I once had a job with Gateway Learning, Inc., the company responsible for Hooked On Phonics. They hired me to run their Web development and systems integration back during the beautiful dot-com bubble. This place, located down in the waterfront area of San Francisco, had the look of a seminal start-up. Their pride and joy, a 120-foot square of paper with the database ERD printed on it, hung in a place of honor so that every employee, visitor, and investor could see it upon entering the developer zone. Their “data dictionary” filled two three-inch binders.

I reported to a guy named Fred. He had the position of Vice President of Being French and Developing Software. We worked together for a month. One day he pulled me aside and said to me, “Curtis, I find it hard to trust you because you speak with such short sentences.”

I quit the next day.

Hindsight has revealed that I hadn’t performed what I now see as the most important job of a development manager: managing up. By that, I mean that I did not manage the expectations or needs of my own boss.

Yesterday, I wrote about managing down. Turns out that, in most cases, managing software development teams, “managing down,” kind of runs itself. Unless you’ve out-sourced all of the development and your developers sit 8000 miles away from you. But, if the developers sit on the same floor as you, as long as you can see them, joke with them, look at the code they’re writing, admire whatever loony hobby they indulge, developers will do their best to meet deadlines, write great code, and drink all of the soda/coffee/tea/water in the office.

I now realize, after leading in the soft and fuzzy world of corporate America, that the hardest job of a leader often comes with “managing up.” In short, some bosses, they don’t seem to know how to do … well, anything. Anything worthwhile to you, at least.

That makes them the most difficult to manage.

This article targets people at all levels of employment, from worker bee to executive.

Unless you, like philipmat, have gone the self-employment route; then, as he so eloquently puts it, “[you’re] boss is an asshole.” And, always will be.

Necessary caveat: not my current boss

If you’re reading this,   your name here, current boss  , I’m not talking about you! Really!

Distill and frame your communication

When I worked at KickFire in Saratoga as the Director of Development, I reported to Bruce, the CTO, a visionary if ever I had met one. He wanted to write a series of novels like Asimov’s Foundation series that spanned millions of years. He invented some software to help him organize the events of his fictional universe. It turned out that it had applications in organizing and coordinating real-world corporations’ activities.

Bruce, a consummate 1960s geek, interacted with the world as you’d expect a sci-fi loving, assembly-hacking, libertarian. It took me the better part of six months to figure out the mechanics of a proper interaction with him. It turned out that if I talked with him with an adolescent-like passion about the status of my teams’ work and never directly criticized his decisions, we made the relationship work.

Your boss probably worries about things you don’t even know exist. She knows something about the budget that you don’t. She knows that management has a new strategic plan that will force her to reallocate his already-too-few resources. And, almost every single time, she has her own boss that she finds difficult to manage.

She doesn’t have the same perspective as you have. Most likely, she doesn’t care about the implementation details of the latest project. She cares about the quantifiable aspects of your project. Then, she can include those with the quantifiable aspects of all the other projects that she manages and show them to her boss who has an even wider perspective.

Don’t inundate your boss with details irrelevant to her job duties. Give her your measured results. If she wants details, she’ll ask for them. Have those available.

Learn to summarize well. And, if you’re working for Fred, just make sure your summaries are long-winded.

Exception: Some bosses really like to talk. And talk. And talk. Some of them expect you to participate. Others just like the sound of their own voice. In either situation, you’ll find yourself drawn into tangential conversations. Learn your boss’ expectations with their style of communication and endure the parts that you dislike. Then, vent to your peers but never your subordinates.

Respect them for what they do

As a programmer or a small-team software leader, you probably crack open that IDE pretty often. You can grok code pretty quickly. Your boss, probably not so much.

Bosses can probably describe the methods that they use to make really bad PowerPoint, Excel spreadsheets, and the advanced usages of Outlook. If you didn’t extrapolate from that list of frequently used applications, bosses spend most of their time collating and condensing various streams of communication into other streams of communication. They’re a multiplexer of reports and statuses, compliance questionnaires and change requests.

Admittedly, that doesn’t sound too sexy to programmers like us. I figure that managers get paid more because they have to abandon the fun applications like Visual Studio, TextMate, and the like. Then, their technical skills atrophy. They become readers of MSDN Magazine or one of the many syscon publications, if you’re lucky. Depending on the industry, they may not even read those. Maybe Bloomberg or the Financial Times.

When you see that and sneer or laugh, ask yourself if you would want to do that. Probably not. I know I didn’t think it sounded awesome. Even when I live it, I don’t. Give them the props they deserve, as silly as they seem.

Exception: Some bosses have never written a single line of code in their life. That happens the farther up the food chain you go. Some of them actually fear technology, though they may hold that as a secret. If you find you work for that boss, don’t make them to feel disparaged. Instead, help them to understand what you do.

I spent a year trying to convince a CEO at a former job that he owned a software company. He always retorted, “No, it’s a service company powered by technology!” That may make sense if he ran Accenture. He didn’t. He ran an e-invoice company. The “e” should have clued him in.

Communicate honestly with them

I cannot stress this enough. This makes you a better person, makes the team better, and will keep your boss in a position of power. They like power, those bosses.

If you screw up, tell them. If you succeed at something, tell them. But, if you screw up, tell them.

You might find this difficult. A lot of people lie upward, hiding the bad truth from their boss. They do that because they don’t want to look bad to their boss. They want to appear perfect. I understand that. I hate disappointing my boss, even if I don’t like him. Especially if I don’t like him.

Exception: There is none. Tell the truth.

Understand their level of risk aversion

With each change, something bad could happen: a new bug in the software, some incomplete feature, a chance to fail. Bosses hate that. So, if the software must change, they want it as quickly as they can get it with the smallest number of changes possible. You should figure out pretty quickly the amount of risk your boss will accept. Then, only stray outside of that acceptable amount if you want to fight for the change.

I have found this the hardest of all fights. If you want to do something that represents a perceived high level of risk, you will need to make sure that you’ve worked out your reasons past “it’s something cool that I just read about.” You’ll want to show them a proof of concept, show them how it works, show them why it makes the project better in more than one way.

If you have a good boss, they’ll trust you. If you have a bad boss, you won’t have an opportunity to do it, anyway. If you live with a boss somewhere between those two extremes, then you expect resistance so you’ll need to pick the aspects of change in which you really believe.

Exception: I hate the phrase “it’s easier to ask for forgiveness than permission.” I try to never fall into that philosophy. But, every once in a while, maybe once every two years, you just have to do it. Make sure you choose judiciously. In some cases, it can get you fired.

Can you add to this list?

Thanks for reading this far. A lot of you have unspoken strategies that you use to get along with your bosses. If you have one that you think worth sharing, please post it down in the comments section below for others to read.