5 Tips for Interviewing Your Future Boss

Interviewing is a two way street and everyone knows that the information security market is a “candidate market.”  With more jobs than talent and plenty of positions for most infosec professionals to choose from, it is extremely important to interview your next boss with the same scrutiny as the company is interviewing you.  Making sure you’re not working for an unstable, unpredictable or volatile boss is extremely important.  However, this type of interview must be handled class and savvy.  Here are five tips for interviewing your future boss.

If You’re Happy and You Know It

Set the stage early in the interview by letting him/her know that you’re happy to be in the interview and looking forward to learning more about the position, company and culture.  Ask if they feel there will be time at the end of the interview to ask a few questions of your own.

Understand Expectations

When it seems as if the manager has asked the questions he/she needs to, start by asking this question:  “Within the first six months on the job, what are the top three things you expect to see from me?”  Red flags are raised if your future manager is annoyed with this question or dismissive.  Make sure the expectations seem reasonable based on what you know about the position and the timelines.  If your future boss is focused on new role mastery, reasonable project completion, collaboration with team mates, breathe a sigh of relief!

Team Dynamics or Dynamic Team?

Ask about the team dynamic and if there are any current issues facing the group.  Every team has issues and even great teams go through rough patches.  It is useful for you to know what you’re walking into.  Pay attention to whether you’re getting an honest and balanced answer as well as any hesitancy or long pauses.

Make Mistakes Better

Another critical element is communication and a great question to drill into this is:  “If you had a problem with something I did, how would I know?”  Truthfully, I don’t believe that any of us wakes up hoping to screw up or tick our bosses off, but sometimes it happens.  The real issue is how the situation is handled once the mistake is made.  This is a great time to not only learn about your future manager, but to let them know what communication style works best for you.

Type Your Leader

Ask them to characterize their leadership style.  If this feels too direct, open the conversation by stating that you’ve successfully worked with several different leaders with varying styles and you’re interested in what works best for them.  While most micromanagers won’t come straight out and say, “hey, I’m going to drive you crazy by watching every move you make and criticize you at every step along the way,” they will allude to their true nature as they describe their style.

The goal is to find a situation where your style and goals match those of your future leadership.  Take the time to ask the right questions and get the information you need to make the right decision.  It’s far easier to find another interview than it is to extricate yourself from a poor leadership experience!