5 Things a Great EA Will Do That CEOs Never Have Time For

...and why delegating these is the key to being a better leader

Many leaders, especially first-time CEOs, don’t see the value in hiring a full-time Executive Assistant. They think tools like Calendly, an AI notetaker, and a virtual assistant can provide the same benefits.

I get it. For most of my career, I never had an EA. It felt like a luxury that we could not afford, and that I did not need. Was managing my calendar really a full-time job that I needed to hire someone for? That seemed extravagant. I figured it was easier to do it myself since I knew my own preferences, a sentiment that most of the early stage CEOs I advise share.

About four years into building BetterCloud, I hit a breaking point. My calendar had become so crazy that I was showing up unprepared and late to meetings. My wife didn’t even know when I was traveling for work. Our Head of People at the time told me, “You need to get an EA who can help you organize your schedule and make sure you’re on time.”

Today, I can tell you from experience that the right EA will literally change your life. A great EA will do a lot more than take notes and schedule meetings. So it is not as simple as just hiring anyone. Your EA is a hire you should make strategically, and someone that will serve as a key member of your CEO support team.

Why an EA Is So Important

The real turning point for me came when I heard John Chambers, the former CEO of Cisco, speak at a conference. He explained that his EA not only organized his day and removed work from his plate but also made him 10-20% more efficient and effective every day. To put an EA’s impact in another way:

Having an EA means you will free up an extra 1 hour and 36 minutes of your daily time, or ~20 days each year. You can use this to (sleep / work less / work smarter), and be more focused and present in the core decision making that is a CEO’s job.

Time is the most valuable asset you have. If you’re like me, your days are packed from 8 AM to 8 PM, you’re traveling, and you’re constantly context-switching. People are always asking for your time.

When I hired my longtime EA at BetterCloud, who I worked with for more than six years, I quickly saw how much work could be taken off my plate. Scheduling a year's worth of board meetings with three major investors (all of whom are on 10+ boards), coordinating travel for a three-city customer tour, or rearranging an entire week of meetings on short notice because of an emergency takes real time and thought.

Importantly, when all of those things were taken care of, I no longer had to think about tactical issues like:

• Did I get that 1:1 doc from the exec I’m meeting with tomorrow?

• Have I met with this person before?

• Where do we stand on the board meeting schedule?

• What were the follow-up items we agreed to in that meeting?

• Do I have the deck ready for the all-hands tomorrow?

• Did I book a hotel for that trip I’m taking tomorrow?

Instead, I could focus almost all my brainpower on the core problems and opportunities facing our business. This was a much better, more impactful use of my time and energy. It also allowed me to be completely present in meetings because I knew that if something serious came up, my EA would get in touch with me.

The 5 Steps an EA Takes To Make You 20% Better as CEO

If I have finally convinced you to hire an EA, congratulations. The hardest step is admitting that you have a problem in the first place. 😀

All joking aside, here is what you should do next to drastically improve your life, and chances of success, as a leader:

Step #1: Find Someone You Trust 1000%

The key is to find someone you trust 1000%. Setting expectations around trust is critical. There’s nothing more important than the trust between a CEO and their EA. It’s the only way to make that a successful relationship.

You want someone who enjoys being behind the scenes and can handle complex logistics. You need an EA who can push back and wield authority, especially with execs and senior members of your team. You have to trust this person to do tactical work on your behalf, and believe that they have the ability to become a force multiplier on your productivity.

Finding an EA that you trust inherently is not easy, but it is a critical hire. So you should run your search accordingly. Here are five questions that I would ask during EA interviews to properly vet candidates:

1. Where do you want to be in 5 years?
   This one is especially telling. You’re not looking for a “right” answer, but it helps you understand how they’re thinking about the job and where it fits into their bigger picture. Personally, I like someone who wants to grow into more, maybe HR or a chief of staff type, but still wants to be in a role that supports others and will be happy serving as your EA for at least two years (because there is too much disruption if they move after a shorter period of time).
   

2. What’s a project you’ve worked on that you’re really proud of?
   Doesn’t matter if it was at work or not. You’re looking for someone who lights up talking about organizing something or helping a team accomplish a goal. The best answers I’ve gotten were things like organizing a charity event or running a big summer camp.
   

3. Are you up for a ton of work?
   I usually try to scare them a little. Be honest that it’s one role doing a lot. It’s fast-paced, it’s demanding, and some people will walk away after hearing that. But the right person will lean in.
   

4. What are the first three things you’d do if you joined?
   You’re trying to see if they can think for themselves. Do they talk about meeting people, checking your calendar, speaking with members of your exec team? Or do they wait for instructions on every little thing?
   

5. Who’s your favorite person you’ve worked for, and your least favorite? Why?
   No need for names. You’re just trying to get a sense for the kind of people they thrive under and like to work for, and whether you are a fit.

Step #2: Have Them Take Over Your Calendar

If you are the CEO of a growing company your calendar will inevitably look crazy. Your schedule probably looks something like the below (this is a screenshot of my calendar for a routine week during my time at BetterCloud).

A great EA doesn’t just schedule meetings, or make reservations for you. They will be thinking about and coordinating meetings that are a quarter or a year out (i.e. board meetings) and making sure that they schedule according to your preferences (i.e. back to back all day, 10 min breaks between meetings).

They will proactively manage your time. They will constantly move things around (without asking you) to ensure that they’re removing or working around conflicts (including personal conflicts) and prioritizing the right meetings.

Your EA will have context on the challenges the business faces, and your priorities at the moment. As an example, when you are fundraising they will know who the front-runners for the round are. So if those investors reach out they will re-arrange your schedule and make time. But if you are raising a Series B, and a huge growth fund emails after having already told you their minimum check size is $100M but to stay in touch for future rounds, your EA won’t up-end your schedule to accommodate them. You won’t need to tell your EA to do this, or explain why. They will have the context and just do it because they will be maintaining the spreadsheet of every investor you are talking to, and who on your team has spoken to them.

Step #3: Have Them Coordinate Deliverables

In an ideal world, everyone would get everything done the right way, and on time. But in reality that does not happen. Your EA becomes your air traffic controller for key deliverables.

This includes working with your team on deliverables such as:

• Collecting slides for a board deck and all-hands meetings

• Ensuring your team submits 1:1 agendas 24 hours in advance

• Making sure sales and success people send you briefs of prospects/customers in advance of customer meetings

• Capturing follow-up items from leadership meetings and ensuring they get completed on time.

And it also includes making sure that you, with all the demands on your time and attention, are aware of and on top of your deliverables. This includes being adequately prepared for key presentations and customer meetings, or responding to important emails left unattended.

Your EA will serve as a “double agent” or sorts internally, lending an ear to your team’s gripes about how hard it is to get answers because of your clogged inbox/schedule, and when truly needed and urgent getting you to prioritize responding to the right people.

Step #4: Have Them Take Over Internal Event Coordination

Most companies hold internal events such as all-hands meetings, leadership team offsites, company kickoffs, board dinners, team dinners, and holiday parties. These are just a few examples, but most companies have different people or departments owning these events.

Finding an EA who can take ownership of some or all of them has a couple of benefits, and ensures their ROI becomes incredibly high. It provides another set of eyes looking across the events to find tie-ins and touch points (ex: to company wins, goals, employees or projects to highlight, etc). Given the trust you should have in your EA, it should give you the comfort to take a step back from all the minute details of planning these events so that you can focus on the most important needle movers for your business.

Step #5: Go Beyond the Basics

I worked with my longtime EA Dani for six years, and she became one of the most important members of my support system (alongside my wife Jess, and our CFO Bart). She handled all of my travel, calendaring and logistics like reservations, and she kept me and our ELT on track and accountable to our deliverables. She also coordinated all of our internal meetings like company all-hands, exec offsites and board meetings.

Dani made sure that I understood who I was meeting with, the context, and the last time I met with them, etc. She chased down everyone to get 1:1 agendas completed the day beforehand, so that I could make the most of my time with people. She served as a gatekeeper, ensuring that I only attended essential meetings. She understood the pulse of company sentiment, helping me to understand how people (from our most junior employees, to our execs) were feeling and where we had issues. She made sure I got people critical answers when they were needed.

(Dani if you are reading this, thank you).

But it was the daily digest that she sent me, and all the work that went into putting it together every day, that really made the biggest difference.

The Power of a Daily Digest

Like the presidential daily digest, this is a daily, high-level summary of what is happening, relevant to, and to be actioned by the CEO. Here is an example of the digest that Dani would send me each morning:

In the digest, she’d make sure I understood who I was meeting with, the context and why behind the meeting, the last time I met with them, and would include resources like their linkedin profiles. She would include links to the one on one agendas that she had to chase people down for, or the presentations I was going to use for different meetings.

She was able to preview for me the mood and outlook of people I was meeting with. And every digest had a list of to-dos or decisions I had to make at the bottom.

Free Up 20% of your Time

Here is what other CEOs said about the impact of their Executive Assistants:

1. Nick Mehta, Founder and CEO of Gainsight, emphasizes the critical role of an Executive Assistant (EA), citing his own EA, Erica Mansfield, as the most indispensable team member. He outlines operational practices including a color-coded calendar for meeting types, embedding prep materials directly in calendar invites, and continuous Slack communication to streamline decisions. Mehta also notes the importance of personal-life integration, with his EA managing both professional and family commitments through full visibility on his calendar.

2. Todd Olson, Founder and CEO of Pendo, explains that his EA team plays a key role in company communication by organizing content for biweekly town halls. EAs on the team manage the preparation of town hall decks, ensuring smooth execution. Olson notes this process is supported by a well-established internal team and external consultants.
   

3. Nick Cromydas, Co-Founder and CEO of Hunt Club, relies on his Executive Assistant to compile and finalize the monthly all-hands presentation, ensuring it runs smoothly. While leadership aligns on key themes and content, split between consistent updates and crowdsourced team questions, each leader creates their slides, which the EA assembles into the final deck. Cromydas notes this operational structure has enabled consistency and sustainability in executing high-impact all-hands meeting

4. Jennifer Zuccarini, Founder and CEO of Fleur du Mal, highlights the importance of investing in team culture, a shift that evolved after early years focused solely on brand building. Zuccarini credits her office manager/EA, who also oversees HR and culture, with helping execute these programs. She implemented initiatives like “Employee of the Season,” personalized birthday celebrations, and team events to foster recognition and cohesion.

Imagine never having to worry about any of the tasks above. Imagine never having to context switch into your calendar or chase people for deliverables. Imagine freeing up 10-20% of your time.

That’s the power of a great EA.

For CEOs who still think an EA isn’t worth the investment: If you truly value your time, and believe in the impact you can have on the business when you are properly focused, hiring the right EA will be one of the best decisions you’ll ever make.