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One of the best ways to distinguish yourself among other job applicants is to ask thoughtful, targeted questions during your interview, both in response to questions asked of you during the interview and at the end of the interview, when most applicants are asked if they have any questions to ask of the interviewer or interviewing panel.

Assume you may go through at least a couple of interviews, and use each one to ask questions that will give you additional insight not only into the job itself, but also into your potential boss’s management style and the company’s or department’s culture.

First interview questions – getting the lay of the land

If it’s your first interview, you’ll probably want to ask basic questions about the organization, doing so in such a way that indicates you’ve already gained a good understanding of the employer and its industry (including libraries). For example, “My research indicates that [company] is known for outstanding customer support. Are there ways in which this job supports that effort?” Other questions might include:

  • Is this a recently-created position or one that’s been part of the organization for awhile? (A recently-created position, that is, one that the candidate is going to be creating if hired, can either be a terrific opportunity to shape a new role and tailor it to your strengths to a degree, or a disaster waiting to happen. If it’s a recently-created position find out as much as you can about why the position was created, whose idea it was, and what problems it’s intended to solve. Your goal is to avoid signing on for a “set up to fail” position that lacks the internal political support to succeed.)
  • How would you describe a typical day/week in this position? Is the work flow fairly steady, or are there times of the year when things ramp up considerably? (This may impact whether or not a job is going to work with your life circumstances.)
  • Does this position collaborate with other departments, and if so which departments? What are their mutual goals? (Smart organizations have strategic goals that involve cross-departmental collaboration. This question will help surface that information.)
  • How long did the previous person in this job have the position? How long, in general, have people been in the position? (A high rate of turnover for a specific job indicates serious personnel problems, whether with a boss, subordinates, or the organizational culture in general.)
  • How long did the previous person work with the existing team? (This will give you a better understanding of the team dynamics you’ll be inheriting if you’re applying for a management job.)
  • How would you describe the organization culture at [organization]? If the interviewer’s answer to this question is too vague, you can be more specific in your question, for example, what type of individual fits in best here? What type of individual wouldn’t be a good fit? What strengths are most in demand, in this department as well as within the company overall? (This will help you determine just how well your own strengths align with the organization’s priorities.)

Depending on the size of the employer and its hiring procedures, it’s possible (if not probable) that your initial interview will be with an HR person, rather than the person who’ll eventually be your boss.

In that case, that HR person is likely to be able to answer this first round of general questions, whereas you’ll may find that your more specific questions about management style, communication preferences, and success measurements are best answered by the person who you’d be reporting to should you get the job. We’ll take a look at those “second interview” questions next!

Second interview questions to seal the deal (or avoid a train wreck)

Once you’ve made it to a second interview, both you and the potential employer have signaled a serious interest in each other. Now’s the time to come armed with a set of questions that demonstrate your seriousness, interest in the company as well as the job, and commitment to begin delivering value from day one.

The following questions, intended for your potential boss, will demonstrate both enthusiasm for the position and a realistic sense of its potential challenges.

  • What characteristics or actions do you personally feel are critical for success in this position? Every job posting lists many required skills, but what you want to get to with this question is what your potential boss values as his/her highest priority for the job. For example, if the answer is “collaboration skills,” that signals a much different working environment (and set of expectations) than if the answer were “delivers reports progress to me every day.” Neither is necessarily good or bad, but one response may be a better fit for you than another.
  •  What do you feel are the key challenges in this position? Although the actual challenges you face may turn out to be quite different than the ones a potential boss mentions, knowing his or her perspective gives you a heads-up about what they’ll be concerned about, as well as greater insight into whether these are the kinds of challenges you want or feel competent to take on.
  • What could I accomplish in my first year that would most help the department/company? You want to indicate that you are committed to successfully performing your role at the departmental level, but also want to be cognizant of the larger benefit of your work to the organization. In addition, this question makes it clear that you’re interested in – and responsive to – your potential boss’s leadership and priorities.
  • How do you most prefer to work with your staff? Bosses have (as you know) widely differing management styles, which you’ll need to understand and conform to. For example, do they like daily verbal/written status updates or prefer to just stop by your cubicle now and then for a chat? Do they prefer you exercise your professional judgment when handling tasks they’ve delegated to you, or do they want to be consulted before decisions are made? How and when do they provide feedback? Some bosses only provide feedback in an annual performance review, others prefer to “coach in the moment,” and provide feedback on an ongoing basis. Understanding a boss’s management style will help you understand if you can happily work with that person.
  • What do you most like about working here? If your potential boss can’t come up with any reasons the company is a great place to work, you may want to reconsider the job opportunity. A toxic, unhappy, or bitter boss is almost a guarantee of a miserable workplace. On the other hand, a boss with a positive outlook about the company and his/her work can help create a positive, collaborative, and effective team.
  • Are there any skills you feel I’d need to strengthen to be as successful as possible in this position? This question gives your interviewer the opportunity to mention any reservations he/she might have about your ability to do the job, and also provides you an opportunity to address those reservations. This may mean pointing out additional aspects of your professional background that address a key “gap,” or acknowledging the gap and stating that you’re excited to master that skill (and willing to put in time on your own to do so). Or, it may surface information that leads you to conclude that you simply wouldn’t be happy in the position.

In a first interview, you’re generally asking and answering questions that relate to the alignment of your professional skills with the job requirements, as well as your comfort with the organization as a potential employer. As you progress through a second interview, however, your goal is more about determining whether the person to whom you’ll be reporting is someone you can work with effectively and successfully.

Asking thoughtful questions will help position you as an engaged, smart candidate; listening thoughtfully to the answers can help you determine whether to hop on board or avoid a potential career train wreck.