My Leadership Approach

Leadership is the ability to help a group of people advance from the place they are today as much as they are willing and able to grow.

The first thing you need to know about my approach to leadership is a little context.

Here are some crucial bits to apply to what I’m about to tell you:

  1. I have been working in technology in many ways, but mostly as a software engineer or software engineering manager for over 20 years
  2. I have a degree in education. I wanted to be a teacher since middle school after watching, and being inspired by, great teachers
  3. Despite having a degree in elementary education, I decided not to teach because of how curriculum and evaluation was carried out at a mass scale in US public education
  4. I was in college studying elementary education when No Child Left Behind, a test-focused education platform, was unveiled. I fought against its existence
  5. My ethos is personal development. I care, first and foremost, about growth. Of myself and of those around me. I like to make people better

My Approach

My approach to leadership got its start in the classroom. Shortly after college, I had a class of fourth graders, which is my favorite age. My group was:

  • all different, they had strengths and weaknesses that made them unique
  • they still mostly loved to learn, just as we all were born doing. Some were more engaged than others
  • they all came from different backgrounds, but most came from less advantaged homes. Some had absent parents, others just had a mom. Some had many advantages

We all walking into my room on some clear, bright September day full of optimism. I knew that my job was to take them from where they were that day and push them as far as possible before I let them go on the following June.

Where is Here?

Let’s stop and consider what I mean by where they were when they came into me. Human learning isn’t like feeding information to a computer. Facts go in your head, sometimes leaving as quickly as they come in. Sometimes it stays forever. But, the set of skills that allow you to learn and interact with the world successfully, those tend to persist and can be applied on any material you need to learn. Those are the skills I care about. Let’s apply this to a common scenario in elementary school:

I learned my multiplication tables in second grade. The first skill here is understanding how whole numbers work and why. When I had enough number sense to understand addition and how multiplication was based on that, Mrs. Potter let me work on my multiplication tables. From there, learning my multiplication tables was memorization. It’s a learning skill that isn’t much fun, but it’s important.

What did I learn from this exercise, from number sense to addition to multiplication tables?

  1. How numbers work. The basis for the entirety of math.
  2. How multiplication relates to addition, which is an abstraction of number sense
  3. How to memorize random stuff that’s easier to just trust it’s right because it’s posted everywhere so it’s probably true

Now, what did my teachers test for? My knowledge of my tables. They surely wanted to be sure I got numbers, but the real evaluation was the number knowledge. Does that mean there were kids who learned their tables without understanding math? Yes! There are plenty, and the education system failed them because the right answer to 7x8=56 doesn’t illustrate that I understand that 7 rows of 8 dogs will equal 56 dogs (side note: there will also be at least 4 dog fights).

Another crucial point is where any person is is not clear. We cannot know someone else completely so we approximate a sense of the person before us. Are they confident? Fact-filled? Clever? Scared? All of the above? Measurement of learning is very, very hard. How your subject feels today, what they learned recently, and how much they know about the test will affect evaluations, so it’s all an approximation.

Thus, my idea of who my students were that day was a guess and how they left me at the end of the year would also have been another guess. However, it would have been a very educated guess based on the time I spent with them.

Evolution from Education to Leadership

How does this relate to leadership? It’s easy: teachers are leaders. But let’s chat about my experience a little more.

I walked away from teaching because I didn’t love the idea of testing my kids constantly, especially since the testing doesn’t prove what we think it does. I spent a great deal of time with professors who shared alternative views of education, those outside the norms of public schools. I worked at a Sudbury Valley school, a democratic school where all students and staff determine and enforce rules equally. From there, I found technology and met John Urban.


John Urban was one of my first bosses. Maybe I’ll meet a leader better than him, but so far, no one has come close. He led a large department of contractors who worked across the Naval Research Laboratory in Washington, DC. I was not even 21 working part time for his department when I met him. The first time we spoke, he told me I would leave a mark on the company before I moved on. I was surprised, who was I that he thought that I could leave my mark anywhere? This was the default level of confidence he placed in his employees.

John took care of his employees, but he also expected results. He remembered milestones, he asked after your family, and he always checked if you needed anything to do your job. Every single time he saw you. He was a shield for us, taking the brunt of company communications failures, leadership failures, and advocating for our inclusion in a company whose building we barely set foot in. In return, we thrived. The department grew, adding customers as more branches. Personally, I hated letting him down and did all I could to meet or exceed his expectations.

In short, John is my leadership hero, and as an overhead employee before I found a direct role, I learned from him up close. I learned the kindness, clarity, diplomacy, and reactivity needed to lead. Today, I often ask myself, What Would John C. Urban Do? And I hope with every decision, that he’s proud of me.

My Approach in Technology Leadership

Leading technologists is fundamentally the same as teaching students. There are obvious differences in maturity, motivations, and overall breadth of knowledge. However, I’m still tasked with creating a product, whatever it is, that will make money. And the best way is to get my engineers, colleagues, and bosses from where they are today as far as I can reasonably push them. This is based, in part, on my helping them advance:

  • perceived technical understanding
  • social and emotional skills required to create a great product. Or, if you’re an engineer of course you need social skills
  • ability to plan and execute work independently
  • understanding how and when to ask for help. And that it’s not an indictment on you or your power if you need to ask
  • making sure you, if you’re another leader, have the skills you need to help those near you as best you can
  • assuring you have the learning skills necessary to advance yourself without my prodding, should you want to

I can sum this up by saying, the place I really want to take those around me is to a place where they don’t need me. Instead, I want them to be able to think of me, think about what I would do, and know what they are doing will make me smile.

Does It Have To Be a Test? Implicit Bias
Your browser is out-of-date!

Update your browser to view this website correctly. Update my browser now