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The Emotional Journey of Retiring CEOs

leadership transition retirement tips for a board transitioning a ceo Apr 30, 2024

When a CEO leaves their last career role to begin their "retirement", they go through the stages of loss and grieving. It’s a natural part of the transition process and everyone will experience it differently.

Because the grief experience is so unique to every individual, there is no predicting what your CEO's personal expression will look like.

Over ten years of working with CEOs facing the end of their careers, I have seen that this grief can manifest at any time and, it comes up unexpectedly. If you are observing the wellbeing of the CEO, grief symptoms often look like unusual or uncharacteristic behaviour. It won't necessarily be bad or have negative impact behavior. The importance is for the board and the team to know what is behind the behaviour and have empathy for the situation. With that perspective, those around the CEO can navigate grief intentionally and ensure their leader is empowered throughout their transition.

What are some real-life examples of these behaviours? Here are three that I have experienced.


As a usually calm, soft-spoken CEO was leaving his role, he told me how he had a disturbing experience on the weekend. Never one to be quick-tempered, he found himself throwing objects around. Even worse, it was in front of other people. As he caught himself in mid throw, he realized he was struggling to come to terms with reaching the end of his career. He was angry that he had aged and that this was the final months in his beloved role. By processing the unexpected behaviour, he was able to move through that stage of his grief and get one step closer toward embracing his next phase of life.


Another stage of grief I’ve seen is when CEOs who typically keep their emotions private become expressive during the last weeks of their job. Many times this comes out as a fear of crying at their retirement party or on their final day. They don't want to be the person who has to carry around a Kleenex box. Saying goodbye to colleagues, customers, and partners who have grown to be friends causes those "last time" meetings to be sentimental. Although it may not be familiar to the CEO to be emotional, I encourage them to allow it to happen. Being vulnerable models to others that sharing their feelings at these milestones is a human experience. In other words, because the CEO cares deeply about the people, role, and the impact, sadness in saying goodbye is "normal" and healthy.


The third stage of grief I’ve seen is denial. This is the fight or flight instinct that happens to all of us. In one example, the CEO left town unexpectedly to avoid his retirement party (although he had a second thought and returned on time). I have also seen CEOs choose to focus on a legacy project that is far too large to complete before their final day. Even though it’s difficult to manage denial, it’s a key stage in allowing your brain to process grief without becoming overwhelmed. It is one technique for slowing down their grieving process to a pace the CEO could manage. However, it can cause unintended stress on the team and others.

It’s important to give outgoing CEOs the space and support they need to experience the grieving process in their own unique way.

Letting them work through their emotions makes for a more seamless transition period. The board or team need to balance giving space while watching for behaviours that could be harmful to the CEO (including their reputation) or others. By moving through the grief cycle, a CEO can arrive at a place where they can look forward to their retirement with a sense of peace and accomplishment and, perhaps, excitement.

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