Leadership Dilemmas: Handling Underperforming Team Members

Jon Hoffman
Foundations Of Effective Leadership
8 min readNov 5, 2023

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As a leader we need to engage in the challenging discussions and make the difficult decisions.

Photo by Kelly Sikkema on Unsplash

I’ve recently started reading “Radical Candor” by Kim Scott. In the book’s introduction, she recounted her experience with someone she called “Bob.” Kim had high expectations for Bob when she hired him, believing he would be an exceptional addition to her team. However, it became evident that Bob struggled in his role to the extent that Kim and her colleagues had to put in extra hours to compensate for his deficiencies. Eventually, Kim had to make the tough call to terminate his employment, though this decision came after allowing his underperformance to persist for too long, negatively affecting other team members’ performance and overall morale. I won’t reveal the full story, as it is worth reading to understand the lessons she learned. Anyone who has been in a leadership position for some time has likely encountered similar challenges.

While effective leadership requires motivating and coaching team members to excel, there are times when even the most skilled leaders face a daunting reality not everyone can be successfully motivated or coached. There are situations where individuals have been promoted beyond their abilities or employees struggle to fulfill their roles. In such cases, leaders must make tough decisions that significantly affect their team and organization. This article discusses these challenges and offers practical insights into how leaders can tackle them.

Acknowledging the Issue

When faced with an underperforming employee, the first and most crucial step for a leader is to acknowledge there is an issue. Ignoring the problem can have detrimental effects on the team, leading to a decrease in morale, productivity, and overall performance. By recognizing the issue, a leader can take appropriate action to address it and prevent further negative consequences.

One of the worst things a leader can do is to ignore the issue, as this can create a false sense of security for the underperforming employee. This may lead to a lack of motivation and an even greater decrease in the quality of work produced. Additionally, other team members may feel frustrated and demotivated, as they may have to pick up the slack or compensate for the underperforming employee’s work.

On the other hand, if a leader acknowledges the issue, they can take the necessary steps to address it. This may involve providing additional training or resources to the employee, reassigning tasks, or having a candid conversation about expectations and performance. By taking action, a leader can demonstrate their commitment to the team’s success and create an environment of trust and accountability.

In some cases, the underperforming employee may not be aware of their shortcomings or may believe that they are performing well. In such situations, the leader needs to provide clear and constructive feedback, highlighting the areas where improvement is needed. This can help the employee understand the expectations and work towards meeting them.

However, there may be instances where despite the leader’s efforts, the underperforming employee is unable or unwilling to improve. In such cases, the leader may need to make the tough decision of reassigning or letting the employee go. This can be a challenging and uncomfortable task, but it is necessary for the overall success of the team and organization. It is crucial to remember that in such situations, a leader must assume responsibility for the organization as a whole and take the necessary actions to ensure the organization’s success. I firmly believe that if a leader is unwilling to engage in challenging discussions, make tough decisions, and act in the organization’s best interests, they may not be ready for a leadership role.

Making The Difficult Decision

Making the tough decision is one of the most demanding aspects of a leader’s job, yet it’s an essential part of their role. While it’s crucial to follow your organization’s specific procedures for handling underperforming employees, here are some practical steps leaders can take to address the situation effectively:

  1. Recognize the problem: As soon as you notice that an employee is underperforming, acknowledge the issue and its impact on the team and organization. This is the most crucial step and can potentially be one of the hardest.
  2. Document specific examples: Start by documenting specific examples of how the employee’s work has suffered and doesn’t meet expectations, including any behavior issues you’ve observed. It can be important to note how the employee’s performance issues impact others on their team and the organization itself.
  3. Conduct a meeting: Schedule a one-on-one meeting with the employee to address the situation and gain awareness of their perspective. During the meeting, ask questions to establish the causes of their underperformance. Maintaining a positive and supportive atmosphere is crucial during this conversation. Make it clear to the employee that your intention is to help them, and you are not seeking to criticize or demoralize them.
  4. Develop an action plan: Once you and the employee have discussed the issues and causes, develop an action plan together to work toward a resolution. Remember it is important for the employee to take ownership is the plan. If the employee does not take ownership, then they will struggle to succeed.
  5. Monitor progress: Schedule regular meetings to monitor the employee’s progress on the action plan and encourage further growth. Give the employee plenty of opportunities to explain how they are developing and what is still challenging for them. If the plan needs to be changed, encourage them to make suggestions.
  6. Address non-improvement: If, despite the combined efforts of both you and the employee, there is no noticeable improvement in performance, it is advisable to seek external assistance, such as involving other supervisors or reaching out to your Human Resources department.
  7. Take more decisive actions: If all other approaches prove unsuccessful, you may need to consider more decisive measures, which could involve either reassigning the employee or, in some cases, parting ways with them.

By following these steps, leaders can effectively handle underperforming employees, support their team, and maintain a positive work environment. It’s essential to address underperformance promptly, as it can negatively impact the team and the organization if left unaddressed.

In my experience step 3, the one-on-one meeting has consistently provided a strong indicator of the potential success of steps 4 and 5. When the employee is open to discussion, acknowledges the issues, or at least acknowledges the possibility of an issue, they tend to engage with the action plan for improvement and commit to its implementation. Conversely, if the employee resists or fails to recognize any issues, they typically show little commitment to the action plan and minimal improvement. In such cases, reassignment or termination often becomes the necessary course of action.

Handling the Tough Decision

When all other efforts have been exhausted, and the necessity arises to reassign or terminate an employee, it proves to be an emotionally taxing experience, not only for the employee but also for me as the leader. In my leadership role, I view the individuals who work for me as an integral part of my professional family. I genuinely care about their progress and wholeheartedly celebrate their achievements.

Conversely, when an employee faces challenges or fails to meet expectations, it’s a personal and professional setback for me as their leader. Therefore, when circumstances necessitate reassignment or termination, it weighs heavily on my conscience. However, it’s crucial to remember that making such difficult decisions is sometimes essential for the well-being of the team and the organization’s overall success. This balance between compassion and the greater good can be one of the most challenging aspects of leadership.

Nonetheless, the consolation I find in such a situation is knowing that I have left no stone unturned in my efforts to support and enable the employee to succeed. Having exhausted all avenues for their improvement, I can rest assured that the decision is a last resort, taken in the best interest of both the individual and the organization. While it remains emotionally taxing, this approach aligns with my commitment to ensure that I have done everything within my power to facilitate their growth and success.

In Conclusion

Navigating the challenges of managing underperforming employees is a critical aspect of effective leadership. As we explored Kim Scott’s experience with “Bob” and delved into the intricate process of addressing underperformance, it’s clear that making the difficult decision to reassign or terminate an employee is one of the most daunting tasks for a leader. However, it’s also a fundamental part of the leader’s role, and vital to the success of an organization.

Leaders understand that their team members are more than just colleagues; they become a part of their professional family. A genuine commitment to their success and a deep understanding of how their accomplishments contribute to the organization’s success are what make the decision to address underperformance so emotionally challenging.

When the time comes to make such a challenging decision, leaders find solace in knowing that they have done everything possible to support the underperforming employee. Exhausting all avenues for improvement, leaders can rest easy knowing that the decision is a last resort, made in the best interest of both the individual and the organization. While this process remains emotionally taxing, it aligns with the leader’s commitment to ensuring that every effort has been made to foster growth and success. Ultimately, it’s a testament to their dedication to the team’s prosperity and the organization’s continued growth.

Always keep in mind that as a leader, commitment to the team’s and the organization’s success is paramount. When one team member underperforms, it can lead to frustration and demotivation among other team members, as they may have to shoulder additional responsibilities or compensate for the underperforming employee’s work.

This can lead to lower morale and a decrease in overall team productivity. It’s the leader’s responsibility to maintain a harmonious work environment where each team member feels valued and is allowed to contribute effectively. Addressing underperformance, while challenging, is an essential step in preserving the team’s cohesion and the organization’s long-term success. Leaders must be prepared to make the tough choices when necessary, for the good of the organization.

I have written several books on leadership, software development and robotics, drawing upon nearly three decades of experience in the tech industry as both an engineer and a leader. However, my most cherished role is being a dad. I enjoy anything that keeps me active, especially running, hiking, paddle boarding, and yoga. You can follow me on X (Twitter), BlueSky, and Medium.

If you enjoy my articles, please check out my book on Amazon: Foundations of Effective Leadership

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