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Joys of middle management

Published on Sep 10, 2022

🛫4 mins to read

  • notes
  • management
  • process

Conventional wisdom paints the idea of a middle manager as taking shit from both sides. You are simultaneously managing up and down.

corporate flowchart

Things are great when both your reports and your leaders are aligned, then you are at that cruising altitude where everything is smooth sailing.

When things start to crack is when there is tension or misalignment between what the engineers think is needed and what management wants to be done next. Typically boils down around things like tech debt or re-architecture which are all better in the long term but have no quantifiable metrics in the short term.

However, I’ve personally witnessed some of the best managers operate in this zone of tension. They are honest and direct but also kind. They are capable of saying no upwards and downwards when it is appropriate to do so.

Understandably, this is a hard thing to do. It’s tightrope walking trying to deliver features that will provide value to your leadership while ensuring that your reports are happy and doing their best work.

I’ve taken notes from observing a few of my favorite managers and there isn’t a real silver bullet but I wanted to note these down so it serves as a reminder that middle management can be rewarding if you focus your efforts in the right direction.

Manager # 1

Lead by example

Everyday, he would personally work on cleaning up tech debt from the codebase. Admittedly these were simple things but it really encouraged everyone on the team to take on such projects because he was leading by example.

Suggestions over prescriptions

As an engineer, the most gratifying experience is when you figure out how to solve a problem. This is also why it’s hard to provide help to such folks because you don’t want to prescribe a solution. An elegant way manager # 1 dealt with this was to provide pointers on where to look for solutions.

Compare how X is achieving this

What does Y product do in a similar situation

It’s a creative way of steering you in the right direction without a heavy hand.

Saying a loud and clear “No”

I admired the way manager # 1 said no. It was clear, direct and unambiguous. And he would say it to anyone and everyone when warranted. This includes technical discussions but more importantly ones around deadlines, when to deploy, when an engineer is too involved with his / her work.

Serve as an umbrella

I love managers who act as shields and prevent any office politics from entering the realm of their team. This doesn’t mean they brush things under the carpet but rather be honest about what’s going on but also ensure that those dynamics do not affect you or your work. This also means, as long as you listen to your manager, you don’t have to worry about timelines or delivery dates as they are ensuring they communicate that responsibly to stakeholders.

Manager # 2

Encourage ownership

She encouraged when team members took ownership of projects and allowed them to lead when they are capable. This means providing direction, aligning the team around this person as well as providing PR support when it is appropriate to internal peer teams.

Even when projects weren’t officially sanctioned, if the team feels like they can pull it off, standing behind them and encouraging them to push along is great.


My favorite part about any project is there is a problem that needs to be solved. How to do it is an engineer’s domain. When it gets done is what the manager cares about. If you have a really solid understanding of each others’ styles and estimates are reliable, it’s great for both people to stay in their lanes.

She only stepped in when things seemed to go out of control but was happy to remain oblivious to implementation details as long as things were chugging along. It’s the perfect mix of how involved a manager ought to be.

I don’t care how you do it as long as it is done

Reduces red tape

Anything process, technology or purchase-decision wise that could help reduce red tape is taken upon. Anything that is dragging the team down is swiftly dealt with and

Manager # 3

Being available

Being available is something so simple yet overlooked, especially in a remote world. Responding to messages as soon as possible and addressing any concerns without leaving them hanging. If you are told they will get back to you, there is no need to follow up. They will get back to you. Such a great way to build trust.


Unblocking people is one of the duties of a manager. Being able to either involve yourselves directly or pointing people in the right direction in a timely manner is not an easy thing to do. Doing so shows people how invested you are in the project’s and the team’s success.

Providing context

Providing context is such a huge skill in a manager’s toolbox. Being able to provide a big picture or paint historical context on tasks, projects and deadlines goes a long way. It goes along very well with saying no. By adding some context, a no can land much softer because there is valid reasoning behind it.

Common traits


All were great listeners. All conversations had a real “what can I do to help” vibe which is not merely saying those words but meaning it. Taking feedback seriously. For example, does the team ask for meeting-free days? Let’s get on it.

Sometimes things aren’t doable but an explanation or providing context as to why goes a long way over brushing aside or not paying attention. Also, it is hard for people to always come up with solutions. Asking if doing X will help goes a long way.

Honest and direct

Taking a radical candor approach to feedback. When things don’t work, address them directly, specifically in a blameless manner. Provide feedback so the person has sufficient time to course correct. If things aren’t working, being direct about it. Collect feedback from the team, find your stars and help raise them to the next level. Find your weak links and show them how they can change approaches to become better. Leave no one behind.

Care personally

Have a specific interest over your personal career trajectory. This one is great as they are advocating for you outside of your meetings, showcasing your achievements and how it has helped the company. They also have specific feedback that will help you become a more rounded contributor to the team. This feedback is delivered with empathy and ahead of time, not as an excuse to not give you a promotion.

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