Supporting a new executive?Here’s how to make the first 30 days count.

Executive assistants are so much more than someone managing your calendar. They make sure your time goes on the most important parts of your business, your people and, in many cases, your life. That is no mean feat.

In some organizations, they run the show from behind the scenes, making decisions happen by getting the right people in the right place to make the right call. I’ll walk you through what an EA’s first few weeks with a new executive can look like, so you get a glimpse of their world. If you’re an EA reading this, I hope you find a few useful nuggets to take away.

A recent LinkedIn post about a well-paid EA role in London ended with a joke: somebody should build a tool that does all this autonomously. The replies from EAs, chiefs of staff and executive search specialists came thick and fast. Calendars, inboxes and travel are only the visible part of the role. What makes an EA exceptional is judgement: deciding what deserves a leader’s time, protecting their attention, and being trusted with things nobody writes down. I agree with them.

In this piece: why the first weeks are so demanding, the questions worth asking early, a CMI model for agreeing what you decide, where Time OS takes routine admin off your plate, and a working agreement to fill in with your executive.

Because you’re learning a person while running their week. Their priorities, the people who matter to them, how they like to be briefed, and when they need protecting from their own diary. None of it pauses while you learn.

The diary is often where you’re judged first. Prialto’s 2025 Executive Productivity Report asked executives which tasks their assistants handle, and scheduling came top, at 79%, ahead of travel and inbox management. People notice a smooth week long before they see the judgement behind it.

Many EAs are learning more than one leader at once. The US Bureau of Labor Statistics notes that “many executive secretaries and executive administrative assistants support more than one manager in an organization.” Two executives means two sets of priorities, two sets of people and two sets of habits.

Sources: Prialto, 2025 Executive Productivity Report · U.S. Bureau of Labor Statistics, Occupational Outlook Handbook

The questions that tell you what to protect, and who comes first. These five are a good place to start.

1. 1.What does a great week look like for you? It tells you what to protect before you know who to say no to.
2. 2.Who always gets time, and who should come through me first? This map of people is the part no handover note ever fully captures.
3. 3.When do you do your best thinking? That’s the first block of time to protect.
4. 4.How do you like to be briefed? Before each meeting, at the start of the day, or in writing the night before.
5. 5.What should I never move without asking you? Your first list of decisions to discuss, which you’ll shorten as trust builds.

If you get time with the person who supported this executive before you, ask what they wish they’d known in their first month. It’s often the most useful half hour of the handover.

The Chartered Management Institute’s guide to successful delegation starts by agreeing boundaries at one of three levels: decide only after discussion, decide then report, or decide alone. Most EAs start at the first level with a new executive and earn their way to the last. Agreeing the levels out loud makes that progress visible to both of you. Pick a stage to see how it maps.

Each move up a level is trust earned, and writing it down means it doesn’t have to be renegotiated every time the diary gets busy.

Source: CMI, Successful delegation

On the repeatable part, so more of your week goes on the judgement calls.

1. 1.Booking pages for routine meetings. One-to-ones, intro calls and reviews get booked on your executive’s real availability, without a chain of emails.
2. 2.Rules set once. Meeting hours, buffers and daily limits hold for every booking, so you’re not defending the same gaps every week.
3. 3.Group polls for the big ones. Boards, offsites and leadership meetings get a time that works, and nobody needs an account to vote.
4. 4.Protected time that stays protected. Focus time and out-of-office with auto-decline turn away clashing invites with a message you’ve agreed.

Can I book straight into my executive’s calendar?

Time OS doesn’t book on someone else’s behalf today. Your executive connects their own calendar and owns the booking pages and settings, and you set them up together. That setup session doubles as a good first-week conversation about how they like to work.

In my view, the best tools give an EA back the hours that go on logistics, and leave the judgement where it belongs: with you.

Fill this in with your executive in your first proper sit-down. Each part matches one of eight things worth settling in your first month, and the meter fills as you agree them. The card shows which Time OS setting can take care of each routine rule, and you can print it or save it as a PDF. Nothing you tick or type is stored or sent.

Where do you start?

1. 1.Book a proper sit-down in week one. Thirty minutes with the five questions above.
2. 2.Agree your levels. Which decisions you discuss, which you report and which are yours.
3. 3.Set the routine rules in the tool. Hours, gaps, limits and booking pages, so the admin runs while you get to know the people.