Nobody teaches you this part. You spend so much time learning how to manage calendars, coordinate travel, and keep everything running smoothly that one of the most critical skills in the entire EA toolkit gets completely overlooked.
How to talk to your executive.
Not small talk. Not status updates. I mean really communicating. Advocating for what you need. Raising concerns. Asking for clarity. Pushing back when something isn’t working. Doing all of that while maintaining the respect of someone who is busy, senior, and operating under enormous pressure.
It sounds simple. It is absolutely not simple. But it is learnable and once you get it right, everything about your working relationship gets easier.
Understand How They Receive Information
Before you can communicate effectively with your executive, you need to understand how they actually process information. Some executives want the bottom line first and the details only if they ask. Others want full context before they can engage with a recommendation. Some prefer a quick verbal conversation. Others want things in writing so they can think before they respond.
If you’re not sure how your executive prefers to receive information, pay attention. Watch how they engage in meetings. Notice when they seem impatient and when they seem fully engaged. And if you’re still not sure, just ask. “I want to make sure I’m communicating with you in the way that works best for you. Do you prefer I come to you with a quick summary or full context?” That question alone will tell your executive a lot about how thoughtful you are.
Lead With the Point
Your executive’s time is precious and their attention is constantly being pulled in twelve different directions. When you need something from them, get to the point quickly. Not abruptly, but efficiently.
Instead of building up to what you need with a lot of preamble, lead with it. “I need five minutes to discuss Thursday’s board prep” is better than a two paragraph email that eventually gets to the same request. Respect their time and they will respect your communication.
Come With Solutions, Not Just Problems
This is one of the most important habits you can build as an EA. When you bring a problem to your executive, bring at least one proposed solution with it. Ideally two or three options with a recommendation.
“We have a conflict on Thursday. The board call and the client lunch are at the same time. I can move the client lunch to Friday, reschedule the board call for next week, or see if we can do a 30 minute call with the board before the lunch. I’d recommend moving the client lunch to Friday since the board call has more attendees. What do you think?”
That is the difference between being reactive and being strategic. Executives don’t want to solve the problems you’re supposed to be managing. They want to make a quick decision and move on. Make it easy for them.
Ask for What You Need Directly
This one is hard for a lot of EAs because we are wired to be accommodating. But there will be times when you need something from your executive in order to do your job well. Access to information. A decision that’s been sitting too long. Clarity on a priority. Feedback on your performance.
Ask for it directly. Not apologetically, not buried in a long email, not hinted at and hoped for. Directly.
“I need fifteen minutes on your calendar this week to align on Q4 priorities so I can manage your schedule effectively.” That’s it. Clear, professional, and framed around how it benefits them.
Most executives respond very well to direct, well framed requests. What they don’t respond well to is vagueness, hinting, or having to read between the lines.
Pick Your Moments
Timing matters enormously when communicating up. A conversation that would go well on a calm Tuesday morning might go completely sideways if you try to have it right before your executive walks into a high stakes meeting.
Learn your executive’s rhythms. Know when they’re most receptive and when they’re most distracted. Know what their stress triggers are and give those moments a wide berth for anything non-urgent. The same message delivered at the right moment lands completely differently than one delivered at the wrong one.
Know When to Put It in Writing
Some conversations should happen in person or over the phone. Others are better in writing, especially if you need a decision documented, if the information is detailed, or if your executive is the kind of person who processes better when they can read and think before responding.
A good rule of thumb is that anything requiring a quick yes or no answer can usually be handled verbally. Anything more complex, or anything you need a record of, should go in writing. When in doubt, follow up a verbal conversation with a brief written summary. “Just following up on our conversation. We agreed to move the client lunch to Friday. I’ll send the updated invite shortly.” Clean, clear, documented.
When You Need to Push Back
This is the part that makes most EAs nervous. But here’s the truth. Knowing how to respectfully push back is one of the most valuable things you can do for your executive and for yourself.
If your executive is about to overcommit their schedule, if a decision is being made without information you know is relevant, if something is being asked of you that isn’t reasonable, you have both the right and the responsibility to say something.
The key is how you say it. Not defensively, not emotionally, but calmly and professionally with their best interests at the center of the conversation.
“I want to flag something before we confirm this. If we add this to Thursday, you’ll have back to back commitments from 8am to 7pm with no breaks. I’m happy to make it work if that’s what you want but I want to make sure you have the full picture first.”
That’s not insubordination. That’s exactly what a great EA does. And most executives, when they’re working with someone they trust, genuinely appreciate it.
The Bottom Line
Communicating up is a skill. It takes practice, self awareness, and a genuine understanding of the person you’re supporting. But when you get it right, it transforms the working relationship. You stop feeling like you’re always waiting for direction and start feeling like an equal partner in making things work.
Your executive needs you to communicate well. Not just to receive their communication, but to send it back clearly, confidently, and effectively. That’s the partnership. And you are absolutely capable of it.
What’s the hardest part of communicating with your executive? Drop it in the comments. You are definitely not alone.
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