Interviewing Your Future Boss: Startup Founders. Don’t fall into the trap of viewing the startup interview as a one-way evaluation process of a founder assessing an endless sea of great candidates. A unicorn is perhaps unique, but working for the wrong one isn’t necessarily going to advance your professional prospects.
In a mission-driven company, the importance for the candidate of understanding the founder’s “why” cannot be understated. As Peter Thiel once famously asked, “Why should the 20th employee join your company?" (FN1) A job candidate evaluating a mission-driven company should be discerning whether the founder(s)’s “why” is compelling enough. Does it interest you? Does it spark your loyalty, obsession and resilience? Is the founder team emboldened on a true mission, answering an authentic call to adventure?
💡 Let’s flip the script. Instead of answering the founder’s questions about hiring top tier talent, how should a top candidate assess a startup’s leadership team and the nature of the opportunity? What are the key signals for sustainable success? Long-term vision? Personal mission? Is there an underlying authentic conviction and connection with the underlying mission?
Notice that this inquiry isn’t about the compensation package, 401(k), stock options, or fringe benefits.
There’s no shortage of advice on how to benchmark market norms for that part of your candidacy. But those secondary questions quickly become moot if the founder team can’t provide strong answers when you assess them.
Test for the Founder’s “Why.” Savvy startup leaders dig into a candidate’s motivation. Let’s probe into theirs. After all, as Thiel points out, “talented people don’t need to work for you; they have plenty of options… Why would someone join your company as its 20th engineer when she could go work at Google for more money and more prestige?” (FN2)
Candidates should ask:
“Why this company, and why now?”
“What (unique) problem is your team obsessed with solving?”
“Why do you think you're the one who can drive a solution?”
Look for answers grounded in personal experience, obsession, or earned insight—not generic passion. A founder who speaks from lived conviction is more likely to build something worth joining. Momentum is great, but without a sustainable passion, it’s difficult to channel energy and carry it forward.
In addition, look for founders driven by a true mission and equipped with the right capabilities to tackle its core challenges. Do they possess the proven knowledge, skills, and judgment to deliver a successful outcome? For instance, a seasoned research scientist is a more likely biotech founder than a military cadet — but what if that military leader once oversaw scientists working at a DARPA lab?
Nike — Running Toward a Movement. Consider the story of Nike co-founder, Phil Knight. He’s so much more than a “shoe dog,” and Nike is way more than another shoe manufacturer. Knight’s bold vision set his company’s mission to serve athletes and inspire a running movement. Nike’s mission extends well beyond designing unique shoes. Knight established a bold ambition for his team: creating a global running culture. His earliest hires consisted mainly of former runners. Running obsessives. One of his first key hires regularly corresponded with hundreds of runners, and when he opened the company’s first retail store in southern California, it was a shrine to runners! Knight’s co-founder was one of the leading American track & field coaches. The Nike team felt the pain of bad shoes and the joy of a runner’s high. Little doubt that the Nike mission was embedded in the DNA of its earliest teams, laying the foundation for not merely a manufacturing leader but a cultural juggernaut. (FN3)
Starbucks — Building Coffee Culture. What about the journey of Starbuck’s founder, Howard Schultz? Inspired by a visit to Italian coffee houses, Schultz aimed to create a welcoming “third place” between work and home, making coffee culture a part of American life and eventually unleashing a global coffee culture. (FN4) The Starbuck’s mission encompassed building a community, requiring more than mere baristas. Instead, these team members became ambassadors working with a belief in their organization’s mission. Commenting on his team’s passion, Schultz said, “When you're surrounded by people who share a passionate commitment around a common purpose, anything is possible.” (FN5) The earliest Starbucks teams bought into Schultz’s vision, even before there was a business case for $5 lattes in paper cups.
Follow the Vision Trail. You need to walk away with clear answers about the founder’s vision for this startup. Is the founder thinking in decades—or weeks and months? Has the founder articulated a clear vision of the company’s long-term purpose and market impact? Is the founder building a team focused merely on funding and features, or do they talk about building a generational company?
Of equal importance, is this company’s mission aligning with your own personal mission? You may be too late to join this founder as part of the founding team, but you’re staking your career progress on its success. There is often high opportunity costs associated with taking a role at a startup.
Be honest with yourself about your own goals. If this new opportunity isn’t aligned with your own long-term objectives, it’s just a food job. Sometimes, that’s fine. We’re not always operating with leverage at a point where we can pursue our mission. But it’s not enough for anybody ready to embark on a true mission.
Check for Cultural Ownership. Early employees define their startup’s DNA. As a candidate, you should consider asking:
“What kind of people succeed here—and why?”
“What are the most important cultural norms on your team?”
Strong founders understand the type of behavior encouraged and rewarded at their companies. And what won’t be tolerated. Vague, performative answers = red flags.
Demand Clarity on Execution Philosophy. Execution risk kills startups. Strive to understand it better by asking:
“How do you make decisions under uncertainty?”
“How do you balance speed and quality?”
These aren’t trick questions.
Founder’s Learning Framework. Startups inevitably face challenges. How will this founder team avoid repeating yesterday’s mistakes? Probe them about their influencers and influences – mentors, coaches, advisors and lessons learned – to serve the aim of avoiding repetition of past mistakes. Ask:
“Who do you turn to when you need guidance?”
“What’s the hardest feedback you’ve received?”
Humility and self-awareness aren’t soft skills. Founders who aren’t married to their original hypothesis wear the humility to turn to Plan B, iterate and pivot towards new solutions. These are essential survival traits.
What to Look for When Interviewing a Founder. A good founder can pitch. A great founder can articulate their mission with clarity, demonstrate their credibility to execute a business plan and attract a following.
Mission Clarity. Can the founder team clearly explain why they’re doing this — and why it matters?
Credibility to Execute. Does the founder team have personal or professional experience that fully align with the problem being solved by the startup?
Team Culture Fit. Are they attracting people who believe in their cause — and can also build it?
✳️ Key Takeaways. The best startup interviews are two-way streets -- mutual and reinforcing mission focus. As a candidate, you’re not just offering skills—you’re trading energy, risk, and time. Don’t join a startup unless its leadership team is obsessed with the mission, clear-eyed about risk, and radically intentional about building the future. A great founder doesn’t just want to hire you. They invite you to believe in their vision and enable the mission.
You’re Not Just Joining a Company. You’re Joining a Movement. If the founder team isn’t fighting for a mission that they deeply care about and don’t have the skills to make real progress to achieve it, that’s a red flag. And if they’re not attracting a group of like-minded people with similar drive and commitment? Walk.
Melanie Perkins & Canva: Democratizing Design. Melanie Perkins, while teaching design programs at university, recognized the complexity of traditional design tools. She carried with her firsthand empathy for user frustration. This insight led her to democratize design with the creation of Canva, which aims to make design accessible to everyone. Perkins articulated her mission, “We wanted to empower the world to design, and that meant creating a tool that was simple, intuitive, and collaborative.” (FN6) Her firsthand experience with design education informed Canva's user-friendly interface, enabling users worldwide to create professional-quality designs effortlessly.
Luis von Ahn & Duolingo: Making Education Free and Accessible. Luis von Ahn, a computer science professor and inventor of CAPTCHA, co-founded Duolingo to provide free language education globally. His strong technical background in computer science and passion for accessible education drove the platform's development. Von Ahn is noted for saying, “Our mission is to develop the best education in the world and make it universally available.” (FN7) Duolingo's gamified approach to language learning reflects von Ahn's innovative spirit and commitment to educational equity.
Yvon Chouinard & Patagonia: Environmental Stewardship Through Business. Yvon Chouinard, an accomplished climber and blacksmith, founded Patagonia with the aim of producing high-quality outdoor gear while minimizing environmental impact. Chouinard wasn’t a fashion executive, but rather an alpinist who built what he needed for the mountain. His deep connection to nature influenced the company's ethos. Chouinard is noted for saying, “Patagonia exists to challenge conventional wisdom and present a new style of responsible business.” (FN8) His dedication to environmental activism is evident in Patagonia's initiatives, such as donating profits to conservation efforts and implementing sustainable manufacturing practices.
Wanted: A Founder with an Authentic Mission and Skill Alignment. These founders exemplify the power of aligning personal passion with professional expertise:
Phil Knight channeled his love for running into building a brand that embodies athletic spirit.
Howard Schultz unleashed a passion for coffee into a global movement that changed the daily habits of millions across the planet.
Melanie Perkins leveraged her design education experience to simplify design tools for the masses.
Luis von Ahn utilized his computer science background to make education accessible worldwide.
Yvon Chouinard integrated his environmental values into a business model promoting sustainability.
💡 When interviewing founders, look for this synergy between their mission and capabilities. A strong connection often signals a deeper commitment and a higher potential for impactful success.
About the Author: Kevin R. Davis is a 2x General Counsel who offers business stakeholders strategic guidance aimed at optimizing their operations, including implementing lean legal systems, improving risk management processes, undertaking business transformations, fundraising, engaging in strategic planning and handling exits. Kevin publishes a weekly newsletter, The Savvy Startup Advisor™, which provides guidance for startup success. Earlier in his career, Kevin worked as a corporate attorney with Kirkland & Ellis, LLP and as a legal executive of Publicis Groupe. Kevin is a graduate of Northwestern University School of Law and Northwestern University.
Illustrations by Juliette Davis. Help tip the scale in favor of our talented illustrator, a graphics design student, Juliette Davis: https://buymeacoffee.com/savvystartupadvisor.
Nothing contained in this article should be construed as legal or investment advice. This article does not create an attorney-client relationship between any reader and its author. Neither the author nor the publisher is responsible for updating this publication to consider any changes in applicable laws. Nothing in this article is based upon the author or publisher’s experience with any specific individual or organization; any resemblance to actual persons, places, or events is purely coincidental. If legal advice or other professional assistance is required, the services of a competent professional should be sought.
References
FN1 / Thiel, P. (2014). Zero to One. Crown Publishing Group. (p 120).
FN2 / Thiel, P. (2014). Zero to One. Crown Publishing Group. (p 120).
FN3 / Knight, P. (2016). Shoe dog: A memoir by the creator of Nike. Scribner.
FN 4/ Schultz, H., & Gordon, J. (2011). Onward: How Starbucks fought for its life without losing its soul. Rodale Books.
FN5 /Schultz, H. (n.d.). When you're surrounded by people who share a passionate commitment around a common purpose, anything is possible [Quote]. Retrieved from https://quotefancy.com/quote/1404127/Howard-Schultz-When-you-re-surrounded-by-people-who-share-a-passionate-commitment-around.
FN6/ Perkins, M. (2023). Canva celebrates 10 years of empowering the world to design. Startups Magazine. Retrieved June 19, 2025, from [Startups Magazine]
FN7/ von Ahn, L. (2014, October 9). Our mission is to develop the best education in the world and make it universally available [Video]. YouTube.
FN8 / Chouinard, Y. (2005). Let my people go surfing: The education of a reluctant businessman. Penguin Books.
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