Leadership Job Hunt — Six Tips on Interviewing Your Interviewer
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It’s brutal right now. Job hunting. Looking for a new leadership role in the best of times is a challenge. Right now however, it can feel like an endless quest.

You’ve searched. You had all the alerts on all the job boards. You’ve filled out countless applications. You’ve networked. You’ve posted online.

Rejections and ghosting have all been endured.

Then the moment. You get the call. You charm during the initial “meet ‘n greet” phone screen. You are asked for an official interview.

You know you must be ready to answer their questions. If that’s the end of your prep work you are missing a full half of the process. An interview is not a one way street. It is a dialog. A conversation. You must be as prepared to interview them as they are you.

More interviews are won and lost in the moments after, “So do you have any questions for us?”, than before.

Go in ready with these six questions as your base and you’ll be moving strong to the win column.

What are the first challenges this position will face on day one? This question serves two purposes. First, you get a feel for their own self-awareness of their company. Can they answer with confidence the tasks you will have on your desk the first day? If not, or if they paint some “everything is awesome” picture, that’s a red flag. Second, you need to know if there are items in waiting you have no professional desire to tackle. That’s OK, but you need to be honest with yourself about it. What do you expect to see from this role in the first 30–90–180 days? This is a natural follow-up to question one. A healthy company with clear vision will know that your first 30 days are spent learning, by day 90 you should have general prioritized plans, and by day 180 some of the high priority plans would be in motion. If they cannot articulate that idea to you, that’s a problem. Are there resources already allocated to tackling your known challenges? While no company would say a hard “no” here their ability to provide insight into the support your role will have should exist. They should be able to discuss at a high level the dollars, people, and/or vendors they are capable of lining up. Hesitance to answer, talking around the answer, those are signs you will be tasked with doing it all with very little. Is that an obstacle you wish to take on? Only you know, but you’ll at least know. When we get to the one year anniversary for this role, what will make you look back and say, “Yeah, this was a great hire, I’m glad we have you here,”? This question takes the front line ideas and answers already given, then pushes for how they as a company define success. You cannot be successful in a company that does not know how it defines that very success. How do the teams this position will lead feel about an external person taking the helm versus an internal candidate? This is a great question to get a feel for the culture of the company. If you’ve been a leader any amount of time, you’ve taken on a team that had a member apply for and not receive a promotion to that leadership role. It can be an uncomfortable situation. Has the company considered this and worked with the team to make a positive transition? How are leaders here empowered to help their teams with professional development and career progression? Strong teams made up of high performers need new challenges, opportunities, and advancement. The tools you are given to facilitate that progression will be a pillar on which you can build success. Companies that cannot identify how they help or do not have plans in place will create roadblocks to your building and leading a strong team.

These questions are by no means a be-all, end-all of things you can and should ask, but they give a foundational position on which to go after that, “What questions do you have?”, opportunity.

Do not hesitate to flip the script and interview your interviewer. Strong, healthy companies see doing so as a positive, not a problem.

Good luck!
['Jon Santee']
['Job Hunting', 'Job Search', 'Interview Tips', 'Leadership', 'Interview']