“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.

Why Emails Don’t Build Culture: What Research Says About Real Communication

When goals are slipping or alignment feels off, most leaders start with an email.
It feels efficient — a quick check-in, a list of reminders, a few encouraging words. But research consistently shows that when it comes to real organizational change, email isn’t enough.

The Myth of the Perfect Email

Email is great for logistics and updates — but when we use it to build culture, it falls flat.
That’s because culture isn’t built through information; it’s built through connection.

Psychologists and communication theorists have found that we interpret meaning not just from words, but from tone, body language, timing, and feedback. When those cues are missing, messages can feel colder, flatter, and less urgent — even when they’re well written.

What the Research Says

Media Richness Theory (Daft & Lengel, 1986) explains that some communication channels are “richer” than others. Rich channels — like in-person meetings or live video — allow for immediate feedback, emotional cues, and clearer understanding.
“Lean” channels — like email — are great for data, but weak for dialogue.

Similarly, Karen Byron’s (2008) research on email communication found that emotion and intent are often misunderstood in emails. Even short, neutral messages can be interpreted as negative when tone cues are missing.

So when leaders send “How’s progress on our goals?” emails and hear nothing back, it’s not necessarily disengagement — it’s that the message didn’t invite conversation.

What Meetings Do Differently

Meetings aren’t just for updates — they’re for meaning-making. When people meet to discuss goals, they have the chance to:

• Ask questions that clarify assumptions.

• Hear how others are interpreting the same priorities.

• Build shared understanding — and shared ownership.

It’s the social construction of clarity that matters. You can’t get that through reply-all.

When to Email vs. When to Meet

Use email for:

• Quick updates, reminders, or summaries

• Sharing data or reference documents

• Confirming decisions already made

Use meetings for:

• Launching new initiatives or strategies

• Checking in on goals that require collaboration

• Exploring barriers, questions, or concerns

The key is to match the communication method to the task complexity — not the leader’s convenience.

Final Thought

Email informs. Meetings connect.
And culture is built on connection.

If you want people to care about the goals, you have to create space where they can see how their work fits into the story. That story can’t live in an inbox — it has to live in conversation.

VibeCheck Insight

• Use email to document decisions, not make them.

• Build recurring meetings for reflection, not just reporting.

• Remember: culture grows where communication is human.

When Strategy Stays on Paper: What Strategic Planning Really Reveals About Organizational Culture

Recently, I’ve been researching strategic planning and its effects on organizational operations. What I’ve found is that strategic planning only makes a real impact when it’s done differently — when it’s inclusive, clearly communicated, and not limited to a traditional 3–5-year lens.

Too often, strategic planning is treated like a formality. A board retreat happens, a vision document gets produced, and a few goals are written down somewhere that most people in the organization never see again. On paper, that looks like strategy.
In practice, it often looks like confusion.

Who Drives the Plan?

In many organizations — schools, nonprofits, and businesses alike — strategic planning is driven by the board and the Chief Executive Officer (CEO). That’s not necessarily wrong, but when those two groups are the only ones involved, something important gets lost.

The goals may exist, but the ownership doesn’t.
When strategy isn’t clearly communicated or tied to daily work, there’s little accountability or alignment. The plan becomes a leadership artifact instead of a shared roadmap.

A Common Story: The Plan That No One Remembers

In one organization I observed, a strategic planning process was rolled out with enthusiasm and structure. There was a designated point of contact who tracked progress and kept things organized. But when that person left and a replacement stepped in, the communication rhythm stopped.

The only follow-up came months later, when a senior leader emailed teams asking for updates on the goals that had been set.
The problem?
When staff were asked about those goals, most didn’t know what they were. Some didn’t even know any goals had been set at all.

The issue wasn’t the framework — it was the lack of follow-through and communication.

Why Traditional Strategic Planning Falls Short

The traditional 3–5-year strategic plan assumes stability — steady leadership, predictable budgets, and consistent priorities. But that’s not how most modern organizations work anymore.
Teams shift, priorities change, and external pressures evolve faster than any five-year plan can predict.

When plans aren’t revisited regularly or communicated widely, they quickly become irrelevant.
And when they’re created by leadership without broad participation, they fail to capture the perspectives of the people closest to the work.

Strategic planning shouldn’t be an event — it should be a living practice.

Strategy as a Living Culture

A good strategic plan isn’t a product — it’s a process that builds shared understanding.
That means:

• Involving more stakeholders in the planning itself.

• Talking about the goals often — not just during annual reports.

• Revisiting and revising when conditions change.

When organizations make strategy part of the culture — not just a leadership exercise — staff feel ownership, communication improves, and accountability becomes organic.

Without that connection, strategy doesn’t drive operations — operations drift without direction.

What This Teaches Us About Culture

When people don’t know the goals, it’s not a motivation problem — it’s a communication problem.
When plans fade after leadership changes, it’s not a systems issue — it’s a culture issue.

Plans don’t fail because they’re bad. They fail because they’re silent.

VibeCheck Insight

When organizations say their strategy “isn’t working,” it’s rarely the framework.
It’s usually because the culture around communication and ownership wasn’t built.

1. Involve more voices in the planning process.

2. Keep goals visible and discussed.

3. Treat strategic planning as ongoing, not episodic.

That’s how you move from strategy on paper to strategy in practice.

Reflections of Beginning Leadership

Recently, I’ve been reflecting more and more about my experiences in leadership and coaching leaders. I have made some big mistakes along the way. There are so many instances that I can think of that I regret but there are also things that I am proud of.

When I was in Army Basic training, we took turns being the squad leader and although I don’t remember the exact thing that a person said but it was along the lines of “You can either lead by respect or by fear.” I’m sure if I looked this up I might be able to find the context around this. For me, the quote struck me…..so much of leadership in the beginning was trying to make sure that people respected me and I was going about this with threats and authoritativeness and it’s completely ineffective.

The folks who work for you, might do what you say but they don’t respect you. They will work around your rigid rules and go around you. Eventually, if you are lucky and self reflective you might learn that it’s not about telling people what to do but instead working with people to decide the best course of action. This to me, seems like the secret sauce, but believe it or not, there are a lot of people who don’t want to be included in the decision making process. With that being said, it is apparent that balance is key, but you don’t learn that from any class or any book. You have to try and fail and then try again. I think what is important in that process is that you acknowledge when you realize you are wrong and you actually make the change. We can sometimes live in our fear of not being taken seriously iff we change our minds, but we are working with humans and to continue doing things that don’t work is demoralizing.

If I were to redo some of my beginning leadership journey, I would look at the concepts presented in the book by Brene Brown “Dare to Lead”. Because the work that you do as a leader is so important but it’s also emotional and taxing. You have to be able to self reflect and take feedback but you also have to be confident in your abilities.

Regardless, you can do this….but if you can’t do it with love then don’t move into leadership.