My former CEO used to get hangry every day around 2 PM, right before his most important calls. It took me three weeks of watching him snap at perfectly reasonable questions to figure out the pattern. Once I started having protein bars ready at 1:45 PM, our afternoon meetings became 50% more productive.

That’s anticipation in action. Not mind-reading. Just paying attention and taking action before problems become fires.

If you want to move from “helpful assistant” to “indispensable partner,” mastering anticipation is how you get there.

Why Anticipation Matters More Than Efficiency

Executives don’t just want things done fast. They want to never have to think about certain things at all. When you anticipate well, you remove entire categories of problems from their mental load.

The difference between reactive and anticipatory support:

• Reactive: Your executive asks for the Johnson contract, you find it
• Anticipatory: Before the Johnson meeting, you put the contract, the amendment from last quarter, and notes from their last conversation on their desk

The payoff is massive. Executives who trust their EA’s anticipation delegate more, share more context, and include you in higher-level conversations. You become part of the decision-making process, not just the execution.

7 Strategies to Anticipate Like a Pro

1. Map Their Daily Patterns and Pain Points

Track these specific behaviors for two weeks:

• What time do they hit their energy wall?
• Which types of meetings drain them most?
• What recurring tasks do they procrastinate on?
• When do they skip meals or work through breaks?
• What questions do they ask repeatedly?

Then build solutions around the patterns:

• Energy crash at 3 PM? Block 15 minutes and have their preferred snack ready
• Always running late from board meetings? Build in 20-minute buffers
• Forget to eat lunch before investor calls? Calendar reminder at 11:30 AM

2. Read Their Communication Before They Send It

Get copied on or preview these items:

• All emails going to board members or key clients
• Presentations before major meetings
• Contracts before they’re signed
• Meeting agendas they’re supposed to review

Your job: catch issues before they do

• Typos in client-facing documents
• Missing attachments
• Scheduling conflicts they haven’t noticed
• Key information that should be included but isn’t

3. Know Their Top 10 People Inside Out

Create profiles for their most important relationships:

• Board members: their priorities, communication preferences, recent conversations
• Direct reports: current projects, performance issues, personal situations affecting work
• Key clients: contract renewal dates, relationship history, decision-making style
• Family members: important dates, preferences for personal scheduling

Before any interaction with these people, brief your executive on:

• Recent developments they should know about
• Topics to avoid or handle carefully
• Opportunities to strengthen the relationship
• Any action items from previous conversations

4. Master the Art of Pre-Problem Solving

Every Friday, spend 30 minutes on this exercise:

• What could go wrong next week?
• What decisions will they need to make?
• What information will they need that isn’t readily available?
• Who might demand their time unexpectedly?

Then take action:

• Book backup restaurant reservations for client dinners
• Prep talking points for likely conversation topics
• Gather background information on people they’re meeting
• Clear calendar flexibility for urgent items

5. Build Your Executive Intelligence Network

Cultivate relationships with these key people:

• Their assistant from their previous company
• EAs supporting their board members
• Administrative staff in departments they work with frequently
• Reception/security staff who see visitor patterns

These relationships give you advance warning about:

• Mood shifts after difficult conversations
• Industry developments affecting your company
• Relationship dynamics with key stakeholders
• Scheduling conflicts before they become emergencies

6. Create Systems That Think Ahead

Set up automated alerts for:

• Contract renewal dates (90, 60, and 30 days out)
• Employee anniversary dates and birthdays
• Quarterly board meeting prep deadlines
• Travel document expiration dates
• Important industry conference deadlines

Prep template responses for common situations:

• Meeting decline scripts for different types of requests
• Travel change request formats for their preferred vendors
• Brief talking points for unexpected media requests
• Standard responses for common client questions

7. Perfect the Pre-Brief

Before every important meeting or call, provide a one-page brief with:

• Meeting objective and desired outcome
• Key people attending (with context on relationships)
• Potential objections or difficult topics
• Background information they might need
• Suggested talking points or questions to ask

Format it consistently: 30 seconds to read, everything they need to walk in confident and prepared.

When You Get It Wrong (And You Will)

Anticipation isn’t about being perfect. Sometimes you’ll prepare for scenarios that don’t happen or miss something obvious. Here’s how to recover:

Own it quickly: “I should have anticipated that you’d need the backup presentation. I’ll have three versions ready next time.”

Learn from it: Keep a “missed opportunities” list and review it monthly to spot patterns in what you’re not seeing.

Adjust your systems: If you consistently miss certain types of needs, build better tracking or alerts.

The Real Payoff

After six months of consistent anticipation, something shifts. Your executive stops explaining context because you already know it. They start asking your opinion on decisions. You get included in conversations that shape the business.

You’re no longer just managing their schedule. You’re helping them think.

That CEO with the 2 PM hunger problem? Six months later, he told me I was the best EA he’d ever worked with. When he moved companies, he tried to recruit me. When I decided to stay, he became one of my strongest professional references.

The protein bars were just the beginning. But the trust and credibility I built through consistent anticipation? That became the foundation of my entire career.

You Might Also Enjoy:

• How to Improve Communication with Your Executive
• Why Emotional Intelligence Is Crucial for Executive Assistants