3 Hard-Learned Lessons on Surviving Leadership Mistakes

3 min read
Mar 31, 2015

Getting (and Surviving) Tough Lessons on LeadershipOf all the leadership qualities that a good manager should have, maybe the most fundamental one is the ability to learn from mistakes. After all, being a good leader is a process, not a single goal, so you must be able to adapt.

It’s not always easy to admit you’re wrong, but it’s undoubtedly valuable. We heard from three managers who swallowed that bitter pill — and gained important insights from it.

Be Adaptable

Andrew Schrage, Founder and CEO of Money Crashers, shared with us what he calls “The best feedback I ever received.” In his case, the feedback came from one of his direct reports. This employee was an older worker who, says Schrage, “had analyzed my management style for quite some time.”

And what did that employee have to say? “He respectfully pulled me aside and told me that I would have much better results if I transformed my management style to the individual personalities of my team, rather than expecting all of them to conform to my singular management style.” Rather than getting defensive or pulling rank, Schrage listened. “It was eye-opening and very helpful,” he says.

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Don’t Underestimate Your Employees

Rusty Shelton, Founder and CEO of Shelton Interactive, also got a lesson from his employees. “I was under the mistaken belief that team members wanted to always be built up, and I focused my leadership style early in my career entirely on highlighting positives,” he says. But “We did an anonymous survey, and the feedback came in loud and clear — they didn’t want me to hold back on feedback. Surprisingly to me, they were craving it because they wanted to improve.”

Honesty is one of the biggest advantages of anonymous surveys. Shelton took that candid feedback and adapted. “Looking back, I was pretty naive,” he admits. “I have gotten much more proactive with calling out both positives and places that need improvement, and I think it’s been good for everyone.”

Open Yourself Up

Dalyla Santos, Managing Partner at Alonso, Perez & Santos, LLP, tells a story from her early experiences as a leader. “As a young, fragile looking, immigrant female manager at a large law firm in Orlando, Florida, I always felt unequipped for the position,” she says. She worked hard to develop the leadership skills that she admired in her own supervisor, as well as reading what experts in the field had to say.

However, “My first year as a manager was not pretty,” Santos concedes. “I ran a tight [ship], and I barely smiled or connected on a personal level with any of my employees. I realized that while the work was getting done, it was not satisfying to me or my employees. I wanted more than anything for my employees to believe in me and to follow me like I followed my own manager.”

In her second year, she worked on developing personal skills by talking with her employees about their families and lives outside of work. But she found it hard not to see the efforts as a chore that meant losing productive work time. “At first,” she admits, “I spent most of the time looking at my watch and faking a smile while they told me about their crazy weekend or their kids.”

Santos persevered, and things got easier as she developed relationships with her employees and socializing became more natural. “I actually was able to balance getting the work done and also getting to know my employees and truly caring for their well-being.” That doesn’t mean her self-doubt disappeared — but luckily, during her third year as a manager, “one of my employees came in my office after a long day and thanked me. He thanked me for not giving up on the department and going the extra mile to make the firm successful but also to make the employees feel the success as well. He told me that he loved his job because of me and everyday he came to work he felt like he made a difference in our clients' lives.”

The feedback was gratifying, but it also pushed Santos to work even harder to become a better leader. And in the end, isn’t that what the best lessons should do?



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