So you’ve been offered a job. That’s great! But before you accept, ask yourself these key questions. If not, the day will come when you wish you had.
I’ve worked with lots of people who have quit a job and are looking for a new job. When I ask them why they quit, they’ll explain the circumstances. Then time and again they’ll say, “I wish I had thought about that before I ever went to work there!”
Indeed. A great deal of trouble could be avoided in our careers if only we would slow down and think about the job we’re about to step into.
But many job seekers become hopelessly optimistic the moment someone offers them a job or a promotion. They’re like teenagers feeling puppy love. They exaggerate the good parts of the job, perhaps even imagining fantasies about what the job will be like. Meanwhile they overlook or simply ignore the less appealing aspects of the position. Then later, when the job proves disappointing, they moan, “I wish I had thought about that before I went to work there!”
When I work with employers who are hiring, I always remind them: the best and least painful time to fire someone is before you even hire them. The same logic applies to anyone considering a new job: the best and least painful time to quit a job is before you take it.
Here are a baker’s dozen of questions to consider before you sign up for a job:
1. Who will I be reporting to?
The number one people quit their job is because they can’t stand their boss (if you’re a manager, you should pay attention to that). But my question is: did you not explore ahead of time what your relationship with that old boss was going to be like? I’m amazed that people knowingly and apparently willingly step into jobs where they’ll have to work under someone they already know they can’t stand. Why do that?!
The truth, of course, is that relatively few managers are actually “bad” managers or “bad” people. Yeah, there are a few incompetent and/or dysfunctional bosses out there. But in the main, the person you’ll be working for is just like you: they’re trying to do a job and earn a living, and part of their job is to manage you.
So the thing you have to ask is: what is my new boss’s management style? Do they tend to be hands-on or hands-off? Or are they more collaborative and likely to treat you as a peer? How often will they expect to interact with you? What will you be able to expect from them? How do they tend to communicate?
Once you’ve gathered some insights into your prospective boss, ask yourself: how well will I function under this person’s management style?
2. Who are the people I’ll be teaming with?
The people you work alongside will be like your second family. You’re going to spend a lot of time around them. And their work is going to affect your work.
In light of that, you might think the question you should ask is: do I like these people. But that’s actually beside the point. “Liking” your coworkers is nice if you can get it, but from the standpoint of work, it’s a bit of a luxury.
The better question to ask is: what will it be like to interact with these people? Are they competent? Do they take the work seriously? Do they appear to be focused on the task at hand, or are they playing silly games behind the scenes? Do they seem to respect each other? Do they seem to function as a team? If (or more likely when) your job is on the line, can you trust them to be there for you? Can you tell anything about how well they communicate with each other?
Lots more I could say about your prospective coworkers. Just consider whether those people look like they can help you be the best you can be in your work, and vice versa.
3. What’s the essence of this job?
In other words, what’s the main thing the employer and the supervisor will want you to do in this job?
That main thing may or may not be spelled out in the job description. I discovered that once working with a guy who had opened up a restaurant. He was advertising for a marketing director, and he asked me to look over the job description. It was pretty lengthy and wordy, and I thought it was too general. Finally I just asked him, “So what will this person have to do to make you happy?”
Without a moment’s hesitation he shot back, “To put butts in seats! That’s what I want to see. Butts in seats.”
What will you have to do to make your prospective employer and supervisor happy? Until you’ve nailed down the answer to that question, I’d be very hesitant to sign up for the job.
4. What am I actually going to be doing on a day-to-day basis?
I find that lots of people pursue jobs and careers based on perceptions about the work (often gleaned from stereotypes) rather than any firsthand knowledge about the work itself.
The best source on that is someone who actually does (or has done) the job you’re considering. How difficult can it be to buy that person a Starbucks and pick their brain about their experience (that’s called informational interviewing, and you can find out more about that here)? You’ll know pretty quickly how well the job is going to fit you.
To go into a job having no idea what that job will actually entail on a daily basis is just foolish. Shame on you if you end up hating it!
5. How is success measured in this job? And how is it rewarded?
Earlier I encouraged you to figure out what it will take to make your prospective employer and boss happy. This question is similar, except that here you want to put a metric on that success factor.
To use the illustration of the restaurant owner above, he rather crassly stated success as “butts in seats.” That’s fine. If I was interviewing for his marketing position, however I’d ask, “How many butts in seats would you like?”
The obvious answer is, as many as I can find. But it would help to define some realistic expectations for that. Say he’s now got 100 patrons a night, on average, showing up to his restaurant. What is his target? 150 patrons per night? 200? 250? 1,000? Within what timeframe? A month? Six months? A year?
Neither you nor your new boss will ever be able to determine whether you’re succeeding unless you can measure your success.
Now suppose I hire on and knock myself out bringing new patrons into the restaurant, and the owner is thrilled with my performance. Aside from my regular salary and compensation, is there any way my efforts will be recognized or rewarded—for example, through a bonus, or an incentive vacation, or an employee-of-the-year award, or whatever?
Not everyone is motivated by recognition. But probably 65 percent of people are. If you’re one of those people, it seems pretty important to know ahead of time if and how your hard work will be recognized once you’ve signed up for the job. Otherwise, you’re liable to feel slighted and disappointed when you do great work, but it goes unnoticed.
6. What’s the history of this job?
Every job has a story. If it’s a job that’s been around for a long time, lots of people have probably done it. If it’s a brand new job, the story is that whoever is the first to do it—presumably you—will be on a giant learning curve.
What’s the story of the job you’re looking at? Why does it exist? Where did it originate? Who has held it before? What was their history in doing the job? What did the previous holder of this job do well? What did they do poorly? How is this job regarded by others in the organization? By others outside the organization?
Some jobs are plumbs, others are prunes. It almost doesn’t matter who has held the job. The job itself seems either agreeable or odious. Be especially careful about the job for which there’s been a lot of turnover. It’s highly likely that that job is poorly designed, or that the expectations for it are unrealistic.
Some jobs are just snakebit. They end up hurting the person who does the job, no matter how hard or how well they work.
I’m not saying to walk away from a job just because it has a history of being difficult. For some people, taking on a tough assignment and succeeding is exactly the right job for them. But go into it knowing what and who has preceded you.
7. What’s the environment like at this job?
When you take a job, you’re planting yourself in an environment. A plant can survive in various environments, but it only thrives under certain conditions. So ask yourself: what conditions will I be operating under?
I’ll never understand the person who comes home after three weeks at their new job and complains, “I can’t stand the open office environment at work! There’s no privacy.”
Oh, really? Like, you’re just now figuring out that an open office format is not conducive for you to do your best work? What were you thinking when you interviewed for the job and saw that it was going to be in an open office, and yet took the job anyway?
You need to go back and review all of the times in your life when you were doing an activity that you enjoyed doing and feel you did well (if you’d like a formal exercise for doing that, click here). Pay particular attention to the environmental conditions or circumstances in which you were doing those preferred activities.
Were you outdoors or indoors, or did that matter? Was there a lot of structure, or lots of freedom and flexibility? Were you on your own or teamed up with others? Was there a need or a problem to solve? Were you working on a project with a defined outcome? Were there hard-target goals, or was it more open-ended and visionary? Was there a challenge you were trying to meet? Was there competition? Was it about making money, or some other objective?
Your motivation will only thrive under certain conditions. Indeed, certain conditions are often vital to a person’s functioning. In the absence of those conditions, the person’s motivation will start to whither. It may ultimately die out altogether.
So ask yourself: will this particular workplace environment provide the circumstances I need to thrive in my work?
8. What’s the culture of the organization?
Culture has to do with the values, language, and tribal customs that a group of people share. In simple terms, culture is “how things are around here.”
One reason people get into trouble when they accept a new job is that they’ve never been outside the culture they are most familiar with. It’s what happened to me when I moved from Dallas to Boston in 1972 to attend college (sight unseen, sad to say). Who knew that Boston in late September would be 45 degrees cooler than Dallas? Or that “regular” coffee means coffee with cream and sugar already added? Or that people don’t ask how you’re doing? Needless to say, I went through culture shock.
A lot of people go through culture shock when they take a new position. Suddenly they get hit with new values that govern how things operate, and a whole new language and different ways of communicating. That’s especially true if they change sectors of the economy, such as moving from the for-profit world to nonprofit work.
Whole books have been written about corporate culture. My counsel is to use informational interviews (see #4 above) and site visits to learn as much as you can about your prospective organization’s culture before you accept a position there. You want to know the relative match or mis-match between your own values and workstyle and those of the organization you will be joining.
9. What is the dysfunction of this organization?
The assumption behind this question is that all organizations have dysfunction. If you find one that doesn’t, don’t join it, or you’ll end up making it dysfunctional.
Dysfunction can range from operations and communications that are merely ineffective to those that are downright pathological. For example, the organization where every decision has to go through someone at the top. Or the organization that spends most of its time in crisis mode. Or the organization that uses newer, younger people to do all the heavy lifting, while the old-timers sit back and enjoy the lion’s share of the profits. Or the organization that once had greatness, but is now resting on its laurels and watching the value of its brand dissipate.
A special case is the entrepreneurial organization. If you go to work for an entrepreneur, realize ahead of time that the venture is an extension of that entrepreneur. So whatever the entrepreneur’s dysfunctions are will manifest themselves through his/her organization and its culture.
I can’t tell you to walk away from a dysfunctional organization, or else you could never work for anybody—even yourself! But to be forewarned is to be forearmed. If you have a sense for how your prospective employer fails to handle communication, conflicts, and workflow effectively, you can at least calibrate your expectations—and also think about ways in which you can perhaps introduce healthier practices to the venture.
10. When I walk around this organization, what do I see?
This question is similar to the earlier question about the environment (#7). But the idea here is to let your subjective impressions have free reign. When you walk into the place where you would be working, how does it feel? What do you notice? What do you see people doing? What’s the atmosphere? What does the place look like? What strikes you the most about the place and space and what’s going on there?
Then having gathered up all those impressions, ask yourself: is this a picture that appeals to me?
When I sent in the paperwork to attend college, they asked me if I had a dorm preference. I checked a box that said no. Big mistake! If I had bothered to visit the school ahead of time, I would have discovered that some rooms were air-conditioned and others weren’t. Coming from Texas, it was a huge problem for me to start out living in a dorm room on a busy street with no air conditioning!
Unfortunately, many people do a similar thing with their jobs. They ignore the simple details that end up making a huge difference in their satisfaction at work (let alone their satisfaction with their work). It could be the paint on the walls. The lighting. The heat. The quiet. The way the cafeteria or snack area looks. The parking. The commute. Even the coffee.
Again some people are more adaptable than others, and some people are more sensitive to their surroundings than others. Just pay attention to what your sensitivities are. You’re going to spend a lot of time at work. You might as well make it a place you can see yourself working in.
11. How do my spouse and family feel about this job and this employer?
They use canaries to tell if the air in a mineshaft is going bad. Well, oftentimes your spouse and family are your canaries telling you that a job is not for you. No, they’re not infallible. But simply as a point of personal responsibility, you owe it to them to listen carefully to their opinion of a job before you sign up for it. After all, they’re going to be affected by how that job affects you. They’re the ones who will have to put up with your moods and complaints and stress level if the job turns out to be a poor fit.
I’ve known employers who insist that their spouse meet a candidate they are thinking of hiring into a key position. If the spouse ends up having concerns, the person doesn’t get hired. Period. Is that fair? I don’t know, but those employers swear by that method.
Well, I guess the same thing could apply in reverse—a spouse and family having veto power over a job you’re considering. Yes, conceivably they might cause you to end up walking away from a good deal. But if they have your best interests at heart, I suspect that more often than not they will prove to be a good sounding board for you, and will see things in a prospective job that may not have occurred to you.
12. What’s the “trajectory” for this job?
In other words, where does it go? What does it lead to? What’s your future if you do well in it?
One of the greatest mistakes people make when accepting a new position is that they only look at the job in front of them, and don’t consider how that job fits into a vision for their life. (Oftentimes that’s because they don’t have a vision for their life. Big mistake!) Every job you have in your career should fit into a bigger picture of where your life is headed. I’m not saying to simply use a job as a stepping stone. No, take the job and acquit yourself well in it. Do good work. Add value.
But where will your hard work in that job take you? Is there a ladder for you to move up? Is there a natural progression, that if you do this job well, you’re likely to position yourself for greater responsibility or new opportunities or a bigger and more interesting challenge?
That sighing sound you hear in the elevator every Monday morning is, in part, the sound of people's motivational wheels spinning like tires stuck in the mud. Of people who are going nowhere. They’re just marking time in a job that lost its motivational appeal long ago. But it's because they have no vision for their life. They’re working and getting paid. But it’s “just a job.”
You can avoid that by reflecting on how the job you’re considering fits into the larger journey of your life.
13. Why am I taking this job?
Notice that the emphasis here is not on the “why,” but on “this job.” Why this particular job?
A common answer is: “Because this is the only job I’ve been offered.” Fair enough. But if that’s actually the answer, is that a compelling enough reason to take the job? If so, that feels a lot like settling, to me.
I know full well that job-seekers can quickly become desperate people. (That’s one of the reasons why you should never, ever undertake a job search on your own, by yourself, as a solo activity.) But desperation is a thief. It can trick you into making rash decisions that get a steady paycheck going again, but inflict a heavy opportunity cost tied to the road not taken.
But whether or not you’re desperate as a job-seeker, the question remains: why this particular job? The idea here is that just as you’re going to work at a job, you want the job to work for you. That is, you want your job to matter, to have a point to it, to express something of who you are. You’re going to try and put the best of your efforts into your work (you are, that is, if indeed the job fits you; if it doesn't, you motivation and energy will plummet).
So the question to ask ahead of time is: will this job allow me to do that? Is this job a good fit with who I am, and what I have to offer, and how I add value, and what matters to me? Is it worthy of me devoting even a day of this brief life I’ve been given?
13a. Let me put it this way. . .
If you just take a job, any old job, and don’t think it through ahead of time, it’s almost certain that sooner or later you’re going to leave that job dissatisfied. If you then come see me, I’m probably going to ask you why you quit. And you’ll give me the reason. And after you do you’ll probably sigh, “I wish I had thought about that before I ever went to work there!”
Now I’m going to commiserate with you and then try to help you find and follow a path that works for you. But as you can see, I’d rather we were able to avoid that conversation altogether!
Question: If you’ve ever disliked a job so much that you quit, what is it that you wished you had thought about before you took that job?
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