What happens when employees start making decisions that belong to leaders.
Have you ever had this happen?
An employee walked into their manager’s office and said, “I’m going to Portugal for three months this summer with my family, and I’ll be working remotely while I’m there.”
They weren’t asking.
They were informing.
The company policy was clear. Employees were expected to be in the office three days a week unless they had received approval for an alternative arrangement. Both the employee and the leader knew the policy, yet the leader hesitated. Instead of thinking about what the organization required, they found themselves thinking about how the employee might react if they said no.
I’ve now heard versions of this story from numerous leaders.
An employee decides they’ll work different hours because it better suits their lifestyle. Another announces they will no longer attend meetings they don’t find useful. Someone else informs their manager they will be working from another country for several months.
The details change.
The leadership dilemma doesn’t.
THE MOMENT LEADERSHIP SHIFTS
What fascinates me isn’t the employee’s behavior.
Employees will always test boundaries. They will advocate for what they want. They feel entitled to make decisions that aren’t theirs to make. They will sometimes make assumptions about what they can and cannot do.
That isn’t the real issue.
The real issue is what happens inside the leader.
Somewhere along the way, empathy, support, and care for the employee experience have become conflated with a leader’s responsibility to regulate employees’ emotional states. Leaders began worrying less about making the right decision based on policy, performance, and organizational criteria, and more about how disappointed, frustrated, or upset the employee might become.
Instead of asking, What best serves the organization and this employee’s development? they began asking, How do I avoid upsetting this person?
That is the moment leadership shifted from authentic leadership to leadership from the adaptive persona.
WHEN EMPATHY BECOMES CODEPENDENCY
Empathy means understanding another person’s experience.
Codependency means becoming responsible for it.
The employee who wanted to spend the summer in Portugal may have had legitimate reasons. Family circumstances may have made the request understandable. They may genuinely have believed they could perform their role just as effectively from abroad. There may even have been a business case for approving the arrangement.
None of those possibilities changed one important fact.
The decision belonged to the organization, not the employee.
When a leader struggles to hold that boundary because they are worried about the employee’s emotional reaction, empathy has crossed into codependency.
HOW THE ADAPTIVE PERSONA CREATES PERMISSIVE LEADERSHIP
This is not authentic leadership.
It is the adaptive persona trying to avoid conflict, disapproval, or emotional discomfort. It is a leader without developed leadership capacities strong enough to have difficult conversations and manage performance.
The adaptive persona wants to be seen as supportive, understanding, and reasonable. It wants people to leave conversations feeling like they are a kind, compassionate human being. It tells the leader that saying no is unkind, that enforcing a policy is rigid, or that holding someone accountable will damage the relationship.
The authentic leader understands something different.
Leadership is not about protecting people from disappointment or bursting their entitlement bubble. It is about putting the needs of the collective ahead of an employee’s agenda. This creates a strong, safe working environment where people know the rules of the game and trust their leader to do the job of managing to performance expectations and policies, not individual agendas.
When leaders organize themselves around preventing emotional discomfort, permissive leadership follows.
THE COST OF PERMISSIVE LEADERSHIP
Permissive leadership rarely looks permissive. It looks like flexibility. It looks like kindness. It looks like being employee-centered.
Yet every time a leader avoids holding a reasonable boundary because they fear an employee’s reaction, they teach a lesson they never intended.
In the Portugal example, the employee learns that organizational policies are secondary to what they want to do if they confidently announce their plans. Other employees notice. They begin testing boundaries of their own, and before long, the written policy means very little because leadership has stopped reinforcing it consistently.
Culture is never built by policies alone.
It is built by the behaviors leaders repeatedly reward, tolerate, and reinforce.
DEVELOPMENT REQUIRES DISCOMFORT
Employees do not become stronger because leaders rescue them from difficult emotions. They become stronger because leaders tell them the truth, hold reasonable expectations, and trust that they are capable of working through disappointment.
Imagine if the leader had responded this way:
“I understand why you’d like to spend the summer in Portugal, and I’m happy to discuss your request. However, this isn’t a decision you can make unilaterally. We have a three-day in-office policy, and any exception needs to be reviewed before plans are made. Let’s explore whether there’s a workable solution.”
That response is respectful.
It is empathetic.
It is also leadership.
The employee may still feel disappointed.
That does not mean the leader has failed.
THE REAL LEADERSHIP QUESTION
One of the most important responsibilities of leadership is developing adults who can hear difficult answers, accept reasonable boundaries, and remain engaged even when they don’t get what they want.
That cannot happen if leaders believe their primary responsibility is to manage employees’ emotional reactions.
Employees don’t need leaders who rescue them from disappointment. They need leaders who hold boundaries, tell the truth, and support their development through difficult conversations.
The next time you find yourself hesitating before enforcing a reasonable expectation, ask yourself one question:
Am I leading from my authentic self, or has my adaptive persona convinced me that my job is to manage someone else’s feelings?
If this resonates with you, my book 𝐒𝐨, 𝐘𝐨𝐮 𝐓𝐡𝐢𝐧𝐤 𝐘𝐨𝐮 𝐂𝐚𝐧 𝐋𝐞𝐚𝐝? explores how leaders become permissive when they mistake managing emotions for leading people. It provides a practical framework for recognizing the adaptive patterns that undermine leadership and replacing them with authentic leadership that builds accountability, trust, and high performance.