You want to get to know your interviewee by asking questions such as the following:
- How did you get involved in this job, organization, or industry?
- What do you like most about it? What has been most rewarding?
- What is most challenging? Was there anything that surprised you?
- What is a typical day, week, or month?
- What skills are most critical to have, develop, and maintain to be successful?
- What personality types are most successful?
- What do you know now that you wished you knew when you started?
Interest in their specific background establishes rapport because it shows you care about them specifically. It also gives you a foundation for questions to ask later because you know more about their experience.
You want to get broader information about the industry, so you ask questions that reflect your research:
- According to my research, the top competitors are [name the competitors]. Am I missing anyone you think is significant? Is there a new player I should know about?
- According to my research, [name a trend, challenge, or innovation] is a major trend, challenge, or innovation. Is this affecting your job or organization? Is this overestimated in the media? Are there are other trends, challenges, or innovations I should be concerned about?
This is why research prior to the informational interview is so critical. You use your research findings as a springboard for conversation. You are not relying on the interviewee to think of everything and be the sole source of information. You are offering ideas, too. Informational interviews also enable you to dive deeper into what you previously researched.
Pick several research findings to test, and choose what to ask based on what level and type of experience your interviewee has. If your interviewee is very experienced and senior, you can ask broad strategy questions. If your interviewee is focused on a very specific area, say technology, focus on technology related issues in the discussion.
You want to get career-related information, such as salary and environment, and a candid sense of your chances in this job, organization, or industry:
- According to my research, it is customary for people in this job to make [name salary range] and experience [name lifestyle, travel, or work culture]. Is that accurate? Are there any nuances to this that are not publicized in general media?
- According to my research, the typical career trajectory is [name different titles you have seen for the job]. Is this accurate? Does this differ by company?
- How would you describe the culture of your organization? Does this vary greatly for companies in the industry?
- According to my research, it is customary for people in this job to have [name skills and experiences]. Is my background of [summarize your skills and experience] competitive? If you knew of an opening for this type of job, would you consider me or refer me?
- What about my background is most relevant to this job? What would I need to do to improve my chances?
These questions enable you to get information on the touchy issues of compensation and lifestyle, as well as candid feedback on your hiring prospects. By offering ideas, you take the pressure off the interviewee to reveal sensitive information. Instead, you give them something to react to. People will also appreciate that you have done some salary research, as they might not have time to see what is happening in the market, and they will want to reciprocate by sharing something they know.
Asking about the competitiveness of your skills and experience is not the same as asking for a specific job.
You should never ask for a job in an informational interview. It is disingenuous because you asked for a meeting to focus on gathering information, not to ask for a job.
In the previous example, you are asking for candid feedback about your job potential. You will not get candid feedback from recruiters or prospective employers during an actual job interview. Recruiters and prospective employers will be concerned about being too critical too soon, angering the candidate, and having the candidate bad-mouth the organization or even sue. Since you will not get explicit feedback during the interview process, try to get that feedback in an informational interview. Asking if your informational interviewee would consider hiring or referring you is much more direct than just asking if your background is good. The measure that matters is whether you are competitive for an open job.
Asking for job potential is still, however, not as presumptuous as asking for a job outright.
For people from a specific organization, you want to fill in your organizational chart with answers to the following questions:
- What department are you in (i.e., the specific name if it’s not revealed in their introduction or on their business card)?
- Who oversees this department?
- How does it fit in with the rest of the organization?
- Is this structure typical, or are your competitors organized differently?
- I am doing research on [name another organization] and trying to find who runs the [name department you want]. Do you know anyone there whom I could ask?
If you are trying to fill out spaces in your organizational chart, you should ask these questions if your interviewee would likely know the answers. If your interviewee is very junior or works in a department with little other contact, he or she may not know, so don’t take it personally if they don’t share any information. You should also ask about other organizations because sometimes insiders do know their competitors. You also might get referrals to additional potential informational interviews.
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