Leadership and Loss

 “It is worth remembering that the time of greatest gain in terms of wisdom and inner strength is often that of greatest difficulty.”  Dalai Lama

A closeup of the eye on a young man with a serious look on his face

I was talking with my friend and colleague, Richard, a few weeks back.  I was recounting the impact of the number of people close to me who had died in the past three months.  As we talked, he paused, and then encouraged me to write about loss in relation to leaders.  It was his notion that leaders often struggle to deal with loss.

Over the next several days I reflected on our conversation and began to incubate where this topic might lead me.  You can judge the value of where it ‘led me’.  If nothing else I know that the writing has allowed me some additional perspective on my own grief and loss.  That’s a good thing, as it has allowed me to return some energy to my soul through understanding that grieving was an integral part of healing.

I look forward to hearing from you, and finding out how your own journey is going, and how your summer is going.

As always, thank you to those of you who provide me feedback.  It is always helpful and appreciated.

Do your best work and be well.


Leadership and Loss

Over the past month I have been thinking about leadership and loss.  As part of my ‘thought journey’ I came across a book by Sylvia Hepler titled, Learning Leadership Through Loss.  In the dedication section of her book she lists 23 items that can involve loss.  They are listed below.

Job terminations

Illnesses or unwanted health conditions

Physical disabilities

Marital strife

Financial loss

Physical, emotional, sexual, or financial abuse

Separation or divorce, death

Substance abuse


Alterations in physical appearance


Deteriorating elderly parents

Mental health challenges

Geographical moves

New jobs


Empty nest

Loss of friendships

Loss of reputation

Loss of respect

Loss of support for significant life choices you’ve made

Loss of living space through fire or flood

As I went through the list, I began to put tic marks next to the ones that I had experienced.  Each one had a memory.  Next to some, I paused to reflect on my deeper sense of loss/pain that I had experienced.  When I completed the list, I realized that I had put marks next to 17 of the 23 items.  That gave me pause.  “Wow, I’ve dealt with a lot of loss in my life.”  Then it occurred to me that many of us, if not most of us, have dealt with a lot of loss in our lives.

There are a couple of things that I have learned in dealing with loss.  The first is being able to ‘sit’ with the loss long enough to understand its meaning and impact on my life.  This took me into my 50’s to learn.  My prior reaction was to try to ‘get over’ or around the loss.  I wanted to ignore the pain.  I wanted the pain to go away.  Then I learned a far greater lesson about loss – if I allowed it the time and space to fully emerge, I would be in a far better place emotionally, intellectually, and spiritually, and, on occasion, even physically.

Sometimes that loss is a person that was close to you.  That ‘sitting,’ in part, is time to reflect on what that person meant to you.  That reflection can often take weeks, months and years to fully understand their impact on our lives.  We are better off when we provide ourselves the space to allow the sadness and grief to emerge as it will.  The point is that each loss will be different.  It will be different in intensity and it will be different in the how and how long you will carry the loss with you.  Some losses will last a lifetime.  That’s okay.

The other thing that I have learned about loss is also about choice – what we do with our ‘losses’ is also about our choice.  If you have read my work for very long, you know that I talk often about ‘choice.’  I would submit that with each loss we can build our strength and capacity of who we are as a person, and who we are as a leader; or, we can allow ‘it’ to take us on a downward spiral for a very long time.

Loss has a way of humbling us.  It is a great equalizer for all of us.  While each loss is different, collectively, loss is a common experience we share as part of humanity.  It allows us to empathize more, to share compassion, to identify and help others to heal.  In our capacity as a leader, it is where we have a chance to connect and strengthen our relationships with our people.

In the end, loss is highly personal, as is the pain associated with it.  As you connect with that pain and anguish it allows you to be more fully human.  Being more fully human allows others to connect with you in a deeper, more meaningful way.  Loss doesn’t define you unless you choose to allow it to.  Yes, some losses are so painful that we may want to ‘opt out’ for a period; sometimes, that is necessary.  That’s okay.  Just understand that the end game of who you are in the world is never about the loss, but the opportunity to shape your story and how you engage and impact others.

I remember watching Tony Dungy after his 19-year-old son died.  There was a sense of peace about him.  I understood that he had a longer view of life and what came next.  Nevertheless, losing a child is the worst thing I can imagine.  I knew that at one level Tony and his wife’s hearts were broken.  They still are.  He chose, however, to not allow his heart being broken to define his life and the other choices he could make to engage the world and use that loss to comfort others; to help them to see a path that allowed them to carry their pain with them without it defining the rest of their life.

There is likely another writing in this topic.  My encouragement, as I end this piece, is that you will allow yourself ‘access’ to your losses and your pain, understanding that within you is the strength to endure the loss and come through stronger and better.  Like many things in life, it is not complex, just difficult.

To a better you…


Of Interest:

Read about how leaders deal with loss.