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5 Questions
YOU SHOULD
BE ASKING THE
INTERVIEWERS
SO THAT THEY
RATE YOU AS:
“GOOD FIT”
1. “What would a truly
exceptional person in
this role do that a good
one wouldn’t?”
Why it works:
→ Forces clarity on expectations
→ Signals you’re aiming to exceed, not just meet
the bar
What to listen for:
→ Are they focused on outcomes or activity?
→ Do they actually know what “exceptional”
looks like?
2. “Where has the
business outgrown the
current approach, but
hasn’t solved for it yet?”
Why it works:
→ Identifies pain without blame
→ Positions you as a future-state thinker
What to listen for:
→ Are they aware of internal blockers?
→ Will they give you permission to challenge
legacy systems?
3. “Which decisions would
this role make
autonomously vs. require
alignment?”
Why it works:
→ Clarifies scope and authority
→ Signals that you’re thinking operationally, not just
tactically
What to listen for:
→ Micromanagement red flags
→ Conflicting answers = misalignment
4. “What would make you
say, 6 months from now,
‘Hiring this person was
the best move we made’?”
Why it works:
→ Shifts the room into outcome visualization
→ Signals ownership from Day 1
What to listen for:
→ Are they focused on inputs or outcomes?
→ Are there clear KPIs tied to success?
5. “What has someone
done in this role
previously that didn’t
work?”
Why it works:
→ Gives you pattern recognition
→ Helps you avoid repeating mistakes
What to listen for:
→ Do they place blame or reflect on systems?
→ Will you have room to experiment, or are they
still burnt?
final
thoughts
Don’t Just Interview:
Lead the Conversation
When you ask these types of questions, you’re
no longer a “candidate.”
You’re a peer.
You’re thinking like someone already in the seat.
Struggling with
your job search?
Book a
1:1 consult
today.
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