The Questions You Should Always Ask Before Joining a Startup
How to separate rocket ships from train wrecks before you sign the offer.
Hey Everybody, real John here. I was meeting with a mentee the other day and he’s building something pretty amazing, I’ll let you know when it is live. But the thought occurred to me, he eventually will hire people and have a thriving business. How can he make that a great place for others and what are the questions THEY should ask before they join him. We all interview and get the offer and are so excited about landing an amazing role. We make sure we like the people and see all the positives of the product. But there are many other questions to ask before you make that leap. Ok, the rest of this is AI generated, but I definitely reviewed/edited it. Enjoy.
Landing a role at a startup feels like boarding a rocket ship—fast growth, outsized responsibility, and the thrill of shaping something from zero to one. But the brutal reality? Many startups flame out. Others survive by burning through their people.
That’s why your interview isn’t just about proving you’re a fit—it’s about finding out if the company is one you actually want to bet on.
Here are the questions that cut through the hype.
💰 Finance & Runway
If the company won’t be alive in 12 months, nothing else matters.
What’s your runway (in months) with current funding?
Who are your investors? Do they actively support portfolio companies?
What’s your burn rate, and how has it changed in the last year?
How concentrated are your revenue streams (i.e., relying on one big client)?
What’s the timeline to profitability?
🖥️ Infrastructure & Technology
The best ideas collapse on weak foundations.
What does your tech stack look like—modern or legacy-heavy?
How will you scale infrastructure if traffic grows 10x?
What’s your approach to data security & compliance?
How do you handle incidents and who’s on-call?
How much technical debt is being paid down vs. ignored?
⚙️ Process & Operations
This determines whether you thrive—or drown in chaos.
How do you define success for this role in the first 6–12 months?
What drives feature decisions—founder instinct, customer input, or data?
Do you run structured sprints/kanban, or is it ad hoc?
How often do priorities change?
How is feedback shared across engineering, product, and leadership?
What OKRs/KPIs are top of mind right now?
👥 Culture & People
At the end of the day, you’re joining humans, not just ideas.
What’s the biggest challenge the team faces right now?
How transparent is leadership with financial and strategic updates?
What’s been the employee turnover this past year?
What are the non-negotiables in your culture?
🚀 Risk & Growth
This separates a real strategy from blind optimism.
What could cause the company to fail in the next 12–18 months?
Who are your competitors, and how do you really differentiate?
What’s your customer acquisition strategy—paid, organic, partnerships?
What’s the long-term vision: IPO, acquisition, or sustainable private growth?
🐢 Final Thoughts
You don’t need to ask every single question, but you do need to probe across categories:
Finance → Are they solvent?
Infrastructure → Will you be building or firefighting?
Process → Clarity or chaos?
Culture → Do you even want to stay?
Risk & Growth → Is this ride worth it?
The right startup can launch your career. The wrong one will chew you up and spit you out. Ask boldly—your future self will thank you.