11 Lessons for Chiefs of Staffs

Inspired by my fireside chat with The Chief of Staff Association last week, I want to share learnings from my 8 years as Chief of Staff to Larry Ellison at Oracle. When I stumbled into this role, I didn’t know anyone else in it, and had to define my own path.

1. The role is seldom clearly defined. It varies greatly across companies and principals — from mostly administrative to leading large teams. It’s helpful to know the expectations beforehand, but don’t expect crystal clarity because there are no clear boundaries. It’s necessary to be flexible, both early on, and as your role changes.
2. To do your job well, you will be stepping on other people’s toes. This is because a large part of the Chief of Staff role is to find gaps and solve problems that exist between roles.
3. Alignment with your principal is key. Behind closed doors, you are your principal’s confidante, sounding board, and advisor. It is your job to push, question, refute. But once a decision is made, you must align with your principal even if you didn’t initially agree.
4. Your relationship with your principal is different from those of their other reports. You will be expected to anticipate needs, handle emotions, be flexible and empathetic. Finding the right principal is key, and figuring out that relationship is unique. Ideally, work for a principal who is complementary to you so you can learn from their strengths and help accommodate their weaknesses.
5. Don’t confuse position power with personal power. Your position power is an extension of your principal. You are using their name and position to accomplish a task. However, this is not the same as the power you wield in isolation. You must understand the distinction and build your own credibility in order to continue your career.
6. Moving from Chief of Staff to Staff is a nonlinear and complicated process. If you’re good at your job, it will be hard to leave it. Often, you may need to continue the COS role while taking on a second role if you want to move out of it.
7. You may have one true boss, but don’t forget about the other senior leadership. Learn the motivations and working styles of the key stakeholders you work with to be successful.
8. You’re unlikely to have “peers” but it’s important to find allies across the company, those who will both advocate for you and give you honest feedback.
9. Work-life balance is variable. Identify your top priorities and work around them. Enjoy the breaks when you get them, even if they aren’t the ones you pick. As you build the relationship, you’ll be able to set your own boundaries better.
10. A lot of what you’ll do is behind the scenes, and you may not get the credit you deserve. A good principal will make sure you are properly rewarded, but sometimes you’ll need to do a little pushing too.
11. Find a community of others with similar roles to learn from and grow with. I’m so grateful to the many I’ve learned from along the way.

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In April 2023, I left Oracle after almost 11 years, serving a number of roles including Chief of Staff to Larry Ellison, VP Global Marketing and Brand, VP Product Strategy and Marketing Oracle Health, and Head of Oracle for Startups and Oracle for Research. This post is week 4 of me sharing 11 things I learned over these 11 years here and on LinkedIn, and I hope you’ll join me for this journey.