Alicia Diamond

Actionable advice for passionate business builders

Actionable advice, tips, and musings from a 2x Chief of Staff & passionate business builder

My life as a Chief of Staff

Why write this?

  • See also “Why I blog”. I write to practice concisely articulating my thoughts, to give my brain the opportunity to make disparate connections, and to hold myself accountable to processing and deeply comprehending my inputs. Sure, I guess you could say I’m forcing myself to write papers after reading.

  • As of the time of this writing, the CoS role is still quite rare in the private sector. Silicon Valley has embraced the role and popularized it, thanks in part of a few famous former Chiefs (Sheryl Sandberg). As of the time of this writing, Sheryl Sandberg is still Silicon Valley royalty…

To successfully support a CEO and drive corporate results, I believe a CoS needs creativity, empathy, compassion and a conscience. A good CoS should be a mentor, facilitator, and consigliere.

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. More about that another day.

As someone living the role, I’m often asked to articulate it to those who have either 1) never heard of a private sector CoS, or 2) never had the right forum to actually understand what the role entails. I enjoy these conversations, especially internally, as they give me an opportunity to educate and to also assess how people perceive my role/the CEO’s role. I find that my role as CoS is equally misunderstood as the CEO’s role, but very few people are willing to admit that they don’t really know what a CEO does day in and day out.

So, what’s a typical day?

  • Attend meetings with my CEO or on behalf of my CEO.

    • I spent 80-90% of my time in meetings. CEO’s are conductors of the orchestra. Effective CEOs don’t do, they orchestrate. As CoS, a big part of my job is to make sure my CEO has all of the information requires to effectively orchestrate. This means sitting in meetings to make sure I get the right information.

  • Nudge. Anyone and everyone.

    • Put another way: hold people accountable. Cat herd. Crack the whip. Whatever you want to call it, a big part of my role as CoS is to make sure people do what they said they were going to do, on or before the deadline they communicated.

    • All three CEOs I’ve served have been astounded by how much nudging is required of his or her team. As Chief Nudger, I’ve grown to expect it.

  • Deep dive, as necessary

    • Continuing with the theme of keeping the CEO informed so he or she can effectively orchestrate, I often spend time deep diving in a particular area. It might be ahead of an external meeting (who are we meeting? what is their background? what’s the 20% of information that will give us a competitive advantage in the meeting?) or ahead of an internal meeting (what’s the background? why does the CEO need to get involved? how are the people involved feeling about this? how are they doing?).

  • Ghostwriting

    • Chiefs are glued at the hip with their CEOs. The difference between an EA and a CoS is that the latter knows both what has to get done and why. In my role, I have all of the context about why something is more important than something else, I understand the nuance that went into the decision-making process, and I know why we chose this course of action over various alternatives. This puts me in a great position to draft internal and external communication to ~90% completeness for my CEO. This includes emails, Board communications (meeting decks, talking points), external presentations, etc.

So, what do you think? What do you want to know about life as a Chief of Staff?

Want to learn more about the CoS role?