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Navigating the Challenges of Difficult Employees: A Guide for Business Owners

In any business's diverse ecosystem, challenging employee behaviors are inevitable. At first, it comes as quite a surprise because your tight-knit team has supported you since inception, and you’ve never had a challenge. You are loyal to your team, and they are faithful to you. But then, you expand, and sometimes a negative nelly slips in. Of course, you will interview with this in mind and hope to reduce the chances of getting a rotten egg, but sometimes it happens. From those who shirk responsibility to individuals who sow discord, these situations test your leadership and impact your business’s morale and productivity. This guide offers pragmatic and emotionally intelligent strategies for business owners to manage difficult employees and foster a positive workplace culture effectively.

Strategies for Handling Common Types of Difficult Employees

The Underperformer

Challenge: Employees who consistently fail to meet their responsibilities can negatively affect team morale and productivity.


  • Set Clear Expectations: Clearly communicate job responsibilities and performance standards.

  • Provide Support and Training: Identify gaps in skills or knowledge and offer the necessary support to fill them.

  • Regular Feedback: Implement a structured system for providing constructive feedback, focusing on improvement and accountability.

  • Performance Improvement Plan (PIP): For persistent underperformance, a formal PIP can outline specific goals and timelines for improvement alongside potential consequences for non-improvement.

  • NOTE: If someone has potential and is willing to work to improve their performance, it is always less expensive to turn an employee around than to replace them. Follow our blog on April 17th, for a more in-depth discussion on how to handle Employee Performance issues.

The Negative Influencer

Challenge: Their pessimism and complaints can infect the workplace atmosphere, lowering morale.


  • Address Negativity: Have a private conversation to understand the root causes of their negativity and address any legitimate concerns.

  • Promote Positivity: Encourage positive recognition among employees and celebrate successes to foster a more positive work environment.

  • Set Behavioral Expectations: Make it clear that while feedback is welcome, constant negativity will not be tolerated.

  • NOTE: Forbidding employees from discussing safety concerns or pay inequities is not legal. Be careful how you communicate your desire for positive communication.

The Lone Wolf

Challenge: Prefers working alone, resists collaboration, potentially causing rifts in team cohesion.


  • Encourage Teamwork: Use team-building activities to foster better communication and collaboration.

  • Assign Collaborative Projects: Encourage projects that require teamwork, highlighting the value of diverse input and cooperative efforts.

  • Personalized Motivation: Understand their strengths and motivations for a tailored approach that integrates their preferences with team needs.

The Disruptor

Challenge: Engages in behaviors that disturb the workplace order, such as gossiping, bullying, or other toxic actions.


  • Enforce a Zero-Tolerance Policy: Make it clear that disruptive behavior is unacceptable, with clear consequences.

  • Conflict Resolution Training: Offer training to help all employees, including the disruptor, manage conflicts constructively.

  • Mediation: In cases of interpersonal conflict, consider mediation to resolve issues amicably and professionally.

The Overambitious

Challenge: May step on others to climb the ladder, including taking credit for others’ work or pushing too hard for advancement.


  • Channel Ambition: Provide clear advancement pathways emphasizing teamwork and ethical behavior.

  • Mentorship Programs: Pairing them with mentors can help guide their ambition positively while reinforcing company values.

  • Recognition: Ensure that achievements are recognized and rewarded, promoting a culture of integrity and teamwork.

Creating a Positive Work Environment

  • Lead by Example: Your behavior sets the tone for the entire business. Demonstrating empathy, respect, and integrity encourages employees to emulate these qualities.

  • Open Communication Channels: Foster an environment where feedback is encouraged and valued, allowing for transparent dialogue about concerns and suggestions.

  • Build a Culture of Recognition: Regularly acknowledging and rewarding hard work and positive behavior can motivate employees and reinforce desired behaviors.

  • Invest in Employee Development: Providing opportunities for professional growth shows your commitment to your employees' futures, enhancing loyalty and satisfaction.

  • Address Issues Promptly: Delaying action on problematic behaviors only allows them to fester. Early intervention can prevent escalation and demonstrate your commitment to a healthy workplace.


Navigating the complexities of human behavior is part of your role as a business owner. Applying these strategies can transform challenges into growth and improvement opportunities for individual employees and your business. Remember, the goal is to manage difficult employees and lead by example, fostering an environment where everyone can thrive and work together to achieve unified objectives.

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