A Simple Lesson in Human Leadership

Joseph Rupp
8 min readNov 2, 2020

I hope I can live up to the examples of two early influences in my career

Joseph Rupp, Sugar High Motivation

Photo By roberthyrons (inserted here for Esther.)

My temporary boss Don bounced into work on the seventh floor of our Glendale office building on Brand Boulevard. I say temporary, because he had been borrowed from his day job in Seattle to work in the Catastrophe Center managing just about any unit they could find for him that was not directly tied to adjusting claims. He reported to the Claims Center Head, Robie (an inspiring figure in his own right), and managed diverse work from the Subrogation to the Call Assistance Unit to Hospitality. He had been on assignment for about 5 months. I reported to him the entire time. I knew he missed home.

I did not know that this assignment constituted pre-training for me, part of a strategy already thought out by our regional leaders to prepare me for my next job. Up to this point, I had been an individual contributor adjusting claims and now, handling Operations work in the Cat Center. I was two years into my career with Safeco Insurance.

He wanted to talk to me. He was extremely excited. I was apprehensive. Each time someone wanted to “talk to me” — said with that inflection and tone of voice — it meant someone was leaving. It was the nature of the work. Our claims center, which had been as large as a region at its height, with over 400 associates, many of them independent contractors, was winding down. And I did not want him to leave. I was learning a ton from him.

We walked side by side through the open space, moving from area to area as he spoke amidst associates performing their duties. He did not like sitting down to chat. That practice alone of walking and teaching was different than other bosses. Serious conversations usually happened inside a cubicle in hushed tones.

“You need to talk to everyone here. When you arrive, you need to make your presence felt. Say, hello, stop and ask about their day and their family. Don’t hide in your cubicle, too many supervisors do that.” He paused to hitch up his pants, he had a habit of stopping mid-sentence and pulling up his jeans. In contrast to our “normal” buttoned up work environment, we wore very casual attire in this setting.

“And be happy, don’t let the stress get to you. It’s going to come and go. Let everyone know you will not let it affect you. Each one of them will take their cues from you. Believe me. The mood of the team follows the leader.” Don sported a thick black bushy mustache that rose and fell as he spoke. It was so prominent you would think of it as a separate character attached to his face. I could not help but notice it moved even more charismatically in this moment. Even his mustache seemed extra happy.

He loved to dispense advice. He also carried a slight twang in his animated voice, courtesy of his hometown of Billings, Montana. For some reason, I found the accent comforting.

“Now, I need two things from you. One, I’m going to be leaving soon, so you need to prepare to take over my duties.” He had a habit of speaking fast and through you. He was a great listener, ironically, but when giving advice, he would get on a roll as if mentally checking off his to do list before the item evaporated. He did not fully appreciate what he had just told me, or if he did, it was part of his strategy to lessen the impact by running through the issue onto the next destination in the conversation.

“You are going to do a great job. People gravitate to you. My advice is to be present. You are ready for this. Speak to them often, even when you don’t think you need to. Over Communicate. I’m serious.” This was excellent advice. I know it seems boilerplate. I get it. But, for some reason, these words of wisdom really struck me. He was making obvious what I already believed I knew.

The power came from his example; he did exactly what he was suggesting to me. In the obviousness of the lesson, it gained power by his example. The bigger point he made was about thinking of those you worked with — make certain you show empathy and courtesy and attention. He suggested I treat everyone, no matter their role, with respect and dignity.

He pointed me to the example of Annie, our senior administrative assistant who came to us as a temporary employee and reported to him. “Look, she’s smarter and more talented than anyone here. She could be running the place. She is excellent. Try to keep her. She makes everyone better by her attitude. She worries about everyone else. She keeps her thumb on the pulse. Listen to her.” He was making a point about equity and attitude. Annie occupied a place as important as anyone in the Cat Center because of the power and proficiency with which she carried out her job — even though she was still working as a temporary employee. She made our jobs easier.

No one was beneath or above, Don. In fact, it was obvious that Don looked up to Annie. Everyone was important. This lesson came home a year later when I hired one of the sharpest and hardest working people I had ever worked with — a custodian who performed grunt work as if he were a superhero. I’ll tell that story in another post. He was an incredible example of hard work and selfless attitude.

Back to Annie. Unfortunately, she left a few months later. I never forgot her example. She exhibited not only an incredible work ethic and sheer knack for efficiency, but she was also kind and joyful. Her presence added a dimension to the work environment that just made it more magnetic. What I did not know at the time, was that a deeply personal experience had shaped how she treated others.

When Esther and I met Annie for a farewell dinner one evening, she shared her experience with cancer. We had no idea. She kept it a secret from everyone. She had beaten lymphoma a few years prior, but the experience shaped how she thought of her place in the world, her contributions and how to treat others. Her life would not be defined by how much money or power she might acquire, but how well she treated others. I remember when Annie narrowed her gaze, looked at Esther and said, “I know you already understand that lesson.” Indeed, my wife had made those lessons clear to me, but an added example can really emphasize the lesson.

Don left the center a week later, after we had completed the second mission. He wanted me to find something entertaining for the troops. He reminded me how hard everyone had been working, especially at the beginning of the Center’s inauguration several months earlier, just after the Northridge Earthquake struck on Martin Luther King Day, January 17th 1994 at 4:30 in the morning — a moment I will never forget as Esther and I lived in a small one room apartment on Scott Road in Burbank, a short seventeen miles from the epicenter in the San Fernando Valley.

Photo by Pandapix

When the Earthquake struck, Esther and I both had the same thought: this is the big one! She just had the thought earlier than I did. The walls in our tiny apartment seemed to simultaneously shudder wildly out of control AND melt. The noise overwhelmed us; we could hear it coming like a train before the waves of motion hit the building. Esther moved much more quickly than me.

Initially, I took the sensation lightly, saying to her in the very first moment as she tried to pull me out of bed, “It’s just an earthquake…” as I shook off early morning slumber. “No, Joseph, this is not just an earthquake. It’s a BIG earthquake. We have to get to the door jamb.” We huddled in the area just underneath the door to the living area for what seemed like an hour. The quaking lasted around a minute and a half.

The moments after the earthquake were surreal. Our apartment complex was relatively new, meaning it would survive because of modern building methods and requirements. But, no one would remain in the building. All of us were too rattled and scared. We congregated in our pajamas and bathrobes outside the apartment on the narrow lawns and concrete walkways fronting the complex. More than once, someone would open their door, crying and rush to their car, parked along the street, get in and speed away. You would hear people saying out loud, “I’m never coming back to this place.”

Of course, when we finally began to move around the city, you could see the devastation wrought by the 6.7 magnitude temblor. You may remember familiar images from T.V. News reports of portions of the (State Route) 118 Freeway shorn in half; a three story apartment complex in Reseda pancaked into rubble and the Bullock’s department store and parking structure in the Northridge Fashion Center crumbled.

All of these images brought home the importance of the work we performed every day. The insurance industry, sometimes rightfully, earns a ton of flack for its performance during different catastrophes (Katrina comes to mind.) I get the skepticism and understand it. However, the flip side is the thousands of stories of those people whose lives have been put back together because of the industry. In our case, I remember that we incurred around 8,000 claims and tallied less than a twenty lawsuits — a testament to how well the company responded to and resolved those claims.

I mention the details of the earthquake to underscore a larger point built into the narrative. Our work and personal lives obviously intersect during normal times and moments of trauma. Don’s message to me about empathy and understanding often served me well later in my leadership career. His was not the only example of transparent and engaged leadership. I have been extraordinarily fortunate to have 15 bosses over my career and each of them taught me something about leadership in their own right — whether they did so by example or in another way. I’ll post a more detailed commentary of those lessons in a future post.

I would not always meet the high bar of Don and Annie’s examples over the course of my career, but the mere fact Don went to the trouble of sharing his perspective and leading by example, made an impression that carried important lessons in human centered leadership — especially at an early stage of my career.

Oh, incidentally, there was a second mission I alluded to in the post. I’ll save that for another time!

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Joseph Rupp

I focus on how to effectively imagine, create and sustain individual and team transformation.