Created

Jan 19, 2023 8:01 PM

The best part of their role was exposure to their executive

“But my favorite part of the job was the late night 1:1 conversations with Reid like the one on the plane from Vegas, where I offered my best candid advice on whatever was on his mind and where I did my best impression of a consigliore-cum-interlocutor as he ruminated on the small and big questions animating his life.” — Ben Casnocha, ex-CoS to Reid Hoffman (from 10,000 Hours with Reid Hoffman)“You get front row seats to growing a company and are a thought partner on major company decisions. You learn how to be an operator / CEO / COO and get a crash course on all aspects of running a business. If you don’t know what you enjoy, it’s a great way to get exposure to every biz function to find out what you like.” — CoS at a high-growth startup“It’s essentially an ‘IC-CEO’ role. You get to work on some really interesting problems and learn first-hand what it’s like to be CEO of a start-up.” — Philip Sorensen, CoS at Nova Credit

Other things CoS said they loved about their roles

CoS loved — the “control tower” visibility they get

“You get to be inside the control tower at the business. You’re not in charge, but you have the broadest view of the entire machine in action, and you’re uniquely positioned to connect the dots across different functions.” — Simon de Jesus Rodrigues, CoS at Curio“Visibility at the highest levels of the company. “ — CoS at 2000 person software company“Having a bird’s eye view as well as worm’s eye view on the organisation.” — CoS at early-stage startup

CoS loved — working on “company-defining” projects

“Variety, breadth, pace of learning, visibility, connections to senior leadership, exposure to company-wide important projects” — CoS at one of the largest companies in the world

CoS loved — having no “typical day”

“I loved that my job was constantly changing — I was always working on something new. Also, I loved getting to spend time with people all across the organization.” David Burt, ex- CoS @ The Atlantic“Getting to touch all the parts of a business, being a mini-CEO, different projects everyday.” — CoS of high-profile sports media company“Ability to have visibility into roles that typically require 10+ years experience, as well as never having a “typical day”

CoS loved — the opportunity for “Leveraged learning”

Sachin Rekhi defines “leverage learning” not by learning by doing yourself, but ultimately learnings from other people’s doing. There’s a lot of leverage learning in the CoS role from how others operate.

“It’s a continuous learning experience, the type that no other role or education program could provide.” — Saumil Shah, CoS at Arm

Being a Chief of Staff can be lonely

“It can be a lonely role! Building a CoS community is crucial to feeling supported in your role.”

“Being a leader can be lonely. Especially for a role like CoS where you are privy to your CEO and President’s thoughts about almost everything. You may not have direct peers and your job is to help shepherd your leaders and you company to achieve your strategic goals. I have been lucky to be surrounded by a team of incredible leaders who understand and support my role as CoS.” — Danika Dougherty, Chief of Staff at Digital Diagnostics

CoS found hard the lack of definition

“The role can be totally undefined by the principal, leaving the person with little to do, or it could become a glorified executive assistant, or it could be a roving project manager, or it could become a bottleneck gatekeeper, or it could be a second-guesser of strategies. I’ve seen all of these iterations.” — Adam Kovacevich in “Chiefs of Staff Are Necessary for Politics, But Not Always Great for Companies”

“How to push back and define my scope for others to respect it.” — CoS at one of the largest companies in the world”

“That there isn’t a clear agenda for things that need to get done. There is a lot of self prioritization.” — CoS at Series B startup

CoS found it hard to have boundaries

“Managing workload. Because my CoS role flexes to many areas of the organization, I don’t have the same boundaries that department leaders do. Sometimes I find myself signing up for more than I realistically can do.” — Danika Dougherty, Chief of Staff at Digital Diagnostics“Learning how to balance the boss / coachee relationship, including when to push back, when to bring feedback and when to lean into her priorities.” — Meghan Kiesel, CoS @ Cisco

What CoS found it hard to load balance

“Work tends to come in batches, so some weeks are intense. Also related, this is particularly relevant for people coming straight from IC roles, you need to learn how to outsource effectively.” — Philip Sorensen, CoS at Nova Credit

More CoS were hired internally than externally

Given that the role is intensely relationship-driven, it’s not surprising that more Chiefs of Staff were hired internally than externally. What surprised me is not by much. One reason could be that smaller companies are hiring for a CoS role but don’t have someone to fill it internally.

“It was initially set as an interim 6-month gig since neither of us knew exactly what I would be doing. It turned into two years. We picked “Chief of Staff” as the job title, even though there was no staff to be chief of yet and even though it’s a title that means different things in different contexts.” — Ben Casnocha, ex-CoS to Reid Hoffman (from 10,000 Hours with Reid Hoffman)

How Chiefs of Staff created the role by “pitching it” internally

“As we’ve started to scale, I asked the GP if I could transition into a CoS role which he said no. I convinced him to let me run a 6 week trial of my doing the CoS role.” — Sibi, CoS @ Earnest Capital“I pitched the role to the CEO in 2014 when I was joining the company of (5). The role wasn’t very prominent in early/growth stage companies and we didn’t have a great understanding of how to define the position, especially at such a new business. We continued to revisit it over the next 2 years as the company grew along with my responsibilities in fundraising, internal comms and other strategic projects that were important to my CEO. As we neared 100 employees, those duties helping to scale the company started to really align with our vision for the Chief of Staff role. We wrote the first (of many) job descriptions and made the role official” — Scott Amenta, ex-CoS @ Spring“I made a lateral move from VP Marketing to CoS. There was overlap between me and the VP Growth, and we needed someone to take on the “special project” and operational work (HR, legal, finance, etc) to relieve pressure on the COO. I’d expressed an interest early after joining in a CoS role, and when the timing was right we mutually agreed to make that transition.” — Megan Wheeler, CoS @ Moves Financial

Creating leverage is the meta-responsibility of the role

Executives have limited time and teams have limited resources which puts a cap on their productivity. Chiefs of Staff amplify an executive or team’s efforts and decisions.

“Give leverage to CEO, coordinate projects to completion (not always owning them), owning strategic projects as an extension of the CEO’s and CFO’s offices. Zig one day, zag another.” — CoS at Unicorn Company

Strategic prioritization, serving as an “information exchange” and “do what needs to be done” projects are main responsibilities

Main CoS responsibilities — Being a strategic prioritization compass

As organisations scale, more priorities compete for the exec’s time. More people, more emails, more projects. They just get more of everything. This pattern applies to CoS roles where a CoS serves a company as well — more priorities compete for the company’s limited resources. Chiefs of Staff serve as a prioritization compass ensuring that resources get directed towards the right priorities.

“I helped conceive, build up, and then run a new organization to amplify and extend Reid Hoffman’s strategic priorities. Working out of the LinkedIn and Greylock offices for almost two years, as Chief of Staff I was involved in many of the decisions Reid made across the different areas of his work: LinkedIn (where he’s co-founder/executive chairman), Greylock (the venture capital firm where he’s a partner), his philanthropic work, assorted public intellectual projects, and political/civic initiatives. I also strategized and executed new, proactive initiatives to increase Reid’s impact in Silicon Valley, Washington D.C., and beyond.” — Ben Casnocha, ex-CoS to Reid Hoffman (from 10,000 Hours with Reid Hoffman)”“Manage priorities: do calendar audits, review and synthesize metrics/ initiatives to support company priority setting.” — Julia DeWahl, Ex-Chief of Staff to the CEO at Opendoor, The Chief of Staff role in Silicon Valley“I also help prioritize the team’s efforts as needed (top-level strategy set by the GP), bring the team together to lead All-Hands meetings, track our KPIs to identify progress, and a bit more (we’re a startup so we all do a lot!).” — Sibi, CoS @ Earnest Capital

Main CoS responsibilities — Serving as an information exchange

Executives attend a lot of meetings — internal meetings, pitch meetings, board meetings. Chiefs of Staff serve as an information exchange taking in inputs from what’s really going on in the business, helping executives make better decisions and creating outputs to communicate those decisions.

“1. Great communication skills: Much of what you’ll do is acting as an ‘exchange’ for information.2. Great interpersonal skills: You’ll most likely work with _a lot_ of people. It’s important you can build trusted relationships with them efficiently. 3. General business analysis skills: It’s helpful to know how to put a good deck or memo together, build a financial model or do data analysis with SQL. That way, you can take the first cut at certain tasks before sending it on to the respective team(s).” — Philip Sorensen, CoS at Nova Credit“Preparing board materials and strategy session decks for the CEO for meetings with the management committee and advisory board, preparing CEO for external speaking engagements (World Economic Forum, conferences, business school classes) as well as internal speaking engagements (investor meetings, firmwide town hall meetings, etc.), researching trends and key themes for the CEO related to the private equity space as well as investment themes of important” — CoS @ top growth-equity fund“The literal title Chief of Staff can be deceiving, as Chiefs of Staff in most contexts aren’t managing any staff directly. However, one of the primary functions of a CoS, having developed strong relationships with key stakeholders, is to be a conduit of information across teams. This might take the form of developing company-wide OKRs and getting buy-in and support for the processes or running point on cross-functional projects that require 3 or more teams with no clear leader. In both instances the CoS supports the organization by freeing information bottlenecks, helping quickly growing teams get visibility outside their functional silos. — Scott Amenta, ex-CoS @ Spring“Oversee staff/internal operations: prepare agendas, take notes, and assign action items at weekly staff meetings, manage the OKR and annual planning processes, support with board meeting prep…” — Julia DeWahl, Ex-Chief of Staff to the CEO at Opendoor, The Chief of Staff role in Silicon Valley

Main CoS responsibilities — “Do what needs to be done” special projects

Special projects are a catch-all term for saying doing whatever needs to be done.

Here’s Megan Wheeler again, “I love the variety. I manage compliance, which is very precise and important due to the legal implications of not being compliant. So there’s a certain amount of stress around managing that. But then I can do something like work with my Office Manager on planning a fun activity for employees, because I also oversee that function. So it’s a mixed bag of strategy and execution, high importance/risk and low importance/risk.”“Spearhead special projects: lead a metrics overhaul, do customer research on an adjacent business opportunity, run an acquisition process, lead the search for an executive hire.” — Julia DeWahl, Ex-Chief of Staff to the CEO at Opendoor, The Chief of Staff role in Silicon Valley

“Master generalists” succeed in the role

“You need the ability to be a “Master Generalist to succeed in the role.”

“Take care of all the big things and little things that need to get done, but that aren’t exactly anybody’s job. Strategy, prioritization, and execution are key.” — Megan Wheeler, CoS at Moves Financial

Caveat: there is no instruction manual for being a CoS

“There is no instruction manual for being a CoS — a lot of it depends on your relationship with the person you are a CoS for and how well you know how they work, how they think, what they are most focused on and prioritize. “ — CoS @ top growth-equity fund

Other qualities of successful Chiefs of Staff

Successful Chiefs of Staff are not “credit-seeking”

“Be humble but confident — your role is NOT to be the star of the show, but rather to help the stars (especially the CEO) shine.” — Megan Wheeler, CoS at Moves Financial

Successful Chiefs of Staff are “Infinite learners”

CoS learn by doing, but they learn even more by other people’s doing.

“Ability to figure it out (both intellectual strength and curiosity to learn a broad range of information AND working independently/autonomously/without guidance to do so).” — CoS at 100 person Series B companyHave the foresight to get things done before anyone else thinks of doing them. Be a self-sufficient learner who makes it easy for colleagues to be self-sufficient — eg, keep on top of comms so employees know where to find information without needing to ask. — Megan Wheeler, CoS at Moves Financial

Successful Chiefs of Staff are trustworthy

“The other is trust — everyone at the organization needs to trust you otherwise you cannot be effective at your job.” — CoS at 100 person Series B company“One of the most important qualities in a Chief of Staff is trustworthiness. If a CEO feels like she can trust her CoS, then a whole new level to the relationship is unlocked. The CEO now has a person she can let her guard down around and get honest feedback from, and, in return, the Chief of Staff often gets a mentor for life.” — Ali Rohde, CoS at an early-stage YC startup

Successful Chiefs of Staff are able to switch context rapidly

When my CEO decided to pivot the company, she was glad I was there to help execute the pivot, but nervous it would be too much stress to put on me. I told her not to worry — that, just like there were wartime CEOs (https://a16z.com/2011/04/14/peacetime-ceowartime-ceo-2/), there were also wartime Chiefs of Staff. That immediately put her at ease — instead of adding to her stress, I was able to show her that I could be a steady partner and take some of the stress off her plate.” — Ali Rohde, CoS at an early-stage YC startup“Be comfortable with rapid context switching, variety and fast pace of the role.” — Megan Wheeler, CoS at Moves Financial

Successful Chiefs of Staff have foresight

“Have the foresight to get things done before anyone else thinks of doing them.” — Megan Wheeler, CoS at Moves Financial1. Be proactive. Don’t wait until things break; get ahead of them. 2. Think for the next 10x today. What happens if the company gets 10x more employees, more products, more anything? Are you ready to support that growth? Be prepared. 3. Over-communicate.” — Sibi, CoS @ Earnest Capital

Going into the role, Chiefs of Staff wish they had…a vision for the type CoS they want to be

“You should have some type of vision of what type of CoS you want to be — be that strategic, operational, HR/People, etc. The role is so nebulous that you need to understand what your strengths are, how you can be most useful, and most importantly, what you’re not going to do. It’s super important that your vision of your role and your principal’s expectations of you are closely aligned. It’s a role that is extremely susceptible to scope creep, which means you need to have periodic (at least quarterly, if not monthly) frank discussions about your allocation. It’s a choose-your-own-adventure type of role, which is both a big opportunity and a big responsibility. — Simon de Jesus Rodrigues, CoS at Curio

Chiefs of Staff wish they had — a clear growth plan in the role

“I wish I had a clear growth plan for my role - often, the need for a CoS comes about when the executive needs additional support on a specific set of processes, tasks, or projects. Once those responsibilities are under control- what other responsibilities is the executive comfortable with handing over and how do those align with the skills you want to develop?” — ex-Chief of Staff at 8000 person company

Chiefs of Staff wish they had — aligned the role with where they want to go with their career

“There are all kinds of Chiefs of Staff roles. Make sure you do your diligence on what the role entails — ask where it sits on the spectrum of Executive Assistant to COO. Try to understand why the company is hiring a Chief of Staff and make sure it aligns with what you want to grow in your career. Try every business function to see what you like, what you’re good at, and what you prefer not doing.” — Chief of Staff at High Growth Startup

Chiefs of Staff wish they had — an exit plan

“To think clearly about the succession and exit plan — I always knew it wasnt a role that has a direct next step, but that doesnt mean working out the next step right now is any easier” — Max Bray, CoS @ Founders Forum“Being a CoS is a point in time — you will go on to do something else afterwards — spend the time gaining skill sets, working on projects, that round out your capabilities and make you a stronger and more compelling candidate for the future role you’re after.” — CoS at 100+ person finance company

Chief of Staffs came from a range of seniority levels

High-pressure experiences prepared CoS well for the role, but they didn’t all come from previous jobs

“Personally, buying and maintaining a home from a young age on my own taught me prioritization and responsibility. Running a home + keeping up a personal life + plus having a job when it’s just you means you’re responsible for everything and can’t rely on anyone else. You can’t let things slip (eg, eating food and a leaking roof are both immediate needs but with different impacts).” — Megan Wheeler, CoS @ Moves Financial“ Prior demanding work environments. Relentless focus on details and producing an A+ quality work product. I served in the Peace Corps which taught me how to be flexible and maintain composure in stressful and challenging situations of all varieties.” — Marcelo Andrade, CoS @ SmartBiz Loans“Previously I worked in corporate strategy, which helped me in the chief of staff role as I tried to come up with frameworks for decisions.” — David Burt, ex- CoS @ The Atlantic“Banking — high pressure and detail oriented nature of the work probably gave me the best work ethic but I think the best experience that prepared me is sitting in and observing partner-led meetings where decision making and questions were being made led me to learn what these senior people are most focused on. You should listen 3x as much as you talk and active listening is an important life skill.” — CoS @ top growth-equity fund

State of Chief of Staff in Tech — 2021