Take the Time to Evaluate Your Career

Decisions in Determining Direction

I co-founded my company about six years ago, and during the course of my employment at Gremlin, I’ve held more roles than I can count. I’ve worked my way all around the career ladder, from an IC position to an executive, managerial role and back again. My current role is CTO, but as my company has brought on more seasoned Product and Engineering leaders, I have transitioned most of my managerial responsibilities and find myself more focused on individual contributions to the company. Change is always difficult, but this go around, I made time and space to not jump into the next problem that needs solving without first taking time to evaluate what I enjoy doing and what my skills position me to do well.

As I thought through the many roads ahead, I reached out to my peer network and was surprised to find that many other individuals had very similar experiences. While many of us found that we very much enjoy interacting with people across the company, we also found that we could be successful in a leadership role without directly managing. Not just that, but many of us considered ourselves to create much more value and be much more effective in IC roles similar to the ones we started in. Not to mention it brought many of us more joy.

Evaluation and Course Correction

Aha Moment:

In the midst of the pandemic, our company went through a reduction in force (RIF) like many others. During this challenging time, we decided to part ways with a high-level executive and the network of managers he hired during his tenure. It was nothing personal; we just realized that while this executive did many things well, he lacked capabilities in a few key areas. Regardless of the reasoning, this change left me with the sole responsibility of not only rebuilding confidence in leadership but also defining a lot of the new direction and strategy.

While orienting to this new role and the previously untread ground, I found it increasingly difficult to manage the now many direct reports, define strategy, and try to get more tangible work done all at the same time. It’s tough for many entrepreneurs who have seen their company through numerous years and countless crises to admit that they can’t do everything, and that realization definitely took its toll, but ultimately it started me on the path of evaluation in terms of the trajectory I wanted my career to take.

Driving from Data

Being very data-driven, I decided to start simple and drew a simple graph with the x-axis representing how much I enjoyed doing something and the y-axis representing how good I thought I was at actually doing it. Then I set to work plotting the tasks, actions, and projects I had worked on over the years and observing how they manifested on the graph. I learned that many of the duties that would traditionally be attributed to managers fell in the two left quadrants of the graph. At the same time, many of the duties normally completed by an IC were plotted on the right side of the graph, primarily in the upper right quadrant, indicating that I not only was good at those tasks and responsibilities, but I enjoyed them as well. That’s when I knew I needed to make a change for the good of the company and myself.

This may sound like an overly simplistic way to try to determine something as complex as determining career trajectory, but drawing dots on an XY chart is where the ease ends. Mustering the courage to exhaustively and honestly determine where those dots actually belong on both axes requires a herculean amount of willingness to introspect and evolve.

Kill Your Ego

• After individuals have worked their way up the career ladder or been thrust into a role due to being early on in a company, they are more often than not unwilling or unable to give up that responsibility. Whether it is building or managing a team, it takes a concentrated effort to suppress the ego and recognize what is best for both you and the company.
• “Very few people can grow as quickly as the company needs them to.” This is some advice I received a while back that really resonated with me and simply means, that while you can work outside of your traditional training or skillset, it is likely that if your company is succeeding, it will need you to grow much more quickly than most people are capable of learning to continue succeeding.