Why you should pick your own boss

Ty Clark asked me for advice on job seeking: The best advice I’ve ever heard about picking a job is to pick your boss first, not the job.

This is challenging since the system of finding jobs is designed the other way: it’s set up to let bosses pick you. Job ads don’t have a field listing a “Boss Suckiness Index (BSI)” or “what % of her reports love or hate her.” At best you talk to your possible boss during an interview, and interviews are mostly BS. Yet by focusing on who your boss will be above most other criteria changes both how you pursue jobs and how happy you’ll be once you pick one.

The simple reasons why your boss matters more than you realize are:

  • A good boss in a mediocre company will protect you and support you on a daily basis.
  • A bad boss in a good company will frustrate and demoralize you on a daily basis.

In the first case, you will learn more and possibly have more opportunities than in the latter. A good boss will recognize your talents and develop them. A bad boss may never recognize what you can do at all, or take advantage of you more than help you. The only upside to a bad boss in a good company is if working for them is the only way into the company after a year you can possibly transfer to a different team, with a different boss, and achieve the best of both worlds (assuming you survive that long).

Most people looking for jobs focus on other criteria such as:

  • Salary. This is important, but beyond your minimum needs it can be a trap. There are many people with $250k salaries who hate their jobs and, as a consequence, their lives. They work with coworkers who were also primarily attracted to salary. If you are thinking long term, or want a high growth career, salary can’t be your primary criteria. Salary is the laziest measure of the quality of a job and therefore the weakest.
  • What you will work on. Many people are attracted to specific projects or roles. I did this for years until I learned hot projects didn’t necessarily make for happy/productive work environments. While I learned much, my career suffered. I watched plenty of people thinking longer term who stayed with good managers rather than chasing cool projects, and they rose in seniority in the company as their managers did.  
  • What your job title will be. Even if you have to work as an intern, if you are talented and work hard a good boss will recognize your ability and move you into a position worthy of your skills. Even if they don’t have another job opening for you, a good boss will have a healthy network and can help place you somewhere that does, with a good manager they know who works there. Chasing the best job title you can get at the expense of who you’ll be working for is a trap: they may never let you leave that job title, no matter how much you outgrow it.

Picking bosses demands having a strong network. You need to cultivate friendships with people in your field where you can share notes on the bosses you’ve worked for. It takes time and research to put it together, but knowing who in your field the good managers are and seeking them out is the best asset you can have for a long and healthy career. If you have one or two companies in mind, investigate who the best bosses are in your job function so you know the landscape, and if the opportunity presents itself, which way to lean if an opportunity arises.

The less experience you have, the harder it is to pick your own boss when you’re hired. That’s ok. Instead ask about how much internal mobility there is: do people move between teams and groups easily? If yes, once hired your goal should be to figure out what things you need to set in motion to give you that choice and to study who is the best boss there for you.

Related: How to survive a bad manager

25 Responses to “Why you should pick your own boss”

  1. Phil Simon

    Nice post, Scott. I find the also true: never take a job with a “good” company if you knew in advance that your boss and you wouldn’t be simpatico. About ten years ago, I spoke to a recruiter at a big company. I soon found out that I’d be reporting to a knucklehead with whom I had worked before. I immediately declined to proceed.

  2. Michael Hafner

    Basically, I agree – but seen from another view, this is also kind of a recommendation to stay quite passive. but that just is one of the dark sides of being employed…

    1. Scott

      How passive this makes you depends on what qualities you seek in a boss. It’s possible to find ones who want you to be agressive and take risks.

      As I said, shopping for bosses depends on your network and if your network isn’t very good going out on your own may be the only way to achieve what you want.

  3. Thomas Duff

    Having just ended a year-long situation with a not-wonderful boss-like person, I can completely agree with you. The replacement should be 180 degrees opposite, and it’s already having a beneficial effect on the group.

  4. Ravi Warrier

    Completely agree. Though, the bigger question is how to select a good boss? Here’s my two cents (or paise, since I come from India :)).

    1. Ask to meet the reports: Most people don’t know they have this option. You can request the interviewer to meet members of the team and you can give a partial reason: to understand the organization’s work culture and job profile better (leaving out, “asking how good/bad you are?”).

    If your would-be boss is interviewing you and you are intimidated, then ask the HR during the HR round to meet with the boss’ team. This time, don’t mention the work-culture if the HR sounds insecure.

    There are no fixed set of questions to ask the team members. I have observed that most people display tells when spoken about their own career path in the team/organization – like how many times they got promoted or got a raise?

    Another line of questioning is asking about innovations from the team – a poor boss will usually avoid changes and disruptions, and hence discourage innovative and creative thinking withing the group.

    One more area of discontent with bosses is when it comes to cross-team collaborations. A bad boss will not have the right rapport with other teams’ bosses thereby leading to high levels of bureaucracy. Ask team members how easy is it working with cross-functional or cross-location people and you’ll get to know a bit about the strings that connect them.

    If you are already in the organization:

    2. I have always (since I took my first job at 17) had a principle: If I can no longer learn from the organization or the boss, I quit.

    If you feel, your boss has taught you everything s/he can, then leave. There is nothing much left in the job for you. And if he’s stagnant, chances are he’ll stagnate you.

  5. A Reader

    Great post, quite accurate in my experience. The only thing I wish to add is that sometimes, probably more often than not, you need to have perspective to truly appreciate the difference between a good and a bad boss and, more importantly, how to spot them.

    Example: I helped my nightmare of a boss interview people for years and watched her repeatedly do a terrible job at screening candidates. Upshot? Anyone that interviews me remotely like she did, I walk out and don’t even waste another minute of my time.

    One more gem, mainly to do with internal moves: I once saw a presentation where the author said something along the lines of: when the weather changes, don’t wait. Leave and be in the first wave of folks that do so, because the best talent always leaves first, on their own terms, not when the shit hits the fan. The reason you’re moving on will be self evident. If you leave when all hell breaks loose, you’re just another rat leaving the sinking ship. Which would you rather be viewed as by other people in the company?

    Had I done these things earlier in my career, I’d be miles ahead of where I am now. Bad leadership can cost you your job and even your entire career, to say nothing of the years taken off your life. As is sometimes paraphrased about good looking, single women; sometimes when people are hiring, it’s only because someone finally had enough of their shit and left. Buyer beware.

  6. Riccardo Bua (@RiccardoBua)

    True words, hard to achieve in reality as it assumes the boss will stay there forever, in my job environment most of the time manager roles are changing within max 3 years and often lot less than that…

    Hence picking a boss might be not the smartest move if you lose him/her within few months…

  7. echo

    I quite agree with your point.

  8. Susan

    This article is spot on. I wish I didn’t know from experience.



Leave a Reply

* Required