Top 10 Questions to ask an interviewer

What does success look like in this position and how do you measure it?

The following is an excerpt from the Nation Best-Selling book: iQUIT – HOW THE WORLD OF WORK IS CHANGING FOREVER AND WHAT IT MEANS FOR YOU – Available today on

All jobs exist for a reason and those reasons ultimately must be measured in order to support and justify their existence. Many people will know, even before an interview process begins, what the compensation is for a position. But what you also need to know, for many reasons including job security, is how you will be measured on your work, and exactly how your work will be deemed successful. The old saying, “You cannot manage what you cannot measure” applies to everything in business, including your job, and the bigger the organization you’re interviewing with, the more important this can be for you.

Larger organizations also have a tendency to create and acquire so many positions over time that they will sometimes hire outside consultants like McKinsey and others to come in and help reduce redundancies, increase efficiencies, and commonly cut overhead. If you’ve ever watched the movie Office Space, you may remember the scene where the consultants, referred to as the Bobs, came in and interviewed each employee, including Tom Smykowski, asking things like, “What would you say you do here?” only to have the employee try to explain and even fight to justify their job. It is also not uncommon to see this happen within organizations who are struggling to grow and/or looking to sell their business and need ways to artificially boost their stock price while reducing their overhead, innovation, and costs—frequently resulting in the rapid downsizing of their workforce. This process is referred to as “carving the pumpkin” because hidden within the veneer of what appears to be a shiny pumpkin (organization) is a hollow shell that, if not quickly sold or acquired, will eventually collapse in on itself. And like all carved pumpkins after Halloween that have no more future value, will eventually get discarded.

So, make sure to ask this question and drill down into the responses if they are not initially clear to you. The last thing you want is to eventually find yourself sitting in front of “the Bobs” having to justify your job when the people hiring you should have done that for you in the first place. And by knowing in advance what success looks like in this role, you should be able to better see the contributed value you can provide and your potential future while working there.


Question #1: Who would I be reporting to and how would you describe their management style?

Question #2: Why is this position now open?

Question #3: What was the growth rate of the business last year?

Question #4: What would people tell me are the top three benefits and top three challenges in this job?

Question #5: If I perform my job well, what are my potential career paths from here?

Question #6: Who is the leader of this business and how would people describe their leadership style?

Question #7: How would you describe the culture of this business and what do people like most about working here?

Question #8: What are the top three reasons previous employees have provided when leaving your organization?


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