Startup Series : Letting Go: A Tough but Necessary Decision in a Startup

Roshni Mohandas
3 min readJul 16, 2024

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Photo by Alex Kotliarskyi on Unsplash

Running a startup often involves making tough decisions, especially when it comes to managing your team. Recently, I had to let go of an employee named Diwakar. This experience was challenging, but it underscored some vital lessons about leadership, team management, and the importance of maintaining a balance between compassion and business needs.

The Backstory

Three months before letting Diwakar go, I had a conversation with him about his plans and performance. Diwakar often sought guidance and needed his work, including code, to be verified by someone else. He struggled to deploy anything independently and seemed to require micromanagement. Unfortunately, this dependency was not sustainable in our fast-paced startup environment.

Challenges Faced

  • Lack of Independence: Diwakar’s inability to work autonomously was a significant issue. In a startup, each team member needs to be a self-starter, capable of handling their tasks without constant supervision.
  • Team Dynamics: Earlier, due to financial constraints, we had to let go of other developers. These developers refused to conduct knowledge transfer (KT) sessions with Diwakar as he lacked basic understanding, further complicating his onboarding and performance.
  • Entitlement Issues: When it was time for Diwakar to leave, he was reluctant to return company equipment and exhibited a sense of entitlement that was detrimental to the team’s morale.

The Decision to Let Go

As difficult as it was, I had to prioritize the startup’s well-being over individual considerations. While compassion is an important trait, allowing it to cloud judgment can harm the entire organization. Diwakar’s performance issues and dependency on constant oversight meant he was not a good fit for our team. It was clear that letting him go was necessary to protect the startup’s interests.

Lessons Learned

  1. Maintain High Standards: It’s essential to maintain high standards for performance and independence. Each team member should contribute effectively without needing excessive guidance.
  2. Protect Team Morale: Ensuring that all team members are aligned in their work ethic and contributions is crucial for maintaining morale and productivity.
  3. Balance Compassion and Judgment: While empathy is important, it should not come at the expense of the organization’s health. Sometimes, tough decisions are necessary to keep the startup moving forward.

Moving Forward

Diwakar’s departure, though difficult, was a learning experience. It reinforced the importance of clear communication, setting expectations, and making tough decisions when necessary. For any startup founder, it’s crucial to remember that while being compassionate is important, it should not override the need for sound judgment and decisiveness.

Key Takeaways:

  1. Set Clear Expectations: Ensure all team members understand their roles and responsibilities from the outset.
  2. Foster Independence: Encourage and support team members to work independently and take ownership of their tasks.
  3. Make Tough Decisions: Do not shy away from making difficult decisions that are in the best interest of the startup.
  4. Protect the Startup: Always prioritize the health and sustainability of the startup, even when it means making tough personnel decisions.

In conclusion, letting go of an underperforming employee is never easy, but it is sometimes necessary for the greater good of the organization. By maintaining high standards, fostering independence, and balancing compassion with judgment, you can navigate these challenges and keep your startup on the path to success.

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Roshni Mohandas
Roshni Mohandas

Written by Roshni Mohandas

Entrepreneur, Data Scientist , Startup , Hustler : 100% follow back