Workplace Strategies Watercooler 2026: Managing, Documenting, and Surviving the Challenging Employee

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Rob Niccolini: We’re here at Workplace Strategies in Austin, Texas. We just finished our session entitled, I Knew You Were Trouble: Managing, Documenting, and Surviving the Challenging Employee. My name’s Rob Niccolini, I’m a shareholder with Ogletree Deakins in the Washington D.C. office, and an employment litigator who has a fair number of jury trials under my belt. And my co-presenter is?

Anne Larson: Anne Larson. I’m a shareholder in the Chicago office. I’m the firm’s biometric privacy guru. I focus on high stakes litigation, such as Biometric Information Privacy Act, otherwise known as BIPA class actions, and C-suite shakeups, executive misconduct and terminations. I recently handled the removal of a publicly traded CEO and threatened claims by a former general counsel and a former COO.

Rob Niccolini: So, we’re going to be talking today about seven different archetypes of challenging employees. Basically, what are the types of challenging employees and some specific suggestions for managing them? And then Anne and I are going to offer some general management and discipline tips, and also some litigation considerations. So, let’s go ahead and jump in and let’s start with the first challenging employee archetype, which is on everybody’s mind right now. Anne?

Anne Larson: Well, first of all, everyone, I want to know, how many of you have received a complaint or a request in the last year with possible AI use? We asked this polling question today at Workplace Strategies, and 84% of the room said yes, 16% said no. So, everyone, welcome to a brave new world, the world of the AI adopter. HR is receiving more and more internal complaints and demands that are well written, polished, and cite more legal authority than a first-year law exam. The AI adopter has discovered ChatGPT, Copilot, and Claude. These AI tools produce lengthy demands and complaints that appear to have been drafted by a lawyer. They use phrases like, “Hostile work environment,” list specific statutes by name, and cite case law. HR and legal read them and say, “Wow.”

This is the new normal, let’s talk about how you spot it. Clues include citing to applicable law by someone with no legal training, unusually well organized and structured complaints, writing with perfect grammar and spelling, but somehow it just doesn’t sound like the way this employee speaks. The key point here is whether or not AI was used, is really irrelevant to how you handle the internal complaint. There’s nothing illegal about using AI to draft a better internal complaint or a better pro se lawsuit. So punishing an employee for using AI or demeaning them, or simply ignoring their complaint or denying it without proper investigation, that’s only going to get you into trouble. It might actually be viewed as retaliation. So, AI generated complaints still need to be investigated and addressed just like any other complaint.

So, how do you manage it? First, don’t overreact to legal jargon. Focus on the actual workplace issue being raised, get to the core, the human core of the problem. Second, request specifics. AI content often uses generalizations without dates and facts. Third, meet face-to-face with the complainant, ask questions and get the facts, remove AI from the equation. One practical takeaway is that, think about these AI assisted internal complaints as a preview of what’s going to soon follow with litigation. AI is fueling pro se lawsuits. Courts are seeing better written, better structured complaints from pro se’s; although they may contain hallucinated case citations. So, the bottom line with where this is all going with AI is another reason to shore up your documentation of problem employees before they file in court.

Rob Niccolini: So, I’m going to talk about our next two archetypes of challenging employees, the bully and the gatekeeper. Let’s talk about bullies first. And let me be clear, true bullying that rises to the level of a hostile work environment has no place in the workplace whatsoever and requires immediate investigation, and quite frankly, discipline, up to and including termination. But when we’re talking about the bully as a challenging employee, we’re really talking about someone who engages in improperly dominating behavior who is pushing around their coworkers, not physically, but often verbally or emotionally. And to the extent that the conduct they’re engaging in is short of actual hostile work environment harassment, it’s still unacceptable and it’s still something that we need to address. Bullies are often driven by ego or insecurity, and the fact that they’re driven by ego or insecurity is something that human resources needs to recognize in terms of dealing with them, in terms of addressing what is the root cause of their behavior.

Ultimately, the best way for dealing with bullies in our experience is directly confronting and calling out their behavior. You need to document specific interactions and concrete examples of bullying behavior. You need to make it clear directly to the employee that they’re unacceptable. And you need to provide clear documentation that if the behavior continues, it’s going to result in discipline, up to and including termination.

The gatekeeper is in some ways a subset of the bully, but very different. Gatekeepers tend to be long-term or veteran employees. They’ve been around a long time, and they have a lot of information. They have a lot of knowledge usually in a niche area. The problem is, those gatekeepers, first, they tend to hoard their information. They actually get their legitimacy and their power in the workplace from the fact that they are the experts in their area. And secondly, because they know a lot about their area, they tend to be very, very change adverse. They don’t like change, they reject change, they fight against change. And in fact, change can challenge their identity and question their underlying power, which is why they kick back so hard at it.
To deal with the gatekeeper, first of all, you need to have an honest discussion about romanticizing the past, about always thinking that the good old days were always better. In some cases, they were, but in a lot of cases they really weren’t, and that needs to be addressed and confronted directly. You also need an honest assessment with the gatekeeper about what works, what we need to continue in our workplace, but also what doesn’t work. This can also involve changes in technology and rejections by the gatekeeper of those changes. And ultimately, we have to recognize that our companies don’t want to lose the experience and knowledge of our gatekeepers, but we also can’t allow them to use that experience and knowledge in a way that essentially constitutes bullying and that prevents us from growing as a company.
So, let’s move on to our next archetype, Anne.

Anne Larson: The next toxic employee we’re talking about is the naysayer. The naysayer has never heard of an idea or program that they cannot shoot down or undermine. Their negativity, complaining, and lack of buy-in pulls others down. A variant that I love is the silent resistor, the master of enthusiastic agreement, followed by devastating inaction. The naysayer undermines company progress by fomenting dissatisfaction and resistance to new ideas. So, how do we manage the naysayer? You need to be upfront and tell them that their resistance to new ideas and programs will no longer be tolerated. You also need to document deadlines and have checkpoints along the way to ensure the work gets done, because their favorite thing is to not do work, to not do their job. So the naysayer needs to ultimately understand that if they fail to meet their goals and deadlines, they’re going to be performance managed out and discharged.

Rob Niccolini: So, I’m going to talk about two more challenging employee archetypes now that again are a little bit related. The first is what we’ve termed the victim, and the second is what we’ve termed the social butterfly.

So first, the victim. Anyone who’s worked in a company, whether in human resources or management, knows the victim and has dealt with the victim. The victim is the person, the employee, who has an excuse for everything. It is never their fault; it is always the fault of someone or something else. The victim uses blaming others as a defense and also as a shield. Nothing is ever the fault of the victim and they accept no personal responsibility for anything that’s going wrong, any goals that aren’t met, any quotas that aren’t met as well.

In order to deal with and manage the victim, you really have to focus on personal agency, the personal agency of the victim employee. You need to be spotlighting future solutions and very much not focusing on past problems. You ultimately need to find a way to break what we like to call the excuse cycle. You need to address with the victim the things that they aren’t doing properly, the performance goals that they aren’t meeting. And to the extent that the victim is trying to turn it back to say why it’s not their fault, why what’s happened in the past justifies it, you need to basically say, “We’re not here to talk about the past. We’re here to talk about the future. We’re here to talk about moving forward in a productive manner,” and go ahead and set those goals very, very specifically.

The social butterfly is not a subset of the victim, but it’s a little bit related to the victim. The social butterfly values personal relationships and interactions far higher than they value achievement or performance. The social butterfly is the person in the workplace who loves the gossip. They’re the person who is almost never at their desk but they’re always in the break room, at the water cooler, out getting coffee, and more importantly, out at other people’s desks talking about what happened. They love gossip, they love to talk about things in the workplace, really, anything in the workplace, other than actually getting the work done.

To deal with the social butterfly can be very difficult because the first thing you have to do is you have to monitor their behavior. You have to be able to say to the social butterfly and confront the social butterfly the amount of time that they’re spending working versus the amount of time that they’re spending talking to other people. The amount of time that they’re spending engaging in interactions that really don’t advance the ball in the workplace. Supervisors hate the social butterfly. Supervisors have to spend so much time monitoring the social butterfly and making sure they’re doing their job, that the supervisors don’t have time to do their own jobs. We have found that sometimes the monitoring is most effective therefore if you use multiple supervisors, if everyone’s keeping their eye on the social butterfly and working collaboratively so no one person is responsible for the monitoring.

And once you’ve engaged in monitoring, once you can establish the amount of time the social butterfly is spending in non-work related activities, you need to confront them with that. You need to lay out for them how they’re wasting their time and you need to specify where they need to be and what they need to be doing and what they shouldn’t be doing as well. It takes persistence and patience to deal with the social butterfly, but if you let them get away with it, you’re losing massive amounts of productivity.

Anne Larson: The underperformer is the most challenging and complicated of our bad employees. Their performance is a rollercoaster. One day they miss every deadline, the next day they hit every deadline. They meet expectations just enough to make you second guess whether a PIP is really necessary. Their unpredictability keeps you constantly guessing.

So, how do you manage the underperformer? We recommend that you review past projects to identify what was done well and what was not to establish a baseline. From there, set standards moving forward with a checklist or guardrail approach to ensure job requirements are consistently met. Now, if that’s not working, you can move to a PIP. Use a PIP to set expectations and ensure that metrics are met. The PIP can either be used to improve performance or to document the performance reasons for termination. And while you’re in the PIP, schedule regular check-ins. Recognize progress where it occurs. Specifically tell the employee what they’ve done well, provide examples of it, but also say what they’re still not doing that is required by the PIP, and tell them specifically what better needs to be done. But if performance remains inconsistent and you don’t think they’ve met the PIP, then stop the rollercoaster and just be done.

Rob Niccolini: So, that’s our summary of the seven different archetypes of challenging employees. Again, them being the AI adopter, the bully, the gatekeeper, the naysayer, the victim, the social butterfly, and the underperformer. Our suggestions for dealing with all of them, we’ve given you some specifics, but it all comes down to ultimately, performance management. So, let’s talk a little bit about some basic performance management tips.

Let’s start by recognizing that addressing performance is never fun. No one likes to do this, but you can’t beat around the bush. Performance issues don’t resolve on their own. They only get worse if you allow them to fester. And so the first tip is, you really do have to bite the bullet and get down to it. As you address performance, the second tip is that you always need to focus on the problem, not on the person. You don’t want to make this personal. You want to make it about improving performance and improving productivity in the workplace. So, you focus on the problematic behavior, not the personality. As you address performance, the next tip is don’t exaggerate or generalize, but use concrete details, examples, and goals whenever possible. Having a discussion with someone about personality traits is only going to result in them being defensive and not open to change. If, however, you’re addressing things in a concrete manner that it’s harder for them to refute, it just makes it easier to come up with a path forward.

And in terms of that path forward, very often you’re talking about disciplinary write-ups and ultimately a PIP, a performance improvement plan. Performance improvement plans are generally going to be 30, 45, or 60 days. We don’t generally recommend going much beyond 60 days. And it’s essentially a collection of goals laid out in writing for what the employee needs to do over that time period to improve their performance and to retain their employment. As I said, a PIP should always be reduced to writing. It’s best if it’s signed off by the employee, but it needs to, as best you can, enunciate concrete goals for the employee to either meet or to show that they haven’t met and termination will be necessary.

Anne, you want to talk about the most important thing related to performance improvement?

Anne Larson: Sure. The old saying in real estate is, “Location, location, location.” In employment litigation, it’s what, Rob?

Rob Niccolini: Document, document, document.

Anne Larson: All right. First, standardize performance reviews and disciplinary write-ups. Make sure your forms show that performance is uniformly analyzed and that policies are uniformly applied. Second, make sure the employee knows the expectations for the job and the consequences of poor performance or misconduct. Disciplinary writeup should have an acknowledgement signature, and if the employee refuses to sign, write in the form, “Employee refuses to sign.” Put your initials, your name, and the date. Keep in mind that the EEOC is very clear on this, that if there is no performance documentation in writing signed by the employee, their view is, it never happened. Third, keep it factual, no gossip, no opinions, no subjective conclusions. Gossip is always unreliable or can be unreliable, so you need to investigate to confirm or refute it with firsthand accounts. You need to support write-ups with specific examples.

For example, I had an incident in the last year where a client had a driver who refused to sign a BIPA consent form. That’s Biometric Information Privacy Act. That statute requires informed consent, that you tell them what kind of biometric equipment they’re being used and they consent to use. He said it caused him emotional distress. So, HR gave him an ADA form to give his therapist to discuss whether or not he was going to request any kind of proposed accommodation. His therapist read it, told him it was no big deal and to sign it. But the bottom line here is that this particular employee was upset that the company just didn’t agree with his position and allow him to get out of signing this BIPA consent. So he leaned into both the head of HR and his supervisor, puffed up his upper body, took his headset off, and then snapped it in his hands in front of them.

So, the bottom line here was that they needed to put him on a final written warning for that conduct and they needed to take those kind of specific facts and examples and put that in the actual final written warning, not just say that the employee engaged in unprofessional conduct and had violated their code of conduct.

Fourth, preserve the best evidence. A photo of a sledgehammer is not as good as the actual sledgehammer. It has much more emotional impact and meaning. Fifth, interview witnesses promptly. Memories fade, stories change, and reluctant witnesses may leave for other employment. And if you figure out that a witness’s testimony is key to your defense, you may actually want to take the lead in drafting a focus statement for their signature. It’s going to be a lot better than the rather meandering statements I often read.
And if you’re further concerned that this employee witness may leave and their testimony is going to be vital to the defense of a charge or a lawsuit, go the affidavit route, and then you draft a good concise focused affidavit after listening very carefully to the witness’s testimony. Have the employee review the affidavit for accuracy and strategize on whether to sign it now or hold the signature to a later date. Because if you have it signed now and you’re in or about to go into litigation, it’s going to have to be produced pretty promptly in written discovery. And if it’s not signed, what you could do is wait and see how the facts play out, see whether or not you need to add further facts or explain facts further in the affidavit before actually signing it. But if you truly think that the witness’s threat in terms of moving on to other employment, it may just be best to get the signature on that affidavit, so you’ve got that testimony nailed down.

Rob Niccolini: So, we’re going to end with a few litigation considerations related to challenging employees and documentation tips. Obviously, the goal is to address performance issues, to address challenging employees, and to improve their performance. But very often, if that’s not possible and we have to terminate them, we can be looking at litigation. And the question is, what can we do to put ourselves in the best possible position to defend ourselves and to defend our company? I’ve been very lucky to try a lot of cases to verdict before juries, and what I’ve always told my clients are the same thing. A jury doesn’t care about legal technicalities. What a jury cares about is, was the employee treated fairly? If the jury believes the employee was treated fairly, that is a case that the employer is going to win. If the jury feels the employee was treated unfairly, then we’re really behind the eight-ball and we’re really fighting an uphill battle in terms of convincing the jury that we should win.

To back that up a little bit, a jury poll, which I find both fascinating and a little bit scary, provides some stark numbers. Whether or not the best evidence of employees’ work performance is the performance evaluation, jurors, 61% say it is. So if you’re looking at a termination and you don’t have any sort of performance evaluations or you don’t have any performance evaluations that show problems, then that jury is going to be very suspicious about the basis for the termination.
Secondly, a question was asked of jurors, is the company negligent if it does not properly document performance problems? A whopping 91% of jurors said that the company is negligent. So, documenting performance problems is not only a best practice, it’s a necessary practice if you’re planning to litigate these cases.

And finally, question asked of jurors, must all companies give employees fair warning before termination? 74% of jurors said yes. Even though legally we’re not required to give any sort of due process rights, we’re not required to give prior notice of termination or the reason for a termination, most jurors believe that if we don’t give fair warning, then we’ve done something wrong.

Anne Larson: Let’s conclude with talking about basic discharge concepts. Any decision to discharge is going to be placed under a microscope, so you need to ask these key questions. Does the performance issue or the offense merit termination? Proportionality matters. So, you need to think through, is some lesser discipline more appropriate, given this employee’s tenure and overall record? Next, is there sufficient evidence to support a termination? You need documentation that demonstrates the facts underlying the decision and what rule or policy was violated. And here’s what I think is very important from a company’s perspective that they sometimes forget to include, which really explains to the EEOC, a judge or jury why this termination was merited. Explain the consequences to the company, why the performance problem or the misconduct, why it had an impact for the company and this discharge was necessary.

Next, did you put your expectations for the employee in writing? Did you inform the employee in writing regarding the disciplinary consequences of his conduct? Was there a fair investigation? Was the investigation thorough and conducted without bias? And then the next is probably the most important question from a legal standpoint and also from the EEOC’s perspective. Has the company treated similarly situated employees outside the protected class the same? If not, that inconsistency is going to give a plaintiff’s attorney his best evidence against you and your company. So, if you answered yes to all these questions, I think you’re in a great position to defend any challenge to your termination decision. And if not, then it’s a good idea to look a little harder at your decision and what documentation you have supporting it.

And on final point about AI, you may want to use it as much as your employees seem to be using it now against you. So feed these questions, your answer and the documentation, and see how AI responds. Is it good enough or do you need more? What’s the answer?

Rob Niccolini: So, hopefully today we’ve given you some helpful and concrete tips on identifying challenging employees, on managing challenging employees and on why documenting performance is really so important not only to improving performance, but also to defending the company if litigation happens afterwards. So, thank you very much for listening and have a great day.

Anne Larson: Thank you.

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