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

Featured

How to Run an Executive Team Meeting That Doesn't Suck

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.

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

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

How Busy Leaders Can Trigger a Flow State and all of its Benefits

In an ever-increasingly complex business world, leaders cannot disappear for weeks at a time to pursue a flow state at an ashram. While a thorough rest and recharge are always helpful, it’s more realistic to look for ways to trigger a flow state that simultaneously drive results in your business.

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

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.

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

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.

Advice From Zainab Ghadiyali for Current and Future Chiefs of Staff

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.

Hey, CXO! You deserve a Chief of Staff!

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?

Kicking Off the New Year, Minus the BS

Tullman uses the crutch of annual budget planning to kickstart this idea, encouraging leaders to be ruthless about how they allocate their resources and to reward only those projects, departments, and individuals that make an outsized impact on the bottom line.

The All-important Daily Stand-up

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.

My life as a Chief of Staff

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.