25 Hard Questions Every Founder Should Ask Themselves

Startup founders share their go-to questions for taking a pulse check on everything from product strategy to co-founder relationships to their own decision making.

QUESTIONS TO REFOCUS YOUR PRIORITIES AND DECISION MAKING

The stakes of every single decision you make in the founder seat can feel extremely high. But it can be hard to parse out which problems are actually worth your extended consideration.

1. Did the work I do today actually move the needle on making the company successful?

A useful question to differentiate between urgent to-dos and distractions — particularly in the 0 to 1 stretch of a startup. This question reminds me to spend time focusing on outputs rather than inputs.

2. If in a year we looked back on this decision, is this the decision that killed the company?

If you find yourself hand-wringing over a decision, stop and ask if this problem could pose an existential threat to the company.

3. How can we shorten the time from hypothesis to insight?

Speed in a startup context isn’t just how fast you ship products — it’s how fast you can test your assumptions.

4. What's the hard part — and am I working on it?

‘The hard part’ is the aspect of a project where if it doesn't work, the whole thing won't work.

5. Is there a way for me to make this a smaller decision than the one I’m considering?

To add some more efficiency to your decision-making process, ask how you can break big decisions down into smaller, reversible choices.

6. What’s the kill criteria for this project?

Just as important as deciding to do something is knowing when it’s time to quit. Set benchmarks that you can observe and adhere to.

7. Are we winning because we’re making good calls? Or are we doing well in spite of ourselves?

Use this question to routinely assess whether you and your team are falsely correlating good outcomes with bad decisions.

QUESTIONS TO SIZE UP YOUR PRODUCT STRATEGY

It’s easy to get wrapped up in the daily minutia, but it’s just as important to evaluate if you’ve created the product you set out to build.

8. What is the customer actually trying to tell us with a feature request?

Probe deeper into the customer’s needs behind a feature request to understand the actual problem.

9. Are we pursuing this product direction due to inertia or because it’s right?

This question reveals product directions that may not align with today's customer or technology landscape.

10. Why won’t this work out?

Identify the potential tripwires of every bet before making decisions.

11. How can we make the product more delightful?

There’s always room for extra delight in your product; create space for those intangibles.

12. When we look at competitors who have failed, how do we avoid repeating their mistakes?

Take stock of both successes and failures to learn what pitfalls to avoid.

13. What's the new product that would terrify us the most if it were launched tomorrow?

Identify the disruptive innovation that could shake your business model and plan accordingly.

14. If I was starting this business again today from scratch, what would I build to win the market?

Avoid the sunk cost fallacy by focusing on what is essential today.

QUESTIONS TO STRENGTHEN YOUR RELATIONSHIPS WITH YOUR CO-FOUNDERS AND TEAM

Reflect on these questions when you find yourself in challenging situations with co-founders or are just looking to improve teamwork.

15. What hurts me more? The fact that they did it in the first place — or that they did it without me?

Understanding your feelings can help navigate trust and care issues within your team.

16. What’s the conversation I’m avoiding?

Identify and name the hard discussions that need to happen within your team.

17. What’s one thing I’m afraid to ask my team but probably should?

Encouraging a culture of openness and curiosity can break down barriers.

18. Is my team missing any context to be able to make good decisions for the company?

Ensure knowledge isn’t trapped within individuals and is accessible for informed decision-making.

19. How does our team now compare to the team last year?

Regularly reflect on team development and individual performances.

20. Am I letting my team members operate in their respective zones of genius?

Empower team members to contribute effectively within their strengths.

QUESTIONS TO CHECK IN AS YOU GROW

When your team grows, revisit these questions to recenter your focus.

21. What’s the next glass ceiling?

Identify constraints that could limit growth and strategize on how to overcome them.

22. If we close 100 more deals that are just like this one, will we be happy or sad?

Evaluate whether the growth opportunities align with your values and vision.

23. Where are we on the continuum of chaos and control?

Acknowledge the balance between maintaining control and allowing creative chaos.

24. What am I doing that I feel constrained by? What could I relax that could make things much faster, better and more scalable?

Identify constraints you can loosen to create better outcomes.

25. What’s one area of growth I’ve been avoiding because it feels uncomfortable?

Recognize that discomfort often lies on the path to growth and improvement.