I’ve been in a Chief of Staff role at a private company for a year now. It’s a tricky role to navigate, and like any role, comes with pros and cons.
- Pro: I work closely with the CFO in a lot of areas.
- Con: Sometimes I feel like I’m pinballed into various tasks.
- Pro: No two days are alike.
- Con: Nights and weekends can get hijacked.
- Pro: I’m privy to most senior leadership information.
- Con: Just because I can see The Table doesn’t mean I have a seat at it.
The biggest con I’ve been facing lately is existential career angst. How am I doing? Where am I going? What skills am I building? The hardest part about being a generalist is the desire for mastery in a team full of specialists. Mastery implies depth, and I’ve always considered depth a measure of impact. But then I read David Hoang’s account of talking to primary care providers—generalists in the healthcare industry—and their broader range of patient care.1
No one can deny the impact of primary care providers. They’re typically the first people we see when we have a health issue. If the issue is beyond their skillset, they’ll refer us to a specialist. But most times, the primary care provider is sufficient. Their broad range is what ultimately allows them to serve more people. Similarly, the impact of a Chief of Staff can extend far beyond the nucleus of our team or department.
Breadth doesn’t have to mean a lack of mastery either, but it does mean reframing our role to consider what mastery as a generalist looks like— some PCPs are better than others, and the same goes for Chiefs of Staff. Ultimately, I’ve found it helpful to view the Chief of Staff role as an apprenticeship. The craft is service.
Service is a form of leadership, whether it’s serving our customers, our teams, or the organization’s mission. Chiefs of Staff can leverage the close working relationship we have with organizational leaders to grow as a Chief of Service. I’ve learned more from observation and feedback than I have from any book or blog post just by being in the trenches day after day with my boss.
On the flip side, Chiefs of Staff are uniquely positioned to serve the person serving everybody else. It’s like a positive feedback loop that multiplies our principals’ impact and shines a light on the impact we can make as their Chief of Staff.
How do we better serve the person serving everybody else? Here’s the most important way: show up.
I remember one week I got a phone call in the middle of an evening workout.
“Phil, I need your help. I need you to tee up Bryce and Chad for me in 20 minutes.”2
I usually keep my phone on loud in case of emergencies, but damn. Now, really? I was pacing up and down the floor like a guy that took too much pre-workout but didn’t know what machine he wanted to use. I called Bryce and explained the urgency— we were up against the clock on a lot of things, but this was the 11th hour. He agreed to make himself available and said he’d get Chad as well. I put my phone away, powdered white from the lifting chalk on my hands, and packed up to schedule the Zoom.
If we’re not there, we can’t serve. This doesn’t mean showing up for the job. Attendance on the job is table stakes. It means showing up when it counts. Showing up when it counts is hard to do because it often butts up against what we actually want to do in the moment. Showing up when it counts means showing up for someone else when it matters. We all know the moments that matter.
Another simple way to improve our service is by reducing Friction. Friction is that hidden force that keeps things from getting done.3 It’s usually created from one of two things: a lack of initiative, or weak connective tissue within an organization.
If our boss has to consistently follow up to make sure something gets done, there’s Friction. If someone in finance is dealing with a problem that could be solved with someone from operations, but the working relationship just isn’t there to pick up the phone and call, there’s Friction. So Chiefs of Staff can reduce Friction by simply doing The Thing without being told to do The Thing, or by having good working relationships to act as a conduit between teams. Keep this in mind, too: you don’t have to know The Thing to get it done, but if you can get the person who knows The Thing to get it done, that’s good service.
Reducing Friction is simple, but not easy. It’s like working out— we all know we need to go to the gym and eat healthier, but unless we build habits or systems, we’re relying on discipline, which comes and goes. I’ve found that daily huddles with colleagues are a great way to promote initiative. State your big win for the day, ask people what concerns they have, and problem solve as a team. Spend 10-15 minutes max.
Try to meet colleagues in person, too. Especially colleagues on different teams. I’m no social scientist, but one in-person interaction is probably worth more than twenty video calls. My company is remote-first, but many early employees lived together to work on-site. As we started hiring more remote folks, we decided to throw an in-person retreat so people didn’t feel disconnected from the action happening on-site. People at my company still bring up our first retreat over a year later with those who attended.
A third way to improve our service is to reinforce. Leaders are foundations for the rest of the organization, like concrete to a building. But did you know that concrete on its own can easily break when cracked? A single crack will compromise the integrity of the whole. It’s a weakness that limited concrete’s use for a long time, but then we discovered reinforced concrete.
Reinforced concrete is two materials in one: concrete and steel. The steel is used as an inner skeleton that can absorb tension. Together, they can withstand greater varieties of stress. Steel transformed concrete into a building material that can be used not just as the foundation for a house, but also as its floors, walls, and roof.
Chiefs of Staff transform their principals into reinforced concrete. We can do this in a variety of ways because stress—and our response to it—can come in a variety of forms, but a good general purpose tool is empathy. What might this person be feeling right now? What concerns or fears might be inducing tension? Reggie Love, former aide to Barack Obama, used to check in on the former President just to make sure he ate three meals a day. And while it might seem trivial to ask my boss, “Hey, have you, like, eaten lunch yet?” I don’t think I’d be a great Chief of Service if I can’t even help him get past Maslow’s first level of needs.
If you’re still on the fence about practicing “service”, I’ll leave you with this quote from Niko Canner at Incandescent:
“Deliberate practice is an opportunity for intentionality and creativity. The intentionality of having a fine-grained focus for one’s practice constitutes its deliberate quality. The creativity required to turn our ordinary “episodes of doing” into opportunities for practice enables us to reach the next level of mastery – much sooner than we might otherwise.”“Always Be Practicing Something“
While service might seem like just another ordinary “episode of doing”, maybe we’re just not giving it the attention it deserves.
So show up. Reduce Friction. Reinforce.4
These are just a few service-minded behaviors that we can practice during our “apprenticeship” to become better Chiefs of Staff.
When does our apprenticeship end? I think the more valuable question is: When does one become a leader? Which is not a question that we should feel compelled to answer— in the end, leaders are defined by the people they serve.
 While I have to credit Robert Greene for inspiring the apprenticeship idea, it made me really excited to see I was not the only one thinking about mastery for generalists. Here’s David Hoang’s essay (now only for paid subscribers).
 While Bryce and Chad are real people, their names were changed for privacy.
 For more on Friction, I highly recommend Shane Parrish’s article here.
 Maybe one day I’ll think of a third “R” word to make these behaviors catchier and more memorable. In the meantime, apologies go to my editor. Sorry, Minnow.
Thank you to Minnow, Anthony, Lyle, and Steven for editing. Thank you to Jackie, Sean, Iavanya, and Dominique for sharing your stories as fellow Chiefs of Staff and contributing to the ideas in this essay.
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