They say people do not leave jobs, they leave bosses. I think that reflects 50% of my reactive career decisions over a 20 year span. And if you looked at my LinkedIn profile, that is an unfortunate number of bosses.
So how do you know how you have a good boss?
Is it because you get free pizza when you are hungry?
Is it because you get a good raise every year?
The sad thing is that most of the things that people like about their boss are the opposite of traits of a good boss. You might be getting a lot of things that make you comfortable, and appear to be valuable on the surface. In fact, the better the perks you are receiving, the more likely you are probably working for a bad boss.
I am going to give you the characteristics of what I see in a good boss and hopefully at the end of this short article you will sit down and ask yourself if you have a good boss or a bad boss.
For me a good boss does three things.
- Makes sure I have the tools to do my job
- Lets me know what his concerns are with his job
- Grooms me for the next step in my career
That probably sounds abstract and nebulous. I will try to break it down.
Item 1: Having the tools to do my job.
Every time I have managed people and I am needed to moderate some sort of disagreement between two coworkers or two different teams, I always make a big deal about it. I always tell people “the last thing you want me to do is make this decision for you” and sometimes I have to privately sit down with a person and explain “You were hired to solve problems, and I am concerned you are spending more time making them”. That is never a pleasant conversation. When I am coming into a role I want to make sure that my boss has given me the ability to do what needs to be done. Do I have hiring authority? A budget? The right people already on a team? The right tools for me to be effective? If something is missing, I need to be able to go to my boss and make sure that I can get those things or else be empowered to create a solution on my own. This is harder than it sounds, but I have been asked a few times to join a company with constraints on my job that make success impossible. I have learned to avoid that situation.
Item 2: Lets me know what his concerns are with his job.
I am probably worse at this than I want to be, and I am sure many people are. The last thing you want to do is to let people who need to believe in your leadership know that you need anything in particular. I have learned to start trusting people with this more and more as I have evolved, and also made it clear when it is something that is a professional concern or a personal limitation. Let’s be honest—none of us are perfect. Sometimes people on our teams do not help us as much we would like them to, and sometimes the solutions to problems are not easily attainable. Being able to separate personal issues from structural business problems is hard, and it is worth having a conversation with people you are working with to make sure those get resolved. This is a lot harder than it sounds in reality but it is valuable because…
Item 3: Grooms me for the next step in my career.
A friend of mine flattered me recently when we agreed to meet for coffee. I asked him why he always makes time in his bay area visits to get together and he pointed out that he considers me a “best athlete” problem solver. I really cherish that feedback.
I often go out of my way to hire “best athletes” for most of the teams I build as opposed to “best athlete” candidates. For the work that I do there are too many unknowns to focus on “best fit”. If I go and find the best person to solve a specific problem for a specific product, nine times out of ten they are going to struggle when we have to pop the clutch and prioritize some sort of crazy emergency issue related to marketplace shifts. This may be a unique problem to startups but I have yet to regret choosing “best athletes” in hiring.
A big part of the value here is in working with the people on your team and getting them to take on more and more responsibility. There was a period of time in my career when I became very mindful about my role and my responsibilities. There was also a period of time, prior to that, when I was a ravenous bulldog intent on doing my job to the best of my ability and chewing through any obstacle in my way to get my work done, often leaving a trail of chaos and bewilderment in my wake.
To anyone who was affected by the latter, I am deeply sorry. In the case of the former, I often ask myself “how do I make sure that if I get struck by a meteor, the company I work for will continue to succeed”. I know that is dramatic, but it is valuable to ensure there is a succession plan for the organization. I have done some minor team rearranging, and also some random schedule adjustments simply for the sake of ensuring that meaningful work can happen without me. As an engineering manager, for example, I was accused (correctly, and fairly) on a few occasions of missing specific meetings on purpose, just to test that people can manage on their own. “Szeder is meddling with the warp core again” was how my peers stated it, and I cannot say it is wrong—but if you continually try to explore space at warp four, you will never need to know what happens if you urgently need to go warp ten.
I hope this was an enjoyable read. I have had some bad bosses in my time and honestly, whenever I manage people I look in the mirror some days and ask myself if I can see previous managers peering back at me. Maybe that critical self-reflection is the best feature of all for a boss to have.
So what do you think makes a boss a good boss? I would love to know!
