Dealing with a difficult employee—whether it’s a bad attitude, lack of accountability, or confrontational behavior—is one of the most challenging parts of leadership.
But before you take action, pause.
The most effective leaders don’t react first—they diagnose first.
If you’re wondering what questions to ask an unhappy employee or how to handle someone with a negative attitude, start here.
1. Is toxic leadership to blame for difficult employees acting out?
Before assuming the issue is entirely on the employee, consider whether leadership may be contributing to the problem.
In some cases, difficult behavior is a response—not the root issue.
Have an open, non-defensive conversation about expectations. When you approach the situation with curiosity instead of frustration, you may uncover insights that completely shift how you handle it.
2. Are you the problem?
Not the most comfortable question—but one of the most important.
As leaders, we all leave a “wake.” As described by Henry Cloud, that wake reflects the impact we have on others.
Is your leadership creating clarity and trust—or confusion and tension?
If the wake behind you is filled with strained relationships, it may be time to look inward. The upside? Leadership is a skill—and it can be improved.
3. What if the poor behavior is related to company culture?
Look beyond the individual.
Is this behavior isolated—or is it something that exists across your team?
If similar attitudes or habits are common, the issue may be cultural rather than personal. In that case, the employee may not even recognize their behavior as a problem.
That requires a different approach—one focused on resetting expectations, not just correcting one person.
4. What if the problem is your management style?
Not every employee responds to the same leadership style.
Some thrive with direct, candid feedback. Others shut down under it.
If your default approach doesn’t match how this person operates, friction is inevitable.
Ask yourself:
Are you adapting your communication style—or expecting them to adapt entirely to you?
Often, the solution isn’t choosing one style over another—it’s learning to flex.
5. How do you ensure confidentiality?
When addressing difficult behavior, how you handle the conversation matters just as much as what you say.
While team accountability can be powerful (as discussed by Patrick Lencioni), some situations require private, one-on-one discussions.
If confidentiality is necessary, protect it.
Shut down gossip, avoid oversharing, and build trust by handling the situation with professionalism.
6. Is there not enough incentive to perform?
Step into their shoes.
Would you feel motivated in their position?
Incentives aren’t just about compensation—they include recognition, growth opportunities, and alignment with meaningful work.
If high-value behaviors aren’t being rewarded, don’t be surprised when performance slips.
7. Is there something going on in their personal life?
You don’t need to pry—but awareness matters.
Sometimes what looks like a bad attitude is actually stress, grief, or personal challenges showing up at work.
Approach the situation with empathy and a willingness to listen. Understanding context doesn’t excuse behavior—but it does inform how you address it.
8. Does the employee feel that there’s no way to develop their career?
For many employees, lack of progression leads to disengagement.
If they don’t see a path forward, motivation naturally declines.
Find out what drives them. If growth matters, look for ways to connect performance with opportunity.
Even small signs of progress can shift mindset and behavior.
9. Does the employee feel that they’re not being challenged enough?
Sometimes difficult behavior isn’t resistance—it’s boredom.
Just like in parenting, people often disengage when they aren’t challenged.
Are you giving this person opportunities to stretch, grow, and take ownership?
The right level of challenge can transform attitude and performance.
10. Does this difficult employee have too much work on their plate?
Overwhelm is one of the most common causes of poor behavior.
Before confronting the issue, evaluate their workload.
Is their role realistic?
Or would replacing them require multiple hires?
If the workload is unsustainable, addressing capacity may solve more than any disciplinary conversation ever could.
Final Thought
Before confronting a difficult employee, the goal isn’t just to correct behavior—it’s to understand it.
The best leaders ask better questions first.
Whether you’re dealing with an unhappy employee, someone with a bad attitude, or a more confrontational personality, these questions will help you approach the situation with clarity, fairness, and effectiveness.
About the Author:
Jonno White
Jonno White is the Founder of Clarity. He helps leaders build high-performance teams and grow organizations that impact more people’s lives. Jonno is the Author of Step Up or Step Out with more than 10,000 sales worldwide. He also hosts The Leadership Conversations Podcast with listeners in more than 100 countries.
