Let me tell you a story about an up and coming go getter, with endless potential, a personality that was impossible to ignore and a work ethic so strong it was only matched by his graciousness and humility.
It’s me, I am talking about myself… again. I have another story about a leadership mistake I got to experience first-hand. This time it was regarding my career development.
I worked in the HR department for a small industrial manufacturing company early on in my career. A couple of months after I started it was time for their annual performance and development cycle to kick off. This meant that year end reviews were conducted, but I didn’t have a review of any kind with my leader because I was so new with the organization.
This organization’s process dictated that once the reviews were completed all employees were required to complete a goal setting form and submit them to their leader. The goal setting form had a requirement that all employees set five goals for the year. The first three goals were meant to be work related goals. These were focused on improving the work that you currently do. What projects, tasks, and supports were you going to be completing?
The fourth goal was meant to reflect team development. How are you going to support the growth and culture of your team? The final goal was a development focused goal. This one was specifically meant to support your personal growth and learning.
While I didn’t have a year-end review, due to my short tenure, I was asked to complete the goal setting form and submit it to my leader to help us track progress for the upcoming year. Overall, the process made all kinds of sense. It was consistent and it created a strong foundation for performance conversations throughout the year. There was only one fatal flaw.
This process only worked if you had educated and engaged leaders. Unfortunately for me, this was not the case. My leader did not fully engage in the process. The first time that we had an actual conversation about the goals I had set was six months after the annual review window, or eight full months after I had started.
She pulled up the goal setting form on her laptop and asked me, “So, which of these can we cross off?”
That moment was pivotal for me, a single sentence that summed up the difference between compliance and commitment in leadership. The system wasn’t broken because the form was bad. It failed because the conversation never happened my leader wasn’t committed.
For the work-related goals her question wasn’t ideal, but we had monthly one-on-one conversations and my leader was involved in the work I was doing, so she had a decent enough understanding of the progress I was making on the majority of the projects I had been tasked with. The real issue that appeared was the development goal I had set.
I was looking to progress towards leadership roles in the future. To get there I had set some goals around both formal education courses that could support my learning as well as looking to gain a mentor in a leadership role within the organization. I found an external program that provided the type of learning I was looking for and this program was within the budget allocations of our staff development fund.
I had my application prepared but I needed approval from my leader for funding and the time required to complete the program. I brought it up monthly at our one-on-one’s but my leader would always push it to the next month because she wanted to focus on the task at hand as that was the biggest priority for our day-to-day work. As a result, I missed the application deadline for two different cohorts of the program.
Missing that opportunity was frustrating, but it also taught me something foundational: leadership failure doesn’t always come from bad intentions. Sometimes it comes from distraction, disconnection, or the inability to prioritize development over deliverables.
Great leaders still fail sometimes, but in doing so, they learn how their mistakes impact others. They don’t just own the outcomes, they learn from the missed conversations, the forgotten check-ins, the assumptions that people “are fine.”
That’s what this story is about. Not a poor leader, but a missed moment, a lesson in what happens when leadership becomes purely transactional. Every leader I work with now hears me say: “This process only works if you show up for it.”
Reflection
Leadership is often more about presence than perfection. The biggest mistakes often come from assuming people are growing without actually talking about it. Learning through mistakes means recognizing those blind spots and turning them into milestones.
If this story resonates with you, download my free eBook ‘Mistakes or Milestones’ to explore more real leadership lessons, or book a 15-minute discovery call to start building growth-focused leadership habits in your own organization.
