Jacob Kaplan-Moss

My questions for prospective employers (Director/VP roles)

Last time I was looking for a job, I wrote up a list of questions I wanted to ask prospective employees. I just ran across the list again, and figured I’d share. I was looking for a senior management role (Director/VP-level) in Engineering or Security, so the questions are sloped in that direction.

Also note that I was in a fairly strong position; I didn’t need the a job immanently. So, I was able to ask fairly direct, challenging questions. You may have a lower risk tolerance and want to scale some of these back.

What does success in the role look like?

What’s my boss’s (or board’s) expectations for me?

What are the strengths and weaknesses of the org as it currently exists?

What’s the degree of managerial discretion in the role?

What’s the history of the role?

What are the businesses goals for organization?

What’s the business’s financial picture look like?

D&I is important to me; what is the org doing here?

Tell me about the executive leadership team:

Tell me about the organizational structure…