🔎 Role Fit and Hiring Process
Who to ask: Hiring Manager & Recruiters
Goal: Show you care about being successful in the role
What are the main reasons you all are hiring for this role now?
What problems does you all need to solve in the next 6 to 12 months?
What does doing a great job look like at 3, 6, and 12 months?
Which skills do you expect someone to have on day one vs learn over time?
What would make someone a top performer in this role?
Why might this role not be the right fit for someone?
How do you usually evaluate whether someone is doing well in this role?
⚙️ Engineering
Who to ask: Peers and Hiring Manager
Goal: Show you care about working with a strong team and can execute
What are the team’s top priorities right now and why?
What do you wish the team had more time to do?
What are the biggest engineering challenges at the moment?
What keeps you up at night? Aka what challenges is the org facing that you want to improve/fix?
What's your favorite thing you've worked on during your time here?
How do engineers work with product and design day to day?
What does professional growth look like for engineers on this team?
What does the current tech stack look like? How do you decide when to bring in new tools or frameworks?
🦄 Product
Who to ask: Recruiter, PMs, Leadership
Goal: Show you think like an owner and care about building the right thing
Who is the core customer and what problem are you solving for them?
What really sets this product apart for the customer?
How do you know the product is working for customers?
What is driving the roadmap right now?
How do you all decide what is “good enough” to ship?
How does customer feedback actually make its way into engineering decisions?
Is there anything you'd change about how your team works to make the team more effective?
🚀 Business & Strategy
Who to ask: Leadership
Goal: Show you are able to have high level discussions about things that matter
What part of the business is growing the fastest right now?
What does the team do unusually well compared to competitors?
How do new ideas usually get tested here?
How does the company make money today? Who is the target customer?
What challenges do you all run into when customers are deciding whether to buy?
What makes customers switch to you instead of sticking with what they already use?
How do customers usually find you all?
How predictable is the sales cycle / where do most new customers come from today?
What would be hardest for a new competitor to copy?
What part of the business is hardest to scale and why?
How do outside factors like regulation or policy show up for the business?
💰 Funding and Financials
Who to ask: Leadership or Recruiter later in the process
Goal: Show you are a high level thinker who is thoughtfully assessing the business
What are you choosing to focus/spend on, and what are you intentionally not doing yet?
What would a great next 12 months for the company look like?
What milestones matter most before the next fundraise?
What do you think the next funding round might look like if everything goes well?
What’s the current burn rate and runway?
How do you think about spending and investment at this stage?
How much funding has the company raised so far, and who are the main investors?
What were the valuation and key terms of the last round?
How are you thinking about timing for the next fundraise?
Have there been any recent layoffs or cost cuts, and what came out of that?
💜 Culture and People
Who to ask: Hiring Manager, People Team, Future Teammates
Goal: Show you care about joining a thoughtful, high performing team
How would you personally describe the work culture here?
What habits make someone successful here over time?
What’s the most common feedback people get here?
What kind of urgency does the team operate with day to day?
What kind of person tends to do really well here, and who tends to struggle?
How do different teams collaborate on projects within the company?
What kind of work gets noticed or rewarded the most?
How does the company think about diversity and inclusion these days?
👀 Real Talk
Who to ask: Leadership, peers and/or backchannels (people you trust)
Goal: Show you are a curious person who is assessing the company in depth
What do you want the culture to look like one year from now?
Where do you think the team still lacks clarity?
What do you wish more candidates asked about?
What kind of person would be unhappy here even if they are talented?
What’s something that looks chaotic from the outside but works well internally?
What tends to slow the team down more than it should?
Questions You Might Want To Skip and Why
Heads up: if work-life balance is your top priority, we totally get it — and this section might feel uncomfortable to read. But we're including it because our goal is to help you get your dream offer, and we don't want well-intentioned questions to accidentally work against you. — Lexi
The following questions aren't dealbreakers, but they can make hiring managers hesitate. They're tempting to ask because they come from a reasonable place, you want to make an informed decision and spot red flags.
(See The Work Life Balance Paradox on the Leopard blog for more nuance on this topic.)
Here's what many candidates don't realize: the Q&A portion of an interview is still part of your evaluation.Your questions reveal how you think, what you prioritize, and how you approach problems. When questions focus too heavily on personal needs too early in the process, they can raise concerns, even if unintentionally.
Where things can go sideways in a hiring manager/team's head:
Can they handle the ambiguity of startup life? (Questions suggest they expect structure, predictability, or clear boundaries that don't exist yet)
Will they be flexible when plans change? (Seem rigid about role, tech stack, or ways of working in an environment that demands adaptability)
Are they more interested in what they'll get than what they'll give? (Focused on benefits, perks, and guarantees before understanding the problems to solve)
Are their priorities in line with our values? (More concerned with titles and recognition over shipping and solving problems)
The good news: you can still get your questions answered without raising these flags. The key is reframing them to show you're thinking like someone already on the team:
Instead of asking what the company will do for you, ask:
How you can contribute: "What does success look like in this role in the first 90 days?"
How decisions get made: "How does the team prioritize when there are competing urgent needs?"
What the team values: "What traits do your highest performers share?"
How the company operates: "How do you balance moving fast with making thoughtful decisions?"
A Final Note on Work Life Balance: If work-life balance is genuinely your top priority in this job search, that's completely valid. Some of the advice in this section may not apply to you, and that's okay. Just know that even companies with excellent work-life balance care about how candidates approach the role. The best candidates at balance-friendly companies still lead with contribution and curiosity.
Yellow Flag Questions
About Work Life Balance:
How strict is the return-to-office policy?
Is there good work-life balance?
Do people work late a lot?
How many hours per week do people typically work?
Can I leave at 5pm every day?
How often do people work on weekends?
What are the core hours I need to be available?
Is this role high-pressure?
How stressful is this job?
Will I be expected to be available after hours?
How fast-paced is the environment?
How often do people work more than 40 hours a week?
If there's a production issue at 9pm, am I expected to jump on immediately?
Financial Concerns
Is the company doing okay financially?
How much runway do you have left?
Are you going to make it to the next funding round?
When will you be profitable?
Are investors happy with your progress?
Job Security:
Will this role definitely still exist in six months?
Has this position had high turnover?
Why did the last person leave?
Am I replacing someone who was fired?
How many people have you laid off this year?
Burnout & Sustainability:
How does the company prevent burnout?
What happens when someone is clearly overworked?
How sustainable is the pace long-term?
What's the culture around taking breaks during the day?
Do people feel guilty about not working evenings and weekends?
How do you handle it when people need to slow down for their mental health?
Is there an expectation to always be "on" and high-energy?
What's the typical tenure—do people burn out and leave quickly?
Promotions:
How long does it typically take to get promoted from this level?
How much time do engineers typically spend in meetings?
What's the expectation around synchronous collaboration versus deep work time?
How much product thinking is expected from engineers?
How often do team members actually get promoted?
How often are people actually paid their end of year bonuses?
