Most of my clients are CEOs, and most of them have an executive assistant (EA), but over the years I've worked with early-stage founders getting their very first EA, as well as long-time leaders seeking a new person who's a better fit for their evolving needs. I've seen many times how the right EA can have a tremendous impact not only on a leader's effectiveness, but also on their state of mind and their sense of well-being. In my experience a CEO goes through three stages in the process of obtaining the right level of executive assistance:
Stage One: Any Assistance At All
It can be a quantum leap for a CEO to get any assistance at all. New ventures are typically lean and scrappy, and founders and other early-stage leaders pride themselves on their willingness to roll up their sleeves and do whatever needs to be done. Hiring support staff too soon in a company's development can be perceived as a poor use of limited capital or a potential sign of self-aggrandizing leadership. But if the company experiences any success at all, eventually the scarce resource isn't capital--it's the leader's attention. At that point a CEO who's spending time on tasks that could be delegated to an EA isn't being "lean and scrappy"--they're stubbornly clinging to an outdated job description and hurting the business as a result.
But even when an early-stage CEO realizes that getting assistance would actually benefit the business by freeing up their energies for tasks that only they can accomplish, they may still not be ready to hire someone in a full-time capacity. A common solution is to designate an office manager or someone in a similar role as a part-time EA. This has its limitations--see below--but at the very least the CEO will benefit from the added administrative capacity.
If you're a CEO without any assistance at all...
- What's the return on your attention during the course of a given day?
- How much time do you spend on tasks that are "urgent but not important"?
- How might a part-time EA help with this?
If you're a CEO who's begun working with a part-time EA...
- Remember that people aren't mind-readers--communicate your intentions when you delegate.
- Help your EA prioritize the tasks you assign them relative to their other responsibilities.
- Working with an EA is a learning process--ask for candid feedback early and often.
If you're a part-time EA who's just begun working with a CEO...
- Your CEO may need to learn how to utilize your capacity effectively, and this process will be accelerated via your feedback.
- Don't assume that tasks delegated by your CEO take precedence over other responsibilities (or vice versa)--collaborate with them to balance your priorities.
- Early-stage leaders can be haphazard about scheduling 1:1s--emphasize the value of a consistent cadence for these meetings.
Stage Two: Dedicated Assistance
In the next stage, the CEO realizes that they need dedicated assistance. The part-time EA/office manager (or equivalent) can provide a substantial boost to the CEO's level of organization and productivity, and yet such a role comes with constraints. The problem is often one of status. In most organizations an office manager is a relatively low-status role whose occupant has authority over various domains, but who is also expected to accommodate the preferences of senior leaders and external stakeholders.
Asking such a person to provide a CEO with executive support creates a dilemma whenever they have to interact with such figures in the course of those duties. As office manager, they lack the status to push back on the (often powerful and assertive) people who want access to the CEO--and the predictable result is that the CEO's calendar may be well-organized, but it's too busy, and it reflects other people's priorities, not necessarily the priorities of the CEO. The solution is a full-time EA, someone whose sole responsibility is to provide the CEO with executive support.
This change has a number of effects: The CEO's dedicated EA is generally a role afforded sufficient status to enable them to interact with senior leaders and other figures in a way that allows them to prioritize the CEO's needs, rather than simply placating the people who want the CEO's attention. A dedicated EA can focus on developing the skills required by the role rather than spreading themselves across a range of unrelated responsibilities. And a dedicated EA can become a CEO's trusted ally, not merely an extra set of hands, although this requires both parties to invest in the working relationship.
If you're a CEO without dedicated assistance...
- Do you have sufficient time for reflection and strategic thinking?
- If not, how is work you should stop doing getting in your way?
- How might a dedicated EA help with this?
If you're a CEO who's begun working with a dedicated EA...
- This may become your single most important working relationship--make the effort to onboard them into the role and to get to know each other as colleagues.
- Reflect on and actively communicate your work style preferences--you may want to document this in a "How to Work with Me" manual--and seek to understand your EA's style as well. (But note the potential pitfalls of the "Manager ReadMe" doc.)
- Your EA's effectiveness is contingent on their status--pay attention to the subtle ways you promote (or diminish) their status with other executives and external parties.
If you're a full-time EA who's begun working with a CEO...
- One way to think about your role is helping the CEO manage one of the company's most important resources: their attention.
- If your CEO is like my clients, they're a "happy workaholic," and they don't expect to live a balanced life--but they may need help in setting boundaries.
- Everyone wants the CEO's attention, and they want you to say "yes" to their requests--so it's essential to learn how to say "no."
Stage Three: Professional Assistance
In the final stage of the process, the CEO realizes that they need professional assistance. When a CEO hires their first dedicated EA, several factors may result in the adoption of an expedient solution. Although the CEO has come to believe that a dedicated EA is a good use of resources, they may feel obligated to be economical--they find it hard to justify a high level of compensation for a role with "assistant" in the title. Or the CEO is reluctant to embark upon yet another formal search process--they're probably already running one or more searches for other leadership roles--so they often look within the organization or their personal network to find someone who's trustworthy, capable, and available, even if those candidates don't view an EA role as a long-term position.
But these choices limit the pool of potential candidates, with predictable results: If a skilled EA feels under-compensated, or if they accepted the role while maintaining other professional aspirations, they'll almost certainly find preferable opportunities relatively soon and move on. In order to break this cycle, a CEO needs to hire a professional EA who views the role as a career path, and this often entails running a formal search for the position, along with a significant increase in compensation.
If you're a CEO without professional assistance...
- To what extent does your current EA view the role as a viable career path? How does this affect their commitment to your working relationship?
- How long do you expect your EA to remain in the role? How prepared are you for them to leave?
- How might a professional EA help with this?
If you're a CEO who's begun working with a professional EA...
- How much more might you delegate to them?
- For example, do they have access to your email? Could they respond to certain messages as your proxy?
If you're a professional EA...please contact me, and tell me how to improve this post--I'm sure you have some ideas that would make it more useful.
Three Alternatives
Remote: Many of my clients have worked with a remote EA, in some cases to maintain a relationship with an assistant who needed geographic flexibility, and in others to have access to talent in lower-cost markets. This arrangement seems to work best in the first and second stages above--a junior employee serving as a part-time EA or an early-stage dedicated EA--but there have sometimes been limits on the extent to which a remote EA can serve as a full-fledged professional assistant.
Virtual: A variation on the remote EA is the virtual assistant, in which a platform provides access to an aggregated talent pool and assigns one or more individuals to a user. My clients have had mixed experiences with these services--in some cases they provided a low-cost way to delegate basic administrative tasks, but in others the quality of results didn't justify the effort required to get up the learning curve.
Chief of Staff: An increasing number of my clients are opting to hire a Chief of Staff, typically in addition to an EA, but occasionally in lieu of one. Again, the issue of status is relevant--the Chief of Staff title typically confers a degree of status that allows the role to serve as a CEO's proxy not only via email, but also at meetings and even speaking events. But while this may offer a leader greater flexibility for a period of time, my observation is that Chief of Staff candidates almost always view the position as a short-term stepping stone to an operating role, so it's no substitute for a long-term relationship with a professional EA.
In Closing
It's worth noting that I'm not the only one who thinks CEOs should pay more attention to the EA position:
One hire that most startups make too late is the exec assistant. Founders should not do their own scheduling, travel or presentations.
— Jeremy Liew, Partner at Lightspeed (@jeremysliew) May 31, 2017
EAs are on my mind at the moment because I send a thank-you to each of my clients' assistants during the holiday season to express my appreciation for all they do that makes it possible for me to work with their boss. I couldn't manage my coaching practice without them, and from the bottom of my heart I am truly grateful.
For Further Reading
Growth, Profitability and Return on Attention
Gary Klein on the Elements of Intention
Building a Feedback-Rich Culture
Building a Feedback-Rich Culture from the Middle
How to Think (More on Open Space and Deep Work)
A Checklist for Someone About to Take on a Tougher Job
The Most Productive People Know Who to Ignore
Happy Workaholics Need Boundaries, Not Balance
Learning How to Say "No" Is Part of Success
The Subtle Art of the Executive Assistant (Molly Young, New York, 2021)
- "A...paradox embedded in the job is that the skills required of an executive assistant--a strategic mind, iron discipline, a talent for empathy, and a knack for crisis mitigation--are identical to the skills of a capable CEO. Such talents can be directed at a birthday cake or a ten-year growth plan. It often occurred to me that if the CEO were to die in a tragic accident, Emily would be best qualified to replace him. I wonder if the thought ever crossed his mind."
Resources on the Executive Assistant Role (Maïa Cybelle Carpenter, 2018)
Elevate the Executive: Evolve the Executive Assistant (Maïa Cybelle Carpenter, 2018)
One of the Most Important Hires You'll Make: Hiring Your Executive Assistant (Ryan Caldbeck, 2021)
Photo by Tomas Sobek.
