By Thomas Thompson, LSLO Certified Leadership Coach

“I’ve come to a point in my life where I’ve accepted my sex life is just going to be a C+.”  These words hit me from the 41 year old guy next to me at the Rockies game recently.  Over brats and brews, watching the Rockies take an 8 run lead (then lose in extra innings), we found ourselves in deep waters of conversation.

And I wondered, how many other leaders are carrying weights like this, but never give voice to them?  Never process them, never open that part of their lives? What are the conversations leaders are not having?

Leaders are moving at warp speed: juggling responsibilities, careers, and family.  And while urgent conversations can force themselves in to today, crucial conversations get snoozed for a future day…one that may never come.  Conversations about parenting, marriage, legacy, transition, stages of life, sustainability, and who we are truly becoming.

It is the conversations we are not having that are holding us back from our greatness.  Sure, we can plow ahead on auto-pilot without these conversations. But to seek flourishing, to push into a better future, to truly know ourselves, we need to lean in and talk.

Over the last few decades of working with leaders, I’ve been unearthing these conversations.  Helping people find a table to talk about the life they have versus the life he would love.

What are the conversations leaders are not having?

  • Conversations about the stage of life they are in, the stage of life they just left, or the stage of life that they are entering into. So life becomes what happens to them, instead of them partnering with their own future.
  • Conversations about their fears, their failures, about their deepest worries.  How to handle their anger, sadness, and grief.  I cannot recall the last time I heard someone, unprompted, use the word, “grief.”  Yet I know millions are carrying these unnamed emotions with no outlet.
  • Conversations about sustainability.  This is something easy to ignore early on in life, but sneaks up on us.  Am I living a pace I can maintain?  How can I stay in for the long haul?
  • Conversations about God.  What is important for leaders to think about when it comes to God and His role in their lives? How is their journey with God taking shape, and shaping them?
  • Conversations about who they are supposed to be, but not conversations about who they are truly becoming.  What is the life they would love?  Are they living it?  Are they becoming the person they’ve longed to be, or just going through the motions?

How can we help leaders have these conversations?

Engaging leaders in these conversations requires three things:  Space, Time, and Intentionality.

  1. THE RIGHT SPACE — A conversation around a boardroom looks very different than one around a fire pit.  A conversation under fluorescent lights takes shape a different way than a conversation at sunset in the Rocky Mountains.  Life changing conversations are shaped by the right space.
  2.  THE RIGHT TIME — Leaders need time to process their thoughts, and they need to be in the right time of their lives.  The conversation with a 28 year old focuses on different issues than a conversation with a 48 year old.  A well-asked question with the gift of listening can unlock and unpack.
  3. THE RIGHT INTENTIONALITY — We all need sherpas who have walked the way, who can skillfully unearth our hearts, to help us go from where we are to where we want to go.  People whose knowledge and experience not only guides us to our own best practices, but can offer us a “peek around the corner.”  Who approaches us with intention.

Go back to my buddy’s ballpark confessional. The conversation was in a relaxed SPACE, where we had the security of a baseball game to allow us to slip into serious conversation.  We had five hours of baseball TIME to share together.  And there was INTENTION, as questions connected to life prodded revelations.

What are the conversations YOU are not having?  What is holding you back?  If is finding the right space, the right time, or someone whose intention it is to give you the attention you need?  Take the next step and start unpacking the life that you would love.

Thomas helps people have the conversations they are not having, so they can move towards the life they would love.  If he can serve your story, please reach out to him at