Assistants Talk Too Much. Executives Don’t Talk Enough. Let’s Discuss.

If there’s one thing I’m obsessed with, it’s communication—our habits, our tendencies, our wins, and our absolute faceplants—particularly when it comes to executive-assistant communication.

I also pride myself on being a pattern recognizer. I live for that moment when I can say, “Wait a minute… I’ve seen this before.”

And after years of coaching and training Assistants and Principals in partnerships that range from thriving to downright dysfunctional, I’ve noticed a communication issue that’s… let’s say, consistent.

Assistants talk too much.

Principals barely talk at all.

I’ve seen it, I’ve done it, I own it.

Assistants: You Ramble When You’re Unsure

Assistants—when we’re nervous, unsure, or uncomfortable—we ramble. If we don’t know the answer, we talk circles around the gap. If there’s an eight-second pause, we pounce on it like a fire drill. Boom—there we are, filling the silence with whatever pops into our heads.

When asked where we are on a task, we give every gory detail like we’re narrating a crime scene.

And, spoiler alert: Principals don’t need that.

Principals: You’re Saying… Nothing

On the flip side, Principals are chronic under-communicators.

(FYI: I almost wrote “absent”,” but I behaved.)

When we (the assistant) finally get a meeting—which, let’s be real, is FAR. TOO. RARE.—it’s often vague, rushed, and confusing. We leave with a “deer in headlights” expression, wondering: What the hell do they want me to do?

Details? Skipped. Key players? Unnamed. Timelines? Missing. And then we’re told to “book that conference in that place by the water with the speakers…” What?!

Let’s break this cycle. Here’s how both sides can get better.

FOR PRINCIPALS & ENTREPRENEURS

“People can’t hear what you don’t say. Thinking isn’t communicating.” —Frank Sonnenberg

A strong partnership requires aligned expectations, clarity, and context. Clear communication is the foundation of an efficient, empowered partnership. Here’s how to lead yours better:

Start with the WHY

Especially for complex projects with multiple moving parts—what’s the endgame? What’s the priority? What problem are we solving?

Don’t just throw tasks over the fence without sharing the strategy. Assistants aren’t mind readers, but we are expert pattern spotters. When we know the why, we become an extension of your brain.

Instead of: “Set up a call with John.”

Try: “I want to explore a potential partnership with John’s team. It’s still early, but I’m trying to gauge if he’s serious.”

Now your Assistant knows to keep the tone exploratory, not lock you into a commitment, and maybe even take a pre-call to collect intel.

Context helps us prioritize, prepare, and prevent problems you don’t even see yet.

Connect the dots (and the people).

You know the players. We don’t. Your Assistant doesn’t have access to your internal Rolodex unless you open it up.

Give us the lay of the land. Who’s connected to what? Why does this lunch meeting matter more than the finance review? And if the real answer is “Because I can’t listen to the CFO one more time this week,” then thank you for your honesty. Now I know not to book him before a holiday weekend when you’re fried and cranky.

Share your shortcuts, even if they seem obvious

You’ve accumulated years of experience, lingo, and industry knowledge. Your Assistant doesn’t have that same executive vantage point—yet. Don’t assume they know what you know.

This CEO story? Still one of my favorites.

He flew into a rural Texas farm and told his EA to have someone pick him up from the local runway and take him to a client’s property. She booked a car service.

He was baffled—“Why didn’t she just call a local farm to send a truck?”

Why? Because no normal human thinks like that unless they were raised on a farm or are starring in a cowboy movie. If you don’t tell her how things work in your world, she’s going to make the most logical choice based on her world.

I may or may not have laughed. I said, “I’ve been an EA my whole life and there’s a zero percent chance I would’ve thought to call a farm and bother them to send someone in a pickup.”

Unless you grew up in ag life, that’s not a natural solution. But now that she knows? She’ll never forget it. Whether it’s healthcare, higher ed, or farming—don’t assume. Teach her once, and she’s got it.

The TL;DR (Because I know you just want the quick overview):

You’re not too busy to communicate—you’re too busy not to.

If you want support that actually supports you, you need to give your Assistant the raw materials. Stop handing off puzzles with missing pieces. Your ROI starts with clarity.

FOR ADMINISTRATIVE PROFESSIONALS

“Wise men speak because they have something to say. Fools speak because they have to say something.” —Plato

Great communication is not about proving your value—it’s about delivering value. Your Principal doesn’t need narration. Here’s how to level up your side of the partnership:

Ask for the WHY

Don’t settle for vague assignments. Ask, “What’s the purpose of this?” or “What’s the goal?” It’s not annoying—it’s strategic.

When you know the destination, you can be smarter about the route. And when something goes sideways (because it will), you can reference the goal when explaining what changed.

“I prioritized Project B because you told me it had tighter deadlines and more visibility with leadership.”

See? Strategic, not defensive.

Answer the question they asked

Not the question you think they meant. Not the story that leads up to the answer. Just—the answer.

Simon once asked me, “Did you reschedule that call?” I gave him a four-minute saga about reaching out, hitting the wrong email, figuring out it was the former assistant, etc.

He blinked and said, “Mo… did you reschedule the call?”

I said, “It’s in the works.” He said, “Thanks.” Boom. Done.

It wasn’t that I wasn’t working hard. I just didn’t need to deliver a post-mortem.

Lesson learned: answer the question first. If they need more, they’ll ask.

Get over your pause-a-phobia

Some of us fear silence like it’s the plague. I’m not saying that I’m that type of person, but I’m that type of person. But I have learned over the years that more words ≠ more value. One sharp sentence is stronger than ten fluffy ones. Repeating yourself, over-explaining, or over-sharing signals a lack of confidence—not thoughtfulness.

Next time you go to speak, ask: Is this actually helpful, or am I just filling space?

Be crisp. Be clear. Be strategic.

The TL;DR (because I know you have like 10,000 other things to focus on right now):

The value of your voice comes from its precision—not its volume.

Ask smart questions, pause when needed, and let your clarity be your currency.

MORAL OF THE STORY:

Clear communication isn’t about talking more—it’s about saying what matters.

Whether you’re the one giving direction or the one carrying it out, the strength of your executive-assistant partnership depends on your ability to listen, clarify, and adjust.

Want a step-by-step way to upgrade your communication and partnership right now?

Take my Effective Communication Course and start saying what really matters.

Because when both sides show up with intention, magic happens—and the whole business runs better because of it.