Every workplace has that employee—the one who seems to thrive on chaos, misunderstandings, or just an inexplicable desire to make every Monday feel like a full-blown crisis. In 2025, with hybrid work models, generative AI, and ever-evolving workplace norms, handling a difficult employee has become less about stern talks in corner offices and more about strategy, empathy, and yes, a touch of humor.
Here’s your guide to navigating the stormiest of workplace waters—without sinking your ship.
Step 1: Pinpoint the Issue (Hint: It Might Not Be Them)
Before you dust off your “Tough Love” managerial handbook, take a step back. Sometimes, what seems like an employee problem is actually a system problem. Are expectations clear? Is your feedback consistent? Do they have the tools and resources needed to succeed? As Dr. Linda Hartwell, workplace psychologist, says, “Behavior often reflects the environment. Fixing the system can fix the individual.”
For example, hybrid work environments can lead to miscommunication. Is your “difficult” employee truly problematic, or are they struggling with unclear instructions over Slack or Zoom? Once you’ve ruled out systemic issues and the problem persists, it’s time to dig deeper.
Step 2: Have the Talk (Not the Dreaded One, the Productive One)
Difficult employees usually fall into two categories: the “Unaware” and the “Unbothered.” For the former, it’s about pointing out specific behaviors and their impact. For the latter, it’s about clearly defining consequences. Either way, avoid the temptation to sugarcoat. As leadership coach Marcus Reeves puts it, “Clarity is kindness. Ambiguity? That’s just setting them up to fail.”
Prepare for the conversation by documenting examples of problematic behavior and how it affects the team or organization. Then, approach the talk with a solutions-oriented mindset. For example, instead of saying, “You’re always late,” you could say, “I’ve noticed you’ve been late to meetings three times this week, which delays team progress. How can we work together to address this?”
And if the conversation starts feeling tense, add a little humor to lighten the mood. “I need to address this because you’re too talented to let this issue trip you up—plus, I’m running out of stress balls.” Humor can disarm defensiveness and keep the dialogue constructive.
Step 3: Leverage AI and Data to Stay Objective
Welcome to the future! Tools like performance tracking software or AI-driven engagement platforms can help you identify patterns. Is Linda always late after meetings with Bob? Is Bob consistently disengaged after reviewing TPS reports? With data, you can separate fact from office gossip.
However, don’t become a “Robo-Boss.” As HR expert Nia Alvarez says, “Data can guide you, but empathy seals the deal.” Combine insights with human understanding to get a full picture. Use data not as a weapon but as a lens to identify and address root causes.
For example, generative AI tools can even simulate potential solutions based on past scenarios. Imagine asking your HR AI assistant, “What interventions worked for employees with similar patterns of behavior?” It’s like having a workplace oracle—just without the incense.
Step 4: Create a Plan (and Stick to It Like It’s New Year’s Day)
Once you’ve identified the problem, it’s time for a plan. Set clear goals, measurable outcomes, and regular check-ins. For instance, if tardiness is the issue, agree on specific steps—such as adjusting their start time or implementing a shared calendar reminder—and monitor progress over a set period.
“Difficult behavior rarely changes overnight,” warns organizational consultant Paula Green. “Consistency is key—even if it’s tempting to give up and just buy more stress balls.” Regular follow-ups show the employee you’re invested in their improvement and hold them accountable.
Also, celebrate small wins along the way. If the employee makes noticeable progress, acknowledge it. Recognition is a powerful motivator. It’s not about ignoring past issues but about reinforcing positive change.
Step 5: Build Team Resilience
While addressing the specific employee, don’t forget about the rest of the team. Difficult employees can sometimes affect morale, productivity, or even workplace culture. Hold team meetings to foster open communication and address concerns.
Team-building activities, even virtual ones, can help rebuild trust and camaraderie. Think beyond awkward icebreakers and consider collaborative challenges or group learning sessions. As remote and hybrid work persists, maintaining team cohesion requires intentional effort.
Step 6: Know When to Cut Ties
Let’s face it: Some people are like glitter—impossible to work with and impossible to remove entirely. If you’ve exhausted all options and the employee’s behavior continues to disrupt the team, it’s time to part ways.
Be respectful but firm. As leadership guru Simon Sinek says, “Firing someone is not about giving up on them; it’s about protecting the team.” Ensure you’ve documented all steps taken, both for fairness and to safeguard against legal challenges.
While letting someone go is never easy, it’s sometimes the best decision for the health of the team and the organization. Remember, it’s about creating an environment where everyone can thrive.
Step 7: Reflect and Learn
After resolving the issue—whether through improvement or parting ways—take time to reflect. Could the situation have been handled differently? Are there preventive measures to avoid similar issues in the future? Difficult employees often leave valuable lessons in their wake.
Consider hosting a retrospective meeting with HR or leadership to discuss what worked and what didn’t. Continuous learning and adaptation are the cornerstones of effective management.
Final Thought: Don’t Forget to Laugh
Dealing with difficult employees can be frustrating, but don’t forget to find humor in the chaos. As one seasoned manager put it, “Sometimes you just have to laugh. After all, stress balls are replaceable—your sanity isn’t.”
In 2025, handling difficult employees is about blending traditional wisdom with modern tools and a dash of humor. Stay calm, stay clear, and most importantly, stay human. And if all else fails, remember: there’s always coffee—lots and lots of coffee.