Working relationships

Working with an executive assistant

A good partnership gives you room to focus and someone you can rely on. It starts with a shared understanding of the work, including the decisions, access and context that make it possible.

Anastasia Tonisheva· SEPTEMBER 2026· 7 MIN read

Who decides what

Three kinds of decision, and the shorthand for each one. Write your own version of all three; they are agreements, never a ranking of either person.

Working with an executive assistant should make your days feel more manageable. Someone knows what's happening, follows through on the details and can help you think ahead while you're occupied with something else.

Getting there takes a little more conversation than handing over your calendar.

If you're new to the relationship, you may not know what to delegate. You might know you need help without knowing how that help should work. Your assistant may be experienced and still need to learn which things matter to you, what they can decide and how you prefer to stay informed.

That's a reasonable starting point for both people. You don't need a perfect system on day one. You need a useful first agreement and a way to improve it together.

Agree on what you'd like them to own

Start with the parts of work you want to stop carrying alone.

Perhaps meeting preparation keeps happening at the last minute. Requests from the leadership team arrive through several channels. Travel planning interrupts your day, or follow-ups depend on you remembering to ask again.

Discuss which of those your assistant will own, where they'll help and what belongs elsewhere. The title won't answer that for you. The U.S. occupational profile for executive administrative support includes a broad mix of research, coordination, reporting and operational work, but an individual role still needs an agreed scope. O*NET occupational profile.

Then describe what a good result looks like. For meeting preparation, that could mean relevant material is ready in advance, missing information is flagged and you can quickly see what you're being asked to decide.

Ask your assistant where they can contribute most, what they need to learn and what may not fit their role or available time. An experienced assistant may see a better way to solve the problem. Someone newer may need more guidance before taking it on independently.

You can build from either starting point. The agreement needs to match the person you've hired.

“Keep my mornings clear” is a useful preference. “I need uninterrupted mornings to finish the investor materials before Thursday” gives your assistant something to work with when a conflicting request arrives.

One describes the arrangement. The other explains what it's protecting.

Share enough business context for your assistant to make sensible choices: the current priorities, the people involved, the deadlines that genuinely matter and the changes that could affect them. Include sensitive context only where it's appropriate to the role and their access.

When you override a decision, explain the reason. Was it a standing preference, a temporary priority or an exception for this situation? Otherwise, your assistant may carefully repeat a choice you only wanted once.

The same goes for information you pick up elsewhere. If you make a commitment over lunch or change a deadline during a call, find a quick way to pass it on. A short voice note can be enough. Your assistant shouldn't have to reconstruct a decision they weren't present for.

Make authority clear to both your assistant and the team

Giving someone responsibility without a clear ability to act can create more interruptions for both of you.

You might agree to something like this:

Handle it independentlySchedule routine internal meetings within the agreed hours and priorities.

Handle it, then keep me informedMove a flexible internal check-in within the same week and include the change in the usual update.

Check with me firstDisplace a board or client commitment, approve spending outside the agreed limit, or communicate a sensitive decision.

These are examples to adapt, not rules for every role. The useful part is making the differences explicit. Agree on what happens if you can't be reached, too. Silence should only count as approval where you've specifically agreed that it does.

Your team also needs to know what your assistant is handling. If you ask them to coordinate the leadership agenda, explain that to the people supplying the material. Let those people know which requests come with your backing and which decisions still come to you.

Provide the practical access that goes with the responsibility. That might include calendar permissions, the relevant files, approved booking arrangements and someone in finance or IT who can help. Use proper delegated access rather than informal password sharing.

Your assistant should be clear about their authority as well. Acting on your behalf doesn't automatically mean speaking for you on every issue.

Choose communication habits you can both maintain

A beautiful task board won't help if you never open it. Equally, passing every request in a hallway conversation can make it difficult to keep track of the work.

Choose a practical combination. You might send requests by voice note while your assistant keeps the shared list current. Or you might both work directly from a simple list. Agree on where the latest status lives so neither person has to search several places for an answer.

Give urgent work a clear route. Explain what counts as urgent and what response is needed. A message at 9 p.m. can mean “please handle this now” or “I'm sending it while I remember.” Those shouldn't be indistinguishable.

For a new partnership, a weekly 30-minute conversation is a useful starting point. Use it for upcoming priorities, decisions holding up work and anything that needs adjusting between you. Simple progress updates can be sent beforehand. If the meeting has to move, reschedule it or agree how the necessary decisions will happen that week.

The exact rhythm can change. In an ASAP conversation about executive partnerships, executive assistant Naomi Birman describes adapting communication arrangements to different leaders and circumstances. Her practitioner experience is a useful reminder to test what works together rather than insist on one ideal setup.

Make progress visible without creating a second job

The executive needs confidence that things are moving. The assistant needs enough visibility for workload and priorities to be understood. Neither person benefits from a lengthy report explaining every action taken.

A short update can cover what's finished, what's in progress and what needs a decision. Include recurring responsibilities as well as new requests. Coordinating an onboarding, maintaining a process or resolving a supplier issue still takes time, even when the executive didn't assign it that morning.

Be precise about completion. “The supplier has been contacted” means something different from “The delivery date is confirmed.” Make it easy to see when work is waiting on someone else.

Over time, review whether the support is having the intended effect. Are you prepared earlier? Are fewer commitments being missed? Can your assistant handle agreed work without repeatedly stopping for permission?

Don't judge the partnership only by how few questions reach the executive. A timely question can prevent an expensive mistake. Look at whether the right matters are reaching you, with enough information to decide.

Talk about AI as part of the work

An assistant might use AI to compare proposals, prepare research, improve an internal process or draft communications. Its usefulness extends well beyond the inbox and calendar.

Discuss the actual applications. Which tools are approved? What information can be used? Which outputs need checking? Can anything be sent or changed automatically, and within what limits?

If your assistant proposes an experiment, give it a clear purpose and a little room to be tested. Agree on how you'll tell whether it helped. Equally, an assistant should flag limitations and avoid presenting unverified AI output as completed work.

When automation recovers time, decide together how to use it. That might mean better coverage, fewer late evenings or room for a process improvement you've both wanted. The fact that one task becomes faster doesn't tell you how much additional work the role can absorb.

Leave room for honest adjustments

Some friction will come from learning each other's preferences. Some will come from unclear expectations, insufficient capacity or a genuine gap in skills. It helps to identify which one you're dealing with before trying to solve it.

If a handover goes wrong, review what was understood, what information was available and where the process failed. Agree on a specific change. Both people should be able to acknowledge a mistake without the conversation becoming personal.

Repeated problems still need addressing. Clear expectations and support make it easier to distinguish a fixable misunderstanding from a performance or fit issue. A close working relationship needs accountability on both sides.

Make time occasionally for the role itself. Which work is going well? What does your assistant enjoy? What would they like to learn, and what opportunities can you realistically offer? Some assistants want to deepen their expertise in executive support. Others hope to move toward operations or another role. Ask rather than assume.

Discuss practical boundaries too, including availability, backup coverage and any personal support included in the job. Clear agreements protect reliable service as well as personal time.

A useful place to begin

For your next conversation, each of you can bring one answer to this question:

Bring one answer each

What keeps coming back to the executive that we could handle differently?

Choose one example. Agree on the result, what your assistant can decide, the information they need and when you'll review how it went.

That gives you something concrete to learn from together. As the arrangement becomes dependable, you can hand over more with confidence.

If you'd like a structured way to work through the wider conversation, our Working Together playbook helps you discuss the role, working preferences and shared agreements.

Where this comes from

Written from practice and checked against public documentation on 8 September 2026. Source links sit beside the claims they support.