What to Delegate to an Executive Assistant, and in What Order
A ninety-day sequence for handing work over — what goes first, what should never go, and how to tell whether delegation is actually working.
Delegation fails more often from sequence than from selection. People hand over the hardest thing first, it goes badly, and they conclude that delegation does not work for them.
This is the order that does work, why each stage sits where it does, and the categories that should stay with you regardless of how good your assistant becomes.
The principle: cheap mistakes first
Every delegation is a trust experiment. You want the early experiments to be ones where being wrong costs almost nothing, because that is how both sides learn quickly — and how you find out early if the match is wrong.
That means starting with work that is high volume, rule-based, and cheap to get wrong, then moving toward work that is low volume, judgement-based, and expensive to get wrong.
Weeks 1–2: Calendar
Always first. The rules are explicit, the volume is high enough to reveal a pattern within days, and a scheduling mistake is embarrassing rather than damaging.
Hand over: scheduling and rescheduling, conflict resolution, buffers and travel time, meeting length defaults, recurring meeting hygiene, and the decision about which meetings can move.
Write down the rules before you start. What is a hard no. What gets 15 minutes and what gets an hour. Which people always get accepted. When your no-meeting blocks are and whether they are truly immovable.
Typical return: four to six hours a week. This stage alone often justifies a fractional assistant.
Weeks 2–4: Inbox triage
Second, and only triage at first — sorting, flagging, filing and surfacing. Not replying.
Hand over: categorisation, unsubscribing, routing to other people, flagging what needs you, and drafting replies for your approval.
The drafting stage is where the relationship is really built. Expect the first week of drafts to be wrong in tone. Correct them specifically rather than rewriting silently, and it converges quickly. Once you are approving without editing, let them send.
Weeks 4–8: Travel and logistics
High value because it is the work you least want at 11pm on a Sunday.
Hand over: full itineraries, flight and hotel booking against documented preferences, ground transport, rebooking during disruption, expense capture, and visa or documentation deadlines.
Document preferences once: airline and alliance, seat, how early you want to arrive, hotel type, whether you want the cheapest option or the one closest to the meeting. This is a fifteen-minute document that pays for itself in the first trip.
Weeks 8–12: Projects and follow-through
The stage where an assistant stops saving time and starts creating it.
Hand over: deadline chasing, meeting preparation and briefing notes, action items and follow-up, vendor management, CRM hygiene, research and first-draft documents, and light project coordination.
What not to delegate
Some things should stay with you regardless of how good the relationship becomes.
Relationships where you are the product. Investor updates, key client relationships, anything where the recipient is buying your attention specifically. Your assistant can prepare it. They should not be it.
Judgement calls with asymmetric downside. Hiring and firing, pricing decisions, anything legal, anything that would be expensive to reverse.
The work only you can do. Strategy, product judgement, the actual thinking. If delegation is not buying you more of this, it is not working — you have just moved the busyness.
Anything you cannot describe. If you cannot explain what good looks like, you are not ready to hand it over. That is a signal about your own clarity, not their capability.
How to tell it is working
At ninety days:
- Hours returned per week, honestly counted
- Categories of work that no longer reach you at all
- Things handled that you found out about afterwards — and were handled well
- Whether you are managing them more or less than at week four
If you are managing them more, the problem is usually missing documentation rather than a bad hire.