Should You Be A Manager?

How do you become one? Should you want to?

What Else is There?

Often, this track is pursued by default. Management = career progress.

As someone who’s had broad range of manager types, I believe it is tragic when the wrong people reluctantly become managers because it’s the only track to money, esteem, or influence. Like driving after a few beers, this mistake is not just to their own detriment. Others stand to suffer.

Leveling is an increasingly-used strategy to create a non-management, independent contributor (IC) track that can be just as lucrative or rewarding. But providing an IC track only presents a choice. Many still seek the context to make that choice correctly.

The decision is a personal journey; the job, an acquired taste. Accordingly, I wanted to share my own experience and inspiration down this path.

How NOT to Pick a Track

One form of case study is watching a totally-garbage management structure operate. My career started in Investment Banking, where the path is:

1. Analyst
2. Associate
3. Vice President
4. Director / Executive Director
5. Managing Director

Behind all the crisp shirts and fancy jargon, these titles are performing pretty familiar roles. Allow me to translate:

1. MSOffice & Research Servant
2. Quality Assurance; Servant Babysitter
3. Marketing & SDR
4. Sales
5. Operations & Business Development

Each title typically has a many:one reporting structure to the one below it. Promotion is a function of time, and to a lesser extent, internal respect.

Some thoughts:

First, in what world is someone good at all these jobs, in this sequence?

Second, how can you simultaneously run an excellent team and develop their careers if your reports’ goal is always to leave their current specialty?

Last, notice that there are no role-veteran managers. Nobody who has continuously [worked as an IC, managed/grown, become excellent at hiring] specifically one role for 20 years straight. Instead, specialties are grown out of. In the best case scenario, an IC is excellent in their current specialty, but is managing reports to an entirely different job. Even worse, the expectation is that these IC’s manage in their free time, which in banking, is nil.

Finding Better Manager-Inspiration

Candidly, I sometimes lament the earning potential and prestige of a career in finance I left. But probably my favorite tradeoff in favor of entrepreneurship is that nothing’s sacred. Everyone’s trying to either borrow best practices or design things from scratch until it works for them. Managing included.

For me, management was not an innate passion. Yet as I started to build and grow businesses, I began to value it more and more. When I noticed a lot of mediocre management all around me (both internally and externally), I saw an opportunity for differentiation and excellence.

Specifically, here was my journey and the related reading that inspired me:

1. I was a founder of a company that gained product/market fit and was looking to scale. I learned my main job was to repeatedly replace myself with better specialists. I don’t remember specifically what I read, but it was basically this argument (but would have been written around 2010).
2. As we began to scale, I experienced the battle for good talent. I was particularly inspired by Paul English after a rec from Jim Moran.
3. I got fixated on how to build the machine that builds the company. I got into stuff by Jim Collins after a rec from Eric Wheeler.
4. I realized that leadership maxims and management tactic copy/pasting was a loser’s game. I decided I needed to design what was right for my teams. I really loved the Netflix Culture Doc as an example that is brave and committed to purpose-driven culture design. Not to copy ;)
5. As I got good at hiring, I had the opportunity to manage phenomenal people, and watch them become superstars. What an epiphany!

A Great Reason Not to be a Manager

Note that I’m not trying to beat the Manager track drum. In fact, I have one core problem with it I haven’t been able to resolve. I do my best work, far and away, on a Maker’s schedule, not a Manager’s schedule. ¯\_(ツ)_/¯

Considerations for the Aspiring Manager

So, what if your own version of the journey above is yet to start? What if you’re later in a career as an IC, but still on the fence about management? Here are a couple things I think you should keep in mind:

First, only pick a management track if you think you can succeed at it. Unfortunately, cultures/personalities vary so much that there isn’t a singular definition of success. For me, these qualities apply broadly to a good manager:

1. Ensures reports know what success looks like in advance

2. Helps reports succeed in figuring out how to get there

3. Connects success to a sense of purpose and accomplishment

Second, only pursue management if it gives you personal satisfaction, not to add another collection to your trophy case. For me, I thought about what it might be like to pursue my above framework to be a good manager:

1. I believe isolating value from noise is the single hardest, most strategic, most important, and most interesting part of a new venture

2. I absolutely love collaborative problem solving

3. I started connecting success to purpose for myself (by writing my own resume bullets every quarter). I felt invigorated and deeply wished that for others

A Passion Found Through the Growth Mindset

Hiring and managing great people has been a revelation for me personally. For the first time in my career, I have felt a higher purpose in my job, and a passion that survives the swings of business cycles and product pivots.

Note: It’s also a case study of how passion is built, not found.

I can’t recommend that feeling enough.