The Chief of Staff Role is the Greatest Career Hack Ever.

Chiefs of Staff race to the top of the ladder and experience life as a CXO relatively early in their career. As Chiefs, we can use our unique perspective to ask ourselves “is this where I want to be?” and, if not, use the vantage point to plot a strategic path elsewhere in the organization.

During my two tours as a Chief of Staff, I:

  • served three (!) CEOs

  • helped a founder step into the CEO role and led the company through a seamless leadership transition

  • worked in a venture-backed company and a family-office-funded incubator

  • worked in software, data, direct-to-consumer products, B2B services, sourcing, & manufacturing industries

  • built a team of brilliant generalists that I led through strategic initiatives and tactical challenges across a portfolio of companies

  • learned how to fundraise, build & re-build teams, and effectively manage a Board of Directors

Articles for Chiefs of Staff, from my life in the trenches as a 2x Chief

Articles
Alicia Diamond
How to Run an Executive Team Meeting That Doesn't Suck: 5 Tips for Running Effective Executive Team Meetings
Alicia Diamond

I’ve sat through exec team meetings every week for the last 4 years. Some good, most okay, some downright bad. The better meetings all happened to include a meeting leader focused on making the most out of the time. The worst? They relied on the group to figure it out on the fly.

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Alicia Diamond
Alicia Diamond
How to Leverage your Chief of Staff Experience to Find a Dream Job
Alicia Diamond

Here’s how I approached my job search, and found my dream job, without knowing exactly what I wanted.

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Alicia Diamond
Alicia Diamond
A Chief of Staff Could Have Saved Away and Steph Korey From Her Own Worst Behavior
Alicia Diamond

After reading The Verge's article, relief that I wasn't Steph's Chief of Staff quickly turned into fascination. I couldn't stop thinking about all the ways an experienced Chief of Staff could have helped the Away team and, perhaps, saved Steph from her demise.

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Alicia Diamond
Alicia Diamond
There Has Never Been a Better Time To Be a Chief of Staff
Alicia Diamond

Imagine getting to be the first Chief of Staff at a company. You get to define the role for the company and for the entire team, CXOs included. I’ve gotten the chance to do this and while it’s not easy, it’s immensely satisfying work for the right personality.

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Alicia Diamond
Alicia Diamond
Advice From Zainab Ghadiyali for Current and Future Chiefs of Staff
Alicia Diamond

While she’s not a Chief of Staff, her approach to an unconventional (and seemingly meandering) career is an inspiration for curious generalists like Chiefs of Staff.

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Alicia Diamond
Alicia Diamond
Hey, CXO! You deserve a Chief of Staff!
Alicia Diamond

I know, you’re not POTUS. Nor are you a decorated General. But, the Chief of Staff role has expanded into the private sector. The early adopters of this new role are quietly reaping the results. It's an edge for the modern executive. Couldn't you use an edge?

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Alicia Diamond
Alicia Diamond
The All-important Daily Stand-up
Alicia Diamond

I adopted a system I called “scrum-lite” that revolved around a daily-standup, a whiteboard, and many many post-its. I was like a fish out of water managing my ballooning team, including a second layer below me, and I needed a system that would give me confidence in both our progress and direction. 

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Alicia Diamond
Alicia Diamond
My life as a Chief of Staff
Alicia Diamond

I’ve served as a CoS twice, in two different companies, and under three CEOs. I suppose somewhere in the CoS world I earned a special Girl Scout-style badge for having transitioned CEOs as a CoS.

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Alicia Diamond

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