My Biggest Leadership Failure and How I Overcame It
Failure is often among the best lessons in the power of humility and vulnerability.
When I interviewed for a seat on a company’s board, a selection committee member asked about one of my leadership successes.
I replied, “Can I tell you about a leadership failure?”
That failure, which I now consider a massive disappointment in my behavior at that time, was the catalyst for the work I do now.
Many people, especially those in leadership positions, can view being vulnerable and admitting failure as a weakness, but research shows the opposite to be true. According to a study in the Harvard Business Review, becoming a failure-tolerant leader can foster “a culture of risk-taking that leads to sustained innovation.”
In my case, accomplishments and accolades were the trophies that masked my insecurities. Subsequently, I developed a habit of taking on significantly more responsibilities than I could handle well. I lost sight of my values — the courage to trust my instincts to do my best without trying to control the outcome of each situation. Failure ensued.
One morning while in a critical meeting with employees from one of the three departments that reported to me, although I was physically present; mentally, I was disconnected. My attention was divided between an impending deadline and making the next meeting on time while feeling ill-prepared for both. I couldn’t keep the juggling act up any longer. Feeling rudderless, I realized my failure and need to recalibrate.
Bottom line: I no longer had the right motivation or bandwidth to effectively lead my team, which meant I was failing them and the organization. So I recommended to my boss a restructure that would result in the department with the most developed employees reporting to someone else, allowing me to focus on the remaining two. And she agreed. My failure was not thinking through the unintended consequences for each team member impacted by the transition.
Although the intent was to “right my wrong,” the change I unwittingly suggested cost one of my employees their job.
Within days following the announcement, I had an in-person meeting with the employee and explained the severance package. Once I finished speaking, they said, “Wow, this worked out well for you.” That was a defining moment — my legacy as their leader. I was mortified and humbled by a perception that wasn’t accurate, but our relationship now was too fractured for a retort.
After providing much-needed time and space, I called and extended an invitation to lunch so I could look them in the eye and say, “I am so sorry for the pain that I caused you. It was never my intention, but it doesn’t negate that my actions caused great pain.” And I did.
We are now friends, which never would have happened if I had not humbled myself, drawn power from vulnerability, and took responsibility for my decisions that negatively impacted her and her family.
By saying yes to things that gained me validation and a specific title within the organization, I had allowed my ego to overtake my good judgment. That wasn’t being a leader. And indeed, it was not the leader I wanted to be.
Ultimately, I changed my failed leadership narrative by:
Acknowledging and addressing the personal insecurities that contributed to my professional failure as a leader.
Accepting responsibility for “overreaching” by taking on more responsibilities than I could handle well.
Acting respectfully and quickly to rectify the situation for the well-being and advancement of the individuals and organization.
Apologizing to my team and others who were impacted by my actions.
Reclaiming my identity as an individual independent of the position I occupied.
Returning the focus to my values, intrinsic motivation, and the organization’s mission.
Silencing my internal critic by remembering that no one is infallible.
If you live long enough, you will make your own mistakes. In the meantime, if you listen, you can learn from others. Those self-proclaimed sentiments have been invaluable tools on my path to becoming a transformational leader. Now, my values and the organization’s mission motivate and guide my decisions instead of perceived opportunities to magnify my extrinsic worth.
And following a vote based on the selection committee’s recommendation, I am now a board member and serve on the leadership committee.
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