So you’ve realized the disconnect wasn’t about effort. It wasn’t even about skill. It was about expectations—ones you never said out loud.
Now what?
Most people wait until frustration boils over. Then they say something reactive. Or they don’t say anything at all, but quietly recalibrate their trust.
It doesn’t have to go that way.
You don’t need a reset conversation or a formal review. You don’t need to apologize for having preferences. You just need to start sharing what you’ve now realized.
And the sooner you do that, the faster everything starts to work better.
Because here’s the thing: your EA wants to meet your expectations. They just need to know what they are.
What most executives are afraid of
When we talk to founders and executives about this step, we often hear the same hesitation.
“I don’t want to micromanage.”
“I don’t want to hurt their confidence.”
“I want them to be able to figure it out.”
That makes sense. You hired someone capable. You want them to lead, not wait for instructions. But here’s what’s also true: setting clear preferences is not micromanagement. It’s leadership.
You’re not telling them what to do. You’re showing them how to work with you.
And that clarity is a gift. Because once they have it, they can make better decisions, anticipate your needs, and work with confidence.
Say it before it becomes a correction
The best time to share a preference is before it becomes a problem. The second-best time is now.
Start small. Be honest. And frame it like this:
“I realized I never said this out loud, but…”
“Here’s something that makes a big difference in how supported I feel.”
“This might seem small, but it helps me focus and move faster.”
These aren’t performance conversations. They’re partnership conversations.
They’re the kind that build momentum. And trust. And mutual respect.
5 ways to put this into practice today
1. Adjust the cadence of updates.
If you’re getting updates too frequently – or not frequently enough – say so.
“Can we shift this to one summary each Friday? That would help me stay focused during the week.”
2. Reframe how you want to receive information.
Maybe you don’t need background, just the action. Or maybe you want the “why” behind a recommendation.
“This works, but next time just include the decision and your recommendation.”
3. Set a default for how you want issues flagged.
Give your EA a way to surface urgency without overexplaining.
“If something needs my input today, just flag it with a 🔴 in Slack. Otherwise, drop it in the daily digest.”
4. Share how you mentally process your day.
Help your EA support your flow, not disrupt it.
“I like to start my day with a clean slate—could we move non-urgent updates to afternoons?”
5. Say thank you when they land it.
Positive feedback is powerful clarity. Don’t just correct the misses—celebrate the hits.
“This is exactly the right level of detail. Keep doing it this way.”
Let them in on how you think
One of the simplest ways to strengthen your working relationship is to narrate your preferences when they come up in real time.
When something feels just right, say so and explain why.
“This is perfect. I love when it’s this concise.”
“This kind of heads-up makes my day easier.”
“Thanks for flagging this. I appreciate your eye on it.”
And when something almost works but misses, frame it as a clarification not a complaint.
“This is helpful, but next time, I’d love it in X format.”
“Can we switch this to weekly instead of daily? That rhythm works better for me.”
“I know I didn’t mention this before, but here’s what I’d prefer.”
These moments don’t just shape output. They shape culture. You’re showing your EA what matters to you and giving them a path to meet the mark.
Clarity doesn’t kill autonomy. It fuels it.
The more context you give your EA, the more they can act independently. The more invisible preferences you make visible, the less they’ll have to guess.
And the less guessing, the more momentum.
This isn’t about controlling every detail. It’s about removing the friction that keeps great work from happening. It’s about giving your EA the inside view so they can lead alongside you—not behind you.
And when that happens? Everything moves faster. Everything feels smoother.
Because you’re not just getting support. You’re building trust.
Coming next week
We’ll share how to give feedback in a way that deepens partnership instead of causing tension—so you can keep growing together, not apart.
