I Score Low on Manageability; Bosses Love Me Anyway

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Relationships with bosses are the stuff of legend. Everyone has a story of a boss’ behavior that positively boggles the mind. Or a tale of a relationship with a boss that was an unextinguishable dumpster fire.

But for me, such stories have been few and far between. (Thankfully! Whew!!) In fact, in my career, the vast majority of my relationships with bosses have been terrific. That includes bosses of all different styles, strengths, weaknesses, preferences, and idiosyncrasies.

And I’m not a prototype perfect employee. I’m opinionated, I have no poker face, my energy is spazzy, I get bored easily, and I lack any semblance of patience. Evidence-based personality assessments show me to be far below average when it comes to “manageability” and quite above average when it comes to being “enterprising.” I like going my own way, which means the boss has their hands full.

Yet many of my former bosses would count me among their favorite staffers. It’s not because I’m a swell guy (though certainly I am!). It’s because, I’ve picked up and practiced some habits that tend to make bosses really love having me around.

Those habits are second nature for me today, so at times I fall into the trap of thinking they are easy and obvious. Yet I observe smart, dedicated people who don’t practice them and thus are stuck in a rut with their boss. This article is my effort to help.

Pursue these habits if you want to be a go-to, valued member of your boss’ team.

Do what you say, when you say, no exceptions. This one seems obvious, but it’s an area of struggle for no shortage of hardworking people. It can plague conscientious managers who are inclined to overextend themselves just as easily as it can plague individuals who struggle with basic accountability. If you take on a task or accept an assignment from the boss, do it. Do it by the date they want, or deliver it early. But never late. Don’t make your boss remind you to do it. And don’t assume your boss has forgotten just because they don’t mention it for awhile. Don’t commit to a task if you’re not completely confident you can do it. Be assertive and firm on that, which takes practice. But once you commit to something, get it done.

Impression you’ll make on the boss: “This person really produces. When the going gets tough, I want them in my corner.”

Map status updates to your boss’ preference. Don’t ever put your boss in the position to ask, “What is the status of that project / assignment / task?” If you hear that question, you’re not keeping them as apprised as they want. That’s stressful for your boss, and it sends a signal that you don’t know the basics of keeping key stakeholders informed and involved. When you accept an assignment, ask, “How often and in what way would you like to receive status updates on this task?” Do exactly what they tell you.

Impression you’ll makes on the boss: “I love that I don’t need to wonder what this person is up to or if what I asked for will actually show up.”

Be proactive when the news is bad. If you are likely to miss a deadline, if you’ve dropped a ball, or if you just made a whopping $250K mistake, tell your boss proactively and quickly. Don’t let them hear it from someone else. Don’t make them discover it for themselves. It stinks to admit that you can’t get something done, or that you screwed up. But it doesn’t stink as badly as your your boss finding out and then wondering if you’re trying to hide it. Be honest and transparent, even — especially — when the news is bad.

Impression you’ll makes on the boss: “I wish everyone were confident enough to be honest with me like this person is.”

Adhere to the 70–80–90 rule. Decades ago, my boss Susan Mirvis (who I affectionately called “SuSu”) tried to convince me to stop going to the mat in defense of every single opinion I had. She said, “The fact is, you’re right somewhere around 70% of the time [which, in retrospect, was comedically generous]. I’m right 80% of the time. And Jeff [who was her boss] is right 90% of the time. So, maybe you could knock it off.” By and by I got it, and I came to think of her advice as the 70–80–90 rule. Even as an executive leader, if I disagree with the president or the CEO, I make my opinions known. But in the end, I accept that the boss is more likely right more of the time.

So, say your piece to your boss. But when the decision is made, cease nurturing and stroking your opinions and simply start executing.

Thanks, SuSu! May you rest in peace.

Impression you’ll make on the boss: “This person will speak their mind, which I like. But in the end, thankfully, they help me by just shutting up and doing what needs to be done.”

Prioritize making your boss successful. I asked my friend Chris Goudeseune, the senior director of strategy & projects at the American Council on Exercise, to tell me his secret for cultivating a great relationship with the boss. It’s something Chris has a knack for. He said, “The trick is to be relentlessly inquisitive about my boss’ pain points. I ask them probing questions about their concerns and priorities, trying to get to what they most want to achieve. I acknowledge what I hear, commit to help, and take action. And then I repeat the whole process.” Practice Chris’ rule. Mine for your boss’ most fundamental priorities. Then as much as you can, focus your effort there.

Impression you’ll makes on the boss: “This person gets it at a level that most others don’t. Their career is definitely going going places.”

Don’t, under any circumstances, get defensive. This was the hardest of these habits for me to reliably adopt. But it was sorely needed. It’s quite possible that nothing annoys your boss more than your defensiveness. They don’t want to hear you reexplain, for the third time, why you did that thing they’re not wild about. You won’t convince them of anything, certainly not while you’re in fight-or-flight mode.

When under pressure from the boss, keep it cool and focus any responses on the future. Accept their feedback without caveat. Simply respond, “I’m clear. Thank you.” Then ask questions like, “What would you like me to do next?” Or, “What do you think I should do differently next time?” And be open to what they say.

Impression you’ll makes on the boss: “I’m so glad I don’t have to walk on eggshells with this person. They are secure enough to handle the truth. So, the truth they will get.”

…

If your boss is the rare one boss is a complete and total jerk, putting these habits in place will help, to a degree. But probably only to a degree. Or they won’t, which is a subject for another day. Know that I feel for you.

But chances are your boss is like most — a decent but imperfect human who is doing the best they can. If that’s the case, you practicing these habits can make all the difference.

This article was originally published in The Innovation on Medium.