30 Questions You Can Ask in Your First 30 Days as Chief of Staff

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When you step into the Chief of Staff role, the temptation to jump in and start fixing things is strong. After all, you were hired (or promoted) to make the organization run better. But here’s the truth: your first 30 days aren’t about fixing. They’re about learning.

This is the moment to listen, gather perspective, and build trust. The smartest Chiefs of Staff treat their early days like a research phase. You’re uncovering not just what’s broken, but also what’s working—and what matters most to the people around you.

To help you get started, here are 30 questions you can ask leaders, peers, and front-line staff in your first month.

Questions for Leaders (your principal and their directs)

  1. What do you see as the biggest priorities for this team right now?
  2. Where are we winning? What’s working especially well?
  3. What’s not working as well as it could?
  4. What would you change if you had a magic wand?
  5. What do you wish the team spent more (or less) time on?
  6. Where do you see the biggest risks ahead?
  7. What are the biggest opportunities we’re not fully seizing?
  8. How do you prefer to receive updates and information?
  9. Where do you most need my help in the next 90 days?
  10. What’s one thing you wish everyone on the team better understood about your role?

Questions for Peers (other Chiefs of Staff, EAs, functional leaders)

  1. What does collaboration between our teams look like at its best?
  2. What’s been frustrating or difficult about working across teams?
  3. How do decisions typically get made here?
  4. What slows things down?
  5. What would make communication between teams easier?
  6. Who do you see as informal influencers that I should build relationships with?
  7. What’s something you wish new Chiefs of Staff understood right away?
  8. Where are we duplicating effort across teams?
  9. If you could streamline one process, what would it be?
  10. How do you prefer to work together day to day?

Questions for Front-Line Staff

  1. What makes you proud to work here?
  2. What gets in the way of doing your best work?
  3. What’s one thing you’d change if you could?
  4. Where do you see wasted time or effort?
  5. What’s working well that leadership may not notice?
  6. If you could share one piece of advice with me as I start, what would it be?
  7. How do you usually find out about decisions or changes?
  8. What’s one thing that would make your job easier?
  9. Who’s someone I should talk to if I want to understand how things really work?
  10. What does success look like for you in your role?

Lead with Curiosity

Your first 30 days as Chief of Staff aren’t about having all the answers—they’re about asking the right questions. When you show up with curiosity, you earn trust and uncover insights that no dashboard or report could ever capture.

Listen first, learn deeply, and then you’ll know what’s worth fixing.

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