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?
Sincerely,
Bob
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.
- I’m just curious.
- I wonder what’s important to you.
- I want to be sure I focus on….
- I want to bring value to our customers.
- I want to focus my energy on important things.
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.
- “I want to be sure I understand how I earned this position.”
- “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. - “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.
- “That’s helpful. I wonder if…?”
- “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:
- What would you like me to know about you?
- What are some tipping points in your leadership journey?
- How can I make your job easier?
- What is your vision for our organization?
- What are some of the qualities of the best people you ever worked with?
- Who do I need to build relationships with? Think about inside and outside your organization.
- What would you do if you were in my position?
- What advice do you have for me?
- How do you define success personally?
- How can I help you do your job better?
5 Tips:
- Bring a notepad.
- Take notes.
- Ask follow-up questions.
- Nod your head.
- Express gratitude. “Thanks for saying that.”
Follow-up:
Follow-up in a week or two. Share your impressions. Explain what you noticed.
- “I’ve been thinking about our conversation.”
- “When you said __, it had a big impression on me.”
- “As a result of our conversation. I plan to _. Does that align with your thoughts?”
Summary:
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,
Dan
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.
Great questions, Dan! As the trainer of Executive Assistants, I would add: How are you on your worst day? How do I win with you? How do I lose with you?
Thanks Bonnie. Love the personal nature of your questions. Sometimes we focus too much on results and too little on people. Cheers
Here are some question I would ask.
1.What are the top three biggest challenges the company faces?
2. What do I need to know about the senior leadership team to add value and be an effective team member and leader?
3. What do you expect me to accomplish in the next 6-to-12 months.
4. What’s the best way for us to share information?
5. Who are 3-to-5 people I should interview to increase my understanding of our customers and competitors?
I appreciate how you consistently bring practical suggestions, Paul. #2 is one of my favorites. It reflects an interest in the big picture.
These are amazing questions! I think they are valuable for anyone entering a new role! I myself and moved into a new role and plan on asking some of these exact questions in my next 1:1!!
Glad to bring value, SB. I’ll keep these questions in mind for 1:1s. Thanks.
There are some really great ideas in this post! I might ask questions that help me learn more about the CEO. I’d especially want to learn more about whether they lean toward a more risky approach in their decision making or if they remain more conservative. Learning more about the person who heads the organization would help me understand how I might move forward to align with their vision and approach.
Great point, DJ. I began thinking “alignment” about the second sentence in. Then you used “align” in your last sentence.
The notion of landing strip in intriguing. I’d like to hear more. I’ve had it where people had no idea where I was flying in from. That gets “security” anxious!
Sounds like you got it, Rob. Help people know where you’re coming from. The idea of the safe landing strip comes from my tendency to ask questions like a machine gun. After a while, people wonder what the heck I’m after. Heck, I’m not smart enough to be after something. I’m just curious.