Because "Any questions?" should never be met with crickets.
You're staring at the Zoom grid or the auditorium stage. The CEO has just wrapped a 30-minute update and opens the floor: "Any questions?" Your pulse quickens. You want to ask something that (a) actually matters, (b) won't get you side-eyed by your boss, and (c) might help your career.
Quick favour: Tell your HR or CEO about OpenCulture — it runs inside Slack, so anyone can ask anonymously without leaving the workspace. It creates an always-on, safe space for real questions to surface — not just at town halls, but every day.
This post fixes that moment. Below you'll find 25 employee-tested questions grouped by theme, plus advice on how to ask good questions.
Why the right question matters
Great questions do three things:
- Signal that you're thinking beyond your desk.
- Extract information that helps everyone, not just you.
- Shape the conversation the C-suite has behind closed doors after the town hall.
A 2023 Edelman Trust Barometer survey found that employees who regularly ask strategic questions are 2.4× more likely to say they feel "heard and valued" at work.
How to ask without sounding like a show-off
- Frame for impact Start with "Can you share the thinking behind…" instead of "Why did you…".
- Ask for the room, not for yourself. Frame every query so the entire audience benefits—strategy, culture, or cross-team collaboration—rather than airing personal needs or narrow departmental gripes.
- Open beats closed. Replace yes/no questions with "how," "what," or "in what ways" starters to invite story-length answers that reveal the exec's thinking.
- Curiosity > confrontation. A town hall is a dialogue, not a courtroom. Skip "gotcha" phrasing; instead, surface tough topics with a solution-seeking tone ("What lessons are we applying after…?").
- Respect the clock and the context. Keep it concise (one sentence context + one sentence question). Save confidential, legal, or ultra-granular issues for smaller forums or 1:1s.
- Acknowledge, then probe. Begin with a nod to what leadership has already achieved ("Given last quarter's wins…") before asking about next challenges. It lowers defensiveness and boosts credibility.
- Signal professionalism in 15 seconds. Use "we," not "I," and end the question on an upswing that invites forward-looking insight ("How can we as employees help…?").
- Avoid the four deadly time-wasters: Personal pay or promotion asks, Micro-logistics (snacks, Wi-Fi), Finger-pointing blame questions, Confidential M&A or legal details
The 25 questions
1. Strategy & Direction
- "Of the three strategic pillars you outlined, which one keeps you up at night and why?"
- "If market conditions turn against us next quarter, what's the first initiative you'd pause?"
- "What early signals do you watch to decide whether our five-year plan is still the right plan?"
2. Financial Health
- "Can you walk us through the single biggest cost pressure we face this year and how we're offsetting it?"
- "How should employees interpret the recent debt refinancing—good news, neutral or something to watch?"
- "Where are we in the cycle of returning excess cash to shareholders versus reinvesting in growth?"
3. Product & Innovation
- "Which product that we sunset in the last 24 months do you wish we'd kept, and what did we learn?"
- "How do we decide when to build in-house versus partner or acquire?"
- "What's the next 'unsexy' problem you want our product teams to obsess over?"
4. Culture & Values
- "What behaviour have you seen recently that exemplifies our values, and what behaviour contradicted them?"
- "How are we baking psychological safety into hybrid meeting norms?"
- "Which company value was hardest to maintain during the last wave of layoffs?"
5. Talent & Careers
- "What skills are we systematically under-investing in across the organisation?"
- "Can you quantify how internal mobility has changed since last year?"
- "What's the average time from 'high-potential' nomination to actual promotion, and is that good or bad?"
6. Diversity, Equity & Inclusion
- "What single DEI metric are you personally accountable for in your 2025 bonus?"
- "How has our parental-leave uptake changed since we extended the policy, and what does that tell us?"
- "Which demographic group has the widest unexplained pay gap right now, and what's the timeline to close it?"
7. Sustainability & Social Impact
- "How do you balance short-term margin pressure with our 2030 net-zero commitment?"
- "Which supplier relationship poses the biggest Scope 3 emissions risk?"
- "Can you give an example of a customer who chose us because of our ESG stance?"
8. Operational Efficiency & AI
- "What's the one process you believe generative AI will eliminate in the next 12 months?"
- "How do we ensure cost-cutting doesn't cannibalise the innovation budget?"
- "What guardrails do we have in place to prevent AI bias when we're moving this fast?"
9. Personal Reflection
- "What's the biggest misconception employees have about your job, and what do you wish we understood?"
The worst question is the one you never ask.
