The Skill That Changed My Work: Anticipation

There’s a point in every Executive Assistant’s career where the job shifts.

At first, so much of the work is reacting. Requests come in. Calendars change. Emails pile up. You respond as fast as you can and hope you’ve caught everything.

But over time, something clicks: the real value isn’t in how quickly we respond. It’s in how intentionally we anticipate.

Anticipation isn’t guessing. It’s pattern-spotting.

It’s noticing that a certain type of meeting always leads to follow-up work.
It’s recognizing when an executive is taking on too much before they realize it themselves.
It’s building buffers into calendars before things start falling apart.

Eventually, the day stops feeling like playing defense. You’re designing the flow instead of chasing it.

A few things that helped me get there:

• I ask “what happens after this?” constantly. Every meeting, trip, decision, announcement. There’s always a downstream effect.

• I build in recovery time on purpose. No one thinks they need it until everything is on fire.

• I listen for subtext. Often what sounds like a simple request is actually connected to something bigger.

Anticipation gives everyone around you breathing room. It creates steadiness. And it builds a level of trust that no tool can replace.

We won’t always get it right. But the more we practice it, the more we shift from “supporting tasks” to genuinely supporting people.