Demystifying the Chief of Staff Role

Since starting at Drift, I haven’t had one coffee chat that didn’t at some point lead to the following question: So... What is a Chief of Staff? What do you do here?

This curiosity doesn't just come from inside of the company. I have spoken with countless students and professionals that have reached out through LinkedIn or mutual friends, and although I've enjoyed those coaching conversations, it's been tough to truly scale my knowledge and experience efficiently. My hope is that this post demystifies the Chief of Staff role and allows me to get as much of this information to as many people as possible.

?? WARNING ??

This post is meant to help ambitious professionals considering taking on a Chief of Staff role or senior executives considering hiring one to support them. What I say here is not a one-size-fits-all. It's based on my experience and the experience of others I've spoken with over the years.

So ... Let's jump into it. ??

Having now been a Chief of Staff for 3-4 years across multiple companies, continents (shoutout to my London blokes ????), and contexts (CEO, COO, and CTO), there are a few frameworks I use to better put the role into perspective.

Let’s start with answering the biggest question: What is a Chief of Staff (CoS)?

WHAT IS A CHIEF OF STAFF (CoS)?

This role used to be primarily used in the military to help give young leaders a chance to sit at the feet of generals to learn how things get done at the highest levels (see: aide-de-camp). The CoS experience was meant to be a developmental sprint (1-3 years), and afterwards, the emerging leader would be put back into the organization with a fresh perspective and skill set that they could bring to problems. 

Currently, the role has gained a ton of popularity, but most people (employees and executives) don’t know what they’re looking for until they've gained experience as a CoS or with a CoS working under them. 

Here are two frameworks I use to put the role into perspective.

Framework #1 - Experience

There are different types of Chiefs based on their level of experience: Senior Level, Mid-Level, and Junior Level.

Senior Level ~ Chief of Staff (15-20 years of experience): more senior Chiefs become what is typically called a “clone” of the executive. (see: White House Chief of Staff). They typically have decades of relevant experience, and they’re responsible for running the executive’s office: 

• Partnering with the head of personnel on key staff hiring
• Developing and running the organization’s “operating system”
• Understanding and reporting on business unit operations
• Managing communications (internal and external)
• Assisting with corporate development and fund allocation

To get these things done, they often have their own Chief of Staff (Deputy CoS) and their own executive assistant ("EA"). They frequently partner with the Head of Communications and other top executives that work with the principal they support (c-suite, department leadership, etc.). 

Common Next Steps: After 1-3 years, Chiefs at this level typically go on to run a piece of the organization, take up a role in the c-suite or become an advisor (official or unofficial) Ex: Jack Lew in the Obama administration held the role for one year, and then went on to run the Treasury department. 

Mid-Level Chief of Staff (5-15 years of experience): more mid-level Chiefs aren’t quite ready to become a full “clone” of the executive, but they have enough experience to take a number of special projects and administrative responsibilities off of their principal’s plate. They’re typically responsible for some if not all of the following: 

Administrative

• Partnering with EA’s to ensure scheduling and meeting prep is handled
• Running the principal’s staff meeting and tracking follow-up items
• Drafting communications (internal and external): all-hands meetings (kickoffs, town halls, etc.), board meetings, executive team updates (when department heads report up), company emails, etc.

Special Projects 

• Running and improving the organization (or department) “operating system”: quarterly and yearly planning via OKRs, offsites, etc.
• Understanding and reporting on business unit operations: weekly, monthly, and/or quarterly reporting
• Assisting with cross-functional strategic matters: M&A analysis/integrations, strategy research, fundraising (with smaller private companies), international expansion, etc.

Common Next Steps: After 1-3 years, Chiefs at this level exit into a number of options, but the options vary widely based on their prior experience and the opportunities available at the company.

Junior Chief of Staff (<5 years of experience): more junior-level Chiefs are typically years away from being a proper “clone” of the executive, but they’re typically hungry enough to take 1-2 special projects and many of the administrative responsibilities off of their principal’s plate. They’re typically responsible for some of the following: 

Administrative

• Partnering with EA’s to ensure scheduling and meeting prep is handled; in smaller organizations, the CoS will sometimes take on all of the EA’s responsibilities for a short period of time until an EA can be hired.
• Running the principal’s staff meeting and tracking follow-up items
• Drafting communications (internal and external): all-hands meetings (kickoffs, town halls, etc.), board meetings, executive team updates (when department heads report up), company emails, etc.

Special Projects (no more than 1-2 of these items at a time)

• Running and improving the organization (or department) “operating system”: quarterly and yearly planning via OKRs, offsites, etc.
• Understanding and reporting on business unit operations: weekly, monthly, and/or quarterly reporting
• Assisting with cross-functional strategic matters: M&A analysis/integrations, strategy research, fundraising (with smaller private companies), international expansion, etc.

Common Next Steps: Similar to the mid-level CoS, the options vary widely based on their prior experience and the opportunities available at the company. After my first stint as a Chief of Staff, I was given the opportunity to work in London ????, but I've seen others use the role to change functions.

Here’s the second framework I found through the McChrystal Group. I've found it to be incredibly helpful, and it’s explained in much more detail Do you need a Chief of Staff?.

I did not create this one, but I reference it often. ??

Framework #2 - Career Development and Impact

Figure 1: This four-quadrant chart maps the journey and full potential of a Chief of Staff originally published in One Mission (Fussell 2017).

If you're curious to learn more, I recommend taking one of their CoS courses here: McChrystal Group Programming.

In terms of development, most principals want to place Chiefs in quadrant four (Q4) immediately, but unless the CoS is already coming to the role with an understanding of the industry, company, and employees, this is a hard task for a new Chief of Staff.

A good framework and development plan should pull a Chief’s effectiveness and output from Q1 (assist with execution) to Q4 (strategic thought partner) over time.

More experienced Chiefs will move through these quadrants quickly, but a more junior Chief may never leave the first 2, which is normal.

If you want to learn more about the role, feel free to check out this podcast I did with Maggie Crawley which compares the Product Manager role to the Chief of Staff role. 

Build with Maggie Crowley: Episode #80

Lastly, we’re hiring a new Chief of Staff here at Drift. It’s an incredible opportunity to work for some of the best in the business, so if you’re interested, please reach out to our Director of Leadership Recruiting, Keith Pescosolido at [email protected].

Good luck, and Godspeed. ??