3 Questions to Ask Your Next Boss


Photo by  Amy Hirschi  on  Unsplash

Photo by Amy Hirschi on Unsplash

Interviewing is a pleasure for some and a pain for most. One of the key differences between how you perceive this experience may reside in whether or not you “interview the interviewer” versus feeling that the process is one sided with the employer in control.

When you feel that you have little or no power, many experiences can be nerve wracking, uncomfortable, and intimidating. This is why it is so critical to empower yourself during the interview process.

One of the easiest ways to get confidence, project power, and execute a better interview is to ask intelligent and incisive questions. Here are three questions every candidate should ask the hiring manager during their next interview:

1. Can I speak with a current employee who is in the same or similar position as this role?

This question is incredibly potent for several reasons, but how the question is answered is as valuable as the answer itself. By requesting to include another team member in the process, you are challenging the format and the hiring manager will show you how they handle unique challenges. Do they simply say “No” or ineffectively struggle to come up with how to handle your request? Maybe they are extremely process oriented and are unable to adapt or maybe they lack influence within the organization. All of this is incredibly valuable data that will help you decide if this is someone you want for a boss. And you’d want to speak to a current team member in a similar role because they will generally give you a good sense of what it’s like on the inside and can help you understand success, corporate morale, challenges inherent to the position, etc. 

2. Why did you choose this company as your next great opportunity?

The best bosses, like the best employees, are in the driver’s seat of their own career and will answer a question like this in a detailed and convincing manner. They will share with you how they approached assessing the company and from this you will learn a lot about what is important to the hiring manager. Being aligned with any supervisor is critical and will only make for a better engagement. Imagine, however, if the response to the question is….”Well, it’s a short commute.” or “I was unemployed and needed a job.” In both cases, the answer has nothing to do with the company, its mission, or career development. You may want to think twice before accepting this position if you are ambitious and career motivated as this manager may not be the right person to work for at this point in your career. 

3. Can you tell me the history of this position within the company?

This question is often overlooked but incredibly important. Is the role newly created because of strong corporate growth? Have the last three incumbents been fired or quit because of internal factors or market conditions? Maybe the hiring manager has unrealistic expectations for this role. Without knowing and understanding the history of why the position is open, you have no datum by which to assess the potential of the role or risk. 

Use these questions during your next interview and take some of the pain out of the process. Recognize that, in the current economy, companies need top talent and employees can be choosy. Candidates have the power and when you get comfortable “interviewing the interviewer,” you will be on the path to getting the job that you want.


Written byAustin Meyermann, Founder and President of Hunter Crown, LLC


Looking for your next great opportunity?

Have hiring and/or recruiting needs?