When a long-term employee leaves suddenly and shares a list of grievances, it can be jarring. It’s easy to feel defensive, misunderstood, or even betrayed. But beneath discomfort lies an opportunity for reflection, growth, and a deeper understanding of the human dynamics that shape our organizations.
Recently, I received such an email. It was candid, emotional, and filled with observations about leadership, culture, and change. I responded with gratitude and respect, acknowledging the courage it takes to speak up, even after a departure rather than during it. And that timing matters. Feedback shared after departure, while still valuable, limits the opportunity for dialogue, resolution, and mutual understanding.
This experience prompted me to reflect on several truths that often go unspoken:
1. Feedback Is Courageous but Timing Matters
It takes bravery to speak up, especially when the feedback is critical. But the most impactful feedback is shared while the relationship is still intact. When there’s still room to listen, learn, and adjust. When feedback comes after someone has already left, it’s often too late to change the outcome. It closes the door to dialogue, turning potential growth into a missed opportunity.
2. Perception Isn’t the Whole Picture
Employees see the world from their vantage point, and their experiences are valid. However, leadership decisions often involve layers of context that aren’t always visible across the organization. Budget constraints, legal obligations, strategic pivots, and personnel histories all influence choices. What may appear as favoritism or inconsistency may be a carefully considered, though imperfect, decision made with the best available information to support company goals.
After last year’s engagement survey, one employee chose to identify themselves and share their thoughts directly. That conversation opened the door to a meaningful dialogue. As we talked, there were several light bulb moments, many “I had no idea” realizations. The employee began understanding the rationale behind certain decisions, and how others’ backgrounds and experiences shaped those choices. It was a powerful reminder: that perception is not the whole picture, and that open conversation can turn misunderstanding into insight.
As Daniel Boorstin said, “The greatest enemy of progress is not ignorance, but the illusion of knowledge.”
When employees assume they know the full story without seeking clarity, it can lead to misjudgments and missed opportunities for growth.
3. Favoritism or Strategic Fit? The Unseen Layers of Leadership Decisions
One of the most common critiques is perceived favoritism in promotions or hiring. It’s easy to look at a decision and say, “That person didn’t deserve it,” especially when the full context isn’t visible. But leadership decisions are rarely made in a vacuum. Behind every promotion or leadership appointment is a complex evaluation of education, experience, strategic value, and contributions.
At ReEmployability, we’ve seen time and again how employees grow into new roles by becoming the solution to a business need. Whether it’s resolving a critical operational challenge, cultivating a key client relationship, or quietly demonstrating leadership behind the scenes, these contributions often shape new opportunities. Many of our roles have been created in response to this kind of proactive impact.
Yes, we’ve hired friends and family. Sometimes it works, and sometimes it doesn’t work. But these individuals are often held to higher standards—not just by leadership, but by their families. What employees don’t see are the coaching sessions, performance reviews, and tough conversations that happen behind the scenes. Leadership isn’t about visibility; it’s about impact. Judging personal relationships as favoritism overlooks the accountability and intention behind those decisions.
Why put someone in a position that could ultimately lead to failure? That doesn’t make good business sense. This is essential. Employees must trust that their leaders are making decisions with integrity and intention. If that trust is broken, it’s important to seek clarity, or, if alignment can’t be found, to respectfully opt out. Staying in a culture you don’t believe in only breeds resentment and disengagement.
4. Tenure Doesn’t Always Equal Alignment
There’s a common belief that tenured employees are the “bread and butter” of a company. They carry institutional knowledge, loyalty, and deep relationships. But tenure can also breed resistance to change.
Consider the “Monkeys, Ladder, and Water” parable: five monkeys are placed in a room with a ladder and a banana at the top. When one monkey climbs the ladder, all are sprayed with cold water. Eventually, the monkeys stopped trying. New monkeys are introduced, and even though they’ve never been sprayed, they continue the behavior, beating any monkey who tries to climb the ladder. Why? Because that’s how it’s always been done.
This is the illusion of knowledge at work. Habits formed not from truth, but from repetition and assumption.
While the story is fictional, its message is powerful: we often resist change not because it’s wrong, but because we’ve been conditioned to fear it. Tenured employees may unknowingly perpetuate outdated norms, discouraging innovation and fresh thinking.
This resistance often shows up when key responsibilities shift from one team to another. These changes are not about redefining someone’s job. They’re about aligning roles with evolving business needs. Strategic realignment ensures that the right people are focused on the right priorities, even if it means letting go of legacy structures. When employees view these shifts as threats rather than opportunities, it can stall progress and create unnecessary tension. At ReEmployAbility, we’ve seen this dynamic play out many times over the past 21 years. As business evolves, roles shift to meet new priorities. These changes aren’t about redefining jobs—they’re about aligning with strategic needs. When viewed as threats, these shifts stall progress. We always consider the “Get it, Want it, Capacity to do it” philosophy to guide decisions. And while it’s never easy to see good people leave, there’s a sense of pride in knowing they’ve gained experience and knowledge in an industry that has served me so well. Many of them remain in our industry, and I’m proud of that. Some grow with us. Others move on. Both paths are valid.
5. Leadership Is Lonely and Often Misunderstood
Leadership decisions are rarely simple. Each one is carefully considered. Not only for its immediate impact, but for how it will shape the organization’s future.
Today, ReEmployAbility is experiencing a record-breaking year, and I believe that’s no accident. Thanks to a strong leadership team whose insight and integrity have driven our growth.
In the early days of the company, I leaned heavily on a small, close-knit group of employees who helped shoulder the weight of our expansion. Their dedication laid the foundation for everything we’ve built. Today, I’m proud to lead alongside a broader team of professionals who collaborate, contribute, and share the responsibility of decision-making. Our choices are no longer made in isolation. They’re shaped by diverse perspectives, mutual accountability, and a shared vision for ReEmployAbility’s future.
I understand that for some of our tenured and former team members, those who were part of that original core, it may feel personal when their voices aren’t the loudest in the room anymore. That shift is real, and I want to acknowledge it with empathy and respect for the contributions they’ve made along the way. Change can be uncomfortable, and I’m truly sorry for any pain it may cause. But I also trust the growing team of leaders that walk beside me, guiding the business with purpose and integrity.
Leadership means protecting the organization from internal instability, navigating pressures, and making decisions that may not be popular, but are necessary. These complexities are often invisible but they’re essential to long-term success.
6. Culture Is Everyone’s Responsibility
A healthy culture isn’t built by leadership alone. It’s shaped by every conversation, every act of kindness, and every moment of accountability. When employees feel silenced or undervalued, it signals something is broken. But fixing it requires participation, not just critique.
Building a healthy culture requires humility—the willingness to admit we don’t know everything, and the courage to ask questions. Boorstin’s insight reminds us that progress begins when we challenge our assumptions.
At ReEmployAbility, we’ve made a deliberate effort to embed the principles from The Ideal Team Player by Patrick Lencioni into our culture. We believe that the most effective team members embody three essential virtues: humble, hungry, and smart.
- Humble team players focus on the success of the team rather than personal recognition. They share credit, admit mistakes, and value others’ contributions.
- Hungry team players are self-motivated and always looking for ways to grow, contribute more, and take on new challenges.
- Smart team players have strong interpersonal awareness. They understand group dynamics, communicate effectively, and navigate relationships with emotional intelligence.
These traits aren’t just buzzwords, they’re now the foundation of how we hire, develop, and assess our team. We’ve found that when people possess all three virtues, they naturally contribute to a healthier, more collaborative environment. And when someone is missing one, it becomes harder to sustain effective teamwork.
As Patrick Lencioni writes: “Leaders who can identify, hire, and cultivate employees who are humble, hungry, and smart will have a serious advantage over those who cannot.”
Culture thrives when feedback is welcomed, when trust is mutual, and when everyone, leaders and team members alike are committed to growth.
Final Thoughts
I’m grateful for the feedback I receive from employees, even when it comes too late to change the outcome. It reminds me that leadership is a journey of constant learning, and that every voice matters, even the ones that challenge us.
I hope employees everywhere recognize their power. Not just to speak up, but to do so with courage, timing, and a willingness to engage in hard conversations before the goodbye. Trust your company. Ask questions. Share your concerns. And if you find that alignment is no longer possible, opt out with grace and integrity.
Because the health of an organization depends not just on its leaders but on everyone’s willingness to build something better together.
“The greatest enemy of progress is not ignorance, but the illusion of knowledge.” — Daniel J. Boorstin
