How and Why I Became a 'Manager'

March 16, 2017

After my previous post about my approach to technical interviewing, I received some requests to write more about my career path. In this post, I’m will attempt to answer a question I get asked somewhat regularly: Why did I stop writing code and become a manager?

How did I choose Software?

Before we can dive into why I became a manager, we need to explore a bit more about who I was. Growing up, I loved Legos. I would spent hours building custom lego creations. As I got older, my family got a Commodore 64 and I spent hours playing cartridge games, watching Zaxxon fail to load from cassette tape, and typing in programs printed in computer magazines.

While I was in High School, I ran a dial-up BBS on a computer made from parts cobbled together from old computers and occasional purchases from Computer Shopper. I took all three classes in our computer lab at the High School: Typing, BASIC Programming, and Computer Drafting. Typing was the most important of those three. When I exhausted every class at the High School, I took a Turbo Pascal class at the local community college. If I wasn’t already convinced (I was), after that I knew I wanted to write software for a living.

I went to the University of Illinois to study Computer Science. Studying Computer Science at UIUC was the fulfillment of a dream for me, but I quickly made a small change. During my Freshman year I switched to Computer Engineering. This was precipitated by my experience with the Introduction to Algorithms class. It involved way too much math and theoretical thinking. I just wanted to learn was how computers worked. The Computer Engineering program offered a lot more low-level classes and less theoretical programming classes. My favorite class was our microprocessor design, where we started with basic logic gates and built up to a pipelined processor, including writing a program and running it on the processor. My second favorite class was x86 Assembly programming. I was happy with my choice to switch to Computer Engineering, and it put me in the position I dreamed of as a kid, I got to get paid to write software.

Did I like Software?

After graduating I started working for a consulting company. They did a great job of training new college graduates with a well-defined self-directed training course in C++. That was, practically speaking, the first and last time I got paid to write C++. The world was quickly transitioning to the web and Java. I was among the first members of our staff to learn Java for new projects, and being a primary Microsoft shop, a little J++ as well.

It was amazing. I was learning something new every day, and getting to build applications that real people were using every day. It was also when I first learned to dislike process and management.

This is probably best exemplified by a quick story. On the first project I had an opportunity to lead, I was asked to document the object model. According to our process, this involved opening up Microsoft Word, and defining each class and public method, including method signatures and JavaDoc formatted documentation in Microsoft Word. I thought it was a complete waste of time, I was frustrated that management didn’t understand software development, and I just wanted all the ‘useless’ people to get out of the way and let me build software.

I had another experience that furthered my distain for anyone other than developers. We were implementing Enterprise Application Integration (EAI) software written by Active Software for one of our clients. This involved moving data between several different enterprise systems. The pattern we used was to define a single message format for each data type that would contain all the data that could be consumed by every end systems. Active Software called this a ‘Canonical Message’. However, apparently the client didn’t understand what the world ‘canonical’ meant, and I spent the better part of an afternoon and the entire evening in a conference room with the entire project team attempting to come up with a new way to describe a canonical message without using the word canonical. It drove me CRAZY. I wanted everyone to get out of my way and let me go build something.

I swore I would never do anything but write code.

What Changed?

Fast forward a few years, and I had built up a solid skill-set, primarily in Enterprise Java but also a solid understanding in C#.Net. I learned how to build websites in Oracle Application Server 1.0, proprietary frameworks, Enterprise Java, Spring, and other variations.

I loved learning new frameworks. Each one brought solutions to problems I had struggled with, and as I learned, a new set of problems.

And ultimately, this was the primary factor in my evolution. After a while, a new framework brought a quick review and shrug instead of excitement and a deep examination.

My focus over this period was building enterprise applications running inside large companies. These are important systems and 'fun' to work on, but at the end of the day are largely reading data from a database, displaying it in HTML, capturing some changes, and writing data back to the database. It got old, especially when I became somewhat disillusioned with the evolution of the frameworks.

During this time, I also got to spend a lot more time working directly with clients. While this is often a frustrating experience, it allowed me to learn about a lot of different companies, industries, and business models. I came to respect the challenges that they each faced and the solutions that they had developed.

These factors caused me to pick my head up and look around at the world I lived in, and wonder what else I could be doing.

What Did I Know?

After spending close to a decade working primarily for consulting companies, I had broad but shallow knowledge of a lot of industries. I had worked for Fast Food, Manufacturing, Insurance, HR, Logistics, Banking, Financial Exchanges, and Retailers. I knew a little about a lot, but I didn't have deep knowledge of any. I realized that what I really understood was the consulting industry.

This worked out well since I currently worked for a consulting company. I looked around I started seeing other problems I could solve. Luckily, I was part of a fast-growing company with the trust of the ownership.

It started small. We had a small project and needed a part time PM. I stepped as the technical architect, but I also worked with the client to make sure we were delivering what they needed, and keeping them up to date on the project status and the challenges.

I also learned how the owner interviewed and I started helping out as the company was growing quickly and he was doing more interviews than he could handle alone.

I built trust and over time I took on more responsibility.

How Did I Learn?

I often get asked how I learned how to manage a company. The answer is pretty simple: just like I learned how to code. I read a lot and learned through trial-and-error. I also had great mentors.

This is an example conversation I often had with the owner of one of the companies:

Me: We should be doing X.

Him: Why?

Me: Because <a lot of reasons I thought made sense>.

Him: No.

Me: Why?

Him: Because <a lot of reasons I had not thought about>.

I would take what he said and reformulate my pitch based on this new information. It would often take several iterations before I either got a yes or I became convinced my idea wouldn't work for our company.

The great thing about the owner was that nearly every yes was followed by "go do this, I'm holding you accountable". This was a great way to grow my responsibility and take ownership of my ideas and see them through.

This conversation happened a lot, and over time I really understood what he cared about, and what his overall philosophy was. I agreed with much of his philosophy, but not all of it. We had many spirited discussions over the years, and I came away with a well developed philosophy of my own.

During this time, I expanded my reading habits beyond technology. I started reading business books, articles and anything and everything that taught me about how businesses worked. I learned about public companies by reading their 10K filings. I took a deeper look at our clients and tried to learn why they made decisions that I had previously thought were… strange.

And That Was That?

My transition to 'manager' wasn't over. My family decided to relocate to Colorado. Starting over in a new city with almost no professional network, I chose to go back to senior technical positions where I was actively writing code. I still have a passion for building software and, luckily enough, skills that were still valuable. But I eventually grew restless and started looking for a way to leverage my broader skills.

Then a very important event in my story happened: I took the family to Disney World. No, I didn't have an epiphany on my tenth ride on "It's A Small World", we only rode it 3 times. Instead, I met the CEO of Xcellent Creations on the flight home and found an opportunity to leverage the expertise I'd developed over the years to help grow a small mobile shop into an industry leader that we eventually sold to WPP.

Ultimately, I enjoy solving problems and building things. Whether those are Legos, software, or organizations, it doesn’t really matter. What matters is that it that the problems are challenging and that I’m working with great people.

My hope is that the organization that we’ve built today does for our employees what my past companies did for me. I want to help our team expand their skills, take on new challenges, grow as individuals, and view the world differently. And along the way, ship great apps.