Realizing You Know Nothing About Management and Then Overcoming It

Problem

I was the first time founder of a company and over the course of six months where we were hiring and onboarding a team of around eight people, I realized that I didn't know anything about management. My entire career up until that point had been as an engineer and as a product manager at Google. Google, however, doesn't have people reporting into PMs. I was responsible for managing the product, organizing the specs, and working cross-functionally, rather than doing the hiring, firing, management coaching, and so on that I was now expected to do in this position. I felt overwhelmed like I couldn't keep on top of everything that was happening, and that we weren't really moving or making progress at the rate that I wanted to. Having grown up with a natural sense of Jewish guilt that everything is my fault, I used that to propel me forward in figuring out a proper management solution on my part.

Actions taken

I took a step back and realized that I could be better, that it was in fact my first time doing this, and in a bout of luck shortly after having this conversation with myself, I got an email that changed my course of action. It was an invitation to a management summit sent by one of our investors. Two weeks later, I found myself at this day-long seminar, of speaker after speaker, in a San Francisco classroom. Being a very skeptical person by nature I felt that most of these speakers had very fluffy presentations that were not offering me much in the way of actionable advice. Just as I was thinking this seminar would be a letdown and a complete waste of time, a speaker by the name of Johnathan came to the front of the room, redirecting my attention with a strange but captivating phrase - "Please allow me to transparently manipulate you". In the next 15 minutes, I scribbled down what must have been 14 pages of notes. Everything he was saying made sense, it was actionable, and I generally liked the way he viewed the world. He then wrapped up his speech by saying he had to rush off to the airport and I was left sitting there thinking that everybody up until this point had not been so great, but this guy was unbelievable and I needed to talk to him and learn from him. In a swift fashion, I literally ran out of the room and held the door open to his taxi as I implored about his availability for private coaching. He told me to follow up with the organizers of the seminar to get his information and that started a multi-year relationship of management coaching between Johnathan, who is a professional management coach, and myself.

Lessons learned

• Identify your problems and take proactive steps to fix them, even if that means running out of the classroom in the middle of a seminar to chase down the guy that you think might be helpful in doing so.
• The solution to the problem is not a silver bullet. As it turns out, now that I have a few more years of management and hundreds of books under my belt thinking about this, it's actually a really hard problem. It's not something that one can get good at overnight. It's a continuous learning process both in terms of the information you are absorbing from the world and the trial and error of your actual job. So for anybody who is struggling to move from being an IC to a manger, just know that it is in fact difficult and it will take a lot of time, so do not be too hard on yourself. Your main focus should be on getting better by learning and finding resources to help you work through those problems that you are facing. It never really gets easy, but in time, you will become better at it and more comfortable from having seen certain types of problems before and in having read certain books with references you can fall back on.
• When you are managing a team of two or three people, you can sort of fudge it and maybe get away with it. Once you have anything over five or six people, you really have to be thoughtful and deliberate in your management practice. This includes, but is not limited to, making sure everyone is working together without a tax on your velocity due to lack of practice.
• There definitely is such a thing as a born leader. There are people who have a natural sense of confidence, charisma, and articulation. However, there is no such thing as a born manager. To be a good manager is to have practiced the art of being a good manager and have spent time pickling in the pickle barrel. It is learning different managing techniques, experimenting with them, playing with different processes, working with different teams, dealing with different types of personalities and business challenges. It's not until you have had all of those experiences that you can bring that to bear on different types of management problems. It really is a question of experience and education rather than innate knowledge. It is a skill that one has to learn and experience is the best teacher.