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25 Hard Questions Every Founder Should Ask Themselves
Startup founders face a relentless stream of questions every day—from customers, investors, employees, reporters, and yes, sometimes even skeptical parents. Being able to deliver a sharp, on-the-spot answer is practically part of the job description.
Equally important, though, is holding yourself to the same level of scrutiny. Some of the most profound insights—and the changes in strategy, priorities, or behavior that follow—come from asking yourself the hard questions no one else will.
Take Kareem Amin, CEO and co-founder of Clay. One of his go-to questions is simple but powerful: “Are we taking real risks?”
“It’s easy to convince yourself you’re taking risks,” he says, “but if it’s something you don’t fully believe in, something you think you should do, or something with a predictable outcome, it’s not a real risk. A real risk is something you believe in, even if the result is uncertain. You might be anxious, scared of failure, or worried about the shame if it doesn’t work out. We need to know which decisions are real risks, how many we’re taking, and what the possible outcomes are.”
As startups finalize their 2025 plans, this reflective mindset is especially valuable. We asked founders across the ecosystem—first-time builders and seasoned entrepreneurs alike—which questions help them pause, reflect, and course-correct across product, team, and leadership.
Below are 25 questions they return to again and again, organized into four themes:
- Refocusing priorities and decision-making
- Sizing up your product strategy
- Strengthening co-founder and team relationships
- Checking in as your startup scales
Some are daily reminders; others are checkpoints for stormy periods. Either way, they’re designed to help founders navigate the messy, meaningful journey ahead.
QUESTIONS TO REFOCUS YOUR PRIORITIES AND DECISION MAKING
Every founder feels the weight of every decision. But how do you distinguish what truly matters? These questions help prioritize, accelerate, or slow down your decision-making, and keep your focus where it counts.
1. Did the work I did today actually move the needle on making the company successful?
Colin Zima, CEO and co-founder of Omni, uses this question to separate urgent tasks from distractions, especially in the 0-to-1 stage.
“When your startup is tiny, you can’t rely on momentum,” he says. “Whether it’s acquiring customers, shipping a feature, or generating leads, your small team has to execute. This question reminds me to focus on outputs, not just inputs. Trying isn’t enough—you have to create tangible results and cut efforts that don’t contribute.”
Ilana Borkenstein, CEO of M7 Health, adds a shortcut: “Can I explain how this activity contributes to our company’s OKRs in two sentences or less? If not, skip it.”
2. If we looked back a year from now, would this decision have killed the company?
Levels CEO Sam Corcos uses this to filter existential threats from distractions.
“Founders often get pulled into urgent tasks that feel important but aren’t. This question clarifies what actually moves the company forward,” he says.
Often, scattered attention signals a delegation gap. If your team can’t handle certain decisions independently, hire for that role. If the problem is poor judgment of urgency, this question usually clarifies: the answer is almost always “no.” Startups are default dead—you must prioritize ruthlessly.
3. How can we shorten the time from hypothesis to insight?
Speed isn’t just shipping—it’s testing assumptions quickly.
Ravi Mehta, former co-founder of GPTcsv.ai, says, “Startups can validate ideas in days or weeks, whereas big companies take months. We move fast not by increasing velocity, but by reducing latency—the time from idea to impact.”
4. What’s the hard part—and am I working on it?
Wes Kao, former co-founder of Maven, asks this to stay honest about avoiding crucial challenges.
“The hard part is the piece that, if it fails, the whole project fails. Many founders chase parts they already know how to do because it feels productive. But delaying the hard part can make all ‘progress’ meaningless,” she says.
5. Is there a way to make this a smaller decision?
Decision science expert Annie Duke encourages breaking big bets into smaller, reversible choices.
“Ask: ‘If I pick this, what’s the cost of quitting?’ The lower the cost of change, the faster you can go,” she says. This mindset applies whether you have three employees or 3,000.
6. What’s the kill criteria for this project?
Duke emphasizes naming the point at which you’ll quit if benchmarks aren’t met.
“Set specific states and dates. If by [date] the project hasn’t reached [state], I’ll quit. Review this regularly with an advisor—it mitigates the urge to keep tweaking endlessly,” she says.
7. Are we winning because we made good calls—or in spite of ourselves?
Wade Foster, CEO of Zapier, asks this to avoid falsely attributing success to poor decisions.
“Good decisions can lead to good or bad outcomes. Hardening opinions on the wrong conclusions weakens your company’s potential,” he says.
QUESTIONS TO SIZE UP YOUR PRODUCT STRATEGY
Daily tasks can blind you to whether your product is on the right path. These questions help you step back and evaluate your roadmap, vision, and market fit.
8. What is the customer really trying to tell us with this feature request?
Colin Zima digs into the “why” behind requests.
Ask:
- Why do they need it that way?
- What are they trying to achieve?
- How are they doing it now?
“The deeper you go, the more you align customer requests with your product vision,” he says.
9. Are we pursuing this product direction out of inertia—or because it’s right?
Eilon Reshef, CPO of Gong, asks this to avoid autopilot decisions.
“Technology or customer needs may have changed. If we’re stuck on an old path, at least do it consciously. Also ask: what are we missing because we’re too narrowly focused?”
10. Why won’t this work?
Rick Song, CEO of Persona, runs pre-mortems to identify potential failure points before committing to a decision.
“Finding counterpoints reveals scenarios where you might be wrong and helps determine when it would work,” he says.
11. How can we make the product more delightful?
Rahul Vohra, CEO of Superhuman, builds space for joy and delight even in goal-driven orgs.
Ask:
- How can we make it so striking users can’t help talking about it?
- How can we design it so users don’t need to remember to use it?
12. When looking at competitors who failed, how do we avoid repeating their mistakes?
Kevin Caldwell, CEO of Ossium Health, emphasizes learning from failures—not just successes.
13. What product would terrify us if it launched tomorrow? If it doesn’t exist, why aren’t we building it?
Bob Moore, CEO of Crossbeam, learned this at RJMetrics. The insight led to Stitch, a successful spinout.
14. If I were starting this business today, what would I build to win?
Laura Behrens Wu, CEO of Shippo, uses this to sidestep sunk costs and constraints.
QUESTIONS TO STRENGTHEN YOUR RELATIONSHIPS WITH CO-FOUNDERS AND TEAM
Communication sets the tone for any team. These questions help you navigate conflict, trust, and empowerment.
15. What hurts more: they did it, or they did it without me?
Esther Perel highlights that the first is about power; the second is about care and closeness. Understanding this distinction clarifies conflict.
16. What conversation am I avoiding?
Johnathan Nightingale, co-founder of Raw Signal Group, says acknowledging the “elephant in the room” is often the first step to resolution.
17. What’s one thing I’m afraid to ask my team—but should?
Emily Anhalt, co-founder of Coa, uses this to lean into discomfort and foster openness.
18. Is my team missing context to make good decisions?
Shensi Ding (Merge) and Laura Behrens Wu focus on empowering teams by sharing vision and reasoning, rather than hoarding context.
19. How does our team now compare to last year?
Shensi Ding also asks: What percentage of the team is mediocre or bad? Brutal, but necessary for reflection.
20. Am I letting team members operate in their zones of genius?
Ilana Borkenstein ensures her team has space, autonomy, and context to execute in areas they excel.
QUESTIONS TO CHECK IN AS YOU SCALE
As your startup grows, new challenges emerge. These questions help maintain perspective and adaptability.
21. What’s the next glass ceiling?
Eilon Reshef uses this to anticipate limits in market, product, or operations.
22. If we close 100 more deals like this, will we be happy—or sad?
Melissa Nightingale reminds founders that not all growth is good growth. Align growth with team, market, and your own excitement.
23. Where are we on the continuum of chaos and control?
Kareem Amin: find the sweet spot between structure and creative chaos—like dancing without bumping into each other.
24. What constraints can I relax to move faster, better, and more scalably?
Howard Morgan encourages founders to regularly write out constraints and question which can be loosened to unlock creativity and efficiency.
25. What’s one area of growth I’ve been avoiding because it feels uncomfortable?
Emily Anhalt reminds founders that discomfort is where growth happens—be it delegation, insecurities, or personal habits.
These 25 questions are more than prompts—they’re tools to interrogate your priorities, product, relationships, and scaling strategy. The founders who ask themselves these questions regularly often find the clarity, leverage, and courage to steer through chaos and build something lasting.
