When Senior Leaders Retire ~ Reflections


What Just Happened?

I met with Scrappy McGee the other day for a cup of coffee and reflection.  Scrappy recently left a very senior position.   I have had an opportunity over the years to listen and learn from senior leaders.  Here are the three things that are top of mind when reflecting on what they said.

  1. I felt lonely.
  2. I wish I had more fun.
  3. What I thought was important in the moment was nothing more than a footnote.

Loneliness doesn’t mean being alone. #perspective from Scrappy

A person could be right in front of you but a million miles away.   I couldn’t share my thoughts or my feelings in an open way.  I had ideas that were ahead of where other people were and I could express them but they were orders vs discussions.

I felt alone.  I connected with others and it wasn’t like I didn’t have friends but it still felt lonely.   When people saw my title, they were friendly to me but I knew that if I didn’t have the title, they wouldn’t have an interest.  This also became clear when I left my role.

I am not sure what I could have done differently when it comes to the feeling of being lonely.  Some say that if I did my job properly that this feeling of loneliness is to be expected.  I am not sure that people should live this way, it took a toll on me.  One thing that did help me was finding others at my level and spending time with them.

The only way that I managed through my feelings was when I sat down with peer groups and met with others at C-level events.   I also spent some time volunteering.

Being social and having connectivity with others is critically important to being healthy.  I would say that if you are in a leadership position and you are feeling lonely, you must find others at your level with similar responsibilities to spend time with.


Having more fun #perspective from Scrappy

My everyday was an emergency.   The CEO, board, partners, peers and and others pressed on me for results.  In my role,  I had to be a gatekeeper and an enabler at the same time.   When I started years ago at my company,  we had all sorts of events and fun things that we did.   It was a different time, feels like forever ago.    I didn’t want that to change but pressures of the job and the business made it increasingly difficult to allow for fun.  On top of that, people are more sensitive today and what is fun to one person is offensive to another.  It made it easier for me to just forget to have fun.  Since fun created costs and had many drawbacks it became a risk and liability.   People that talk about work life balance in IT are full of shit.  They are the people that don’t know what it’s like to be a global IT leader.   I was on 24 hours a day.  When was I going to have fun?   Looking back, I probably should have made more time for it though.   I think we had some missed opportunities.   Maybe I wasn’t the person to designate what was fun and what wasn’t but the fun committee idea is bad idea.   If there isn’t a little fun at work everyday, these planned events feel forced and just create opportunities for eye rolls.  I think rewinding the clock a little to days where we injected fun every day was better overall.


It wasn’t that important #perspective from Scrappy

A good friend of mine and fellow C-level officer reflected on all the things in her life she sacrificed.   She missed out on her kids growing up and her marriage was a mess.   She became obsessed with the job and she was really good at what she did.   She was the kind of leader who had a baby on a Tuesday morning and had a good handle on all the business happenings by Tuesday afternoon.   She spent 30 years at her company and she lead a line of the business.  When the company was acquired,  she was one of the first to get reduced.   Her attachment to the company and the work she put in over all the years amounted to her termination.  When she left the company, she could only feel the pain of all the sacrifice and the toll it took on her personally.   I think she is still working through it because it wasn’t about the money.   The pressure I felt on the job with the daily emergencies and fires I had to fight amounted to nothing.   I can’t tell you how many nights I worked until 2:00AM on those power points.   It wasn’t worth it in the long run to me.   My advise to myself looking back would have been, let it wait until tomorrow.   There is nothing they can do to you.    If I am advising a leader today, it would be the same thing.   The pressure is on but what are they really going to do to you?


#Thoughts from Howie

My take away from these conversations is to learn from them and practice behaviors that could change make a positive impact.

How can I help senior leaders in my organization who may feel lonely?

How can I introduce some fun everyday?

How can I help my team and myself by framing things properly and appropriately relative to their importance?

What do you think?

Posted in KM.