independent contractor agreement, or any other agreement, make sure that you get legal support in creating a quality agreement that is a fit for your business.

4. Address problems early. 

This is a big one. So many humans are conflict-adverse. 

Which is normal. 

But this will not serve you in business. There are ways to learn to deal with potential conflicts, and the earlier you deal with them, the more you are likely to minimize the potential adverse impacts. 

I highly recommend that you get and read the book Difficult Conversations, by Sheila Heen, Bruce Patton, William Ury and Douglas Stone. 

The earlier you learn to say “this doesn’t work for me,” “That wasn’t what we agreed to,” “I’m seeing a problem here,”  the earlier you create an opportunity to either address it, or stop things (including potentially the relationship) from continuing. 

The longer you let things go (usually by telling yourself, “I think this will get better,” “maybe this will resolve on its own if I give it a little more time,” “I think he / she/ they will figure it out,”) the more invested people become, the wider the disconnect grows, and the bigger the problem gets. 

These problems in business generally NEVER resolve on their own!

5. Check references. 

Don’t hire on a whim. 

Always check references. 

Generally people that will cause problems in your business have caused problems in past businesses, with clients, with professionals or contractors they may hire, etc. 

One of the big red flags is a new hire (or client), talking about the problems they had with a past employer or client. The phrase “if everyone else is always the problem, maybe the problem isn’t everyone else” is appropriate here. And for some people in life, everyone else is always the problem! 

Avoid those types. 

You can’t always suss out the bad apples by checking references, but you can also ask the potential hire “when have you had a conflict or a problem with a past client or employer, and how did that resolve?” Victims will keep on victiming. (Yes, I made that into a verb). But it’s true: victims will keep on victiming and when you begin to spot this behavior you can be sure that people who have been past victims will make you the antagonist and will continue victiming. 

Avoid them at all costs. 

Research a potential new client whenever possible – there is so much information available online these days! Especially if it will be an engagement of any significant length, be sure to do a certain amount of due diligence in making sure the working relationship will be a fit.

6. Read a book on personality disorders. 

Like I mention above, I have always said “business is a numbers game” – and while it used to be estimated that 2-3% of the general population had personality disorders, the percentage of people with personality disorders has dramatically increased over time (or perhaps we are better at identifying them), and it is now estimated that between 9 – 15% of people have personality disorders!! 

This means that every 1 in 6 or 7, to every 1 in 10 people, have a personality problem (disorder) that will cause problems in relationship to other humans. 

For something to be labeled a disorder, it has to rise to the level of causing harm and dysfunction in that person’s life: thus, the pattern! Given these numbers, it is increasingly important that you learn to spot these patterns associated with a problematic human. 

The book Understanding Personality Disorders: an Introduction, by Duane L. Dobbert may be a good place to start – it can walk you through some of the warning signs that can be missed.

7. Develop a RELATIONSHIP with qualified legal counsel. If you find yourself in a pinch, you don’t want to have to take the time to find and select legal counsel (which can take some time – while it is an excellent investment in your business, it is rarely quick – just like finding the right doctor for your ailment can take some time).

But if you have a pre-established relationship with legal counsel, you can get assistance addressing these scenarios when they require immediate attention – and it is often the case that there is a boiling point where these scenarios do require immediate attention, and often skillful legal help.  

8. Pay particular attention to information / training / rules on dealing with narcissistic personalities. These can be the most problematic, because nothing is ever “their problem.” Ever.

And they feel extremely entitled to [fill in the blank: bully you, attempt coercion and manipulation, take your business, your clients, your time, your life energy …. you get the pattern.] These types tend not to be rational humans that respond in rational ways to rational feedback or even rational legal influence. And in my 23 years legal experience, it is nearly always the case that “like attracts like.” Meaning that humans challenged in the personality (and often ethics) department select counsel that are also challenged in similar ways. 

“The most unreasonable party drives the cost of litigation.”  – Heather Pearce Campbell

This is another of my quotes that I have shared with clients for decades. (I got my legal start in litigation). This can make things very expensive for you if you are up against someone who is not only unethical, but irrational. 

Which is why “red-flag spotting” becomes SUPER important! 

9. Ultimately, all of the points above are about learning to properly create and hold healthy boundaries in your business. Sometimes the legal system or legal support is required to enforce those boundaries (or create then in the first place). But it’s still about boundaries. And when someone like me has to step into the fray and deal with a mess that might have been avoided by taking some of the steps above, it is always more costly and time-consuming than you think it will be, and it is certainly more costly and time-consuming than many of the alternatives you could have implemented proactively. 

The number of problematic clients and independent contractors that I have had to help clients deal with recently is astounding. Contractors who (with many of the red flags above) feel entitled to a client’s business, a client’s earnings, a client’s life-force energy …. These types will take and take and take. 

Or clients who cross boundaries or demand exceptional treatment, or don’t live up to their side of the bargain, or, or, or …

And they all have a pattern of being a past victim. All of them. 

It has cost one of my clients over $60,000 in legal fees (and we are not even to the first actual hearing!) along with a big chunk of her business. 

It has cost another of my clients months of his life, over $40,000 in legal fees, and has required a significant period of rebuilding. 

It has cost another of my clients thousands in legal fees, and a lot of wasted time and energy dealing with putting up new boundaries, and holding the line.  

Another scenario, which is completely frivolous, has cost a client tens of thousands of dollars, a bunch of wasted time between he and his team, and also, is still not resolved. 

These scenarios have costed all of these clients (and others of my clients) many sleepless nights. 

Victims will keep on victiming. 

If you want to avoid your own sleepless nights:

Get help putting business policies in place, creating contracts to protect your services and your business, protecting your I.P., and as early as possible get strategic assistance with a developing and potentially problematic scenario. For any of these, reach out and schedule a strategic consultation to proactively address these, or other, items that should be on your list. We can cover a lot in our time together.

DISCLAIMER: THE INFORMATION PROVIDED IN THIS POST MAY CONTAIN LEGAL INFORMATION, BUT DOES NOT CONSTITUTE LEGAL ADVICE. NO RELATIONSHIP, INCLUDING ATTORNEY-CLIENT RELATIONSHIP, HAS BEEN FORMED AS A RESULT OF THIS POST. YOU ARE ADVISED TO SEEK THE ADVICE OF AN ATTORNEY LICENSED IN YOUR STATE IF YOU HAVE ANY QUESTIONS.

© 2025 Heather Pearce Campbell, The Legal Website Warrior®