Why Chief of Staff?

I frequently get asked why I am drawn to startups and why I choose to specifically work in this role. I didn’t really choose this role or path, as much as I kept integrating things into my life that felt natural and allowed me to step into work that energizes me.

Having experienced the value of the CoS/founder partnership, I’m a huge advocate for both founders and the generalist-CoS-types who can find great success and fulfillment through it. Here, I’ll share a little of my personal experience. Eventually, I may build out more comprehensive resources.

Why I personally love the role (and why you might too!)…

This is the first role that I’ve ever been in that has put me into a near constant flow state. I credit this to the adaptive nature of the role and the wide variety of tasks that keep me just at the edge of my capabilities.

One of the things I appreciate most is that there is a good balance of strategy, implementation, and relationship building. As it turns out, this is a valuable and complementary asset for founder-like people who produce a lot of unstructured ideas and relationships, without the time or discipline to manage everything downstream of that.

For better or worse, I am a generalist and enjoy having a lot of breadth to my role. This may be a byproduct of having been in the startup world for so long, but I think the startup environment is what pulled me toward it. I’m always searching for the place where I can be upstream of as many issues as possible, so I can do something about the issues and opportunities I see. I also work best in long-term, partnership type of roles, where I can really get to know the people I’m working closest to and use my strengths to support their effectiveness. This role checks those big boxes, along with many others.

Some people call Chiefs of Staff “gatekeepers” but I intentionally do not use this word with my team or when talking about the role, as I don’t like the message that it sends. Yes, the role is about protecting the time of another person, but the goal shouldn’t be to shut people out and keep them away.

I’ve always seen my role as more of an traffic controller or conductor. I’m trying to make sure all the parts are moving and getting where they need to go and, yes, that means redirecting a lot of things. Maybe I’m being too pedantic but I see this term used frequently in the CoS/LinkedIn community and it just feels icky to me.

When people reach out to me asking how to become a Chief of Staff or hire one, I always say that one of the beautiful things about the role is that it never looks the same. It is a highly adaptive role shaped around the needs of the person or people it supports. This is why it’s notoriously difficult to find a good match. These roles and the people who fill them tend to be shaped in very unique ways. This is true of most people, but it’s more pronounced in these support-oriented roles.

Whether you’re seeking a role as a CoS or you are a founder who is looking for a great person to support you, the most important thing you can do is take the time to really understand the alignment and nuances in values, skillset, needs, and personality. Assuming skills and values alignment, also ask yourself:

• Would I want to be around this person? Every day?

• Does this person seem like the kind of person I can respect and trust?

• Do we communicate in a natural, unforced way? Does our energy flow easily?

• Do they inspire me? Do I think I can learn from them?

In my own career, as well as when hiring others, my mantra is: if it’s not a “hell yes!” (on both sides) then it’s a NO.

This assessment can be difficult when you’re under the constraints of a hiring process, but make the time to walk this process thoughtfully, and be honest about how you feel at each stage. If there are hesitations, don’t underestimate them, and be honest with yourself and the other person about where you are feeling that tension.

If you’re hiring for this role: you can find training online to help you suss out skills and defeat bias in the hiring process. These things are important, but so is your gut feeling. Your body can tell you things that your brain cannot make sense of. Listen to that. Every single time I’ve overridden my intuition, I’ve regretted it. And, conversely, when I’ve listened to my gut, I generally do not regret it.