Chief of Staff vs. Executive Assistant: Which Is Best for You?

When startup founders or executive teams are stressed out and in need of support, they’ll often hear from colleagues or advisors who say, “You should hire a chief of staff.” Or, “You should hire an executive assistant.” And to many founders, it isn’t entirely clear what the differences are between these two roles.

While they can seem similar on the surface—or at least seem like the two roles overlap—in general, these positions are markedly different. 

In this article, we’re going to define each of these roles to help you understand the key differences between them, and get a better sense of which option would be best for you.

Below, we cover:

Note: Our unique hiring methodology allows us to find world-class generalists that support executives and executive teams. If you’ve been wanting to hire an executive assistant or chief of staff and you want to shortcut the hiring process, reach out to our team. Specifically, if you’re interested in an executive assistant, click here to get started. You can try an assistant for a month or two and see how you like it. Or, if you want to learn about our chief of staff options, click here. For testimonials from our clients, check out our homepage.

What is a Chief of Staff?

A Chief of Staff is a highly experienced and skilled executive who holds a crucial position in managing the day-to-day operations and administrative tasks of a business or organization. In this role, they work closely with the CEO and other top executives to ensure that the company operates effectively and efficiently. The Chief of Staff acts as a trusted advisor and confidant to the CEO, providing them with support, counsel, and guidance as needed.

Apart from managing the operations and administration of the business, the Chief of Staff also plays a vital role in ensuring that the CEO and other top executives are able to focus on strategic decision-making and long-term planning. They can act as a gatekeeper, screening and filtering information that reaches the CEO and ensuring that they are only presented with the most relevant and important matters.

The Chief of Staff also acts as a liaison between different departments, coordinating communication and collaboration to ensure that the business functions as a cohesive and integrated entity. A good Chief of Staff will serve as a linchpin in the smooth and effective running of a business, facilitating the achievement of its goals and objectives.

What is an Executive Assistant?

An executive assistant is a professional who provides crucial support to high-level executives within an organization.

The Executive Assistant role typically involves:

  • Managing calendars and scheduling meetings.
  • Coordinating travel arrangements.
  • Reviewing reports and handling correspondence.
  • Assisting in decision-making processes.
  • Acting as a liaison between the executive and other stakeholders, ensuring smooth and efficient communication.

Executive assistants are not limited to administrative tasks, however. They often participate in strategic planning, project management, and even public relations efforts, sometimes representing the executive in meetings or events. These responsibilities make an executive assistant an integral part of the executive team, contributing not only to the organization of the executive’s work but also to the broader goals of the company.

This dynamic role demands high organizational skills, strong verbal and written communication, effective prioritization, discretion, confidentiality, and adaptability to manage unexpected issues or changes in plans.

What Does a Chief of Staff Do? 10 Responsibilities of the Role

A Chief of Staff works closely with the CEO and serves as a trusted advisor and confidant. They play a crucial role in ensuring that the business operates smoothly and effectively.

The role of a Chief of Staff can vary depending on the size and structure of the organization, but typically involves a range of responsibilities including strategic planning, talent management, operational management, communication and coordination, risk management, stakeholder engagement, project management, performance monitoring, change management, and financial management.

1. Strategic planning

Working with the CEO and other top executives to develop and implement the organization’s strategic goals and objectives.

2. Operational management

Overseeing the day-to-day operations of the business, including managing budgets, resources, and personnel.

3. Communication and coordination

Facilitating communication and coordination between different departments and teams within the organization.

4. Project management

Managing key projects and initiatives, including ensuring that they are completed on time and within budget.

5. Performance monitoring

Monitoring the performance of the organization and its employees, and identifying areas for improvement.

6. Stakeholder engagement

Building and maintaining relationships with key stakeholders, including customers, investors, partners, and employees, to ensure that their needs and expectations are met.

7. Risk management

Identifying and assessing potential risks and developing strategies to mitigate them, including developing contingency plans and ensuring compliance with relevant regulations and laws.

8. Change management

Managing organizational change, including identifying opportunities for improvement, developing and implementing change management plans, and ensuring that employees are informed and engaged throughout the process.

9. Talent management

Developing and implementing strategies for recruiting, training, and retaining top talent, including creating a positive and inclusive work culture.

10. Financial management

Overseeing the financial management of the organization, including budgeting, forecasting, and reporting on financial performance to the CEO and Board of Directors.

What Are the Key Differences Between a Chief of Staff and an Executive Assistant?

A chief of staff is more akin to an experienced operations or project manager than an administrative assistant. They work alongside leadership teams to carry out special projects and initiatives for the company. Their role requires higher level decision-making, a greater sense of confidence to lead, and deeper expertise in executing complex project management. They are not expected to manage administrative tasks for the executive team.

In contrast, executive assistants provide direct administrative support to chief executive officers, chief operating officers, and other senior executives. They act as their gatekeeper or right-hand, communicating on their behalf with key stakeholders (executive staff members, board members, investors, etc.). And at its core, their role functions to free up executives’ time spent on day-to-day administrative activities, and allow them to focus more of their energy on their core competencies (e.g. product, business development, fundraising, etc.). 

While it would be perfectly reasonable to hire a smart, ambitious college graduate for an EA role, chiefs of staff tend to be further into their careers and have more years of experience when compared to EAs (and the cost to hire them will reflect that).

What Chiefs of Staff Do Compared to Executive Assistants

So far, we’ve discussed the highest level differences between chiefs of staff and executive assistants. Now let’s look at some specific examples of what they each do while on the job. 

Examples of Chief of Staff Responsibilities

The job description of a chief of staff varies widely from company to company. But in our experience, chiefs of staff are often utilized to navigate and solve key business challenges such as organizing and improving current standard operating procedures (SOPs), designing and implementing new ones, or leading new company initiatives.

Here are some real world examples of projects you might ask a chief of staff to handle:

  • Organize and Improve Your CRM System: Analyze current CRM system to determine inconsistencies in how it’s being utilized across various company departments (e.g. sales, marketing, customer success, etc.). Identify issues and create procedures or plans to solve them. Communicate new SOPs for CRM use across the entire organization and oversee that the SOPs get implemented.
  • Implement Human Resources Systems for the Company: Research service options for managing payroll and employee benefits. Present options with pricing, pros/cons, reviews, etc. to the c-suite. Then, manage the implementation of the chosen service, ensuring all necessary actions are taken (e.g. communicating to and enrolling employees, designing employee handbooks, ensuring compliance measures are met, etc.). 
  • Lead the Launch of a Product or Service into a New Territory: Research opportunities and challenges for expanding sales into a new country or region. Determine all necessary legal and operational steps that need to be taken, and oversee the implementation of that expansion.

These are fundamental business objectives that you would only ask a highly experienced and competent professional to manage and lead. They bring to light both the value that a chief of staff can deliver, as well as the experience level that’s needed to take on the CoS role. 

Examples of Executive Assistant Responsibilities

In contrast, you would not typically describe an executive assistants job as leading these sorts of complex projects. Instead, EAs are generally in charge of facilitating day to day administrative functions that eat up executives’ time, such as:

  • Email Management: Fielding and organizing the executive’s inbox. Determining which emails to delete, store, or respond to on the executive’s behalf, and which emails need to be responded to by the executive. 
  • Calendar Management: Handling the executive’s day to day schedule. Booking meetings and appointments on their behalf. Spotting and resolving scheduling conflicts. Prioritizing the executives time based on their preferences.
  • Travel Planning: Booking airline and hotel reservations for business or personal travel. Drafting itineraries and making any necessary arrangements for trips.
  • Research and Data Entry: Performing research, tracking down information, and handling recurring data entry such as expense reports.

Having someone to manage these daily workflows and time-consuming administrative tasks can be extremely valuable, too. It can be immensely freeing for senior-level executives—allowing them to spend significantly more time on the work that drives their business forward.

How Should You Decide Whether to Hire a Chief of Staff or an Executive Assistant?

Now that we’ve laid out the concrete differences between chiefs of staff and executive assistants, choosing the right option for you depends on your needs, preferences, and budget.

In the current state of your business, which is overwhelming you more? Is it the need to organize and establish systems and procedures that are fundamental to running your company (e.g. HR, customer support, CRM, etc.)? Or, is it the constant influx of daily messages and meetings that’s bogging you down from focusing on the work you want (and need) to be doing?

Phrased another way, what would you prefer to be delegating? Would you prefer to pass off entire projects to be managed by someone else? Or, would you prefer to pass off your calendar and email inbox to focus more on managing those projects yourself?

There isn’t a right or wrong answer, both chiefs of staff and executive assistants can be transformative for your business—given that you hire the right person (more on this below)

The best option for you comes down to your needs and what you want help with.

The other factor to consider is budget, because the costs do vary between the two roles. As we’ve discussed in a previous article, the cost of an executive assistant ranges from $50K to $150K per year for a US-based EA, or $12K to $90K for an international EA. Whereas, the cost of a chief of staff ranges from $180K to $400K in all-in compensation.

For some companies, the cost differences might play a role in their decision. But both chiefs of staff and EAs can deliver substantial ROI when you take into account the annual value you could deliver to your company with the time you gain back by hiring them. 

Can an Executive Assistant Become a Chief of Staff?

When choosing between an executive assistant and chief of staff, an additional factor to consider is that EAs can become chiefs of staff. So, there is the option to bring someone on as an EA, allow them to take on more responsibilities as time progresses, and eventually offer them the opportunity to move into the chief of staff role. 

This is something that often happens organically, and it can be a great option because the gradual progression over one or more years allows EAs to learn the in’s and out’s of your business, earn the trust of you and your leadership team, and develop the relationships and operational knowledge that it takes to be successful in the chief of staff role. 

But regardless of which option you choose—EA, chief of staff, or EA with hopes of them becoming your chief of staff—the number one factor that will determine the success of the engagement is hiring the right person. And this is where companies run into issues. 

How to Hire an Executive Assistant or Chief of Staff

Executive assistants and chiefs of staff are both what we call generalist roles. One leans more towards administrative professional, while the other leans more towards project or operations manager. The absolute best people for both of these roles have a similar underlying set of traits and abilities. Specifically:

  1. Problem Solving Ability: General intelligence and the ability to figure things out in new and complex situations.
  2. Key Character Traits: Organized, reliable, detail-oriented, team-oriented, high integrity, analytical, assertive, etc.
  3. Communication Ability: Excellent verbal and written communication skills. A confidence and ability to communicate on your behalf or alongside you with key people (team, board members, investors, strategic partners, etc.).

In our experience, for both roles, these are the traits and abilities that predict success on the job. However, most companies don’t have effective methods for evaluating these. There isn’t the equivalent of a coding challenge for EAs and chiefs of staff.

Most companies rely primarily on resume review, interviews, and reference checks when assessing candidates for these roles. But these are simply insufficient for concretely measuring abilities like problem solving, or traits like reliability and detail-orientedness. And the inability to measure these qualities leads to inconsistent results when hiring for these roles.

It’s not uncommon for companies to invest significant time and effort into hiring EA or CoS positions, only to hire someone who looks great on paper but doesn’t perform well on the job. We wrote at length about this problem in our founding story, which you can read here

To solve this, we’ve used our backgrounds in behavioral science and assessment design to develop an in-depth hiring methodology that concretely measures the key qualities we shared above (e.g. problem solving, communication, key characteristics). 

We use a tailored combination of the following when assessing candidates:

  • Quantitative assessments: Tests that allow us to evaluate candidates accurately on key generalist abilities. 
  • Structured interviews: A strategic interview process to cross-compare candidates on the qualities and abilities that matter.
  • Work sample projects: Mock projects to see the quality of their work, based on the types of tasks or projects they’re likely to do on the job.
  • Communication exercises: Exercises to evaluate candidates on key communication skills. 
  • Reference and background checks: A structured approach to interviewing candidates’ references.

By using additional assessments, exercises, and work sample projects, we’re able to see the quality of candidates’ work before they’re hired. And as a result, we don’t have to rely on hopes or best guesses when hiring. We know when we hire someone that they have what it takes to succeed in the role.

Historically, our focus has been on hiring executive assistants. But because of our rigorous hiring methodology which allows us to find the absolute best EAs—we hire roughly 1 out of every 1,000 candidates—the EAs we offer are the ones who are on the career path to becoming chiefs of staff. We’ve had numerous cases where our EAs did in fact move into CoS roles for our clients.

In addition, through assessing tens of thousands of candidates every month, we also come across candidates who are already at the CoS level—so we’re now offering chiefs of staff to clients as well.

If you’re a founder or executive interested in trying out one of our EAs, you can try one for a month or two and see how you like it. We require no long-term commitments. 

Here’s how to get started with us: 

  • Step 1: Complete our form to let us know your needs. 
  • Step 2: If you’re a good fit, we’ll set up a call to discuss our service with you.
  • Step 3: Our team will hand pick an assistant who we think will be a great fit for you based on your needs.
  • Step 4: Our talent team will guide you through the onboarding process over 2-3 weeks.
  • Step 5: For a flat monthly rate, you get a world-class assistant that equates to a full-time employee (40 hours of remote work per week, with no long-term commitment needed).

Alternatively, if you’d like to try one of our chiefs of staff, click here to fill out our form.

For the executive assistant role (and chief of staff role), there is no better strategic partner than Persona. We’ll handle all your administrative duties and ensure you can spend your time on strategic projects that matter. For testimonials from our clients, check out our homepage.

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