During my first day at a new job, my new hire class was introduced to the CEO for a small “Ask Me Anything” session. As an introvert, I am not particularly good at being put on the spot, especially in what felt like such a “high stakes” situation. My class of 9 was round-robined with everyone asking smart questions about company strategy, growth, culture, etc. When it came to my turn, I blanked. I could not think of one question. He point blanked me and I clumsily stumbled over my words and replied with “I’m still thinking of one…”. This was not the kind of first impression you want the CEO to have of you.

Luckily that afternoon he happened to host a larger “Ask Me Anything” session with New Hires from the past 6 months. I had a few hours since that morning to prepare some well contemplated questions that I hoped would allow me to redeem myself.

Hopefully if you find yourself in this situation you’re able to respond with more grace than me but in case you find yourself at a loss for words feel free to lean on the list below in your next “Ask Me Anything” session for ideas.

  • What professional development books have been most influential to you?
  • How much of your success do you attribute to being lucky vs your efforts to create success?
  • What is the biggest piece of advice you have for someone within their first 6 months of joining the organization?
  • Where do you see the company in the next 10 years? What are the main differences? And what things do you see not changing?
  • What differentiates the high potential employees from the average performing employees, in your opinion?
  • Which departments in the organization are experiencing the most growth from a hiring/headcount perspective?
  • What is the biggest area of opportunity for our product/ service?
  • What is your daily regimen and how do you think that contributes to your success?
  • What keeps you up at night? (Work related, what is the biggest thing on your mind for the organization?)
  • How would you describe your leadership style?
  • How do you hold yourself accountable for what you try to achieve day to day?
  • What podcasts do you recommend?
  • Who inspires you?
  • What is the biggest threat you see for the company?

If you have any other questions you think would be good to add to this list, feel free to comment your ideas below!


Hey Money