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Even in the face of disheartening transformations, the connections forged and the values instilled continue to ripple through time, reminding us that our legacies are built in the space between human beings.
Great leaders know when to embrace uncertainty outside their teams but prioritize creating clear paths and shared goals within, ensuring everyone moves forward together.
Leadership is built on beliefs, lessons, and experiences—big and small—that shape how we guide others. Here’s a collection of truths I hold about leading people, from embracing imperfection to cultivating clarity, empathy, and courage.
People's names matter, and it's worth taking the time to get them right.
Declaring calendar bankruptcy every now and then is a good thing.
Buying our first house was a dream come true, but it quickly turned into a costly lesson about ignoring problems. What we thought was an insurmountable expense turned out to be a simple solution, teaching me the importance of recognizing and challenging limiting beliefs.
When my son gamed our potty-training system to maximize cartoons, I realized something: measuring the wrong thing drives the wrong behavior. The same is true in software development—if we focus solely on output, we risk missing the outcomes that truly matter.
While most people settle for the first workable solution, designers dig deeper, exploring a multitude of ideas and embracing risk. This is their superpower.
The tension between designers, developers, and product managers often feels like a struggle for dominance—but what if that tension is the key to building great products?
A friend from a past company recently reached out, stirring up memories of a remarkable culture and a CEO who epitomized leadership excellence for me.
I was surprised to learn that things have taken a disheartening turn after a new CEO was named. The new CEO has reshaped the company into something unrecognizable from the vibrant, people-centric environment it once was. As my friend tells it, what was once a haven of trust, empowerment, and innovation has become a cold, authoritarian machine where people are viewed as disposable.
Hearing this, I couldn’t help but feel for the former CEO. His professional legacy seemed under siege, deliberately dismantled by the new leadership.
I’ve experienced similar shifts. I’ve watched from a distance after leaving a company as teams and practices I painstakingly built have eroded—sometimes naturally and sometimes by deliberate sandblasting.
Initially, it hurt. I felt like my contributions were being erased.
As time has given me space and perspective, I’ve come to accept that change is inevitable. If my former CEO had stayed, the company I loved would still have changed. If I had stayed, the teams I built would still have changed. Perhaps not so dramatically, but nobody in the history of humankind has ever built something that can escape the changing force of time.
While it’s sad to see a place I loved go through painful changes, the truth is that my former CEO’s legacy is unblemished. His influence has rippled beyond the small company he led, inspiring countless others to adopt his human-centered approach. I have watched with pride as dozens of my former coworkers have taken what he taught them and become successful entrepreneurs in their own right. I’ve also watched others walk my path, taking those same lessons into larger organizations. I wouldn’t be surprised if the companies that have benefited from people shaped and influenced by my former CEO number in the tens of thousands.
Legacy, I’ve learned, isn’t defined by the policies we set, the processes we design, or the products we ship. Those things seem so important in the moment, but with time, they are revealed to be fragile and ephemeral.
Legacy is forged in the space between human beings. My legacy is in the relationships I’ve built, the people I’ve invested in, and the good I’ve done for and with other people.
And that will outlast everything.
