Leadership transitions rarely fail because of poor strategy. They fail because of poor entry.

I was recently sitting in on a meeting at an organization that had just appointed a new senior leader.

This, of course, is familiar territory. A leader is brought in to address a specific challenge. They arrive with mandate, momentum, often an augmented budget and, hopefully, a small cohort of trusted colleagues. What matters most in these moments is not what the new leader intends to change — but how they listen before they speak.

The first ninety days of leadership are not a performance window. They are a permission window. They determine whether people will offer you their insight, their patience, and eventually their trust. That is why experienced change leaders conduct listening tours. Some do formal focus groups. Others prefer informal breakfasts, hallway conversations or unannounced pop-ins. The specific tactic matters less than the signal: I am here to learn how this place actually works.

Not every approach resonates with every employee. What matters is that there is something for everyone. These early interactions serve as reconnaissance. They allow leaders to read the emotional landscape, understand where confidence lives, and identify where it has quietly eroded.

During this phase, discretion matters.

Every new leader has moments of surprise — sometimes disbelief — when encountering legacy systems or entrenched behaviors. Those reactions are inevitable. But they belong in private conversations with a trusted inner circle, not in the public square.

At the meeting I observed, that line was crossed. The new leader opened by sharply criticizing the previous leadership team. Systems were described as broken. Quality was framed as inconsistent. The organization, it was implied, had been poorly run.

The intent was understandable. The leader was trying to signal alignment with those who had felt unsupported. The subtext was meant to be reassuring: We see what you’ve endured. Things will be different now.

Intent is not impact.

The previous leader was widely respected — known as diligent, kind and constrained by structural challenges beyond their control. The room knew this. So, instead of relief, something else emerged: defensiveness.

People didn’t say it out loud, but you could see it happen in real time. Postures stiffened. Faces hardened. An invisible line appeared between the speaker and the audience. The wall went up.

By the time the meeting ended, a problem that hadn’t existed an hour earlier now did. Stakeholders gathered afterward, frustrated not by the change agenda itself, but by the way it had been introduced. Trust had been quietly withdrawn.

This is the paradox of change leadership: every system you inherit — no matter how dysfunctional it appears — represents someone’s best effort under constraints.

There will always be individuals who were harmed by the status quo and others who felt protected by it. The way a new leader speaks about the past determines whether people will grant them permission to shape the future.

Generosity lowers resistance. Contempt, even subtle,  creates it.

Generosity does not weaken authority. In fact, it accelerates it.

Leaders who navigate transitions well tend to follow a similar pattern. They are explicit about what they do not yet know. They acknowledge what worked, even imperfectly; and, rather than diagnosing problems in isolation, they ask the organization for systemic insight:

 “If you were in my role, where would you begin — and why?”

These questions do more than gather information. They restore dignity.

Empathy and effectiveness are not competing forces. They are complementary ones. Leaders who enter with humility create space for momentum. Leaders who enter with judgment create friction that must later be undone.

The most effective change leaders understand a quiet truth: you do not earn credibility by dismantling the past. You earn it by respecting the people who survived it. When that respect is present, the room doesn’t need to be convinced. It opens and welcomes you in fully.