“She’s Going to Be Your Legacy”: What One Employee Taught Me About Growth, Grace, and Systems That Fail People

While interviewing for an executive assistant position, I met a young African American woman who seemed to have a lot of potential. She was personable and charismatic, but there were other, more qualified candidates for the position I was looking to fill. I couldn’t offer her that job, but I wanted to offer her another opportunity—one that gave her time to grow—and she started that job with a lot of enthusiasm.

Over the next few months, her lack of experience became glaringly obvious. I had assumed my proximity would be helpful and that I could coach her to become the model employee I knew she could be. She made mistakes, arrived late, kept a tab open with Netflix running on it, and there were just so many instances I couldn’t keep up with.

Her supervisor had wrongly assumed that, because I had championed this employee, he couldn’t follow the progressive steps of discipline. By the time I learned she had not been meeting expectations, he was frustrated and called me to say, “She’s going to be your legacy—you have to let her go.”

Eventually, that cross came to bear. I saw her years later, and it looked like she was thriving—I was happy for her. But I couldn’t shake that quote: “She’s going to be your legacy.”

This was a company I had helped grow from just nine staff and two sites to over thirty learning centers in the span of two years. I had worked with community partners to establish easier pipelines for enrollment and coached leaders from a range of backgrounds. And yet, the way he saw it, none of that mattered—I was throwing it all away to support this one person.

What he meant as an insult—“she’s going to be your legacy”—stuck with me because he was right, but not in the way he thought. My legacy wasn’t that she failed; it was that I tried to make room for someone the system wouldn’t have. It showed me how quickly organizations praise growth in numbers but resist growth in people. If I had to choose again, I’d still give her the chance—but I’d make sure I built the support she needed to thrive.

Too often, we assume that people arrive fully equipped with the skills they need to succeed. But the truth is, those skills must be developed—and that development requires time, structure, and belief.

The VibeCheck Reflection

At VibeCheck, we see this story play out every day—organizations that want to champion emerging talent but don’t have the systems in place to sustain that growth. Leadership programs, onboarding, coaching, and feedback loops are often reactive instead of intentional.

When employees struggle, it’s rarely a “people problem.” It’s a system problem.System problems can be fixed—with honest data, transparent conversations, and a commitment to build environments where people can actually thrive.