Chief of Staff Coaching: Key to Great Executive Teams
The Chief of Staff role has become increasingly important in the corporate world as more and more companies understand the value of this versatile position. After all, the CoS helps streamline decision-making, drive strategic initiatives, and connect leadership with the entire organization.
However, the Chief of Staff position remains a frequently misunderstood role. One of the main reasons I wrote my book, An Insider’s Perspective on the Chief of Staff, was to help get the word out about what this role truly is (and isn’t). When people hear the term “Chief of Staff,” they should think of a “high-level, senior strategic role,” not a “glorified executive assistant.”
For many Chiefs of Staff, the role can feel like a juggling act, balancing day-to-day operations and high-level strategy with the practicality of executing those strategies. The CoS is an advisor, sounding board, and problem-solver who must build and maintain relationships across the executive leadership team and various communication channels. Meanwhile, they need to make sure the Chief Executive Officer (CEO) has the tools they need to lead the company.
Because there is no single clear-cut path to success in this pivotal role, coaching has become an invaluable resource for Chiefs of Staff at all stages of their careers. Whether you’re a first-time CoS getting your feet wet at a tech startup or a seasoned professional looking to boost your leadership skills, good coaching provides the actionable feedback, strategies, and insights — not to mention the confidence — you need to excel.
Finding (and Landing) the Right Chief of Staff Position for You
The first step to excelling as a Chief of Staff is finding the right role in the right organization. The Chief of Staff position can vary dramatically from one company to the next — factors like company size and stage, industry, leadership structure, and more can really shake up expectations.
Consider the Company's Stage
Let’s use the company stage as a specific example. At a startup, the role of Chief of Staff has a jack-of-all-trades, Swiss Army knife feel to it — an expert generalist, if you will. Think of it as having cross-department perspectives and insights that few others in the company have.
You’re often responsible for everything from project management and administrative support to financial oversight and helping hire initial team members. At a mature org, the CoS can oversee data analysis and high-level strategic planning, manage board meetings, track the development of new products, and more.
Focus on the Principal-CoS Relationship
A strong principal match is a key component of finding the right Chief of Staff role. The CoS-principal relationship is foundational to success in this strategic role, yet too many people overlook its importance during their job searches.
While elements like the overarching company culture, your salary and benefits, and even vacation policies might seem important (and they are!), the direct one-on-one relationship between a principal and their Chief of Staff can be the difference between a job you love and a job you can’t wait to quit. Trust me — I’ve seen both sides of this equation and this can make or break the role.
A truly great Chief of Staff has to understand their CEO’s thought process, blind spots, decision-making skills, and communication preferences. You certainly don’t need to be best friends, but you need to be aligned on important issues and have plenty of common ground for decision-making purposes. Coaching provides candidates with assistance in asking the right questions during the interview process and figuring out if the role is a perfect fit.
Find the Right Chief of Staff Coach
As you can see, there really isn’t a universal job description for the Chief of Staff, which is part of why coaching is so valuable for these professionals. In short, a good coach can help you decide what kind of Chief of Staff you want to be. With a structured coaching process, you can assess your strengths, weaknesses, career goals, and leadership styles to identify the best opportunities.
Overall, executive coaching can help you figure out what kind of Chief of Staff you need and want to be. It can help you answer questions like what type of company you want to work at, the type of culture you’d best contribute to, and what to listen for when chatting with potential employers. Maybe you already have a good idea of how to answer these questions, but it never hurts to have a trusted sounding board to bounce things off of.
Craft a Compelling Narrative
Because the role of a Chief of Staff is so varied in its concept and execution, you need to craft a strong narrative about why you’re the perfect person for the position. CoS candidates come from a variety of backgrounds in consulting, operations, finance, and even executive assistant roles. With this in mind, you need to bring forward your experience and demonstrate the qualities that will make you a great CoS.
A Chief of Staff mentor helps candidates put together a cohesive professional story that explains why they’re ready for such an important role. This includes developing a strong story arc for both LinkedIn and your resume and preparing “talk tracks” for networking and interviews.
A well-crafted narrative can help you secure the job and lay the foundation for success. It doesn’t need to be a particularly long narrative either! We’re not writing the next War and Peace here. Think of this as the trailer to a movie they can’t wait to see.
Thriving in the First 90 Days as a Chief of Staff
Once you step into a Chief of Staff role, your first 90 days will be critical as you establish credibility, build relationships, and set clear expectations for yourself. Due to the CoS role’s lack of straightforward definitions, you will need to create your own blueprint. If you need some help, I specialize in helping people write their Chief of Staff playbooks for success.
The most immediate priority as a new Chief of Staff is building a strong relationship with your principal. You must quickly learn how they think, make decisions, and prioritize tasks. A great coach can help you navigate this dynamic by providing effective communication strategies to help you build the deep trust you need with the executive team.
This relationship-building echoes throughout the organization, as you’ll need to familiarize yourself with all key stakeholders. Some companies have never had a CoS before, so your colleagues might not even know what to expect from you! If you don’t properly manage expectations, you could be misunderstood and underutilized. Coaching helps new Chiefs of Staff address this challenge by clearly defining their role, setting boundaries, and demonstrating value early on.
Another critical component of the first 90 days is identifying the organization’s real priorities. Job descriptions and initial conversations might outline certain expectations, only for the reality of the role to catch you by surprise. A skilled CoS can assess where they’ll add the most value and deliver quick wins to establish credibility and build trust.
Developing a Leadership Presence and Executive-Level Communication Skills
It’s important for a Chief of Staff to have an executive presence — the ability to communicate with authority and make strategic decisions under heavy pressure. How you show up every day and present yourself to your colleagues can make an even bigger impression than the details of your resume or educational background.
A Chief of Staff must be able to adapt their communication style to a wide variety of audiences. You’ll need to effectively communicate with your boss, the board, colleagues, vendors, strategic partners, clients, and maybe even the press. This is where my “Communication Blueprint” comes in — it’s a step-by-step guide that helps you effectively frame conversations and present solutions that resonate with your audience.
Managing strong personalities is another key challenge of the CoS role. There are always some big egos roaming around the C-suite, and knowing how to manage them is vital. With a strong coach, you can learn how to navigate difficult conversations and influence decision-making processes at your organization.
Becoming an Indispensable Long-Term Strategic Partner
As a Chief of Staff gains experience and familiarity with their new organization, the responsibilities can shift from executing short-term plans to developing a strategic advisory role. In this phase, the CoS moves beyond simply being the CEO’s right hand and begins shaping the company mission and direction.
Many effective Chiefs of Staff take on additional responsibilities like leading special projects, driving strategic planning, overseeing business transformations (like mergers and acquisitions), and recruiting for management positions. A great Chief of Staff can balance high-level strategy and tactical execution, helping the organization stay aligned and focused on its long-term goals.
One of the biggest challenges at this stage is figuring out the next steps. Unlike traditional C-suite positions, the Chief of Staff doesn’t always have a crystal-clear career trajectory. This is something I love helping my coaching clients with. We can discuss…
What types of projects and initiatives you should be working on
Defining your specific role and avoiding overlap with executive assistants (EA), human resources (HR), and the Chief Operating Officer (COO)
Explaining your particular role to yourself, your boss, your colleagues, and external parties (including those in your personal life)
Working with senior executives and EAs
How to recruit and hire for other key leadership roles
Becoming the go-to strategic partner for your principal and the entire team
Whether you want to grow within your current company or transition into a new role elsewhere, a strong coaching relationship can provide clarity and confidence in your career decisions.
What a Chief of Staff Coaching Session Looks Like
With Next Level Coaching, sessions typically revolve around skill sets and scenarios. We can start your coaching hours by discussing a general skill, such as communication, confidence, or problem-solving. Then, clients often have a specific, real-world situation that ties into that skill. For example, they might be feeling overwhelmed and struggling to prioritize their tasks, or they may need assistance with best practices for a personnel issue or a challenging upcoming conversation.
My coaching style prioritizes helping Chiefs of Staff feel confident and sure-footed in their roles. It’s all about being able to trust yourself and shape your own unique role. When you have a coach in your corner, you have someone who you know will always support you and have your back.
You might be surprised by how helpful it can be to have a coach who truly gets the business world but isn’t in your actual organization! After all, you’ll never have to worry about our conversations getting back to anyone else at your company — you never have to watch what you say. It’s a judgment-free zone, and a dedicated time just for you.
My goal is to provide you with the practical and tactical tools you need to do the job well, without any of the fluffy buzzwords no one knows what to do with. When I coach Chiefs of Staff, lots of our conversations revolve around discussing whether they see all the options available in the role and providing suggestions on how to shake things up a bit.
Take Charge of Your Chief of Staff Role
Whether it’s your first time in the role or you’re a seasoned professional, the Chief of Staff position is dynamic, challenging, and rewarding. However, because the role is so unique and often poorly defined, many Chiefs of Staff struggle to find their footing and navigate their career trajectory.
A successful CoS is much more than a mere executor of tasks. They’re a strategic partner, problem-solver, truth-teller, and highly trusted advisor to the CEO. Some great Chiefs of Staff eventually climb the corporate ladder into C-suite roles, leadership positions in specific departments, or even their own entrepreneurial ventures. Others remain in the CoS role long-term, evolving the position itself into a senior leadership role within the organization.
Leverage Expert Advice to Maximize Your Contributions
Great business coaches like Laurie Arron, Tyler Parris, Max Serrano, Michael Bungay Stanier, and Emily Sander (that’s me!) can help a Chief of Staff grow their influence and confidence. Dedicated coaching helps Chiefs of Staff at every stage — from searching for your dream job to onboarding to long-term career growth — by providing practical, actionable strategies for success and a trusted sounding board. It’s important to note that, unlike most coaches, I’m a specific expert in Chief of Staff coaching.
Not only have I been a Chief of Staff before and written a book about it, but I also host a podcast with frequent Chief of Staff interviews: Leveraging Leadership. I’ve spoken to hundreds of current Chiefs of Staff, coached Chiefs of Staff and their principals, and helped organizations set up and position the CoS role.
Get Started with Next Level Coaching Today!
Helping Chiefs of Staff become the best versions of themselves is what I do. It’s what I love to do. I’m incredibly passionate about helping Chiefs of Staff define their roles and give the position the gravitas, influence, and seniority it deserves. In short? I help Chiefs of Staff write their own playbooks for success.
If you want to develop the unique blend of skills and confidence needed to thrive as a Chief of Staff, reach out today to schedule your free intro call! After all, everything starts with a good, friendly conversation. Let me help you find your next role or become a great leader in your current CoS position!
About The Author
Emily Sander is a C-suite executive turned leadership coach. Her corporate career spanned Fortune 500 companies and scrappy start-ups. She is an ICF-certified leadership coach and the author of two books, An Insider’s Perspective on the Chief of Staff and Hacking Executive Leadership.
Emily works with early to senior executives to step into effective leadership with one-on-one coaching. Go here to read her story from seasoned executive to knowledgeable coach.