On Working for the Wrong Boss

You’ve been living with this for a couple of years. You have a job that’s enviable: a company you like, a leader in its field with a culture you genuinely admire; high compensation, higher than you could readily replace; leadership of the function in which you’ve made your career. But you aren’t sure what to do. It isn’t that your boss is toxic. He’s smart. He’s competent. He’s ethical. He genuinely wants to keep you. But he’s the source of frustration and unhappiness you never thought you’d feel in a job like this.

I don’t want to talk away the magnitude of what you’re feeling. The issue feels serious because you seem consistently diminished. You’re holding yourself back from advancing ideas that you believe would make a difference. You’re feeling at odds with your principles – not in a moral sense, but in the sense of your ability to make things work the way they should. You recognize that there may be a number of areas in which your boss is right, but regardless, you bump up against the places in which he tells you no not as occasions for learning but as places where you’ll never learn what would have happened if you had the latitude to act. It is as though you are living in a smaller world of possibilities, hemmed into a shorter horizon of time than you’re capable of mastering.

There are three paths you can take.

1.  Stay, and transform the situation. Tell yourself you have a year. Write out a description of what better would look like, and commit that if you don’t achieve this improvement within a year that you’ll leave. Better might be a change in your reporting relationship, or a change in the way the reporting relationship works – the decisions you make, the access to top management you have, the way that you and your boss relate. Be specific. Be vivid.

Once you’ve written this description, make it your first priority to achieve this change. Cut corners elsewhere if you need to. Take risks. It’s simply a matter of rationality. You know if you don’t achieve the change that you haven’t been achieving by acting naturally, you’ll have to leave – so turn the dial up much further than is comfortable as you transform or renegotiate the context.

Like with any big goal, evaluate progress often.   Every sixty days, synthesize whether you’re tracking toward achieving the change you described within the year you gave yourself. If you aren’t, ask yourself what’s not working about the approach you’re taking. Try harder or try differently. Don’t fail by inaction or by default.

2.  Stay, and transform yourself. Alternately, decide that – at least for now – the problem isn’t your boss, the problem is how you’re letting him affect you. Perhaps you can’t change him, but you can change the way that you’ve come to feel constrained and diminished. That’s something in your head.

Perhaps a touchstone here could be a passage from Karuna Kayton’s book The Misleading Mind, about Lama Atisha, an Indian Buddhist teacher making the trek to Tibet:

The trip took months to prepare and months to complete, involving hardships we can barely imagine today. Among the party traveling to Tibet was Atisha’s personal cook, who was known as a very difficult person to get along with. And indeed, the Tibetans found him rude, crass and unfriendly. But even worse, the cook’s terrible behavior did not merely extend to the Tibetans, but even to Atisha himself. The Tibetans just could not understand why Lama Atisha would keep such an unsavory person as his cook. Wasn’t travel hard enough?

However, Atisha never showed any sense of intolerance, anger, or embarrassment over his cook’s behavior. Then as now, traveling can sometimes bring out the worst in people, and the Tibetans were impressed that Atisha showed only affection for the cook. Finally, though, they couldn’t stand it, and they asked Atisha why he did not fire the man and send him back to India. Lama Atisha replied, “He is not just my cook; he is my teacher of patience.”

Decide what you’re “hiring your boss” to teach you. Make your priority to learn that lesson from the situation. Prioritize that even above your performance in the job. The performance will come. Your own reorientation toward the situation will be harder and more important.

3.  Make leaving your central project. You’ve stayed this long because your job has so much to recommend it. Finding something better won’t just happen. Treat your search strategically, not tactically. Give yourself a year. Don’t just do the outer work of positioning yourself, building your network to the next level, seeking out situations beyond your comfort zone. Do the inner work as well of asking whether the assumptions you’ve made are really valid. Do you really need to earn what you’ve assumed you do? Does prestige matter in the way you’ve prioritized in the past? Where do you really excel, and might you best fit a job different from the ones you’ve held in the past?Take your emotional energy out of the job you’re in to invest it in your search. When there are trade-offs, ask yourself what will really matter two years from now, when you’re a year into a new job. Anything that won’t matter from that vantage shouldn’t matter to you now. Of course you’ll care from that vantage to look back and feel satisfied that you handled your work and your transition with the utmost professionalism. Deliver that. But disinvest from the everyday of your work, and focus on an image of yourself of someone who is already on the way to being elsewhere.

Whichever choice you make, choose. You can’t steer an easy middle way between these three paths, because they each require you to engage in a very different way with the day-to-day events of work.

  • Along the first path, everything that happens is material from which to fashion the best approach you can to transforming your situation. You need to stretch yourself to make of your circumstances something you’ve never yet made of them. This requires constant, strategic attention.
  • Along the second path, what happens is material for personal reflection and inner work. Why are you reacting as you are? What assumptions do you have? What patterns do you fall into? How can you experiment with feeling and acting differently?
  • Along the third path, what happens is simply to be addressed expediently, delivering on your personal standards in the least demanding way so that you can focus your attention outwards. You want neither to become too absorbed in the strategic possibilities of your current situation, nor too absorbed in your own reactions. Both are distractions from your real work, which is out in the broader world.

If you choose strongly, you can still from time to time step back and either reaffirm your choice or decide to choose differently. Perhaps you take the third choice, but you realize that what you’re seeing on the outside causes you to value what you have in your current role more. You can then decide to work on yourself or to stay and transform your situation. Or perhaps you take the second choice, and as you gain emotional distance from what you’re experiencing, you unlock energy you can use to transform the situation. At any given moment, though, know what you’re after – and bring the best of yourself to that particular path.

There’s every reason to believe that along any of these paths you can address your central problem: that something about this relationship with your boss that has diminished the way you engage with work. Each of these paths is an avenue for growth. Each gives you a chance to take ownership of what matters most. Each requires more from you than you’ve recently felt you knew how to give – which is exactly the standard to which you should hold yourself.


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