Alicia Diamond

Actionable advice for passionate business builders

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

There has never been a better time to be a Chief of Staff

About once a week, a want-to-be Chief of Staff reaches out to pick my brain. If you’re interested in the role - which I’m guessing you are since you’re reading this! - you’ve hopefully sent a few of these types of messages yourself to get some firsthand intel from existing Chiefs. If you haven’t already done, so let’s talk!


I love to talk about the role with prospective Chiefs, new Chiefs, and leaders thinking of hiring a Chief. I’ve seen how the role can make a meaningful impact on the leader and the business at large. Selfishly, I believe the Chief of Staff role promotes my personal mission of building more, better businesses by:

  1. helping today’s leaders to be the best they can be and do the best they can do for their companies

  2. creating a rich talent pipeline of people who have seen firsthand what it’s like at the top and who may choose to pursue the corner office eyes wide open 

Why do I love these conversations with future Chief of Staff? 

Because they’re an opportunity to talk about a few of my favorite topics: the Chief of Staff role, organizational structures, and artful concerns. The conversation always naturally evolves into the other person articulating why they want to support a CXO or how they think they could improve their current company “if only” or what they will do differently when they become CXO one day. 

For anyone inclined to pursue the Chief of Staff role, there has never been a better time. Why?

The Chief of Staff role is burgeoning, but still loosely defined. 

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. If you’re considering joining a company as their first Chief of Staff, I have some advice for you.

The world is waking up to the awesome power of the Chief of Staff role. Investors and Board Directors recognize that the role is a smart investment in their executive’s future success. 

If you want to accelerate your career or leapfrog up the ladder to see what life is like as a CXO, there is no better role than Chief of Staff. The same is true for anyone curious about how a Board of Directors operates, or how a C-suite functions, or how any individual functional area operates from the top down. Investors and boards are driving the adoption of this role after they see how it can successfully influence a CXO’s performance and overall sanity. I was fortunate to interview with one of our Director’s before joining my last company, and that initial relationship supported my continued presence during our CEO transition.

While a Director or Investor may champion the role, they likely don’t have a clear definition of how to implement the role. See also my point above. For the right person, this is an excellent opportunity to define how exactly the company leverages a Chief of Staff. In my experience, the external stakeholder who suggested a Chief of Staff will likely be happy to introduce Chiefs from their network to support you in your new role.

People still don’t know what a CoS is, so you get to own how you’re perceived.

This might be a negative for some people. My husband is an architect, so I get to see firsthand how people latch onto his job and ask questions like “what building have you designed? Are you working on anything cool? Oh, a hospital! Exciting!"

On the other hand, I get to teach people about my role. More often than not, the person responds by saying “I need a CoS!” or “My CEO needs a CoS!” at which point I tell them to let me know when they’re hunting because I always have people in mind. I enjoy these conversations because it gives me a chance to promote the awesome power of the Chief of Staff role. One of these days, I’d love to hear that one of these unsuspecting conversation partners went on to suggest a Chief of Staff to their CEO and got all the credit for the genius idea.

Which brings me back to why I love these conversations with would-be Chiefs of Staff: 

  • I love to educate people on the role.

  • I love to strategize with them about how they can evolve their current role to better position themselves for a CoS role elsewhere.

  • I love to explain how my two CoS roles have been totally different, yet both were based on the same foundation.

  • I love to connect them with other Chiefs in similar fields or send them an article. And if they get scared and decide to pursue another route? Great! I just saved them heartache.

If you’re interested in the role, I encourage you to reach out. Seriously! I love to talk about this topic. But in preparation for our conversation, here are a few common questions I get asked:

What did I do before becoming a Chief of Staff?

The short version is that I was a happy generalist with a variety of titles. I have consistently pursued roles that rewarded curiosity and horizontal growth. I’ve strategically  approached in growth mode, with fuzzy 5-year plans, who needed people who could grow with them wherever and however they grew. More often than not, these jobs were described as ones that required people to “wear many hats”. This is the type of work I most love to do and it just so happened to have trained me well to be a Chief of Staff

What did other people do before becoming a Chief of Staff?

We’re all different, and you should talk to as many of us as possible (I’d be happy to make some introductions). Some common themes include: pursuing a new, loosely defined opportunity at one’s existing company, pitching a CXO to create the role, and discovering the opportunity through patient research.

How did I find my Chief of Staff jobs?

Through conversations. I knew that I wanted to remain a happy generalist and I knew that I wanted to be closely aligned with my next company’s values and mission. The Chief of Staff role is often all-consuming. I want to feel good about how I’m investing my time and I knew that I would need the natural energy that comes from supporting a cause you believe in.

I connected with as many people as possible in and around the Chicago tech community (one of my criteria). I wanted to hone my pitch and to get recommendations about companies from people in the know.

What can I do to help a future Chief of Staff?

I always offer to make intros or invite them to a local meet up, or at the bare minimum send them to the resource page I built out for this very reason so they can continue to read up on the role. I encourage them to keep talking and exploring, even inside their current organization

We’re all standing on other people’s shoulders, whether we acknowledge it or not, so I like to do my part to reward the folks who reach out to learn and gain an edge. I always ask in return that they pay it forward a few years down the line.

So, what do you want to know about the Chief of Staff role?

Despite what you might be assuming, I absolutely love these conversations! Yes, I might ask you to chat before/after business hours, or if you want to meet up in Chicago, it’ll be in the 7 am hour at a coffee shop on my way to work. But, if you make the time to come out or connect during your personal time, I promise to make it a great use of your time.

Alicia Diamond