20 Questions to Ask Before Joining a Startup
Vetting a startup is hard — you're evaluating the company while still impressing interviewers. These 20 questions help you decide whether a startup fits what you actually want: compensation, career growth, or culture.
Before you apply anywhere, decide your top priority in a new role. For most candidates, it's one of three things: compensation, career, or culture. These goals overlap — wanting more cash and a better culture aren't mutually exclusive — but one will matter most. Pick that lens first, then use the questions below.
If you want maximum cash with minimal risk, tech giants (Meta, Amazon, Apple, Google) still offer the highest compensation. But if you love startups — or want equity upside — the questions in each section help you vet whether this company is worth the bet.
If you want to make more money
Compensation & financial stability
If you'd rather take a chance at being an early employee at the next breakout company than employee 85,000 at a tech giant, you need to understand both your immediate earning potential and whether the company will still be around — and whether your equity is actually worth something.
- 1
“What is the salary range for this role?”
A higher range means more upside in negotiations.
- 2
“How are raises calculated and awarded?”
You want raises to be common, not exceptional.
- 3
“How do bonuses work?”
Look for generous bonuses tied to plausible goals.
- 4
“Do you have product-market fit?”
Without PMF, there's no guarantee of real revenue.
- 5
“What is your current growth rate?”
Your earning potential grows with revenue.
- 6
“What is your runway?”
Longer runway means more financial stability.
- 7
“What percent of the company do these shares represent?”
Ask after you receive an offer. Percentage of ownership matters more than share count.
Tip: Benchmark your offer with salary tools before you sign. Ask about liquidation preference and exit price only after you have an offer in hand.
If you want to advance your career quickly
Growth, brand & long-term trajectory
Instead of thinking only about money today, think about how this startup will affect your career years from now — your room to grow inside the company, the network you'll build, and whether the role moves you toward where you want to be.
- 8
“What progression do you envision for someone in this role?”
You want a company that plans for your growth.
- 9
“Does this role contribute to higher-level decisions?”
More responsibility early means faster growth.
- 10
“Will I be able to learn new skills and technologies in this role?”
Avoid roles stuck maintaining legacy systems.
- 11
“What are the founders' backgrounds?”
Founders with successful exits are valuable relationships.
- 12
“What are the backgrounds of the people on my team?”
World-class teammates strengthen your network.
- 13
“Is this startup in the field I ultimately want to work in?”
Ask yourself — don't settle for a detour if you know your destination.
- 14
“Does this startup have the sort of role I'd ultimately like to be in?”
Don't accept a different role hoping the company will create your dream job later.
Tip: Research the company's brand yourself. Being an alum of a well-known startup opens doors long after you leave.
If you want a great culture above all else
Values, communication & flexibility
For many candidates, a culture that fits their lifestyle matters more than maximizing income or title. Culture starts with values, shows up in how people communicate day to day, and is reflected in policies on remote work and time off.
- 15
“What are this company's core values?”
Strong cultures have values deeper than buzzwords.
- 16
“How are these values reflected in company processes and policy?”
Culture shows up in real business decisions.
- 17
“What kind of people — who are otherwise successful — don't work out here?”
A strong culture means some talented people simply aren't a fit.
- 18
“What is the general level of socializing?”
Know whether a chatty office energizes or drains you.
- 19
“Do team members have structured 1-on-1s?”
Critical if you need a formal channel to leadership.
- 20
“What is the policy on remote work and vacation?”
Check whether founders and employees actually use time off.
Tip: Look around the office (or video calls) and ask whether people in similar life situations to yours seem happy and supported.
Never ignore red flags
Choosing one priority doesn't mean ignoring the others. A company in great financial shape can still fail with a toxic culture. A company with amazing culture will fail if it can't make money.
You can ask all 20 questions and simply weight the answers toward what matters most to you. No career move is risk-free — but evaluating a startup through these three lenses gives you the highest chance of landing in the right place.
