Who I'll Never Be and Why
I'll never measure up to these two guys, former bosses and now treasured friends, but I'll never stop trying
Today I’ll share two stories. They feature the same two men, former bosses, now old friends.
The first story occurs in the cavernous glass lobby of a hotel in downtown Los Angeles. In this story, one of the managers says five unbelievable words.
The second story takes place on the mezzanine level of a restaurant in San Francisco a few years later. It’s during a company holiday party. I’m seated with the two bosses in a greasy leather banquette. From the beginning of the story to the end, only two words are spoken. These devastate me so completely that I have scarcely stopped thinking about them since.
The theme of the stories is emotional intelligence. In them, I’ll introduce two gentlemen who are my role models fpor empathetic, thoughtful, generous leaders.
Great leaders fit towering acts of service into tiny gifts of generosity. If a manager has ever done something like this for you, you’ve learned these moments can carry extraordinary meaning. If this hasn’t happened to you, it’s important you do something like this for somebody else. Otherwise you’ll be depriving yourself of this important lesson.
Lasting trust is built this way, resulting in true fellowship, camaraderie, and partnership between leaders and their teams. That’s what has been achieved between me and these two guys.
There are no peacock displays of charisma or inspiring “let’s get ‘em” speeches in these stories. Nobody relied on their executive presence or podium skills. Nobody managed up.
It took less time for these acts to transpire than it did for you to read this introduction. I suppose that also proves these two guys are better leaders than I am a writer.
Ok, let’s get on with it.
I was working for a small company, and it was then acquired by another company. This was in-between financial crises, back when this kind of thing still happened. We flew out to the big company’s annual conference where the acquisition was being announced.
After the big reveal, a bunch of us were hanging around the hotel lobby in the early afternoon. We were hung over and disoriented from the sudden change in our circumstances.
I was talking with of our co-founders and a product manager from the big company. It may be more precise to say that this PM was talking to us.
He was a very nice fella, this guy. He was excitedly explaining his product, showing us some demos with a mix of enthusiasm and pride. He was talking about how our stuff was going to work with his stuff.
His mouth started moving quickly, in a little bit of a blur. As he was doing his demo, I snuck a quick glance at my colleague, the co-founder. The look confirmed what I feared: We had no idea what this guy was talking about.
I closed my eyes for a moment and hoped the lobby would stop rotating. I tried wishing that we could disappear suddenly and reappear anywhere else in the world.
The hotel lobby was a half-mile wide. Why did it feel like there was nowhere to run? Somehow I noticed a door opening on the far side of the lobby. A column of light fell through it and struck the silhouette of my boss and his partner walking in the door. I remember thinking “Oh thank God, maybe they’ll get us out of this.”
Before I could even complete that thought, I saw their posture stiffen. They’d observed me and my colleague in our predicament. I saw one guy lean over to the other. Now they’d adjusted their course — they were headed in our direction. “Oh fuck.” I thought, “We’re in trouble.”
They arrived at our table, and they interrupted our conversation. One boss looked at me and he inclined an eyebrow in my direction. Addressing the PM, he said “Can I borrow these guys?”
This boss had been on the main stage of the conference with the CEO of the big company this morning. It was like Harry Styles had just walked up and asked for my autograph. The PM closed his laptop, made a tiny popping noise and vanished. The bosses led us off to another table and sat us down.
We took a deep breath, and awaited our stern lecture about the unauthorized conversation. We didn’t even realize we had been rescued until the bottle of Champagne arrived and we saw the bosses we grinning at us.
They’d smelled our terror from across the lobby and realized they had to save us. They calculated they could easily pluck us free without being rude. The whole thing was an elegant and beautiful act of service. They were deservedly proud of their performance, and we celebrated again together.
It still brings a tear to my eye.
One more quick story from the same pair of bosses. It was several years later. Both of the boss guys were going to be leaving the company. They’d very generously decided to put me in charge of the team.
It was the night of the big holiday party. It would be their last, and my first as the newly-minted leader. A lot of feelings were being felt.
At some point I picked up the habit of trying to be among the first to leave an off-site event. Since then, I’ve made it part of my own coaching to advise managers that team bonding events are primarily for team members to bond with each other — not for managers to bond with the team.
I think it’s generous and wise for a leader to think of team events this way. At a certain level of seniority, leaders operate best at a professional distance from their team.
Being “one of them” is not as useful to you as it is for the team to be led by someone who maintains that bit of distance. It is also smart for a manager to avoid inappropriate social entanglements like the ones that befall the players in the above video.
Back to the holiday party. An annual tradition was for the bosses to go from table to table and thank everybody for their contribution that year. This was another kind and generous gesture that offered a personal connection between the management and the staff at the end of each year.
It was starting to get late, and the time had come for the two bosses to make their tour. I was sitting with the bosses at their table. The one boss guy set down his drink and turned to other guy and said “Are you ready to go do the ‘Thank you’ thing?”
The guy looked back at him. He looked over at me, extended a finger in my direction and said “Take Matthew.”
It took me a minute to compute the meaning of the gesture. My mouth fell open. My jaw hit the table. A carefully curated mélange of olives were set asunder.
The effect of sending me on the end-of-night “Thank you tour” was to reinforce my position as the new leader of the team in the eyes of the team. He was trading his own “so long” opportunity for the chance to solidify my succession.
The thoughtfulness and sensitivity of this choice and the impact it had on me has been reverberating through my life, my professional relationships, and my management style ever since.
It’s meant so much to me, it’s a bit hard to explain. The time we’ve spent together hasn’t stopped resonating more than a decade later. Not all of the effects are good! It’s humbling to the point of exasperation for he bar set at a level that I know I can never achieve.
It’s not only these actions. Both men have a years-long track record and reputation of equanimity, poise, and generosity. They’ve earned my respect, and they’ve set the standard by which I measure myself as a leader, a manager, and in some ways as a man. There are a quite a lot of people out there who’ll say the same thing.
Those are two stories about these two guys. I haven’t named them because I’ve calculated they prefer privacy to praise at this exact moment. They know who they are. Plenty of people who matter know it too.
To those of you who happens to recognize these folks from my stories, or who recognize their big hearts, big brains, generous and kind spirits, elegant and empathetic choices, and quick wits, I’ll tell you what you already know. You’re fortunate to have them, or to have had them, in your orbit.
There are few like them, and there are no equal. Thank you, fellas. Keep up the good work.