Why It’s Important To Manage Your Boss

Keep them informed, make them look good, and make your opinions count.

Derwin Dexter Sy
The Startup
6 min readDec 6, 2019

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Photo by Hunters Race on Unsplash

If it hasn’t been very clear from my other posts, I just want to say it again. I’ve spent a substantial part of my career as, yes, a middle manager. It’s a role that gets a lot of flak and ridicule. It reeks of bureaucracy. To be clear, I’m currently in a flatter organization, which means being “line”, “middle”, or “top” management doesn’t really mean a lot. But I have to defend the role of a middle manager, in any case.

Being a middle manager is not as easy as it looks. The hate often comes from the fact that it’s a little hard to understand exactly what they do. Oftentimes, you’re not sure how they were qualified (you’d probably guess tenure and often, you’d be right). And unlike top management, middle managers don’t really seem to have much of a say in issues that affect the entire organization. (While this is true a lot of times, it’s often self-fulfilling and can be corrected, as I will explain later.)

The hard part

So what’s the big deal? Can’t we just go on hating on middle managers?

Before anything, the challenge of “managing upwards” is definitely not exclusive to middle managers. Everyone in the organization needs to do that. Regardless of where you are at in your career, you have to manage your boss.

That said, the reason I bring up middle management in the intro is due to the fact that while managing upwards is hard enough, you can probably imagine how much harder it would be to manage upper management folks. Essentially, the root of why we like to hate on middle management is simply because it’s a really tough job, and a lot of people simply fail in that role.

Me, the middle manager

You can’t really manage your team well unless your boss buys into how you operate. Photo by İrfan Simsar on Unsplash

My actual title at the time was department manager, and that meant I was managing a department of around 50 people, divided into 4 sections or teams. Each section had their own manager (for the lack of a better term, a line manager). Our division manager (one up from my role on the org chart) had resigned and the company decided not to hire a new one for a while. So technically, I was reporting to the president directly, or at some point to a general manager, both of whom managed the entire company.

My role, as with any middle manager, was two-fold. One was to manage my team, and that meant directly managing the section managers as well as indirectly looking out for our team members. On the other hand, I also had to manage upward and make sure my boss, the president or GM, was aligned.

That second role proved to be the bigger challenge. Incidentally, you can’t really manage your team well unless your boss buys into how you operate.

Did I do a good job at it? I like to think I did. While not all the decisions or initiatives I had for my team pulled through, I did get a lot of positive change effected. Most importantly, I feel I earned the trust of our upper management through my efforts, regardless of the success rates.

Great, now what do I need to do?

The following tips apply to anyone who has a boss. Yup, that’s basically everyone other than the self-employed. Here are some things to try to build better trust with your manager and to make your life at work way easier.

Just a side note though, I know a lot of people rag on their bosses and maybe that’s justified. I personally have been lucky enough to have worked with mainly well-meaning (if difficult) managers, except in one particular case which I won’t detail here. If you happen to have a boss from hell and you’re convinced there’s no redemption for him or her, these might not work out that well for you. If you’re in this situation, I’d say it’s worth taking a look at your options by now.

Understand their informational needs.

Managing upwards means figuring out what information would be useful for your boss to do his or her job well. Photo by William Iven on Unsplash

I think what irks most bosses is being in the dark on important issues. If your boss has a boss, he or she will likely be asked about how certain things are going. It’s important to have a good understanding of what kind of information would be useful and sufficient in that situation.

In a great article about organics and mechanics, Rands characterizes micromanagers as typically well-meaning managers who simply haven’t gotten the information they need. Managing upwards means you need to figure that part out. Asking them definitely helps, though as in many matters with people, it’s probable they likewise don’t know for sure. Learn by experimenting and switching up your reports once in a while. See which one clicks with them.

Keep them informed.

So you’ve figured out what kind of information they need. Now just give that information to them. Regularly. Unless explicitly told not to, over-communicating with your boss is often the safer call.

In larger organizations, escalation is often the oil that keeps the machine running well. If you’re having difficulties with the work you’re doing, let your boss know and more often than not, they’ll be glad to help you. It’s their job after all.

Give them feedback.

360 feedback is a controversial topic, but it’s actually risky only when there’s politics involved. Photo by Nik MacMillan on Unsplash

360 feedback is a controversial topic, but it’s actually risky only when there’s politics involved. Regardless of whether you have a formal process to give your managers feedback, do it anyway. The best feedback is always one that’s real-time and given immediately after it’s merited. Your boss made a decision you don’t like? Say so, but offer an alternative as well. Feedback that’s not actionable is just plain complaining.

Of course, this may require a bit more tact to pull off gracefully when dealing with your boss. But if you haven’t already mastered tact, it will be important for you to learn, regardless of whether you’re dealing with your team or with your manager.

Make your opinion on issues heard.

Wherever you are along your career, it’s always important to have your opinions heard. Photo by Steve Johnson on Unsplash

In “ Originals “, Adam Grant points out the dilemma of a “middle manager”. Essentially, you’ve got tenure and you don’t want to risk that on strong, controversial opinions. On the other hand, you’re not quite on top yet and might need to fight to get your opinion heard. Here’s where the problem of “not having a voice” begins.

Wherever you are along your career, it’s always important to have your opinions heard. You don’t have to push hard or risk your career for them. But you have to say them out loud. Regardless of how people take it, it’s always going to be a factor to some extent.

Sounds familiar?

If you’re a manager or leader who’s never had a thought about managing upwards, all of this might nonetheless sound familiar. That’s because it is exactly the same as what you need to do to lead your team. The truth is, managing upwards is really no different from managing a team.

Sure, the stakes are higher and intimidation factors might come into play (though hopefully not). The people you talk to are possibly less or more stubborn (hopefully less). In any case, what you need to do is no different. So just take those management skills and use them to the best of your ability on the people supervising you, and you should do fine in this area.

This is the first of my series on the challenges of being a middle manager. It’s an underappreciated job, but in some organizations, it’s a vital role. Keep posted for more posts on this topic and if you have some happy stories (or horror stories) from middle management, I’d love to hear them!

Originally published at https://techmanagement.life on December 6, 2019.

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Derwin Dexter Sy
The Startup

I’m an engineering manager and entrepreneur who loves exchanging ideas and helping others become better at what they do. I run a blog at techmanagement.life