Interviewing with a Former Boss or Coworker

If you network well, there’s a good chance you will eventually interview with a former boss or coworker.  This can feel awkward.  The interviewer has firsthand knowledge of many of the experiences and accomplishments from your background.  They also know about your failures and weaknesses.  Preparing for an interview like this can be difficult. 

When you prepare for an interview with someone that you know well, you need to approach the interview just like any other interview.  Prepare examples of your experience from both the times you worked with them, and when you worked apart.  Don’t assume the person will remember all of your accomplishments from the time you worked together.  It is likely, they have forgotten many of the details. 

The experiences you gained after working together are also important.  You should provide a clear picture of what you have been doing, and what you have accomplished.  Discussing your recent experiences provides an opportunity to show how you have learned and grown professionally.  The interviewer will know your weaknesses.  Showing you recognized these weaknesses, worked to improve on them, and succeeded in developing in these areas can be very impressive in an interview.

You can expect some of the interview to be very conversational, with the two of you reminiscing.  This is good but don’t forget you’re in an interview.  Focus on listening and answering the questions asked. 

When you interview with a former coworker, you have one big benefit: you are a known entity.  Hiring managers want to make a great hire, but often are more worried about avoiding a bad hire.  Knowing a person will be able to meet expectations, even if they aren’t a super star, can be the tipping point in a hiring decision. 

There is one question you can ask that could improve your chances: “What about this position will be more difficult for me in comparison to the job where we worked together?”  The goal of this question is to uncover any reason the interviewer might reject you.  You may not be able to overcome this, but at least you will have the chance to address it. 

If you ask this question, be prepared for some criticism.  You’re asking the interviewer to tell you why they think you won’t succeed.  If you get defensive or argumentative, you will almost guarantee that you will be rejected. 

There’s a chance the objection will be something you can’t overcome.  For example, the hiring manager wants a technical skill you don’t have.  In this situation, there’s only one thing you can do.  You need to express your commitment to learn the new skill quickly.

The other scenario involves and objection in an area where you have gained experience and skills since working with the interviewer.  The interviewer will picture you exactly as you were when you last worked together.  Your challenge is changing the picture.  Show the new experiences and accomplishments you have had.  If you do this effectively, you will show how you are more capable than in the past.