How a Career Fail Became a Lasting Lesson in Leadership

How a Career Fail Became a Lasting Lesson in Leadership

I have a knack for learning things the hard way – can you relate? Here’s a tale of a time when I wanted to succeed so badly, I failed to recognize my own limitations. Like all good stories, this one includes a hero who demonstrated true servant leadership amid a disaster I’d created for myself.

Let me set the scene. I was brand new in my client service role at a claims administration company and utterly thrilled to have been assigned to the largest account. I was eager, excited, and ready to do a great job.

Every three months, we provided the client with a stewardship report, which is corporate speak for, “here’s lots of data to say where we are today, and what we recommend moving forward.”

As extra preparation for my role, I dutifully attended one of these meetings and observed my predecessor’s presentation. The exchange felt straightforward, and I began imagining how I would impress everyone with my own delivery.

But when we began to plan for the next quarter’s meeting, my boss suggested he would drive, and I could ride shotgun.

Well, I didn’t want to ride shotgun. I wanted to grab the steering wheel and drive us past an imaginary checkered flag. I was ready to impress my new leader and flex my exemplary skills. Who needed to ride shotgun? Not this girl.

While confidence and eagerness are wonderful characteristics for anyone in a new role, I got ahead of myself; I didn’t listen to my leader’s gentle cautions. He was telling me I wasn’t ready, but mentally I had already turned on the ignition. He was advising me to fasten my seatbelt and I was focused on shifting into high gear with my foot on the gas.

He cautioned, “It’s not as easy as it looks.” He reassured me, “You’ll still have a role in the meeting if I take the lead.” He said everything but, “Hey Val, you’re over your skis!” I continued on, at full speed.

In hindsight, which so aptly arrives with immense, chagrining clarity, I should have been asking lots of questions instead of simply wanting to forge ahead. But this leader knew I meant well. He knew I was smart and talented, and he didn’t want to crush my spirit.

And what he did next will always stay with me: he saw the learning opportunity, my persistence and, let’s face it, premature ego, and he let me go.

“Wait, what?” you might be thinking. “He let you fall on your face?” Not at all. He made sure I could fail softly, without the client ever noticing a lapse. He prepared by making sure the meeting had a fraction of its usual attendees, and he prepared to spot me if I began to slip.

The presentation kicked off beautifully, but within minutes the client had questions. Questions I hadn’t anticipated. Questions I didn’t know how to answer. I froze. I felt the heat rise in my neck and face, and my stomach began doing flips. It was clear I possessed neither the context nor experience in the program to talk about the why behind the statistics I’d presented.

That’s when I witnessed true servant leadership. My leader suspected this outcome and had prepared to give the presentation himself. When I froze, he jumped in and explained both the exhibits and the data drivers. The meeting was successful, but not because of me.

As I regained consciousness and nodded in all the right places, I silently chastised myself and dreaded the conversation that was sure to follow.

Once the clients departed, I anticipated a gentle but firm, “I told you so.” But that didn’t happen, either. My leader was ready with encouragement only. “Now you know what it’s like,” he said kindly, “and I know you’ll be ready next time.” He never mentioned the incident again, and he never told anyone else about it, either. He picked me up, dusted me off and we moved forward as a team.

I learned three great lessons:

Listen! When someone with more experience and situational knowledge is encouraging or discouraging something, trust their expertise – especially when you know they have your best interests at heart.
As a leader, have the courage to allow a determined teammate to fail. He clearly saw what was going to happen, and when his cautions fell on deaf ears (see lesson no. 1), he allowed me to go forward instead of crushing my spirit. Then he planned for a soft landing so the experience – and that ah-ha moment I had in front of the client – didn’t have to be devastating.
A servant leader roots for their team and can be trusted to cushion a fall. By responding with encouragement and discretion, rather than running to the water cooler to share the drama at my expense, he showed me how he was in my corner. I never had to wonder whether he had my back.

What could have been a humiliating career fail taught me lessons I’ve carried to this day. That’s the thing about experience: we really do learn from it, especially when it’s a tough life lesson. I’ll always be thankful I had a terrific leader who had my back and helped me navigate the speedbumps. Thanks to the heart-stopping experience of momentarily floundering, followed by his steady counsel and support, my future presentations were top-notch.

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