I started out my career under 2 bosses, one who was my boss in the organizational chart and was more-or-less, a hands-off manager, and one who was actively looking for PM help on their team and lobbied to move me within their organization.
They clearly liked what they saw in me in my early days in product management, and perhaps also wanted leverage in their own position. Leverage is a great thing, if you know how to handle it. I’ll call this boss-type the “leverage-seeker”. Leverage-seekers typically are looking out for their own careers and there are plenty of such people in middle-management at most organizations.
Unless your personalities match perfectly, there is little-to-sometimes-negative value to be gained from leverage-seeker bosses. In this case, the career-trade is improperly balanced. The boss has more to gain than the value he or she is providing. My suggestion, in this and all imbalanced relationships, is to get out of it as quickly as humanly possible. Look for an exit route. Perhaps this is a horizontal move at your mid/large scale company or perhaps it is an upward/horizontal move to a startup in the same industry or another company of the same type in the same industry. Perhaps it is a new start in an industry that is beginning to take off. Whatever it is, recognize that moving is of paramount importance so don’t waste your time trying to have a “clean” disconnect. The earlier you are in your career, the higher the cost of sticking with a leverage-seeking boss. You are, in effect, sacrificing the compound returns in your mid and late career by remaining in a situation where there is potentially negative value to you and all the value you do provide will get re-labeled as someone else’s work. The only exceptions to this rule are if you are working in an industry you are truly passionate about and are still experiencing increasing returns to learning (within that industry).
Principle 1
Don’t let your boss determine your career path. Your career is yours and a good boss will act as a coach to help you recognize your strengths while enabling you to help the organization and yourself.
Principle 2
If you see your career only serve someone else’s career within an imbalanced relationship, find alternatives as soon as possible. Don’t wait for a clean exit.
Founder Bosses
Soon after graduating from my middle-manager, leverage-seeking boss, I was rewarded with a Founder boss. Founder bosses are great, if you can handle limited guidance and are a strong performer. I feel I was lucky to experience having a founder boss early in my career as this is the role I’ve always imagined for myself. Despite the soul crushing realities and the crazy rollercoaster ups and downs, the independence of being a founder is second to none.
The key area to learn about founder bosses is that their expectations of themselves tend to carry forward to the people around them. Imagine if Elon Musk was your boss.. I’m certain that he has set seemingly unachievable goals for himself. This is what good founders do. They are visionaries and are known to set their sights high. They tend to see things that do not yet exist and expect nothing but the best from themselves, and this spills over to the people they work closely with. My advice is to not think of this pursuit of excellence as discouraging, but to learn from it as much as possible.
Don’t expect to be coached or mentored significantly by founder bosses. Founders are often juggling so many things at the same time that they barely have time to remain sane..
If you do learn anything from founder bosses, it will mostly have to do with decision-making (why they choose a certain company or investor) and whatever area they are already specialized in. This could range from things like partnership-development to infrastructure architecture.
Founders are not always great at hiring. This can be hit or miss. Align with founders who have tremendous skills in what you are trying to get better at.
If you are trying to become a better software architect or CTO, align with the technical founder(s). If you trying to become a better marketer or growth hacker, align with the marketing focused founder(s). If you are trying to improve your pitching/networking skills, align with the BizDev founder(s) or the founder(s) who usually prepare the pitch-deck and present to investors.
Optimize for what you want, but make sure to actively pursue it. Founders are busy people with busy schedules. It is your responsibility to make the most out of your 1:1s and the projects you get to work on.
Principle 3
Own your interactions with your boss. Don’t leave this up to chance or scheduling conveniences. Make time for a regular check-in and ask how you can improve in the dimensions you want to become great at.
The cost of this will implicitly be taking on responsibility in areas that you don’t want to polish. It is important to recognize this as the cost of getting what you want. If you feel this tends to continue longer than is right, you can recognize that you are in an imbalanced relationship. If you detect that the give/get matrix is unfair, it is time to move.
Lasting relationships, personal and workplace, are built on a foundation of balance and trust. Trust is built or damaged based on repeat encounters in life. Try not to erode trust and aim for well-balanced relationships for the long term.
Great Bosses
I’ve had numerous other types of bosses over the years, ranging from deeply technical and kind bosses, to more pragmatic bosses who are detached. Fast forward a few more years and you get to my current boss. I could not say enough good things about my current boss, but I’ll summarize with this statement.
“Great bosses are as invested in your success as they are in their success”
I’m currently at what I would describe as “Peak boss” (similar to peak oil from my economics classes). Once you think you are at peak boss, try to ensure you don’t mess it up. The P( better boss | your experience ) is quite low when you are at peak-boss, and it is important to maintain strong ties with the people who have invested in your success, especially “peak bosses” :)
This does not mean remaining in a role just due to your boss or sticking out through a tough time in a startup purely due to one relationship. This does mean acknowledging the value you have received and being ready to provide value back in whatever way your future self is able to.
It is important to build bridges throughout life and your career.. Life itself can be thought of as a graph or a network of bridges, some though air, some through water, some within us and some that extend across continents and worlds.
Principle 4
Recognize the people who have invested in your career early and often.
While you may have read this with the lens of “the importance of having a great boss”, if you recognize how important it is to have a great boss, you will likely work hard to be a good one yourself.
