Meaningful Conversations

One of my weekend rituals is connecting with my mother and my father. Over the years, our conversations have evolved from simple status reports about what’s happening in my world to deep, meaningful conversations that I cherish.

As I reflect upon those conversations, I see a parallel to my one-on-one conversations with direct reports as a leader and how I made those more meaningful over time as well.

Conversations With My Mother

The Saturday Morning Run Club was among the many gifts of my friendship with Jack Grubbs. He and I ran together for several years. When he moved away, we continued running together virtually, getting on the phone as we started our runs from our respective locations. As my marathon mileage increased, I found I had more time to talk than Jack, and I added my mother and sister to the group. When Jack passed away, Mom took over the pole position, and now she is usually my first conversation on a Saturday morning run.*

I often find myself in “status-report” mode when talking to my mom. I search my memories to think about what we talked about last week and what has happened in my life since then, and then I proceed to give her a brain dump of the events that have unfolded—and she does the same.

In recent months, however, our conversations have evolved. There will always be some updates about what’s happened in my life, but we spend less time on the facts and more time on the experience.

My mother began clowning when I was in junior high. As a clown, she offered healing to others through laughter and joy and healing for herself as she transitioned out of marriage to my father. She continued to clown through retirement, hanging up her boots a few years ago.

Earlier this year, she was approached with an opportunity to bring “Nurse Sparkle” out of retirement and begin clowning at the local hospital again. At 81 years of age, my mother now spends several hours every Wednesday visiting patients at the local hospital and spreading joy.

These stories are now the most fulfilling moments in our weekly call. I’m often brought to tears hearing the richness of her connection with patients and their families and how a few minutes of her time brightens their experience. I know my mother in a way I never knew her before, and I could not be more proud.

Conversations With My Father

Dad and I do not talk while I run – we’ve tried, but the background noise is too much for his hearing aids. We typically connect on Sunday afternoons. Our connections have not been as consistent as my conversations with my mother, but as of late, they have become very consistent – to the point that he will text me if he doesn’t expect to be home when I usually call to make sure we find a time to connect.

My father’s junior high contribution was to introduce me to philosophy. He asked me to read The Story of Philosophy by Will Durant over the summer. This took root and led to me adding a philosophy major to complement my computer science studies at William & Mary. I never felt particularly good at philosophy, but I enjoyed it.

Growing up, I longed to have deep philosophical conversations with my father. In my childhood and even my college years, I never quite felt up to the task. Our conversations were also more “status-report” when we connected.

Now, as with Mom, that has changed. There is often precious little in the way of status reporting in our conversation, and to the extent that there is, it typically has a greater purpose. The status report opens the door for a broader discussion around some topic.

My father is now regularly exposed to my philosophical meanderings on topics ranging from the nature of the universe to spirituality, enlightenment, and quantum mechanics. There are times when he tells me our conversation was the best conversation he’s had in a long time. We both leave the call feeling enriched, fulfilled and loved.

Your Conversations

I invite you to reflect upon the nature of your conversations, personally and professionally. Are they status reports, or is there a deeper connection?

If you are a leader, consider your one-on-one conversations with your direct reports.** Early in my career, my one-on-one discussions were filled with status report updates, not unlike my early conversations with my parents. I encounter this with my coachees regularly. This is a tremendous opportunity to shift the conversation and have a more enriching working relationship.

I work with an executive team who recently made this a priority. They were not getting enough one-on-one time with the CEO, and when they did, that time felt very tactical. The team agreed to adopt a brief written weekly status report that captured the highlights of what they accomplished, what they were working on in the coming week, and what their impediments were where they needed support.

They also had the foresight to put their status reports in a shared location where each team member could read their peers’ updates. The CEO committed to weekly one-on-ones with each of them and to reviewing the status reports beforehand.

When we connected to debrief a month later, I was excited with the results. Their one-on-ones and their team meetings were far more effective. Everyone had a greater awareness of what was going on in the organization, and their precious meeting time was devoted to solving the impediments, getting up in the balcony, and thinking strategically rather than status updates.

Putting It Into Practice

I invite you to choose one regular conversation and identify a shift to make it more meaningful.

  • Be curious about their experiences.
  • Watch for falling into “status-report” mode.
  • Professionally, shift your one-on-one conversations from status to deeper topics such as professional development.


I am an executive coach and life coach with software executive roots in higher education and EdTech. I coach because I love to help others accelerate their growth as leaders and humans. I frequently write about #management, #leadership, #coaching, #neuroscience, and #arete.

If you would like to learn more, schedule time with me.

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* The “Josh’s Is Running” text message group now has six members. There is an implicit understanding that Mom gets priority on Saturday mornings.

** If you do not regularly have one-on-one conversations with your direct reports, please schedule time with me and be prepared for a very uncoach-like lecture.

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