I sport a straggly beard and unkempt hair (which I assume to be dashingly handsome). I wear jeans and a T-shirt to work. Looking at me it would be hard to guess that I am a military veteran, that before I worked on tech startups I was a Nuclear Submarine Officer in the Navy. After five years of active duty service, entering the civilian/entrepreneurship world was bumpy. Some skills were useful and some had to be thrown out a window. Knowing how to raise a periscope or shoot a torpedo doesn’t get used in tech very often. A lot of skills don’t translate well. However there is one that sticks out as particularly helpful: the importance of a critical self-assessment.
What is critical self-assessment exactly?
Critical self-assessment, or CSA, is the ability for a person to look at their own behavior and actions with a critical eye and judge themselves for what qualities are good and what aren’t. It is the first step in any self-improvement cycle.
I used to be really bad at CSA
One of my first evaluations as a junior officer included a long paragraph describing how bad I am at critical self-assessment. My reaction was one of disappointment, but not surprise. At the age of 23 I was suddenly thrust into a position of substantive authority for the first time. My direct reports were seasoned, intelligent, and dedicated experts in their field. How could I manage these people as a newbie direct out of school?
I did what many young officers mistakenly do, I relied on positional authority and faked bravado to assert myself in a leadership position. Put another way: I was faking it until I made it. There were two problems with that strategy: (1) everyone around me knew I was faking it and I looked like an ass and (2) it was really hard to admit to and acknowledge my mistakes. The mistakes I made (there were many) felt personal and embarrassing. I relied on a leadership methodology that wouldn’t let me acknowledge when I was wrong.
How I Started Becoming Better At Self Assessment
Thankfully, I had a fantastic mentor and boss at the time (shout out to Rich McMunn) who helped coach me through my poor critical self-assessment skills. He taught me how to look at my own capabilities and performance critically and then work on how to address those faults. That last sentence was the nicest way to sum up what was one of my most difficult periods of my career; trust me, it wasn’t nearly as pleasant as that sentence sounded.
I was stubborn and the lesson was hard learned. I imagine it is hard learned for many young junior officers thrust into positions of leadership and authority for the first time. Unfortunately it isn’t learned at all by many aspiring entrepreneurs.
The ability to look at yourself and acknowledge faults was incredibly valuable as a submariner- that’s the first step towards improvement. As an entrepreneur, it is even more valuable.
Entrepreneurs need to learn this skill
There is no silver bullet when working on CSA, it takes hard work. In my opinion the first step is easy: take time to observe your own behavior and how it affects your team. Follow that up with soliciting your colleagues for honest feedback. Soon you’ll be able to identify your own strengths and weaknesses effectively.