Good Leadership
self-awareness, empathy, and a growth mindset
“It’s people that make the difference – little people like you.” — Frank Shirley
This quotation comes from an old holiday classic, National Lampoon's Christmas Vacation. Main Character, Clark Griswold, has a clueless boss, Mr. Shirley, who decides to cancel holiday bonuses to save money. He ends up changing his mind after a comical/farcical series of events that form a subplot leading to the climax of the movie. If you haven’t seen the movie, the quotation is funny because Mr. Shirley, despite ultimately restoring bonuses, still remains clueless. He still can’t remember his star employee Clark’s actual first name, and his comment about little people making a difference is his reason for restoring bonuses. Movies like Christmas Vacation and Office Space, despite being old movie classics at this point, are still relevant because they comically highlight the absurdity of bad leadership that permeates companies of all sizes today.
So, if Mr. Shirley is a bad leader, what does a good leader look like? Well, that’s the subject of many future newsletters, but let me offer you three points of behavioral evidence of a good leader:
People observe a good leader acting and communicating with high integrity around everyone. There’s no difference in how this leader behaves around their teams, peers, boss, or friends.
People regularly see a good leader demonstrating vulnerability and humility, and others model the same behavior.
People feel comfortable providing feedback directly to a good leader and are willing to provide that feedback in front of other people without fear.
These are external points of evidence that reflect internal traits: self-awareness, empathy, and a growth mindset.
Take a moment and think about the best leaders you’ve worked for and with. Have you seen these visible measures in action? Have you seen a leader show these behaviors most of the time, even if they struggle from time to time? Now think of the worst leaders you know. Contrast the evidence above with what you’ve probably seen: politics, self-absorption, ego, and often a complete disregard for other humans.
A few years ago, I had dinner with the CEO and co-founder of a multi-billion dollar company* to talk with him about the role of CEO. He told me CEOs needed to be a bit psychopathic to do the job. As an example, he relayed a story from a visit to one of their company’s satellite offices. They had a couple of teams they were letting go, and the site manager didn’t want to handle the firing. So he ask this CEO to do it, and the CEO said, without any hint of empathy, that he gathered the team members together, fired them all, and then went about the rest of his work for the visit.
Firings and layoffs are part of any leader’s job. Yet, we’ve seen a lot of “handled the wrong way” examples here in 2022, and for a leader to claim that psychopathy should be a required trait for handling such leadership situations is entirely wrong thinking. I generally respected this CEO, and I was disappointed to hear his perspective.
There is a prevailing attitude in tech startups that “leaders and employees should do anything they have to do for the success of the business.” Certainly, in many situations, I would agree. After all, it’s a business, not a family, and building a company from scratch is not for the faint of heart. It’s exhausting, scary, all-consuming, full of huge ups and downs, and often thankless work. Can leaders exhibit the three traits above and still build massively successful companies, or do we need larger-than-life, ego-driven, temperamental personalities to change the world?
I think extreme personalities tend to make the headlines, but I believe that the empathetic, self-aware, growth mindset-oriented leader can build billion-dollar companies, and I believe this type of leader is essential for the health of the business world.
This newsletter is going to explore many aspects of leadership and building startup companies. I’m a former Tech Executive with 20+ years of management experience in multiple high-growth startup companies. These days I’m a startup company advisor, executive coach, and angel investor. I have a passion for good leadership, and I believe it’s possible to get excellent and incredible outcomes from your teams, departments, and companies while still being the kind of leader that people respect and want to work with. I started this substack to share the years of learnings, successes, and failures I’ve had over my years in leadership roles and to give you some advice for being a better leader yourself. Along the way, I’ll keep referring back to this leadership model as I share stories and tips for being a good leader.
*For obvious privacy reasons, I won’t share the names of people or companies in my posts without their explicit permission. I will also obscure specific details and blend some stories to protect the guilty.