So you want to be a chief of staff…

Almost two months ago, I moved into a new role as Operations Manager for our Infrastructure organization (the Chief of Staff title was off limits for various weird reasons). It’s my third stint as a CoS, having served 2 years at Amazon and not quite a year at Twitter in the same role. Historically, it’s been both my favorite , and most stressful & frustrating, job. I’ve had to re-learn the role for every environment, and it’s rare when the same challenges appear a second time.

I recently read Chief of Staff… by Tyler Parris. He’s managed to synthesize a good deal of the benefits, roles & responsibilities, and strategic advantages to hiring a CoS. It’s a great book, and I wholeheartedly recommend it. But it’s written from the Executive’s point of view. I’m still looking for a book describing what an ideal CoS experience should look and feel like from the candidate’s perspective. This is my take at the most important aspects that people don’t tell you about the role.

The Definition

Parris does a great job at the basic description: a chief of staff is a catch-all role, filled by someone with exceptional organizational and people skills, who handles all manner of tasks not covered by an existing member of an executive’s leadership team or administrative staff.

Very succinctly written, and accurate for most CoS roles. Ask someone who’s held the title what they really do, and you’ll receive responses such as, “I herd cats”, “I run the day-to-day”, “I’m essentially a process manager” and “I live in spreadsheets and one-pagers”. A few of the projects I’ve driven at various companies include

• headcount justification and planning processes
• regular reviews of key metrics with various teams
• recruiting process updates, and org-wide education on it
• org-wide communication
• shepherding regular (quarterly/annual) planning cycles

But this role is so much more than projects… or it should be. Most of my job is about relationships, at least when there’s head space for it.

A good CoS is a connector for everyone else in the organization. They maintain a 10,ooo-foot view while they’re tackling the tactical and recognize overlaps in plans, processes, people, and many other facets of a functioning organization. They have access to people and data at all levels and disciplines, and keep at least one ear and one eye open to gauge the temper of the org.

In the right setting, a Chief of Staff is also an extension of the executive they support. They represent the organization in more tactical meetings with the organization’s customers and partners, freeing senior management to focus on juicier, more strategic subjects. My main goal is to make sure that by the time something makes it to my Executive, it’s well-defined and actionable. I’m far from achieving that goal right now, and that fact keeps me up at night, every night. Including weekends. Pleh.

What does it take?

So what does it take to be truly successful in this role? I had the unique experience of observing a couple of Jeff Bezos’ Chiefs of Staff, a 12–18 month rotational position. These were bright, driven individuals who had already gained broad and successful organizational experience. Essentially, Jeff was grooming them for Greater Things.

These people also ran in the background. In the meetings I was a part of (and don’t get me wrong- there weren’t that many… I was a pleb), Jeff’s CoS sat on the periphery, not at the table. They took copious notes and listened intently to everything Jeff said. Even though they were in a position of immense influence and power, it was never about them. They understood they’d been given a rare growth opportunity, and took advantage of the osmosis effect. Then they worked in the shadows to make sure any Jeff Points were addressed quickly & with minimal to no intervention from the boss.

Being a Chief of Staff isn’t about your own power, importance or ego — it’s about doing whatever you can to help your organization and company. Period. If you want this role because you think you’re awesome or just want everything to go your way, please for the love of $deity, do something else.

Okay, so aside from checking your ego at the door, what else should you absolutely have before taking this role? It requires all of the soft skills like staying organized, following through, building relationships, etc. Those are known traits though, and this is a post about what they don’t tell you. Here are the things that I struggle with, wish I had more of, and concentrate on improving every day:

1. Patience. Change is hard. People will push back when they don’t understand something, and most CoS’s are implementing processes and encouraging ideas that people aren’t familiar with. Sometimes the push-back is warranted, sometimes it isn’t. But it’s always exhausting. Get some sleep, kid.
2. Time. This isn’t a 9-to-5 job. So my point about getting sleep is fairly tongue-in-cheek. If the people you support are working around the clock (and most managers in the tech industry are), then you have to keep up to avoid an Endless Backlog. Protecting your personal time is a constant battle.
3. Clear communication skills. This is definitely a struggle for me. Your previous experience won’t necessarily translate to what your Executive or the management team needs or understands. You also need to convey the right sense of urgency per item, and as a CoS, much of what you’re tackling is fairly high priority. Avoiding the Crying Wolf scenario is a very delicate operation. That too takes time, and we’ve already established that’s at a premium.
4. Trust. The CoS position is highly-based on having trust in the people you’re working with. Are they going to deliver on their commits so you don’t have to waste time ‘cat herding’? Are they asking the right clarifying questions so they understand what’s expected of them? Are they prioritizing the right things at the right time? More importantly, success in this role depends on the relationship between the CoS and their Executive. If an Executive doesn’t trust their CoS, then they wind up having a glorified Executive Assistant. Building that trust takes time (egads! time again!), and if you’re supporting an overloaded Exec, it will take far too long to start making measurable progress in the role. Thing is, the Exec probably hired you as their CoS because they were overloaded. #chickenandegg
5. A thick skin. As I said above, you have to have a lot of patience & need to check your ego at the door. I routinely spend hours on some new process or spreadsheet, only to have it picked apart and criticized by what feels like everyone- even after canvassing for feedback from them during the process. It’s very frustrating, and it’s been a part of every CoS role I’ve held. There are days when I’d like to just walk away & find a role where there’s a bit more appreciation and a little less fight-or-flight.
6. Flexibility. The Chief of Staff role is very ill-defined across our industry. What you think are your priorities heading into the position most likely won’t be the priorities a month in. There’s a huge ‘discovery’ ramp; your Executive probably hired you because they needed help uncovering the snakes underneath the rocks. Dealing with the ambiguity, having innumerable conversations to fully understand the challenges, and at the same time making swift progress on somewhat major organizational initiatives (that’s always expected of a CoS) is a huge hurdle in the first 6 months. You have to give it time, which we know is at a premium. (egads! time again!)
7. A short memory. All of the above means that if you’re going to stick with the role, you have to shake off a lot of frustrations almost every day. It’s a requirement to keep most of these to yourself- a good CoS sucks it up for the team, maintains a positive outlook and doggedly makes progress, regardless of the frustrations. I’m halfway breaking the rule with this post, so perhaps we should add “dealing with guilt” to the list. ;)

This doesn’t sound great. Why do it?

1. There are bright spots. There’s nothing like the feeling of hearing, “wow, this is so much clearer” (or easier/better/faster/etc) after you’ve invested so much of yourself on something. Or seeing someone use the data you’ve painstakingly collected and interpreted to make a decision on headcount, hiring, organizational development, or any other facet of their role as a leader. It’s akin to seeing your hard work at childrearing pay off by seeing your kid make Smart Choices, and it’s highly rewarding.
2. Because it’s the right thing to do. If you have the necessary skills & knowledge, and you truly care about organizational efficiency over your own interests, the industry needs you. There are very few people I’ve come across who have that profile. No one’s perfect, but you’re probably more perfect for the job than anyone else in your organization.
3. It’s a massive growth opportunity. Yes, you should be as selfless as possible in the role, but don’t overlook the value to your own career. The exposure to running an organization like a business will stick with you for the rest of your working life.
4. It’s character building. Every time I’ve moved into this role, I’ve felt like I was ready. That I knew what I was doing. That I could approach it as a teaching experience for everyone else who may not have the same background. And every time, I’ve gained at least as much — if not more — knowledge than those I’m supporting.

In Conclusion…

My main points:

1. Being a Chief of Staff is a royal pain in the arse more often than it’s rewarding. You can’t be in it for the ‘glory’, because it’s not glorious. It’s a slog punctuated with some bright spots along the way.
2. Don’t take the role unless you’re in it to make everyone else’s lives better at the expense of your own (usually).
3. It’s highly rewarding, challenging, frustrating. All at the same time. It plays with your emotions, so you have to be pretty strong in your ‘caring’.
4. Given the right partners, it can be the most rewarding role you’ll ever have.