From Star Employee to Struggling Leader — A Simple Explanation of Your Manager's Incompetence
No manager wants to be a terrible boss. Yet even with the best of intentions, it's hard to avoid being at least moderately incompetent.
Welcome to the Scarlet Ink newsletter. I'm Dave Anderson, an ex-Amazon Tech Director and GM. Each week I write a newsletter article on tech industry careers, and specific leadership advice.
Free members can read some amount of each article, while paid members can read the full article. For some, part of the article is plenty! But if you'd like to read more, I'd love you to consider becoming a paid member! The original version of this article was published in 2021. I’ve re-written it so that I could share it with today’s audience!
I imagine the most famous movie about the workplace is Office Space. In that fantastic movie, managers are the brunt of most jokes. The main character, Peter, stops caring about his job, and as a consequence, is recognized as a future senior manager. Peter's boss drones on about paperwork, and clearly doesn’t connect with his employees.
In comics, Dilbert features a hilariously incompetent pointy-haired boss, and many gags revolve around the incompetence of management.
Managers have incredible power in the workplace. Your manager is probably the single largest factor in your level of happiness in your job. They control if your job is secure, and if your career is improving or going downhill. They can impact your independence and autonomy by micromanaging, or by not giving you opportunities to grow.
I overheard this conversation years ago, and it stuck with me to this day.
Manager Alfredo - "What my engineers like is to be told exactly what to do. If they are told exactly what to do, they can relax and just execute on their instructions. When they can just focus on execution instead of making decisions, they’re happier."
Manager Susan - "But these are pretty senior engineers, I think they get satisfaction from solving problems. We’re paying them to solve problems, and that’s the fulfilling part of the job."
Manager Alfredo - "No, you don't understand. They prefer to be told what to do. It’s easier that way for everyone."
You know what? If you think your manager is bad at your job, you’re quite likely right. They are probably missing important details in their team’s work, coaching poorly, delegating ineffectively, and in general making a whole pile of mistakes.
I also think that it’s normal, and should be completely expected.
When I say manager, what do I mean?
When I refer to a Manager, and the job of Management, I mean the job of people management. This job means the manager has a responsibility direct other humans in some fashion in the workplace, and their job is to create value in collaboration with those humans.
In almost all situations, while managers have people management responsibilities, they are also rarely only a people manager. They might be the manager of an iOS app team, but the manager is also responsible for the software delivery, quality, goals, vision, etc.
I was once in a management training class (a fairly rare thing at Amazon to be sure), and we were conducting an exercise where we listed all the things a manager was responsible for.
Relatively quickly, we had a massive list of ideas all over the board.
Manager Sally - "So we have project requirements, people performance, people hiring, product definition, launch readiness, press releases, QA process..."
Manager Phil - "I think this would be faster if we tried instead to list the things managers shouldn't be doing."
And that’s absolutely true. If you were to enumerate the entire list of responsibilities of most managers, it would be almost everything possible, with few exceptions.
That alone is a good reason to be poor at the management job. There’s just so many things you’re responsible for. But that’s not really touching on the reason that most managers perform poorly.
Those elusive people management skills
A manager has a collection of responsibilities related to their field, as I mentioned. But once they’re in management, they have a list of people management skills they must also master. Here are a few random ones. You’ll notice that I’m being more specific than most lists of management responsibilities. Because “building a good team culture” means nothing. I wanted to be a bit more specific.
Decision delegating — We all know that bottlenecks are bad. If a project has a bottleneck, you need to do everything possible to get past it quickly. Decisions are bureaucratic bottlenecks. A manager needs to figure out how to identify the few as possible decisions which need their personal judgement, and delegate everything else to their team, or other designated decider. For example, in most of my roles, I had my “number two”, which was the person who was in charge while I was out of the office or otherwise unavailable. I ensured my organizations (and my managers) knew that this person could make decisions if I were unavailable, and was likely my replacement if I was hit by a bus (or less morbid — if I was suddenly promoted).
Creating Balance — A well-balanced team is one which has fewer weaknesses. A manager must be able to recognize gaps in their team, and be able to identify candidates who don’t have the same strengths as their other team members. This might mean that the candidate is weak in a way that their other existing hires are not. In fact, the manager may be personally biased against that type of work style. For example, a manager may enjoy taking action and risks, so their team may benefit from hiring someone who is cautious and plans more. In my personal experience, I almost always ensured my number two be a person with a more cautious and planning personality, to help counter my tendency to move (too) quickly.
Employee Fulfillment — Employees who are growing and achieving their personal goals stay on a team longer, are incentivized to achieve their team's goals, and create a better team environment. A manager must recognize what motivates each employee, and determine if that employee can achieve their goals while on the team. Some employees may need to leave the team, while other employees may need to take on new tasks. A manager must be able to drive employee growth on their team while achieving their team goals. They can’t ignore employee growth, or they’ll end up with a less tenured team, and they can’t overly focus on employee growth, or they’ll end up doing random low-value work simply for their employee’s benefit.
Giving Constructive Feedback — Feedback is critical to recognizing what you should keep doing, and what you need to change to be successful. A key responsibility for managers is communicating clearly and honestly with their employees in a safe place, which will ensure that feedback is heard and internalized. This also includes recognizing when an employee is not ready to hear feedback, or needs to hear it differently.
Conflict Resolution — A team is a group of people, and any group of people will have conflicts. In my experience, once you hit around 50 people in your organization, there will always be an active conflict within your organization. Your team will also frequently end up in conflict with other teams inside your company. Managers have the responsibility to resolve conflicts to ensure that their team can concentrate on achieving their goals. Unfortunately, you can’t always resolve conflicts with great feelings on all sides. A manager needs to be comfortable with uncomfortable, messy human interactions. They must ensure that conflict doesn’t get in the way of being productive.
That being said, how do people build these skills?