“Very Impressed” ≠ “Moving Forward”
At the end of last year, I did a quiet audit of my own work. There were some easy wins, some inexplicably painful ones, and there were the ones that stalled despite everyone being “very impressed”.
The issue wasn’t about resumes or pedigree. It was something less concrete, but somehow still the deciding factor every single time.
There’s a certain quality executives insist they can “just tell” from a conversation, even though they can’t define it, don’t interview for it directly, and somehow still use it to make final decisions.
This issue is about that.
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Judgment.
Not vibes.
Not hustle.
Not being “the glue.”
Judgment is the thing executives are actually trying to sniff out in interviews, even though they almost never say that out loud.
They’ll say they want someone:
proactive
strategic
who “just gets it”
who doesn’t need hand-holding
What they mean is:
Can we trust you to make the right call when we’re unavailable, busy, or wrong?
The Problem: Everyone Says They Have Good Judgment
Every candidate claims they’re:
a thought partner
proactive
calm under pressure
But most interviews are just a highlight reel of tasks:
“I managed calendars, travel, inboxes, expenses…”
That doesn’t demonstrate judgment.
That demonstrates obedience.
High-compensation EAs signal judgment without ever using the word.
How High-Judgment Candidates Signal It (Creatively)
Here’s what I see the strongest candidates do…often unintentionally.
1. They Narrate Their Thinking, Not Just Their Actions
Low-signal:
“I rescheduled the meeting.”
High-signal:
“I chose not to reschedule it immediately because I wanted to see if the decision dependency resolved first.”
See the difference?
Same task. Different brain.
Rule: If your story doesn’t include a decision point, it doesn’t signal judgment.
2. They Name Constraints Casually
People with good judgment think in tradeoffs.
They say things like:
“Given the timeline…”
“Because visibility was high…”
“Knowing how sensitive the stakeholder was…”
This tells the interviewer you’re not executing blindly, You’re weighing risk, optics, and impact.
Executives love this because it’s how they think.
3. They Use Phrases That Imply Trust Was Given
Listen for language shifts.
Instead of:
“I was asked to…”
They say:
“I was trusted to…”
“I had the latitude to decide…”
“My exec relied on me to…”
This subtly answers the question the interviewer is afraid to ask directly:
“Did anyone actually trust you?”
4. They Show Judgment by What They Didn’t Do
This is a big one…and wildly underused.
High-level EAs talk about restraint:
choosing not to escalate
choosing not to interrupt
choosing not to bring something to the exec yet
Example:
“I didn’t bring it to him that day because I knew it would distract from board prep.”
That’s judgment.
And it lands.
Judgment Isn’t Just What You Say. It’s How You Show Up.
Here are non-verbal, no-bullshit signals interviewers notice immediately:
You don’t over-answer questions
You pause before responding instead of filling silence
You don’t overshare context that isn’t relevant
You ask clarifying questions once, not five times
You’re calm when something is ambiguous instead of frantic
People with good judgment aren’t rushed.
They’re deliberate.
Why This Is What Companies Pay For
At lower compensation bands, EAs are evaluated on:
speed
accuracy
responsiveness
At higher bands, they’re evaluated on:
decision quality
discretion
prioritization
how often they prevent problems no one else saw coming
Executives don’t pay more for busyness.
They pay for fewer bad decisions reaching their desk.
Final Thought (Slightly Uncomfortable, But True)
If your interview stories never include a decision point, hiring managers will assume:
you waited to be told
you escalated everything
or you weren’t trusted with judgment
Even if none of that is true.
So don’t just say you have good judgment.
Make it obvious in how you answer, what you emphasize, and what you leave out.
That’s the difference between being impressive and being hired.
Ask a Recruiter
Stuck in your job search? Not sure how to handle a tricky interview question or navigate the hiring process? Submit your question anonymously, and I’ll answer it in an upcoming newsletter.
📅 See you next time!
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Sydney Morris
Founder, N+1 Search
Author, The Offer Letter