Dear Dan: What Questions Should I Ask My CEO

Dear Dan,

I have a new position within our company. Now I report directly to the CEO. What questions should I ask during our first meeting?



Questions invite engagement. Statements invite judgement. Image of sheep in a field.

Dear Bob,

Congratulations on earning a new position. Here’s a list of questions to choose from. I recommend you pick two or three.

Safe landing strip:

The landing strip for questions is the sentence before the question that declares your intention. Questions can feel awkward. People wonder what you’re after. It’s best to tell them why you’re asking before you ask.
The sentence before the question narrows responses. Help listeners focus on your interests.

  1. I’m just curious.
  2. I wonder what’s important to you.
  3. I want to be sure I focus on….
  4. I want to bring value to our customers.
  5. I want to focus my energy on important things.
Great answers to wrong questions are wearisome. Image of a bored dog.

Questions to ask the CEO:

1. What will be true six months from now?

Ask from three perspectives, for customers, your organization, and for yourself.
“I want to bring value to our customers. If I’m wildly successful in this new role, what will be true for our customers six months from now?”

2. What value do you believe I can bring our customers?

Don’t ask, “What value can I bring our customers?” Ask the question from a personal perspective. You might not hear a personal answer, but it’s worth a try.

3. What did you see in me that prompted you to offer me this position?

Don’t sound needy when you ask this question. Use a landing strip sentence.

  1. “I want to be sure I understand how I earned this position.”
  2. “I look forward to serving in this new capacity. If you don’t mind me asking, what did you see in me that caused you to offer me this position?”
    Listen for specific skills, attitudes, and behaviors. Gently ask a second question if their answer focuses on the work.
  3. “That’s helpful. I’m also interested in any specific skills you noticed.” Insert words like, strengths, talents, attitudes, or behaviors in the place of skills.
  4. “That’s helpful. I wonder if…?”
  5. “I appreciate that. Could you say more about…?”

4. What will I not have done if I fail at this position?

Set a timeframe. “Six months from now.”

Don’t sound insecure. Build a safe landing strip. “I want to be sure I understand the key success factors of this role from your perspective.”

10 Possible questions:

  1. What would you like me to know about you?
  2. What are some tipping points in your leadership journey?
  3. How can I make your job easier?
  4. What is your vision for our organization?
  5. What are some of the qualities of the best people you ever worked with?
  6. Who do I need to build relationships with? Think about inside and outside your organization.
  7. What would you do if you were in my position?
  8. What advice do you have for me?
  9. How do you define success personally?
  10. How can I help you do your job better?
Image of light through tree branches.

5 Tips:

  1. Bring a notepad.
  2. Take notes.
  3. Ask follow-up questions.
  4. Nod your head.
  5. Express gratitude. “Thanks for saying that.”


Follow-up in a week or two. Share your impressions. Explain what you noticed.

  1. “I’ve been thinking about our conversation.”
  2. “When you said __, it had a big impression on me.”
  3. “As a result of our conversation. I plan to _. Does that align with your thoughts?”


The goal of your first conversation with the CEO is to set a tone. Resist the temptation to look smart. Over-confidence is arrogance. Show up with passion, confidence, and a learner’s spirit. A little humility serves you well.

I wish you success in your new role.

You have my best,


What questions could Bob ask when he meets with the CEO for the first time?

Still curious:

2 Ways to Ask Questions Like an Expert

The Best Leaders Ask Questions That Work

7 Questions to Ask Your New Boss

Author’s note: I suspend my 300 word limit on “Dear Dan” posts.