Ask like an investor, think like a founder.
Written by: Richard, Dragonfly Talent Partner
Compiled by: Luffy, Foresight News
If I need to find a job again, I will use this checklist. If you are interviewing at a startup, you should steal this list.
In my career, I have been fortunate to hear candid thoughts from founders, operators, recruiters, interviewers, internal employees, investors, and job seekers. This is the framework that formed in my mind after listening to various perspectives.
1. Founding Team and Structure
Start with the "people":
- Who are the founders? Do they have successful cases, risk signals, or are they a good fit for the market?
- Have they worked together before?
- Who are the early employees? Are they complementary to the founders or redundant?
- Do they have high-caliber advisors or board members?
Ultimately, even if the company undergoes major changes (which usually happens), you are betting on the "people". Sometimes it's not the first idea that succeeds, but the team that makes the idea a reality.
2. Funding and Development Path
You are exchanging time for equity, so know its value:
- Is it venture capital-backed or bootstrapped? How long can the funding last?
- What stage are they at? Pre-seed? Series A?
- Who is on the cap table? Are investors truly helpful, or just tweeting?
- When is the next funding round? What is the plan?
If they cannot answer clearly, you should not blindly join.
3. Product, Technology, and Progress
What are you actually joining?
- What is the product's real functionality?
- What is currently live vs. a concept product?
- What is the roadmap for the next 6-12 months?
- Tech stack: modern architecture or hastily cobbled together?
- Do they have user retention or churn data?
- Are customers paying? Do they have big clients? Or just a pilot?
Especially in AI, infrastructure, and crypto, you need them to truly solve hard problems, not just hype and jargon.
4. Market and Growth Potential
Your equity is only valuable when the company grows:
- How big is the market?
- What market segment are they entering?
- What is the market entry strategy: product-led growth (PLG), sales-driven, or hybrid?
- Do they have a repeatable growth engine?
- Can you see a credible revenue growth path?
A big market without an entry strategy = showboating; ambition without distribution = fantasy; vision without execution = PowerPoint. Choose your favorite.
5. Mission and Alignment
If you join early, you better truly believe:
- Can the team clearly articulate an inspiring mission?
- Is the vision coherent, or just a collection of buzzwords?
- Is the team aligned on the ultimate goal?
You don't have to "change the world", but you should believe in what you are building.
6. Regulatory and Legal Risks
Especially important in fintech, cryptocurrency, medtech, and AI.
- Are there known or potential regulatory barriers?
- Are they operating in a gray area?
- Are there pending legal issues?
A surprise subpoena could turn your "rocket ship" into ruins.
7. Metrics and Focus
Clarity creates momentum.
- What metrics do they track weekly/monthly?
- Are they truly using data or just going by feel?
- Are they measuring what's important or what's easy to measure?
Sometimes there are no metrics yet, and that's okay. But you should still be able to discern the focus. Jensen Huang and NVIDIA don't have formal OKRs; they just build with obsession.
8. Culture and Hiring
You're not just joining a company, you're joining a team project.
- What are the clear and truly practiced values?
- Is there early employee turnover? Why?
- How do they make hiring decisions?
- Do you want to learn from these people?
Also consider: async or sync culture, remote or in-person. If the culture feels toxic or superficial? Trust your instincts.
9. Founder Psychology
How will they react when things deviate (which will definitely happen)?
- Are they open to suggestions or defensive?
- Have they survived failures, or just rode the bull market?
- Can they attract and retain top-tier talent?
The best founders are not perfectionists, but relentless learners.
10. Risks and Vulnerabilities
No company is invincible.
- What are the top three survival risks?
- What is the weakest link: technology, market entry, funding, talent?
- What are the plans to mitigate risks?
You don't need to avoid all risks, but you need to be clear about your situation.
11. Talent Attraction
Maybe biased, but this might be the most important signal after the founders.
- Are they attracting top talent or just anyone?
- Are former employees still fans?
- Would you bet on this team again?
A strong team will give you room for error, while a weak team will magnify every mistake.
12. The Role Itself
Back to the specific role:
- Does the role match your level?
- Was it suitable two years ago? Will it be suitable three years from now?
- Is the compensation consistent with the requirements?
- Is the job description clear, or do you need to write the JD from scratch?
Often, early-stage/inexperienced recruiting teams only know what they need when interviewing candidates. Be prepared to adapt to their actual needs, or leave.
Actual Actions I'll Take in My Next Job Search
- Background check on founders and hiring managers. Who says only they can do this?
- Use the product or request a demo. Would you pay for this? Or who would pay?
- Talk to customers if possible, ask about real pain points
- Research the cap table and funding history; what signals can you see?
- Search for founders' and team's past podcast, blog posts, and tweets
- Look around, are smart people paying attention to this team?
- Deep dive: GitHub, Twitter, Discord, Farcaster, AMAs
These actions are not aggressive, but informed. The best thing you can do for yourself is to make a fully informed decision.
Final Thoughts
Joining a startup is like writing a check to yourself with your time and career. So, ask like an investor, think like a founder. Ask real questions, do your own due diligence, make wise choices, not emotional ones.
Work is a transaction, career is a portfolio, choose wisely.
