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 immediately. 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?

  • 6 months/1 year from now, if I’m successful, what will be different about team and business?
  • How do you measure success?
    • What were the metrics before?
    • How do you expect them to change?
    • How will I be measured and how often?
  • What would you want me to accomplish in my first six months? First year?

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

  • What’s their greatest concerns about the role as it relates to the business’s goals/plans?

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

  • What are the biggest challenges for the role and its org?
  • What are the biggest strengths currently in the org reporting up to this role?
  • Staff review:
  • who’d be reporting to me?
  • for each of them: strengths & weaknesses
  • any performance issues I should know about?

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

  • How do decisions get made?
  • Does this role have hire/fire power? What’s the process?
  • Does this role have discretion over the budget?
  • What processes/procedures are company-wide, vs can be set by the role?
  • What’s the org’s budget?
  • Does this role have discretion over the budget?

What’s the history of the role?

  • Is this a new role or an open seat?
  • Why did the predecessor leave?
  • Are you considering internal candidates? Why or why not?

What are the businesses goals for organization?

  • How does this role fit into that?
  • How are these goals set? By whom and on what cadence?

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

  • How does this role fit into the financial picture?
  • Would my org be a profit or cost center?
  • What’s the funding situation of the business?
  • Burn rate?
  • Or profit/loss?
  • What’s the business’s exit strategy?

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

  • What’s the current demographics of the company?
  • … of the executive leadership?
  • … engineering?
  • … my potential group?
  • What’s the organization doing to create an inclusive workplace?
  • What’s the org doing to improve diversity?

Tell me about the executive leadership team:

  • Who’s on it?
  • Would I be on it?
  • How does that group make decisions and communicate them to the rest of the org?
  • If I needed to bring something to ELT, how would that work?

Tell me about the organizational structure…

  • … below me (my reports)?
  • … above me (my management chain up to the CEO)
    • … any dotted lines to be aware of?
  • … to my side (my peers under my direct manager)?

See also