curiosity vs. questions
how to actually find out what you want to know
Cameron Murray
July 25, 2025
open role: head of sales
series a startup with $20m in funding led by kleiner perkins
gtm tech, built for cmos and sales leaders
reporting to the ceo, tons of opp for growth
someone who’s led teams but not entire orgs and wants their shot
interested? apply here
penny for my thoughts: curiosity vs. questions
when it comes to interviewing, our natural disposition is to approach each conversation as a qualifier for a set of unchecked boxes.
hiring managers want to know: do they have experience with our icp can they actually hit quota is their track record even real | candidates want to know: does this vp know how to lead will they get in the trenches will they blame me else for their failure |
while the entire point of an interview is to qualify the other side as the right fit, you have to be careful not to stick to the surface and be sure to leave room for nuance.
how do you do that? worry less about questions and focus more on curiosity
same same, right? eh, not really.
questions often lack curiosity.
however, curiosity usually leads to answers.
so what’s this look like?
for hiring managers:
being good on paper ≠ being good in real life
so, you hired a “top performer” and they haven’t had an ounce of success in 9 months… i’d be curious what questions you asked in your interviews to really uncover their strengths and weak points to see how they were a fit (or not).
or maybe you’re struggling to even hire and you keep finding yourself consistently interviewing “duds” on your calls… is it possible that they’re not the problem but maybe your questions are?
rather than asking a surface level question and expecting an intuitive and mind blowing response… try just telling them what you’re wanting to understand.
“i’m looking to understand the success you’ve had in the last few roles and how it translates to our team”
“our team is [insert trait] and finds success [insert action]. tell me about your experience in a similar environment”
it’s not about being etherial and woo woo, it’s about really wanting to understand vs. searching for bullshit surface level answers.
for candidates:
focus on your hiring managers philosophy and their overall disposition toward the things that you care about.
rather than asking about day to day expectations, ask about their management style.
questions what does my day look like what kpis do i have to hit what do you expect from me | curiosity how do top performers leverage your leadership whats your most successful trait as a leader what have you seen work best in this role |
one of these gets you numbers without nuance.
the other uncovers how to best leverage their leadership
a few other questions to try:
“if we looked back six months from now, what would success look like to you?”
“who’s the best person you know in this kind of role and what makes them stand out?
“if i did one thing to make your job easier, what would that look like?”
lean in to being curious and drop the ego in your interviews and i promise you the results will be night and day
tldr:
it all comes down to being curious and truly searching for answers.
making your questions all about wanting to understand will lower the other sides defensiveness and enable better, more genuine conversations.
music for your friday
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