An Important Question To Ask Yourself About Your Career

You might call it the secret question that can reveal your career’s fortune.

If you have ambition and a desire to get ahead, you’ll wonder, daydream, and poke around for ways to progress in your profession.  You’ve probably skimmed the management books at the airport book carousel, swapped tips with buddies over beer or a Bloody Mary, and surreptitiously taken a few mental notes when one of those self-help gurus shows up on TV.  All in the pursuit of a better life for yourself and your family.

So here’s an easy one.  Ask yourself “how’s my boss doing?”

It’s an amazingly simple, but deceptively effective, way for you to think about your own career. I’ve found that your answer to this question says far more about your prospects for advancement and promotion than any other question you could answer.


It shows where your values are.

If you answer the question “how’s my boss doing?” with disgust — a flash distaste for the moral comprises, bad choices, and questionable corner-cutting occurring on your boss’ watch — then you’ve also answered a far more important question:

“Is it time for me to go?”

Because if you’re morally unhappy and disgusted with your boss, nothing can make it right.  You can’t change him, you can’t save her, you won’t be the vehicle of their redemption. You can only leave.

If you are disgusted, your employment is coming to an end. You won’t thrive in an environment where your revulsion is necessarily (and thankfully) holding you back.  It only remains to be determined whether you’ll leave at a time of your choosing, or your boss’ choosing. (Let us hope it is not at a time of the legal authorities’ choosing.)

It’s a very useful indicator of your own performance.

Excepting moral deficiencies, answering “how’s your boss doing?” is mostly a way to answer “how are you doing?”

You see, you probably can’t know how well you’re doing at your own job, because it’s impossible to be the star and the critic of the same show.  You can’t be objective about yourself.

Now the customary answers to “how’s your boss doing?” fall into three buckets: an adequate “OK / pretty good”, an enthusiastic “amazing / fantastic”, or an eye-rolling, huffing, heavy-sighing exasperation that says “not well at all”.

“OK / pretty good”, the most common response, indicates satisfaction on both sides: you’re doing your job, they’re doing theirs, and you’re all on the middling path that avoids the drama of recriminations or delight of rewards.

“Fantastic” is that happy place where your respect and admiration for your boss is a reflection of his approval of you.  You’ve done well, you’re getting positive feedback, and resources are flowing your way as a result.  When others recognise the good within us, it is remarkable how often we return the favour. Conversely, I’ve never experienced a professional giving this happy answer when their own performance is being called into question.

“Not at all well”, on the other hand, typically doesn’t mean what you think it means — that your dire old boss is performing poorly.  Rather, it’s usually a good sign that it is your stuff that isn’t up to snuff.

In my decade of advising job-changing professionals, a negative assessment of your boss, unless sweepingly shared by your peers (and at least some of his or her peers), is a reflection of the poor quality of your relationship with your boss as a result of tensions about  the quality or quantity of your work. And those negative emotions colour everything you see in your superior’s endeavours.

Now, before the flame comments begin licking at the heels of this post below, let me say: I know from bad bosses.  Heck, one of my first employers cracked a new bottle of Chivas Regal at 11:30 every morning: the days weren’t productive, but the ping pong games got easier to win as the afternoon dragged on.  So I know whereof I speak with regards to bosses that are creeps.

But if it’s not a moral issue, and you’re one of the very few in your group disparaging your leader’s performance, your unfavorable answer might mean it’s time to review yourself.

It’s your job.

In modern corporate organisations, your job is to make your boss successful. It’s not to figure out what the CEO is doing wrong, how the guys in the other division could be doing their job better, or where the gals on the company’s Board are missing an opportunity on strategy.  Your job is to make your group, your team, your part of the company, successful.  And the only way to do that effectively and reliably is to make your boss successful.

So if your boss isn’t doing well, that means your group isn’t doing well, and that means that you are not doing well.

That’s why one of the most effective questions you can ask is “How do I help you get a gold star on your review next year?”  It shows both a professional understanding of your job’s goals and a personal empathy that displays an ability to look beyond yourself.

You might think that sussing out where you stand compared to your peers is key to getting ahead.  You might fret over whether Heather, Robert, or Ravi, are getting a leg up on you. Or you could be nervously watching to see if your report gets picked up by the right people at the planning meeting and recognised for the excellent work that it is. Relatively speaking, these just don’t matter.

Your organisation’s best and most reliable source of information about you is your boss.  As the company is assessing your abilities, making room for you in the org chart, or allocating a few plum assignments, the best insights they’ll receive will come from your boss. Peer reviews, 360s, subjective comparisons, and quantitative results can play a part, but your immediate supervisor’s interpretation of that material is predominant.  Your boss’ push forward or pull back is determinative.

So if you’re looking to make the most out of your present role, and build a better future for yourself, I’ve found that for most people, in most careers, in most industries, answering the question “how’s my boss doing?” is the best way for you to get ahead.

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