How Do You Handle a Major Setback or Failure as a Leader?

How Do You Handle a Major Setback or Failure as a Leader?

How Do You Handle a Major Setback or Failure as a Leader?

To provide insights into overcoming significant leadership challenges, we’ve gathered seven personal experiences from leaders, including founders, CEOs, and General Managers. From building trust in a restructuring company to managing non-contributing team members, these leaders share their valuable experiences and lessons learned.

  • Building Trust in a Restructuring Company
  • Refocusing Team’s Attention on End Users
  • Communicating Organizational Change
  • Promoting Transparency for a Unified Vision
  • Creating a Positive Environment Under Pressure
  • Implementing Remote Work Successfully
  • Managing Non-Contributing Team Members

Building Trust in a Restructuring Company

Through this experience, I learned the importance of resilience, adaptability, and effective communication in leadership. I have faced my fair share of leadership challenges throughout my career.

One significant challenge that stands out to me was when I took on a new leadership role in an organization that was going through a major restructure. The team I inherited was demotivated, mistrustful, and resistant to change. The company’s financial situation was also precarious, adding more pressure to the role. It was a high-stakes situation, and I knew I had to overcome these challenges if I wanted to succeed in my new role.


I began by building relationships with my team members and gaining their trust. I also communicated openly and transparently about the changes that were happening and involved them in the decision-making processes. It took time, effort, and patience, but eventually, we were able to turn things around.

Keith SantKeith Sant
Founder and CEO, Kind House Buyers

Refocusing Team’s Attention on End Users

In leadership, you’ll inevitably find moments where the options on the table are not black and white.

On a project running behind schedule, the team was divided on whether to push for an extension or to simplify the scope. I found myself in the middle, understanding both perspectives. Taking a page from user-centric design, I refocused the team’s attention on the end users.

The outcome? We simplified the scope, but did so in a way that kept the most crucial user needs front and center. The decision wasn’t popular, but it was respected, and ultimately it was the right one.

Burak ÖzdemirBurak Özdemir
Founder, Set Alarm Online

Communicating Organizational Change

In navigating a significant organizational change, effective communication was pivotal. Transparently conveying the reasons behind the change, the anticipated outcomes, and the steps for implementation helped in alleviating team members’ concerns and uncertainty.

Facilitating an open dialogue where employees could express their views and questions fostered a supportive atmosphere, aiding in a smoother transition and greater buy-in from all involved.

Amanda MillerAmanda Miller
CEO, Angel Numbers Guru

Promoting Transparency for Unified Vision

Early in my startup journey, I struggled to align our engineering team around a unified product vision. With discrepant perspectives and priorities, progress stalled. I realized I needed to improve communication and collaboration.

I initiated a series of working sessions for cross-functional discussion of our long-term goals. Promoting transparency helped build trust and cohesion. As the team shared ideas openly, we converged on solutions that incorporated diverse needs. Bringing people to the table as partners, rather than pushing top-down decisions, was key.

This experience taught me that inclusive leadership is about empowering others, not imposing rigid control. Uniting people behind a common purpose yields greater innovation than directive mandates.

Ankit PrakashAnkit Prakash
Founder, Sprout24

Creating a Positive Environment Under Pressure

Leading my team through a complicated project with tight deadlines was one of the hardest things I had to do as a leader. The team was under a lot of pressure, which was making things worse. In order to fix this, I made a clear project plan with clear tasks and responsibilities so that everyone knew their work was appreciated.

I also encouraged people to talk to each other freely and held regular check-in meetings to address issues and offer support. We met our goals and made the team stronger by creating a positive and collaborative work environment. This led to a successful project and a stronger team.

Jay ToyJay Toy
General Manager, 88stacks

Implementing Remote Work Successfully

Numerous challenges encountered in the leadership journey have contributed to growth. One particular experience that significantly tested my abilities is worth sharing.

In 2021, our company released a public announcement to hire fresh talent. The intention was to implement a remote working policy, a first for the organization. This posed a formidable challenge.

We tackled this challenge by leveraging digital tools and resources that would enable the facilitation of the process and ensure that communication remained open and equitable for all team members. This proactive approach allowed the company to transition into remote work smoothly. It was a massive achievement.

I witnessed a remarkable change among employees. There was a high level of enhanced productivity, reduced burnout, and improved work ethics.

This achievement demonstrated the ability to lead during transformative times. It highlighted the importance of adaptability and continuous learning in leadership.

Peter BrylaPeter Bryla
Community Manager, ResumeLab

Managing Non-Contributing Team Member

A frustrating challenge in this generation that everyone faces is that team members want to work, but they want to make it quick, too. Using their mouths for the tasks rather than putting in the effort is the worst kind.

When pursuing an MBA, being part of a team was a given. The unanimous decision to lead the team brought with it the challenge of getting managerial tasks done, making presentations, and completing other assignments.

There was a team member who had a habit of getting all the attention during task assignments. She boasted about all the work she could do, but ended up doing 0% of the tasks.

As a team lead, ensuring every task is completed by the given deadline with the best output possible is crucial. It’s important to avoid a cold war within the team. It took a while to involve that team member in the tasks, and assigning her less work than the rest ensured some output rather than getting nothing done. Also, it was important not to hurt her ego at the same time.

This situation challenged the enhancement of Emotional Intelligence.

Fahad KhanFahad Khan
Digital Marketing Manager, Ubuy India

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