The Emotional Undercurrent of Transitions: The True Derailer or Enabler

By Natalie Michael
Managing Partner, CEO Next Chapter

Introduction

When people talk about CEO transitions, they tend to focus on the visible: succession plans, governance frameworks, handover protocols, board alignment. These are, without question, vital. But there’s another layer—often overlooked, rarely discussed—that holds even more sway over the outcome of a transition: the emotional undercurrent.

Over the last two decades, I’ve worked with CEOs, founders, successors, and boards navigating this complex terrain. And what I’ve come to understand is this: it’s not the strategy that derails transitions—it’s the unresolved emotion behind the strategy. Ego. Fear. Grief. Guilt. Attachment. These invisible forces are either quietly shaping a successful exit or steadily eroding it.

Whether we acknowledge it or not, transitions are deeply human experiences. And if we fail to factor in the emotional undercurrent, we risk building plans that look pristine on paper but fall apart in practice.

Why Emotions Matter More Than We Think

It’s easy to underestimate how much emotion drives behavior at the top. We assume CEOs are rational decision-makers, buffered by experience and logic. But when identity and legacy are on the line, emotion is never far behind.

For the outgoing CEO, the emotional landscape can be riddled with complexity. Letting go of a role that has defined you for decades is not a tidy process. It can stir up existential questions: Who am I without this title? What is my purpose now? Will I still matter?

For successors, the emotions are just as potent. Stepping into a high-profile role often triggers performance anxiety, imposter syndrome, or fear of not living up to expectations—especially if the predecessor is revered. They might hesitate to bring fresh ideas or challenge legacy norms, out of a desire to “honor” the past.

These emotional dynamics, left unspoken, don’t disappear. They go underground—and that’s when they become dangerous.

The Cost of Avoiding the Emotional Undercurrent

One of the most common derailers I’ve seen is emotional bypassing: the belief that staying focused on logistics will keep things “professional.” But professionalism without emotional awareness leads to cold transitions—and cold transitions lead to silent resistance, fractured relationships, and cultural dissonance.

I once worked with a CEO who had built his company from the ground up and was stepping down after 25 years. His successor was bright, capable, and chosen with great care. But the transition stalled. Why? The outgoing CEO couldn’t emotionally separate from the business. He said all the right things publicly, but behind closed doors, he was second-guessing decisions, meeting privately with senior leaders, and slow-walking the handover.

He wasn’t malicious. He was grieving. And that grief, unacknowledged, began to erode the successor’s confidence and authority. When we finally named the emotion, everything shifted. We created space for the outgoing CEO to process his identity shift and helped the successor navigate trust-building conversations. Only then could the transition move forward.

Emotions aren’t distractions from the work—they are the work.

The Emotions That Most Often Derail Transitions

Here are some of the most common emotions that surface during leadership transitions—and how they show up:

  1. Fear
     Fear of irrelevance, fear of change, fear of public failure. Outgoing CEOs might fear becoming obsolete. Incoming CEOs might fear not being ready. Boards might fear choosing the wrong leader. This fear can cause people to cling to control, avoid honest conversations, or delay decisions. 
  2. Grief
     Stepping away from a role often involves loss—loss of identity, routine, influence, or relationships. If not acknowledged, grief can manifest as bitterness, micromanaging, or resistance to new ideas. 
  3. Guilt
     Some leaders feel guilty for leaving, especially if the company is in flux or people are emotionally attached to them. Guilt can lead to over-functioning or blurred boundaries. 
  4. Ego
     Transitions are a test of humility. Ego shows up as an unwillingness to let go, a desire to protect one’s legacy at all costs, or a need to still be the center of influence after departure. 
  5.  Excitement (Yes, even that)
    Sometimes, successors are so excited for the opportunity that they move too quickly—overhauling systems, making bold declarations, and unintentionally alienating the team. Their excitement, while genuine, needs to be channeled thoughtfully.

Naming the Undercurrent: Why It Matters

The most powerful thing you can do in a transition is name what’s emotionally true. Naming the emotional undercurrent doesn’t make a leader weak—it makes them honest. And honesty is the foundation of influence.

I often begin transition coaching by creating space for both parties to articulate not just what they think, but what they feel. What are they afraid of? What are they mourning? What are they hopeful about? What do they need to feel respected and secure?

When these conversations happen early and often, the emotional undercurrent becomes a current of trust, not sabotage.

Emotional Awareness as an Enabler

The good news is that emotions don’t have to derail transitions. In fact, when acknowledged and integrated, they can enable deeper connection, clearer communication, and more resilient leadership.

Here’s how emotional awareness becomes a strength during transitions:

  1. Increases Empathy and Trust
     When a successor understands what the outgoing CEO is feeling—and vice versa—they can communicate with greater empathy. This builds trust and softens resistance. 
  2. Enhances Self-Regulation
     Leaders who are emotionally aware can manage their reactivity, stay grounded during high-stakes conversations, and model composure to their teams. 
  3. Clarifies Values and Vision
     Transitions often prompt reflection. What kind of leader do I want to be? What legacy do I want to leave? These emotional questions can lead to sharper strategic clarity. 
  4. Creates a Shared Language
     When boards, executives, and teams can talk about the emotional side of change, it normalizes the experience and reduces stigma. People no longer have to hide behind “everything’s fine.” 
  5. Strengthens Culture
    Organizations that embrace emotionally intelligent transitions signal that people matter—not just roles. This strengthens psychological safety and cultural cohesion.

Practical Tools to Navigate the Emotional Undercurrent

While every transition is unique, here are a few tools I recommend for CEOs and boards:

  1. Transition Coaching
     Engage a neutral third party to support both outgoing and incoming leaders. Coaching provides a confidential space to surface emotion, reflect on identity, and process change. 
  2. Narrative Building
     Help both leaders co-create the story of the transition. When both voices are honored, and the narrative is consistent, it creates a sense of continuity and shared purpose. 
  3. Emotional Debriefs
     Hold dedicated conversations—either 1:1 or in small groups—about how people are feeling. Use open-ended prompts: What are you excited about? What are you unsure about? What support do you need? 
  4. Rituals of Closure and Welcome
     Symbolic gestures—like farewell celebrations, welcome messages, or leadership roundtables—can emotionally anchor the change. They create moments of acknowledgment and gratitude. 
  5. Leadership Integration Plans
    Go beyond 90-day action plans. Include relationship-building milestones, cultural immersion activities, and feedback loops. Think of integration as emotional onboarding.

Final Thoughts: Lead the Inner Transition

At its core, a leadership transition is not just an external shift—it’s an internal one. For everyone involved.

You can’t lead others through change unless you’ve led yourself through it first. That means acknowledging your own emotional landscape, naming what’s true, and making room for both grief and growth.

When we treat emotions as distractions, we invite sabotage. When we treat them as signals, we unlock wisdom. And when we lead from that place—of emotional clarity and inner steadiness—we don’t just transition roles. We evolve as leaders, and we set the stage for something greater than succession: transformation.

About Natalie Michael

Natalie Michael is a trusted advisor to CEOs navigating what’s next—whether preparing for their own exit, developing key talent, or designing a purposeful next chapter. As Managing Partner of CEO Next Chapter, she combines over 20 years of experience in executive development with a unique focus on succession strategy, peer learning & leadership reinvention.

A Master Certified CEO Peer Group Leader with Mackay CEO Forums and Chair of Tiger 21 Vancouver 3, Natalie works closely with business leaders stewarding enterprises ranging from $10M to $6B. She holds a Master’s in Organizational Leadership, numerous coaching certifications, and has authored two books on CEO development. Natalie also serves on the boards of Foundations for Social Change and Wavefront Centre for Accessibility.