Managing difficult employees is among the toughest challenges leaders face. When someone appears unreasonable, combative, or unwilling to cooperate, it can be tempting either to ignore the issue and hope it resolves itself—or to react in frustration and make matters worse.
A more effective approach when managing difficult staff is to treat the situation as a negotiation, not a disciplinary standoff. Negotiation techniques help managers uncover underlying problems, address systemic issues, and encourage behavior change without escalating conflict. The following three guidelines can help leaders navigate the challenge of managing difficult people at work.
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1. Listen to Learn
When employees behave in disruptive or uncooperative ways, it’s often because they are trying—ineffectively—to express legitimate concerns. The manager’s task is not to shut the behavior down immediately, but to understand what is driving it.
Start by clearly naming the specific behavior that concerns you, then ask the employee to explain what’s behind it. If the employee becomes defensive or emotional, resist the urge to smooth things over too quickly. Instead, practice active listening:
- Paraphrase what you’ve heard
- Ask clarifying questions
- Check that the employee feels understood
Repeat this process until the employee agrees that you’ve accurately captured their perspective. Only then should you begin asking questions aimed at uncovering deeper interests and core concerns.
Listening in this way often reveals whether the behavior reflects individual frustration—or broader organizational problems that need attention.
2. Institute Accountability—Early and Clearly
When managing difficult employees, leaders sometimes focus too narrowly on the individual and overlook the organizational structures that helped create the problem. One frequent culprit is the absence of clear accountability.
Effective accountability systems rely on:
- Clear expectations
- Transparent decision-making standards
- Appropriate incentives and consequences
Research by University of California, Berkeley professor Philip Tetlock shows that people make better, less overconfident decisions when they know in advance they will be held accountable. Importantly, accountability works best when it is prospective, not punitive.
That means telling employees early—during planning stages, not after problems arise—that they will be expected to explain and justify their decisions as work progresses. When people know how they will be evaluated, they are less likely to engage in disruptive behavior. And if problems persist, the consequences are clearer and easier to address for both manager and employee.
3. Deliver Feedback That Actually Helps
When managing difficult staff, leaders often assume that delivering feedback is the solution. But as Douglas Stone and Sheila Heen explain in their book Feedback, people frequently struggle to receive feedback productively. Instead of motivating improvement, poorly delivered feedback can leave employees feeling attacked, discouraged, or shut down.
According to Stone and Heen, helpful feedback—the kind that leads to real change—has three essential elements:
Appreciation: Begin by acknowledging what the employee is doing well. Even difficult employees usually bring strengths to their role. For example, someone who frustrates teammates may nonetheless demonstrate commitment, persistence, or high standards worth recognizing.
Evaluation: Next, offer a fact-based assessment of current performance. Evaluations often involve comparisons to expectations, standards, or peers—but should avoid personal judgments. Importantly, don’t rely solely on secondhand complaints. Give the employee a chance to respond and share their perspective.
Coaching: Finally, include coaching—guidance aimed at helping the employee learn or change. Rather than issuing ultimatums, invite the employee into a joint problem-solving conversation. Ask what obstacles they foresee and what support they might need. Employees are often better positioned than managers to anticipate challenges and propose workable solutions.
A Negotiator’s Mindset for Managing Difficult Staff
Managing difficult employees isn’t about “fixing” people—it’s about diagnosing interests, aligning incentives, and improving communication. By listening carefully, setting clear accountability, and delivering constructive feedback, leaders can transform difficult interactions into opportunities for growth—for both individuals and organizations.
Are you managing difficult employees? What strategies have you found helpful when managing difficult employees in your organization?
Claim your FREE copy: Dealing with Difficult People
Discover how to collaborate, negotiate, and bargain with even the most combative opponents with, Dealing with Difficult People, a FREE report from the Program on Negotiation at Harvard Law School.
