“They Reminisce Over You.”
There is something about Pete Rock & CL Smooth’s “They Reminisce Over You (T.R.O.Y.)” that has allowed the song to endure for more than three decades. Released in 1992, it is a record about memory, presence, loss, and recognizing what someone meant after they are no longer there. I have always appreciated the song, but the longer I have worked with executives and organizations, the more I have found myself thinking about its message in an entirely different context.
Organizations do a lot of reminiscing.
A respected senior leader announces that they are leaving, and suddenly everyone begins talking about what that person contributed. Colleagues remember how they could walk into a tense meeting and help people find common ground. Someone mentions how much institutional history they carried. Others remember the people they mentored, the relationships they repaired, or the problems they prevented before those problems ever reached the executive team. The departure announcement becomes a moment of organizational reflection, and people begin appreciating work that had become almost invisible while the leader was still doing it.
I have seen this happen enough times that I have learned to ask a different question when a valued leader resigns. Instead of asking why they are leaving, I want to know when they began to leave.
Those are not the same question.
Senior leaders rarely disengage from an organization on the day they submit a resignation letter. More often, the departure begins months earlier through a series of decisions that are difficult to see if leadership is only measuring performance. Experienced executives learn how to remain productive even when they have become less invested. They continue attending meetings, delivering results, managing their teams, and fulfilling the responsibilities associated with their role. What changes first is not necessarily their output. It is what they are willing to contribute beyond what the job requires.
That distinction matters because some of the most valuable things senior leaders bring to an institution have never appeared on a job description.
Pay Attention When Candor Becomes More Polished
One of the privileges of working with experienced executives is benefiting from what they see before everyone else sees it. After twenty or thirty years in leadership, people develop pattern recognition that cannot be easily captured in a dashboard. They have seen strategies succeed and fail. They know how certain decisions are likely to land with employees. They recognize the early signs of a relationship deteriorating or an initiative moving in the wrong direction.
When those leaders are deeply engaged, they tend to share what I think of as the unfinished truth.
They may come into your office and say, “I cannot prove this yet, but something does not feel right.” They may raise a concern before every fact is available or offer an interpretation that challenges the prevailing view. They are willing to risk being wrong because they believe the conversation is important enough to have early.
When that same leader begins disengaging, the quality of their communication often changes in ways that can initially look like improvement. Their observations become more polished. Their recommendations are carefully documented. They wait until they have enough evidence that the issue is difficult to dispute, and they may only offer their judgment when someone explicitly asks for it.
From the outside, nothing appears wrong. In fact, the executive may seem more disciplined.
What the organization has lost is access to their early judgment.
That loss is difficult to measure, but it can become enormously expensive. A risk that might have been discussed while it was still manageable is allowed to mature. A strategic assumption goes unchallenged for another quarter. An employee issue becomes a retention problem because the experienced leader who recognized the pattern no longer believed it was worth raising before the evidence became undeniable.
Candor is discretionary. Senior leaders decide how much of it an organization has earned.
When an experienced executive stops bringing you what they see before they can prove it, I would pay attention.
Influence Becomes Exhausting When It Never Leads to Authority
I have spent much of my career in environments where influence matters. Government certainly teaches you that lesson. A title may give you authority over some things, but most meaningful work requires persuading people you do not control. Healthcare works much the same way, as do large corporations. Complex organizations depend upon leaders who know how to build coalitions, navigate competing priorities, and move people toward an outcome without relying exclusively on positional authority.
That is leadership.
There is, however, a point at which organizations begin confusing a leader’s ability to influence with an excuse not to give that leader meaningful authority.
I have seen senior executives held accountable for outcomes while being excluded from the decisions that determine those outcomes. They are expected to execute strategies they had little opportunity to shape. They are told to “get everyone aligned” after decisions have already been made elsewhere. Because they are capable leaders, they often make the arrangement work for a while. They call colleagues, build support, repair relationships, reframe the argument, and spend their personal credibility getting people to move.
The organization benefits from all of that invisible work and may conclude the structure is functioning exactly as intended.
The executive experiences something different.
Influence without meaningful authority eventually becomes emotional labor. There is only so long a seasoned leader will continue spending personal credibility compensating for an organizational structure that gives them responsibility without sufficient agency.
When they begin disengaging, they may not complain. Experienced leaders often know complaining will accomplish very little. They simply become more selective about where they spend their influence. They stop making the extra phone call. They stop carrying an argument into the fifth room after it was ignored in the first four. They fulfill the requirements of the position and conserve the rest of their credibility for places where it can actually make a difference.
Leadership may interpret that as a loss of passion.
Sometimes it is simply a rational response to learning that access and impact are not the same thing.
Strategic Whiplash Teaches Good Leaders to Wait
Senior executives understand that priorities change. Anyone who has led through a recession, political transition, public health crisis, merger, leadership change, or significant market disruption understands that rigidity is not a leadership virtue. Good executives adjust when circumstances require it.
What wears experienced leaders down is not change. It is change without coherence.
An organization announces decentralization as a strategic priority, only to pull authority back to the top six months later. Leadership talks about building long-term capability in one meeting and rewards a short-term decision that undermines that capability in the next. A major initiative is introduced with urgency, teams reorganize around it, and executives attach their reputations to making it successful. Then senior leadership’s attention shifts, and the initiative quietly disappears without anyone acknowledging what changed.
After this happens enough times, experienced leaders learn something.
They learn to wait.
The next strategic priority arrives, and they no longer immediately mobilize their teams. They use careful language. They avoid attaching too much personal credibility to the announcement. They may tell employees to continue focusing on existing work until the new direction demonstrates that it has staying power.
From the executive suite, that behavior can look like resistance.
From the senior leader’s perspective, it may be stewardship.
Every major organizational initiative requires people to spend credibility with their teams. When leaders repeatedly ask people to make that investment and then casually abandon the strategy, they should not be surprised when experienced executives become reluctant to spend that credibility again.
What appears to be disengagement may actually be learned caution.
Executive Teams Can Become Too Good at Agreeing
Some of the healthiest executive teams I have worked with were not always comfortable places to sit.
People disagreed.
They challenged assumptions, questioned strategies, and occasionally had conversations that created tension in the room. The difference was that the disagreement served the work. People understood that challenging an idea was not the same as challenging someone’s authority or commitment to the organization.
That distinction is essential because senior leaders are not hired merely to execute. They are hired for judgment.
Yet I have watched executive teams gradually develop what I call alignment theater. The presentation is made, the leader asks for reactions, and everyone appears supportive. The meeting ends with apparent agreement, but the real debate begins afterward. Concerns surface privately. Leaders protect their own functions from decisions they did not believe in, and execution slows for reasons nobody is willing to discuss openly.
The organization has achieved the appearance of alignment without receiving any of its benefits.
Experienced executives eventually recognize when honest debate is no longer welcome. They learn which questions can be asked and which ones will be interpreted as resistance. They understand when leadership wants their judgment and when leadership simply wants endorsement.
Once they learn that distinction, many will adjust.
They become easier to manage.
They also become less valuable.
A senior leader who has learned to keep their best judgment to themselves may continue sitting at the executive table for years. The seat is occupied, the meetings continue, and the organization can convince itself that nothing has changed.
But something important has already left the room.
Some of the Most Valuable Leadership Work Is Almost Invisible
When a respected executive leaves an organization, one of the things that often surprises people is how much work suddenly has no owner.
I am not talking about the responsibilities listed in the job description. Those are usually reassigned quickly. I am talking about the connective work that experienced leaders accumulate over time.
Someone had been mentoring the vice president who was struggling with confidence. Someone knew that two department heads had stopped trusting one another and was quietly keeping their conflict from affecting the rest of the organization. Someone understood why a decision that looked obvious on paper would reopen an old institutional wound. Someone was willing to tell a colleague an uncomfortable truth privately before that colleague made a public mistake.
None of this work appears neatly in a performance report.
That does not make it less valuable.
In many organizations, senior leaders carry enormous amounts of emotional and institutional labor precisely because they are good at it. People seek them out. They become translators, mediators, historians, coaches, and stabilizers. Because they perform these roles without much fanfare, the organization gradually begins treating their contribution as though it were unlimited.
It is not.
One of the quieter signs of disengagement is when a leader stops carrying work nobody formally asked them to carry. The mentoring conversations become less frequent. They stop stepping into conflicts outside their function. They no longer volunteer to help another executive think through a difficult situation. Their own responsibilities continue to be handled well, so the change may attract very little attention.
The job is still getting done.
The institution, however, is becoming more fragile.
Do Not Wait Until You Are Reminiscing
This is where Pete Rock & CL Smooth’s record comes back to me.
Organizations are often very good at recognizing the value of senior leaders once they are gone. The farewell message describes their wisdom, their relationships, their institutional knowledge, and their ability to bring people together. People tell stories about what the leader meant to the organization and how much they will be missed.
There is nothing wrong with honoring someone at the end of a chapter. We should.
I simply think we should become much better at recognizing what people contribute while they are still willing to contribute it.
If I were concerned that a senior leader was beginning to disengage, I would not start by asking whether they were thinking about leaving. By the time someone is ready to answer that question honestly, the organization may already be late.
I would want to understand their experience of leadership.
Where are they carrying accountability without enough authority to influence the outcome? Which conversations have they stopped having because those conversations no longer feel useful? Where has the organization asked them to spend credibility repeatedly without demonstrating strategic consistency? What work are they doing that the institution benefits from but rarely recognizes? Where are they invited into the room but prevented from having meaningful influence over what happens there?
Those questions require a certain amount of humility because the answers may challenge the story senior leadership has been telling itself about the organization.
That is precisely why they matter.
Senior leaders do not need constant praise, and experienced executives usually recognize that not every recommendation will become a decision. What they need is coherence. They need meaningful authority commensurate with their accountability. They need executive teams where honest debate is still useful. They need to know that their experience, judgment, relationships, and institutional wisdom are valued for more than their ability to deliver another quarter’s results.
Most importantly, they need evidence that investing more of themselves in the organization still makes sense.
The best time to discover what a leader contributes is not during the farewell reception.
It is while they are still sitting at the table, still carrying the institutional memory, still mentoring the next generation, and still deciding how much of their judgment, courage, creativity, and influence they are willing to give you.
Because by the time everyone begins reminiscing, the organization may simply be acknowledging a departure that happened months ago.
Keep Your Best Leaders Engaged Before Retention Becomes the Problem
Retaining senior leaders requires more than compensation, titles, and succession plans. It requires an executive culture where experienced leaders have meaningful influence, honest debate is valued, accountability matches authority, and the invisible work of leadership is recognized before people decide to stop doing it.
Through keynote presentations, executive retreats, and strategic advisory engagements, I help organizations strengthen executive leadership, improve workplace culture, and identify the conditions that cause talented leaders to disengage long before they resign.
If your organization wants to keep its most experienced leaders fully invested, not simply employed, let’s start a conversation.