Leading a team is hugely rewarding, especially when you see your team members growing professionally and personally. But let’s be honest, dealing with difficult employees is a major headache, and it’s part of the job, especially when those challenging team members happen to report directly to you.
Managing these tricky situations isn’t for everyone—it demands a strong blend of empathy, assertiveness, and strategic thinking. If you’re not up to the task, just one problematic employee can throw off your whole team’s rhythm.
So let me help you cut through the whining sound of employee excuses and the silence of passive aggressiveness. Here are my top 10 straightforward pro-tips to handle tough employees before things get out of hand. I’ll lay out some clear guidelines and share quick, real-life examples to help you come up with an approach that fits your situation. Ready to get started? Let’s jump right in.
Pro-Tip 1: Set Non-Negotiable Expectations
In my early days of management, I encountered “Steve,” a bright employee who was always behind on his deadlines.
I pulled him aside and laid it out clearly: “Steve, your creativity is valuable, but so is our schedule. If you can’t meet deadlines, I’ll need to find someone who can.”
It was tough but necessary. Clarity from the start prevents a world of confusion later.
Pro-Tip 2: Yes, Listening is Important—But Don’t Become the Therapist
“Rachel” was the kind of employee who often needed to unload personal problems, and while I was all ears and showed empathy, it began to take a toll on her work performance and others within earshot. I
t was clear a boundary needed to be set. I sat down with her and was upfront: “Rachel, I genuinely care about your well-being, but we need to steer our conversations towards work-related solutions. Let’s focus on what adjustments we can make here at work to help you manage your stress better.”
Yes –as managers, our role is to support our team, but there’s a fine line between listening and becoming a therapist. It’s important to remember that while empathy is a valuable trait for any leader, maintaining professional boundaries ensures that we stay focused on our primary goals and keep the team on track.
Pro-Tip 3: Give Feedback Like a Coach, Not a Critic
It’s ok to point out errors and areas for improvement. But how you do that, matters tremendously. “Tom” had potential but his work often lacked attention to detail.
Instead of criticizing, I coached: “Tom, I know you’re capable of top-notch work. Let’s review what went wrong here and how you can fix it.” I showed him the errors and we discussed practical steps to improve. This approach fosters growth rather than resentment.
Pro-Tip 4: Regular Check-Ins Aren’t Optional
Inspecting what you expect, actually is a thing. When “Jack” struggled with new software, it affected her job performance.
I didn’t wait for annual reviews; we started bi-weekly check-ins. “Let’s break down what’s going well and what’s not,” I proposed. This regular pulse check helped Jack address issues before they escalated.
Pro-Tip 5: Push Professional Development—Hard
“Ashlee” was great at his job but shied away from public speaking, which held her back. I didn’t accept his reluctance. “Ashlee, you’re enrolling in a public speaking workshop. It’s non-negotiable for your growth path here.”
It was a push she resented at first but thanked me for later.
Pro-Tip 6: Address Bad Behavior Immediately
“James” was constantly interrupting others aggressively and dominating our meetings, which was stifling teamwork.
I took him aside and got straight to the point: “James, constantly talking over your peers isn’t just rude—it’s counterproductive and kills our team’s collaborative spirit. I need you to rethink how you conduct yourself in meetings. This needs to stop, effective immediately.”
It’s never easy to confront someone like this, but nipping bad behavior in the bud is essential for maintaining a respectful and productive team environment.
Pro-Tip 7: Be the Example—Relentlessly
I noticed “Mark” was frequently tardy, following my occasionally relaxed arrival times. As the manager I must admit I felt being late to meetings at times was a prerogative reserved for the boss. But if I expect certain behaviors, then I need to lead the way.
I tightened up my act: “Team, I expect myself and all of you to respect our start times.” Leading by example sets a clear standard.
Pro-Tip 8: Reward Publicly
After “Lucy” improved dramatically over a quarter, I didn’t just thank her privately.
At a team meeting, I announced, “Lucy’s progress has been phenomenal, setting a standard for us all.” Public recognition boosts morale and sets a benchmark for success. But make a note, rewards and recognition should be reserved for the truly deserving. Trophies for participation, is not what we are going for.
Pro-Tip 9: Promote Teamwork, Even When It’s Hard
“Derek” was the kind of guy who liked to fly solo, and while he was great on his own, his reluctance to collaborate was creating silos within the team.
To break down these barriers and enhance teamwork, I strategically assigned him to projects that not only needed his expertise but also required him to depend on and work closely with others.
I approached him with a direct yet encouraging message: “Derek, your skills are crucial to the success of these projects. We need you to really connect with the team and contribute to our collective efforts.” It was crucial to nudge him out of his comfort zone to foster better integration and collaboration across the team. This move not only leveraged his strengths but also bolstered our team dynamics.
Pro-Tip 10: Maintain Boundaries Like a Boss
“Samantha” had a tendency to overshare personal details, creating an awkward atmosphere not just for me but for her colleagues as well. I addressed it directly: “Samantha, we need to keep our conversations professional and work-related. It helps maintain a focused and respectful environment for everyone.” Establishing clear boundaries is key to preserving a professional workplace.
Being a boss isn’t about popularity—it’s about results. Sometimes, you’ve got to play the tough role, challenge people, and set boundaries against personal oversharing. It’s all about being straightforward, fair, and decisive.
Let’s be real: no one rolls out of bed eager to botch their job and drag everyone down with them. Yet, there are a few who seem to test this theory daily. It’s crucial to recognize that not everyone will change or take your coaching . Knowing when to part ways with an employee who just isn’t working out is also part of the job, and what elevates you from merely managing to truly leading.
…But that’s for another letter.
Sincerely,
The CEO