For years I walked into interviews with a silent assumption: they were grading me. I prepped my answers, rehearsed how I’d tell the story of each project, worried about whether I was good enough. Then, at the end, the familiar line always showed up — “Do you have any questions for us?” — and I’d ask a couple out of politeness: what’s the tech stack, how big is the team. Questions asked to look interested, not to learn anything real.
Louise Deason’s piece resets that whole frame. An interview isn’t a one-way exam. It’s two sides sizing each other up — and that “do you have any questions” moment is the rare stretch where the company drops its guard: it shifts from grading you to answering to you. Ask the right thing right then, and you pull out things no job posting or intro call will ever tell you.
You are not a variable waiting to be evaluated. You are the one doing the choosing — between options that are each flawed in their own particular way.
Deason boils it down to nine questions. After reading them, I sorted them under the four things I actually want to know before I say yes to a place.
Do people here move up, or move out?
What a company says about growth is cheap. What’s expensive is the evidence: when was the last time it actually happened.
You’re probing whether the promotion path is transparent and whether it actually functions. A good answer is very specific: a name, a timeline, the criteria that were met. Red flag: vague talk about “review cycles,” or an admission that nobody’s been promoted lately — a sign the path upward is murky.
This exposes how stable the team is and whether there’s room to grow. What’s worth noticing is the difference: did the people who came before move up into management or a bigger role, or did they leave? Same number on the tenure clock, two completely different stories.
Are they willing to be honest?
The next two questions don’t just ask for the truth — they also measure whether the person across the table is willing to tell you the truth. And how they answer is a preview of the working relationship you’re about to enter.
Most candidates will get back a rehearsed humble-brag in disguise — the “we ship so fast our docs fall a bit behind” kind. A real answer names a real bottleneck, and shows whether this person is straight with you. Red flag: not being able to come up with a single weakness.
This one measures psychological safety — whether disagreement is genuinely welcome. Red flag: silence, “our team always agrees,” or “we trust leadership” — all of which hint at either avoidance or groupthink. A strong answer describes an actual process: concerns get raised, decisions sometimes change, and there’s always a reason attached.
Is this chair steady?
Three questions I used to be most reluctant to ask, afraid they’d sound like I was doubting the place. But this is exactly the part that decides whether you’re still sitting there twelve months later.
Is the team expanding, holding steady, or shrinking — and how safe is your role in that. One telling signal: “I’m not sure, that’s being discussed at the leadership level” means the future of your position is still undecided, at a tier above even your soon-to-be direct manager.
This exposes how unstable the organization is and how erratic the leadership layer can be. A reorg three months ago needs explaining. And the reason is what really weighs: a change of strategy is far from a change of leadership, and both are further still from a reorg driven by poor performance.
Is this growth (new work), a backfill, or a reorg? Red flag: hesitation is data too. A pause before the answer is a cue to dig: “Did the previous person move internally or leave outright?” The answer to that tail end often decides whether the place is worth taking.
Who will I work with, and what does done look like?
Finally, the everyday stuff: the people I’ll sit next to, and the yardstick I’ll be measured against.
This measures the team’s transparency and how much confidence they have in their own people. Here’s the interesting bit: the friction in the response tells you more than the content of the answer. Stalling, hard-to-schedule, or introducing you to the wrong person — all of it reveals gatekeeping habits.
Interviewers always have the first half ready, but few prepare for the “failure” half — so you get an unscripted, more honest answer. It reveals the kinds of failure the company has already tasted: the ambiguity you’ll have to sit with, the politics, or the burnout risk baked into the role.
Don’t ask about pay and comp with the CEO during the culture round, and don’t touch benefits until you have an offer in hand — wrong timing is a bad signal about you. Watch for answers that contradict each other across different interviewers: that’s a clearer red flag than any single question above. And if, over the whole session, they never leave you room to ask — that silence is itself the answer.
Switching sides of the table
What I took away after reading isn’t nine questions to memorize. It’s a shift: from trying to get chosen to doing the choosing. Every company is flawed in its own particular way — these nine just help you learn early where the flaw is, so you can decide for yourself which flaw you can live with.
And there’s a test even shorter than the nine questions: their attitude while you ask. A company that bristles at these has just handed you an extremely valuable piece of information cheaply — that it isn’t worth your serious consideration. The trustworthy place is the one willing to sit down for a real, two-way conversation. Your leverage lives in noticing that.
I wrote this mostly to remind the me of five years ago — the one who sat there nodding along, afraid that asking too much would cost him points. Turns out asking the right question is exactly how you get your footing back.
Read more
- source Nine Questions I Now Ask in Interviews That I Wish I'd Asked Five Years Ago louisedeason.substack.com — the original piece
- source 29 Interview Red Flags (for Candidates & Interviewers) toggl.com — a red-flag list for both sides of the table
- source Bad candidates ask these red-flag questions — what to ask instead cnbc.com — what to ask, and when
- on the blog Notes to use, not to file away the same idea, designed from the other direction