Novice: Master, what is true wisdom?
Master: Exercising good judgement.
Novice: How do I obtain good judgement?
Master: Through experience.
Novice: How do I obtain experience?
Master: By exercising bad judgement.
In other words, you can squeeze some value after the fact from stupid choices, as long as you learn from them and consign them to the past. The big problem in the nonprofit sector is how often people keep making the same stupid mistakes.
Remember that in taking a job, you're exercising the power of choice. Think of landing a job with a boss from hell as a stupid choice, and try to avoid repeating it.
When you look for a job, screen your potential bosses rigorously. The human resources manager and your potential boss(1) should be looking for signs that you're a good fit for the organization, but you should also be looking for signs that the organization (and more specifically, your future supervisor) is a good fit for you. You should be relentlessly search for someone you won't hate and despise after you take the job.
There's no unerring method for picking out a good boss. However, it's a good idea to make use of opportunities, such as the point in the interview where they ask "do you have any questions?" (If you don't have any questions, especially at a second interview, you're probably past any help that I can give you.)
I can suggest some questions to ask prospective supervisors, but before I do, allow me to point out that the questions themselves are secondary. You'll be using the responses to the questions to gauge two things:
- Whether they are forbearing and responsive enough to entertain questions. (If they aren't, it may mean that they lack the time, patience, or openness that will be needed to get you acclimated to a new job.)
- Whether the nonverbal cues that accompany their substantive responses are worrisome or encouraging. (Remember, you're looking for someone who will set you up to succeed.)
- Can you tell me about the best supervisor you've ever had? What made him (or her) the best?
- Can you tell me about the best subordinate you've ever had? What made him (or her) the best?
- Have you ever supervised someone who was not a good fit for the job? How did you handle it?
- Is it easier for a subordinate to get your permission or your forgiveness?
- What are you highest priorities for your subordinates? How important is it to you that they show up on time every day, that they meet long term goals, or that they follow procedures?
- How would you describe your management style?
- Do you find it easy or difficult to explain your expectations for a project before it starts? How do you handle it if you're disappointed with the results?
- May I meet my potential colleagues in the organization?
- May I see the office or workspace that has been allocated for this position?
- A potential supervisor who hates being asked these questions is probably a loser, even if he mouths reasonable and detailed responses.
- A potential supervisor who doesn't know the answer to certain of these questions is either dangerously unreflective or dangerously inarticulate.
- A potential supervisor whose face lights up as he describes a favorite boss or subordinate is probably a keeper.
- A potential supervisor who takes your questions about his highest priorities seriously, without assuming that you are just probing to see what you can get away with, is a keeper.
- A potential supervisor who wants you to learn as much as possible about your working environment and peers before you make a decision is a keeper.
- A potential supervisor who shows interest in these questions but avoids answering them might be a very good person who is operating under constraints, possibly from the human resources staff. If the HR people block you from unscripted contact with your potential boss or colleagues, don't take a job with that organization.(2)
However, if you're really committed finding a job that's right for you, and to implementing your own personal zero tolerance for @$$holes policy, then you need to take some risks in the interview process. You need to gamble that asking certain types of questions, and paying close attention to the verbal and nonverbal feedback that those questions elicit, will serve your long term goal. Your quest is for satisfying work, reporting to people who support and appreciate your efforts, in an organization that is fulfilling a meaningful mission in a beneficial way.
If you follow these suggestions, you will probably decide against going back for another interview with some organizations that look great on paper but would lock you into a reporting structure with an impossible boss. More importantly, I can guarantee that if you follow my advice, you will fail to make the short list for some jobs that would have made you miserable.
And that will be a A Good Thing(tm).
1) In some organizations, the task of reviewing your resume and interviewing you is in the hands of human service professionals rather than your prospective boss. If you can't stand the HR buffoon, it's not necessarily a red flag, since you may never see him (or her) again once you've settled into your job.
2) The reason that the process is tightly scripted could be that the nonprofit under scrutiny for discriminatory hiring practices, or that someone with a lot of power is micro-managing the process from above. You do well to avoid working under either of these conditions.