• Jim Kelly

Your boss works for you

If you’re like most people with a corporate job, you have a boss who more or less defines your work experience. He or she makes up demands, and you have to meet them. There’s a big power imbalance in your relationship, and you’re on the short end of it.


It’s time someone told you how the world looks from the boss’s chair. I’m a few decades into my career, I’ve managed a lot of people, and to many of them I’ve been the boss. Or the boss’s boss. Or the boss’s boss’s boss’s boss.


Take it from me, you have a lot more power in our relationship than you think. Here’s what you need to know to leverage it.


The view from my fishbowl

I got where I am because I used to do your job and was pretty good at it, so I got promoted. Now I’m doing this job and haven’t been promoted out of it. So maybe I’m knocking it out of the park, maybe I’m about to be fired, more likely I’m somewhere in between.


My job is to advance 100 different projects incrementally every day. My calendar is wall-to-wall meetings and very interrupt driven, as on any given day two or three of those projects will be leaking fluid or shooting sparks. I have no time get very deep on any one issue, and it feels like I have no time to think.


In those meetings, I make decisions. Sometimes big ones, but mostly lots of little ones. Like how to respond to a team member who’s doing some things well and some things not so well, knowing that my reaction will be a big deal to them. Or what question to ask about this project to suss out risks or fuzzy thinking.


I got told when entering my first executive role that a third of the decisions I would make would be wrong, and part of the job is getting comfortable with that.


Failure, in fact, is constant in my world. I ask for stuff from my team and people all over the company, and I rarely get what I want. If people knew how to do what I’m asking them for, I probably wouldn’t have needed to ask. So every request I make requires follow-up and spotting failures and course correcting and iterating, more time and focus that are in short supply.


Since I’m in charge, I own all the team’s failures. It’s an emotional challenge. And I bring plenty of personal failure as well. The executive’s great demon is coming to grips with how much and in what way he sucks.


Firing someone— the boss’s most notorious duty — is another failure I own. If only I had managed this person differently, every boss tells himself, we wouldn’t have gotten to this spot. It stings because it’s true: a job is a relationship both parties play a role in creating and both parties can redirect.


I should mention my boss, because he’s even quirkier than I am. The higher you get in an organization, the more likely you’ll find people with very strong strengths and very weak weaknesses. His time is even more fragmented, he has even less time to dig into details, and when he suspects something is wrong his tools for dealing with it tend to be very blunt instruments. So keeping him calm and not feeling the need to intervene is constant, delicate work for me.


How I See You

Our company’s business is spinning straw into gold, but despite the deference people pay me as the boss, I don’t spin a single stalk. I’m overhead, here only because when you have this many straw-spinners, you need roles like mine to keep them organized.


You’re the genuine asset, the one who produces the gold that keeps us all fed. You’re not the only one we have, you may not even be the best one, but you’re a valuable one just the same. In some ways you’re better than I was when I had your job. You’re straw-spinner I’m willing to get behind and push.


You were hard to find. You would be amazed how many supposedly professional straw-spinners don’t know a drive band from a flyer whorl. Or don’t show up to work reliably. Or deal drugs on the job. I spent many hours interviewing people, despite my already-impacted calendar, before I found you and you agreed to come help me. I would hate to lose you and have to go back to square one.


I succeed only to the extent you succeed. My boss watches how much straw my department spins, so whatever level of competence and commitment you bring to the job defines how well I do. No one is banking on your success more than I am, and no one is keener to help you grow.


Note that I’m not actually in control of the success criteria for either of us. Nor is my boss. Success for all of us is defined externally, by the straw and gold markets. If we spin efficiently enough, the company makes money and we’re all succeeding. If not, we’re all failing.


You Control What Gets Done

As you know, bosses are in charge and employees have to do whatever we say. Yeah, in our dreams.


Usually when I ask for something and you say yes I figure you’ll deliver about half of it. Not necessarily because you intend that, but because it’s new and you’re learning how to do it and I didn’t explain it very well and it took longer than either of us expected. Or because you got interrupted by a family problem. Or because you had to help one of the junior spinners get untangled. Or because what I asked for couldn’t really be done, and you had to adapt.


Whatever the cause, the fact is what most matters in our business is output, and you have much more control over your output than I do. Within limits, you define your own work/life balance and your own level of commitment to the job. If you put in a lot of hours, if you take extra effort to keep up on gold spinning innovations, if you figure out how to improve in your job faster, you’ll rise faster in the company. If you put in just the minimum, you won’t.


I can ask you for more, but it’s up to you to say yes or no. I might be the kind of boss who keeps asking for more until you say no, in which case I’m counting on you to enforce limits to keep yourself from burning out.


You can — and should — ask me for things too. I’m just as motivated to do what you ask as you are to do what I ask. I want you to get more done, and I’m eager to help if I can.


How you can put your boss to work

The key to getting the most out of me is to understand my constraints, because they’re heavy ones. Some things are easy for me to do, some things quite hard. If you can break down what you want in terms of the first, I’ll be doing your bidding in no time.


Here’s a ranking from easy to hard:

The boss’s superpowers are surprisingly modest and heavily time-constrained. Break down asks in terms of what’s easy for him or her to do, and you’ll have a valuable assistant.

The ranking is all about time, because it’s by far my scarcest resource; I can be most helpful with requests I can complete on the spot. A former colleague had refined most of his interactions with his boss down to presenting her a piece of paper to sign; he got a lot of leverage out of her.


Author an email for me to forward, ask for an introduction to someone, ask me to bring up network stability in my next meeting with IT. Spending money is one of the easier things I can do, just present me a thoughtful cost-benefit analysis I can bring to anyone I might need to persuade.


Harder are things that involve diving deep into a topic. Ask me for advice on problems you’re having, just be advised that my answers will be hit-or-miss. On the one hand I’ve been through a lot and have the scar tissue to show for it, so I may have useful perspective. On the other I’ll bias toward quick answers rather than probing for many relevant details first. And bosses feel the need to deliver even off-the-cuff guesses with great confidence, so caveat emptor. Weigh the advice for yourself.


Also difficult are requests that involve a lot of follow-through. Getting people to change how they work is rarely a one-conversation project. Even when it’s a single person it takes a series of interactions. When it’s multiple people it involves negotiations, preparation, kickoffs, training, monitoring, refinements — meetings, meetings, meetings.


“Can management keep us better informed about what’s going on?” is what I call a hairball problem. The problem itself is vague and general. It’s not obvious what might solve it, except that someone would need to get a bunch of busy people to change their work habits. That’s a big ask.


Which is perhaps why “communication” is a perennial complaint in every organization. “We really need an intranet site where everyone can find the information they need.” “Get meetings to start on time.” “We need a culture of accountability.” You can bring me a request like this, and while I might sympathize I’ll be unlikely to find a piece of it I can bite off.


Instead get specific, because it’s always easier to solve a specific problem than a general one. Figure out what would fix a particular instance of a problem, and what who needs to do what to make that happen. If you can break down my participation into chunks that are easy for me to do, I’ll be impressed at your proactivity and delighted to help. In other words, imagine I’m an intern with a short attention span, and you have to break the work down for me into well-defined tasks.


By the way, I can’t alter the fabric of spacetime. That’s a curiously frequent request, usually phrased something like “give us more time to develop a proper test suite.” I’m not the time fairy, time is not my gift to bestow. Business is always a race against the clock.


If there’s a scheduling conversation to have about the test suite, it’s really about degrees of freedom that can move. Perhaps you’re asking me to ask the head of sales to swallow a month delay in getting a product to sell but keep those checks coming in anyway? Bring me a solution I can act on, rather than just a problem, and we can have a more productive conversation.


Speaking of conversation, if you didn’t notice yourself, I don’t speak the same language as you. You’re in the details of spindles and bales. The nouns in my world are projects and schedules and milestones and budgets and headcounts. You can easily baffle me by describing your issue at too fine a level of detail, leaving me without a headline I can understand. The more you can up-level to my vocabulary, the easier our communication will be.

Welcome to Management

Humans are a hierarchical species, and our tendency to pay deference to job titles is anchored deep. We’re hardwired to perceive the boss as more powerful than he really is, so there’s probably no escaping it completely. But you can remind yourself that a good chunk of the power imbalance you perceive is in your own head; you have a great deal of power yourself.


The higher you rise in the ranks, the more important “managing up” becomes, because your boss has less time to dig into your domain. Managing the boss actively is essential once you’re in the executive suite, and it can be a force multiplier to get you there.


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