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What the Best Executives Secretly Want from Their Assistant (But Rarely Say Out Loud)

The Strategic Assistant Revolution Continues

Author

Joshua Washington
May 08, 2025

The rarest skill in business is not execution - it’s anticipation.

Joshua Washington, The Strategic Assistant

Hey EA-Pros Community,

Here’s the truth few executives will say out loud:

They don’t just want someone who gets things done.

They want someone who sees what’s coming before they do… and moves.

That’s the level where assistants become strategic. Not because they asked for permission, but because they earned the influence through presence, perspective, and precision.

This week’s edition is a power move.

It’s about identifying the silent expectations of top-performing executives, and exceeding them before the request ever leaves their lips.

Let’s dig in.

Joshua

✍️ Feature Article:

The 3 Things Executives Secretly Expect from High-Level Assistants (But Don’t Always Say)

The higher the executive rises, the more isolated the role becomes.

That creates a growing need for a thought partner, but with far less time (or willingness) to explain what that means.

Here are the top three unspoken expectations great executives have of their assistants:

1. Read the Room. Then Read Between the Lines.

When an executive walks out of a meeting and says, “That went well,” they don’t mean, “File the minutes.”

They’re scanning:

  • What wasn’t said?

  • Who looked skeptical?

  • Where’s the friction?

  • What’s going to create a ripple?

Strategic assistants turn casual observations into business intelligence.

📌 Example: “I noticed the new VP didn’t engage with the proposal, should we prep a backup angle?”

2. Manage the Unspoken Energy

Great assistants don’t just manage time, they manage momentum.

Executives hit emotional dips, decision fatigue, and friction daily. The best assistants don’t take it personally; they take it strategically.

🚀 Tactical Tip: If your exec is distracted or short, ask:

“What’s the one decision you’re carrying that I could help untangle today?”

That one line can reset the entire dynamic.

3. Build a Point of View

The biggest shift from “support” to “strategic” is this:

You stop waiting to be asked.

You start offering your opinion: with thought, discretion, and purpose.

Executives trust those who can think, not just do.

📌Frame it like this:

“Here’s what I’m seeing, here’s what I recommend, and here’s how it aligns with what we’re trying to solve.”

That’s how reputations are built. That’s how trust becomes influence.

🚀 Challenge for the Week:

Pick one recurring meeting your executive leads.

This week, come prepared with one observation + one recommendation - even if unsolicited.

You’re not waiting for authority. You’re earning it.

💬 Executive Coaching Corner

Weekly Wisdom: 

“How do I deliver insights without stepping on toes?”

Answer: The most effective assistants are those who learn how to challenge without threatening, advise without demanding, and speak up without overtaking the room.

Here’s the approach:

Use Context as Your Compass

Always ground your insight in business goals. It’s not about what you prefer, it’s about what moves the needle.

📌 Example: “Since we’re pushing for a 12% revenue increase this quarter, I noticed something in the client engagement plan we might want to reconsider…”

Leverage Strategic Framing

Use language that positions your insight as a value-add, not a correction.

📌 Example: “I know this might already be in motion, but here’s one way I think we could enhance the outcome…”

Know When to Hold the Mic

Not every battle is worth fighting. Timing and emotional intelligence will always beat sheer assertiveness.

High-level assistants aren’t loud—they’re heard.

💡 Inspiring Resources 

🚀 ElevateEA Master Strategy Class – One Week Away!

You’re not missing skills, you’re missing the language of strategic influence.

In 12 weeks, learn how to quantify your impact, lead executive-level conversations, and get recognized for the value you already bring.

⚡ Only offered 3x a year. Few spots left.

Closing Note

In the rush of tasks, meetings, and logistics, it’s easy to forget:

You’re not just reacting, you’re shaping.

Strategic leadership doesn’t start with a title.

It starts with what you choose to notice, speak up about, and take ownership of.

This newsletter?

It’s your leadership gym, designed to sharpen the muscles most people never see, but every top executive relies on.

With confidence and purpose,

EA-Pros Team