You’ve clarified your expectations. You’ve started sharing your preferences out loud. Things already feel lighter.
But sustaining that clarity over time? That requires something most people overlook: feedback that deepens trust, not just corrects behavior.
Not performance reviews. Not sandwich-method praise. Real-time insight that helps your EA do their best work—because now they can see what you see.
Why most feedback misses the mark
The biggest mistake leaders make isn’t being too harsh. It’s being too quiet.
They wait. They hesitate. They soften their language until the message gets lost. Or they overcompensate and drop a one-off correction that feels disproportionate to the moment.
Neither builds trust.
Most feedback sounds like evaluation. But the kind that works sounds like partnership:
“Here’s what helped me move faster.”
“Here’s where I hesitated and why.”
“Here’s how I made that call, and how you can do it next time.”
This kind of clarity lets your EA adjust in real-time—without the sting.
5 smarter ways to give feedback that actually lands
1. Use your own decision-making as context.
Your EA wants to think like you. When you share the why behind your choices, you teach them how to anticipate better.
“I skipped that vendor because they didn’t list pricing up front. Transparency matters to me.”
2. Debrief after key moments—briefly and often.
Don’t wait for a quarterly review. Take 3 minutes after an investor call, event, or launch and reflect.
“Let’s do that debrief format again. The way you grouped the feedback themes helped me stay sharp.”
3. Flag early signals instead of late-stage problems.
Don’t wait until it’s “off.” If a direction feels slightly off-track, catch it early.
“I noticed we’re veering a little tactical in this prep. Let’s anchor it back to the goal.”
4. Focus on what creates flow for you.
Your EA’s job is to optimize how you work. Feedback should clarify what makes your day feel smoother.
“When you pre-draft those updates, I can move 3x faster. More of that, please.”
5. Frame feedback as shared calibration, not personal correction.
Use language that emphasizes co-ownership of results.
“We missed a beat here. Let’s align sooner next time so we both feel good hitting send.”
Feedback isn’t one-way
The strongest partnerships invite feedback both directions.
When you create space for your EA to share what helps them succeed, you signal psychological safety. And with safety comes initiative.
Ask with sincerity:
“What’s one thing I could do that would make your work easier?”
“Are there moments where I’m unclear or inconsistent?”
The best EAs will tell you. And when they do? Act on it.
This is how great partnerships evolve
When you give feedback as a form of investment—not judgment—you shape a culture where learning is constant and collaboration is smooth.
Your EA isn’t looking for perfection. They’re looking for insight. For signals that show them how to support you even better next time.
The goal isn’t flawless execution. It’s mutual growth.
And that happens not all at once, but moment by moment.
Thank you for reading this series
I wrote this series because I kept seeing the same pattern: smart, capable leaders feeling frustrated, and thoughtful, talented EAs feeling stuck. Both sides trying. Both sides missing each other.
And every time, the fix was so human. A quick shift in how something was shared. A little more context. A two-minute conversation that changed the dynamic entirely.
We think of support as a system. But it’s really a relationship. And like any relationship, it works better with clarity, kindness, and care.
I hope this series gave you some space to reflect, and some tools to make your work—and your partnership—a little smoother.
