Photo by Jean-Philippe Defaut ©2018

Resources on the Chief of Staff Role in Business

Maïa Cybelle Carpenter

* This list was published in 2018 and as there have been many valuable updates since then, we've continued to update the list.

Whether you are a CEO who needs to learn more about hiring and working with a Chief of Staff, an Executive Assistant or Strategy Consultant hoping to grow into the role of Chief of Staff, or are simply curious about this role which seems to be popping up quite a lot in tech companies, here is a list of resources. We share these resources with our clients so we thought it would be helpful to share them with the public as well. This list is by no means exhaustive, nor in any order. We have omitted older resources that are out-of-date with the current evolution of the role. If we’ve missed anything important, we welcome your suggestions to add other resources in the comments below.

NOTE: As advocates of eliminating confusion around the wide variety of Chief of Staff roles, we refer you to our recommendation outlined here for a new adaptive role supporting the C-Suite and Founders: Executive Operations.

  1. This article in First Round Review about Influitive CEO Mark Organ’s decision to hire a Chief of Staff is highly recommended. It’s thorough and quite detailed: Why You Need Two Chiefs in the Executive Office
  2. Tyler Parris’s definitive book Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization is also highly recommended. It is well researched and contains countless practical examples for both CEOs and Chiefs of Staff. Tyler Parris Coaching LLC, 2015. Also, this podcast with him is great!
  3. Melissa Wingard-Phillips’ slidedeck, Chief of Staff to the CEO — When, Why and How to Hire One is a useful outline of considerations for a Founder/CEO to think about before hiring a CoS. Slideshare/LinkedIn, September 20, 2013.
  4. Reid Hoffman’s former Chief of Staff, Ben Casnocha wrote a wonderful account of his lessons learned on the job: 10,000 Hours with Reid Hoffman. We like to share this article as it underscores the partnership between the CEO and the Chief of Staff.
  5. Maxine Litre’s helpful article on how to hire a Chief of Staff is particularly useful if you are the founder of a startup: The Chief of Staff Role: How to Find the Right Fit in the Interview Process. CoS Tech Forum, March 4, 2018.
  6. Tyler Parris’ thoughtful article on the difference between a Chief of Staff and a Chief Operating Officer in the OneAccord Partners blog, March 14, 2017.
  7. The former Chief of Staff of CircleUp, Emma Stubbs has written about priorities and efficiency in her role on LinkedIn: What is a Chief of Staff Anyway?- Part I, May 2, 2018 and What is a Chief of Staff Anyway?- Part II, January 18, 2019.
  8. McKinsey’s perspective includes some fascinating case studies in this slide deck, from a roundtable discussion on the Chief of Staff role, March 17, 2017.
  9. Ryan Metcalf, former Chief of Staff to Max Levchin at Affirm, summarizes how he spent his time in the role. What I Learned as Chief of Staff to Serial Entrepreneur, Max Levchin, May 8, 2018.
  10. Rob Dickens, currently the Chief of Staff to the CEO of Autodesk has written this detailed account of his point of view of the CoS role in a tech company. I’ve Logged 10,000 Hours as a Chief of Staff in a Large Tech Company; Here’s my POV on the Role, October 22, 2017.
  11. Alex Benady’s post Nine Reasons You Need a Chief of Staff really highlights the growing need for this type of role across many sectors.
  12. Atta Tarki’s recent article in Forbes Why More CEOs Are Hiring A Chief of Staff highlights that hiring a CoS can free up your time, drive high-value initiatives and foster internal talent development, February 27, 2019.
  13. The Chief of Staff Role — Four Part Overview (One, Two, Three, Four) by Paul Cohen, VP of Strategy at One Medical, May-October, 2018.
  14. The Chief of Staff role in Silicon Valley by Julia DeWahl, former CoS to the CEO of Opendoor, April 29, 2019.
  15. Why Every Startup CEO Needs a Chief of Staff by Dave Bailey is a concise list of examples why founders should hire this type of right-hand support role. This includes increasing productivity by 20–50%, enabling the CEO to focus on where they can add the most value, July 9, 2019.
  16. The Case for a Chief of Staff by Dan Ciampa in Harvard Business Review quotes Parris’ book that I mentioned above and has its own perspective on the types of work Chiefs of Staff may do and the desired impact, May-June 2020.
  17. Measuring the Value of a Chief of Staff by Rob Dickins, Chief of Staff Association Blog, May 2022
  18. The First 90 days as a Chief of Staff by Rob Dickins, March 2019

Maïa Cybelle Carpenter

CEO, Carpenter Consulting Partners, Inc.

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