How to Scale Yourself as a Chief of Staff

The Chief of Staff role is a newer concept to the world of business. In just a short time, it has become a very powerful role. The variations in how companies are using this role, and more specifically, how individuals are using this role for professional development, are really interesting to see. During our summit, we talked with leaders about how they navigate their personal growth journeys—both growing into the CoS role and growing beyond the CoS role.

Andrea Geroldi, Chief of Staff at Rising Tide Capital, started out the discussion by highlighting the natural dichotomy in the CoS role. She pointed out that the Chief of Staff role can be rotational for some and much more long-term for others. While the notion of this role is transitionary—helping growing companies navigate big changes, it doesn’t have to be something that you leave.

Whether you’re in it for the moment or here for the long haul, the key to success in the CoS role is having a purpose and a plan. Andrea says that the best thing you can do is to be strategic. Figure out what you want from the position and work towards that. Be vigilant about your priorities and avoid taking on too much. With all the ambiguity in the CoS role, it can be very easy to pile things on. If you don’t have a direction, you may feel compelled to prove your worth by accepting ownership of everything that comes your way. According to Andrea, that’s the biggest mistake that new leaders make as Chief of Staff.

How to Define your Leadership Strategy

A leadership strategy defines your personal approach to leadership. It provides structure and direction for your career and the opportunities that you accept along the way. The CoS role can be chaotic in some organizations simply because of the lack of structure. Getting clear on your professional goals is one way to balance that.

Here are a few actionable steps that will get you started:

  • Understand what makes a great leader and identify the styles and traits that you want to emulate.
  • Take a self-assessment to understand your current skill level, strengths and weaknesses. Absolutely do not skip this step—we often feel much more self-aware than we truly are.
  • Write a personal vision statement.
  • Invite feedback from others—find out what they see in you and consider how that information fits into your professional plan.
  • Get clear on your priorities and your boundaries—as Andrea said in our panel, proceed with caution. Don’t take on too much. Be strategic about which opportunities you embrace and which ones you politely decline.

Five Steps for Transitioning to a Chief of Staff Role

Transitioning to a Chief of Staff role can be challenging. It’s a new role, but more often than not, there isn’t a clear idea for what purpose that role serves. Eleazar Orellana, Operations Leader for Global Accounts at Amazon Web Services and a former CoS at Visa, shared his easy-to-replicate process for getting into the swing of things.

  1. Remove Invisible Roadblocks
  2. Embrace Day One Culture
  3. Know your Endgame
  4. Ruthlessly Prioritize to Achieve your Endgame
  5. Wash. Rinse. Repeat.

Remove Invisible Roadblocks

The first stumbling block that most new CoS encounter is the freedom of ambiguity. With a lack of structure for their new position, some simply don’t know where to begin. They fall victim to ineffectiveness simply because they aren’t comfortable with the lack of structure. Eleazar says that removing invisible roadblocks helps you get in the right frame of mind for purposeful action.

What is an invisible roadblock? We’re talking about erasing the mental mind tricks of our assumptions and bias. The CoS role is literally an opportunity to break the mold and do things differently. But you’ll have to work hard to remove invisible barriers within yourself and within your team. Here are a few tips:

  • Recognize resistance and counter it with a ‘what if’ approach.
  • Understand how people deal with change and get good at identifying the ‘What’s in it for me” in each situation to help ease the transition.
  • Empower others to be an active part of creating change.

Eleazar says that the transition to a CoS role is about going from doing something to empowering other people to do that thing.

Embrace Day One Culture

Borrowing a trick that he picked up at Amazon, Eleazar promotes the idea of Day One Culture as a pivotal step in transitioning to the Chief of Staff role. In short, it’s a culture built around an operating model that puts customers at the center of every action, decision, goal, and priority within the organization.

Former Amazon CEO Jeff Bezos wrote a now-famous 1997 letter to shareholders boldly announcing that his new operational model would revolutionize the internet. Now, more than 20 years later, we recognize that Amazon’s business model was widely successful, crediting a lot of that success to this Day One Culture approach. Now, it’s time for other companies to take notice and adopt some of these same strategies.

The principles of Day One Culture include:

  • Make your customers your top priority.
  • Focus on high-quality, high-velocity decisions.
  • Don’t be afraid to try new things—experiment, accept failure, but keep trying.
  • Focus on growth and innovation simultaneously.
  • Prioritize long-term, sustained value over short-term wins.
  • Build small, diverse teams with agile capabilities.

Know Your Endgame

This is another way of saying that you need to be strategic. Keep one eye on where you’re going and the other on how you’re getting there. Some of the first steps you will take as a CoS should be planned and deliberate.

  • Map out the organization and begin strategically networking, building the relationships that you will need to get to your endgame.
  • Figure out what you like (and what you don’t.)
  • Leverage your newfound exposure to develop an executive mindset.

Here are a couple of examples that illustrate how the same position can take different approaches based on the goal the individual is trying to accomplish.

The first individual worked in a healthcare startup. Their CoS duties were about 20% process-oriented, 10% people-oriented, and 70% business development-oriented. This individual spent the most time co-owning strategic and competitive initiatives that directly grew the business. This experience leads this individual to transition from the CoS role to start their own successful business and then eventually become a senior-level strategist for other startups.

The same CoS role at a major retailer was held by someone with a strong passion for working with people. This CoS spent about 30% of their time on process-oriented activities like overseeing financial reviews, 50% of their time on people-oriented activities with a hands-on approach towards the Ceo's most important day-to-day issues. And the remaining 20% of their time was dedicated towards business growth and portfolio management. This broad and balanced approach to touching all areas of the organization helped this individual transition into a senior product and strategy role at the same company.

Shanaz Chowdhery, former CoS at Vemo Education, says that the CoS role “is great because you can lean into any direction and learn anything you want. It’s almost like getting an MBA. But, it’s not always perfect because you can get thrown into projects that might not work out.”

Ruthlessly Prioritize to Achieve Your Endgame

As we’ve mentioned before, there is a lot of complexity in growing a new company. The very reason that the CoS role has become a vital component of the executive office in these startups is to help manage that complexity. But it can be a double-edged sword.

While there is plenty of opportunities to define your own path, it can be easy to get lost in the fast-pace of change going on around you. It’s not enough to have a plan or an endgame in mind. In the CoS role, you’ll be pulled a million different directions. In order to survive it—and ultimately to succeed at it, you need clear priorities and great boundaries.

You’ll need to work with your CEO to find a balance between opportunities that help the organization and opportunities that help you achieve your personal career goals. The process of breaking down barriers, defining your path, and keeping up the momentum of the day one mindset is a continual process. Whether you stay in the CoS role for a year or you make it a long-term commitment, this process never ends.

Find a community of support for your professional development with the Chief of Staff Network. Join CoSN today for networking, mentorship, and targeted growth opportunities.

How to Amplify Team Performance and Win as a Chief of Staff

The freedom and flexibility of the Chief of Staff role comes with a great amount of responsibility. It’s possibly more important for you to have highly-visible wins than anyone else in the company because you get the freedom to pursue the path that you want.

Shanaz shared his secret for creating big wins by being a high-profile, empathetic leader. He said that the first step is to understand the pain points and dynamics within the executive leadership team. As a fresh face with access to the executive team, you get the benefit of an outside perspective.

Look at what is looking well and what isn’t working as well. When you find a problem, show up and be the hero to help them get down in the trenches and fix it. Shanaz said he would often do deep dives into individual functions and look for opportunities where he saw a lack of cultural building, a lack of delegation, or a lack of clear direction or strategy.

Eleazar added that, “beyond fixing problems and removing things on a to-do-list, you should aim to operationalize them.” It’s not enough to fix a problem now; you need to prevent that problem from reoccurring by addressing the defect in workflows and processes.

If you’re new to the CoS role, try to get that first highly-visible win within your first 90 days. It’s a really important accomplishment to make sure that you reinforce your executive leadership's beliefs in your potential.

Building for the Future, What Comes Next After the CoS Role

Your success in the CoS role ultimately depends on your clarity about your future. Knowing what you want to do next or being actively engaged in figuring that out is how you will give your role meaningful direction.

Eleazar said that “when you start that first role, you need to set the tone with your boss. Aim to have one or two ideas of where you could take the CoS role within the next twelve to eighteen months.” It doesn’t have to be a concrete plan; the idea is to have a direction that provides some structure that both you and your CEO and embrace because a ‘jack-of-all-trades problems solver’ sounds like a cool title, but probably isn’t.

At the end of the day, the CoS role isn’t about merely being a problem-solver. While you’ll do plenty of that, it’s really about greasing the wheels and being a problem preventer. The exposure to all the different areas of an organization is a gold mine for developing your career.

All the CoS’s that we spoke to at the summit agree—the opportunity to get hands-on exposure to all the different areas of a business and being a key force in shaping how the organization grows is the best part about the job. Eleazar says there is no better way to learn how to manage ambiguity—a skill that will become increasingly useful as technology changes the world.

The most common next steps for the CoS is to transition into an executive role managing people or operations, like a Head of Operations. But that path isn’t set in stone. The CoS opens the door to almost any future you could imagine—CEO, strategist, venture capitalist, and beyond.

The Takeaway on Scaling Yourself as a CoS

The underlying message of our panel discussion on scaling yourself as a CoS is that you need a plan. The CoS position is so undefined that it’s imperative you bring some structure to your position. This isn’t the sort of thing that you’re going to sit back and wait to be told what you’re doing. A CoS role is very hands-on. You need to choose your own path and then work together with your boss to structure your time so that you get hands-on experience in the areas that will be the most beneficial.

Create your own path with the inspiration and support of a community of peers. Join CoSN today to connect with a like-minded network of modern executives.

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