Interviewing the Interviewer to Land Your Dream Gig

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A major hurdle to landing a new position is of course acing the interview. And, while the interviewer is often seen as having the upper hand, the interviewee can be just as powerful. As the interviewee, it’s easy to get intimidated. Your inclination is often to sell yourself. You run through an expertly organized list of accomplishments, why you’re interested in the role and how you plan to grow your career. Though an interview is typically seen as means of getting more information out of the candidate, interviewees should really be taking time to do some due diligence of their own.

Job applications and subsequent phone conversations and interviews take time, so you want to be sure you’re heading into a great opportunity ahead of an any in-person meetings. As you’re preparing for an interview, be sure to develop a list of interview questions for the interviewer and specific concerns before your meeting so that when you finally do meet the interviewer in person, you can bring these questions and concerns to the table in a delicate, thoughtful way. Doing so will show the interviewer you’re serious about the role and that you’ve thoroughly evaluated the position.

Here are the top areas to probe and great questions to ask an interviewer so that you can get the most out of your interview:

Asking about the position in question:

  • It’s important to take the temperature of the position to make sure that the role you’re potentially stepping into is not a revolving door and is one which you can leverage to build your skill set.
  • Questions to ask might include:
    • What is the reason for the vacancy at this time?
    • What do you need this person to do in the role?
    • How will this position contribute to the team’s success?
    • What is the growth trajectory for this position?

Understanding the hiring manager:

  • It’s also important to know the person you’ll be reporting to on a regular basis.
  • Some questions might include:
    • What do you feel is the best way to manage your team for maximum output?
    • How will you define success for this position?
    • What main skill sets or traits do you look for when hiring for your team?

Assessing the culture of the startup:

  • Everyone knows that an awesome company culture can turn a good position into a great one. But, avoid cliché questions like, “why do you like working here?” and “what is it like to work here?”
  • Instead, ask these:
    • Why did you decide to come here?
    • What is it about your position that you enjoy most?
    • What are a few common traits across all employees?

Questions to ask at the end of the interview:

  • Your number one priority leaving the interview should be to obtain as much feedback and clarity as possible.
  • Questions to consider may be:
    • How does my skill set match up against what you’re looking for?
    • Do you have any concerns with my background at this stage?
    • What are the next steps and what is your timetable on hiring for this role?

With these tips in mind, you should feel confident and comfortable in any interview setting. Always remember that an interview is a more structured conversation and that you’re learning just as much about the interviewer as they are about you.


Rose O’Connell is a Talent Specialist at OpenView Venture Partners where she partners with OpenView’s portfolio companies to consult on recruitment strategy and to source and hire the top talent they need to scale their teams. Follow her on Twitter @Recruiter_Rose.

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