The sysadmin workplace: 10 lessons on how to deal with your boss

I had a friend and colleague who told me that, "Technical people don't make good managers." I politely disagreed with him every time he said it. Incidentally, he himself had been promoted through the ranks to manager. He was a good manager, but he was also a good person. His greatest strength was that he knew how to deal with his boss in a positive, professional manner, without being a "Yes" man. It's possible to "tell it like it is," as so many of us system administrators love to do, without being seen as aggressive or insubordinate.

Learn to manage your manager.

Breaking bad

This article is more than just a discourse on so-called soft skills for techies, it is a compendium of lessons learned from a career that could have gone much differently than it did. I've made every mistake in that imaginary but omnipresent book about what not to do for your career. One of my former coworkers once told me that I should write, "Career Limiting Moves for Dummies." So, to say that I wrote the book on bad career decisions was almost a fact. Here are ten bits of advice on how to keep your career on track by learning how to deal effectively with your manager.

Silence is golden and duct tape is silver

I know this one might be counter-intuitive for many, but silence is often the best answer. Have you ever been in a group meeting where there's always that one person who must comment on everything? It's cringy and it's bad. If you find that you're that person, get some duct tape and place it over your mouth during those meetings. Sorry to be so direct, but seriously it turns what could have been a simple fifteen-minute meeting into a painful hour-long torture session. The only time that silence is not golden is when your manager asks you specifically to comment on something, or it's your turn in the round table part of the meeting. Have something prepared that is helpful and constructive to add.

Be prepared

This old scouting motto is a good lesson to heed. Never, ever say "I don't know" to the question of "How is X project coming along?" The same goes for "What's the current status of X?" You can answer "I don't know" to a lot of other questions and it's perfectly valid, but don't make the mistake of being unprepared for a question you should know the answer to and will definitely be asked. Prepare what you'll say and how you're going to say it. Even bad news, properly delivered, can be less devastating than if you just blurt it out with no editing, which brings up my next point.

Self-editing

One of the biggest stumbling blocks for technical people is the inability to self-edit. All of us need a filter. Not every thought that enters our heads needs to translate into words, texts, or social media posts. Learning to say difficult things in an inoffensive and in an unemotional way benefits everyone. Making emotional comments, sweeping generalizations, and using profanity are never welcome in a professional environment.

Practice what you'll say to your boss before you say it. Say it out loud so that you can hear it. Record it and play it back to yourself if you have the time and the inclination to get it just right. I know it sounds silly at first, but I think once you hear yourself saying something it will be an enlightening experience and a valuable part of your self-discovery and self-editing. For example, I accidentally recorded myself speaking to a coworker on the phone and when I played it back I thought, "Oh my goodness, do I really sound that arrogant to other people?". It changed my way of speaking forever. I practiced. I recorded myself practicing. I learned to self-edit in my tone, in my delivery, and in my actual words.

Be friendly to everyone

Someone once said, "Be nice to the people you meet on your way up, they're the same ones you'll meet on your way down." This was, at the time, directed toward actors but it works for system administrators too. You'll find in your career that some of your coworkers will move to different jobs, and at some point in the future, one or more of them might become your manager. It happens. If you've had a good rapport with your future manager, life will be easier for you. Managers are people too. It's likely they were once in your position so they're sympathetic to your workload, your work-life balance needs, and all the stresses placed on you by your job. Be cordial, helpful, and professional with everyone in your circles. It can only help you later.

Reality check: Your manager is not your enemy

Yes, I know, there are bad managers. There are vindictive managers. There are managers who have favorites and so on. Do your job. Don't build a wall between you and your manager. Keep lines of communication open. Keep your manager updated on progress, status, pitfalls, setbacks, successes, and schedules. Fill out your timesheet on time. Schedule your vacation well in advance. Give full attention to your tasks. Your manager has more than just you to manage, so make it easy for them to do so. Your manager is not your enemy but rather a career advocate who can help you succeed.

Managing up

There is a now-famous book by author Roseanne Badowski titled, Managing Up: How to Forge an Effective Relationship With Those Above You, that describes how to work with your manager and make both your lives better. At only 240 pages, Badowski gets right to the point and gives great advice on how to foster your manager-subordinate relationship to your advantage. On the surface, it sounds manipulative and kind of underhanded, but it isn't. You have to manage your career, and part of that management is learning how to effectively interface with those who hold your career advancement in their grasps. I'm not selling the book nor am I even suggesting that you read it. What I am suggesting is that you realize that you are being managed and that you should manage yourself and your manager as well. In Badowski's words, "Everyone is a manager, in one way or another." Learn to manage your manager.

Thou shall not bash

Leave the drama and bashing to reality television. There's no place for either in the workplace. The bottom line is that if you have time to stir up drama and to bash coworkers or managers, then you have too much free time on your hands. Find something constructive to do. Managers dislike pot-stirring, drama, and bad-mouthing. You'll find your career lagging, no matter how good you are or think you are; promotions, raises, and bonuses will go to those who keep negativity out of the workplace.

Toot your own horn

It isn't bragging to highlight your successes to your manager, but take a word of advice from the writing world: Show, don't tell. Managers are busy. When you have the opportunity, tell your manager about your successes. Describe how you worked with other teams to complete a project. Tell your manager how you automated a process. Send an email that breaks down the amount of money you saved the company by using a free software alternative to an expensive option. Have the junior system administrator you trained provide a status report on their success in performing backups or maintenance tasks that relieved you to focus on automation. 

Make your manager look good

This final point is perhaps the most important one of all" Make your manager look good. It's your manager's job to get things done. Your responsibility is to do the things. By successfully doing the things, you make your manager look good to their manager. Praise, bonuses, raises, and continued employment does trickle down. If you can make your team and your manager more successful by beating deadlines, saving money, automating, making a process more efficient, or simply accomplishing regular tasks without issue you will also be rewarded. 

Give your best

You don't work in a vacuum. You work with other people and you answer to a manager. You have a responsibility to your team, manager, and yourself to give your best effort every day. Did you ever have a slacking coworker? It's unpleasant, isn't it?

It's funny that a passing grade in school is either 60% or 70%, depending on where you go, but do you want to work for someone who only gives 70% to you? No. Do you want someone working for you or with you who only gives 70%? No. Don't be that person who only gives 70%. Always give your best. Your team, your manager, and your future all depend on how much you give to each of them. 

Wrapping up

System administration isn't easy work. Managers know this. It isn't easy being a manager. Learn this. Learn how and when to speak. Prepare yourself. Be the kind of employee to your manager that you'd want on your team. Instead of looking to become part of the perfect team, spend your time being the perfect team member. Inspire others to do the same. Give your manager great things to say about you and your team in his manager's meetings. And remember that your manager is part of your team.