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Kenneth G. Hartman

Security Consultant & 
Certified SANS Instructor

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It is common wisdom that the interview process is a two-way street. You should be interviewing the company that you are considering working for to determine if you will be a good fit for the culture and values of the company. If you get a chance to talk to executive management, you will certainly want to be prepared. What questions will you ask? Contrary to popular opinion, I do think that there is such a thing as a dumb question. After all, you do not want to destroy your credibility by lack of preparation. Here is a list of some ideas, but just select a few:

On the Culture & Growth:

  • What kind of person succeeds here?
  • How do you define culture?
  • How would you characterize your management style? and those of the folks on your team?
  • Whose careers have you influenced the most?
  • What do you, personally, do to continue to grow?

On the Future:

  • What are your customers telling you is their biggest unmet needs?
  • How do you see the needs of the company‚Äôs market changing in the next few years?
  • How will the company look different in the next 3-5 years?
  • What excites you the most about the future of the company?

Deeper Questions:

NOTE: Make sure that it is appropriate to ask these questions! These require a higher level of rapport with the person you are talking to.

  • Tell me about {name a key person} who has recently left the company?
  • What about employee turnover?
  • What is the toughest decision that you have had to make recently?
  • What is the most important thing that you are working on right now?
  • What keeps you awake at night?

What to look for:

When listening (and observing) the answers to these questions, I look for honesty and openness. Executive leadership sets the tone for a company. Do the answers convey integrity or evasiveness? Displays of passion are important, but is there also a depth that inspires confidence? Would you hire this management team to lead the company that you decide to work for?