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

• T. Carter Baxter’s questions for potential employers – not specifically for any particular level, and some great questions in here.