50 Questions Every Female Founder Should Ask Themselves

Photo by Lauren Kallen

Photo by Lauren Kallen

In business, we often play by the unspoken rules that someone else set up in our industry long before we arrived - this is especially true for women. It’s hard to break those rules if you don’t see anyone else doing it or the pressure to follow a certain path is incredibly high. Inc Magazine’s current female-focused issue inspired us to write a list of 50 questions every female founder should ask themselves.

We hope this list makes you think deeply about your company, makes you question things you once took for granted, and gets you closer to a life and business that bring you deep fulfillment.

These questions are written from the perspective of one female founder to another, but they can apply to anyone who wants to take a deeper look at their chosen path. 

50 Questions Every Female Founder Should Ask Themselves

1. What rules am I following in my business? Who made up those rules? Are they working for me?

2. What decisions have I made for my business because I “should” rather than I “want” to?

3. What rules have I created for my business because they work for me and my family and my employees?

4. Are my current workplace and hours the ideal setup for me to be happy? If not, how would I prefer them to be?

5. What’s a good reason they can’t be that way?

6. How supportive am I of other women in the business world, including my competitors? 

7. How do I show that support? 

8. How often do I reach out to other women for support? How can I do more of it? 

9. How many times has someone told me I can’t do something?

10. Did I believe them? 

11. Do I still?

12. How much do I believe in myself? 

13. If not 1,000%, what is holding me back and what do I have to do to erase that as quickly as possible?

14. What would I do if I failed tomorrow? 

15. What would that mean about me personally?

16. What did I do today to make my co-founder or employees feel that they love their jobs?

17. What role models have informed my perspective of how a leader is most effective? 

18. What qualities do I personally possess that I feel make me a great leader?

19. How confident am I at negotiating? Why?

20. What is the first feeling I feel when I wake up in the morning? 

21. What does that tell me about the decisions I’ve made?

22. What can I change about my business today that will make me and my employees happier?

23. What do I value more: money or a balanced life? 

24. Do/can I have both? Why/why not?

25. What is my company’s mission? (To “be the best…” is not a mission.) 

26. Is a mission important to me or my employees?

27. What am I afraid to do in my business?

28. How often do I try to do something in my business that I'm afraid might fail? 

29. Has starting a business changed the way I care for myself? 

30. What do I do everyday to take care of myself? 

31. What is the most effective way I’ve found to relieve stress?

32. How often do I do this?

33. What do I want my employees to say about me and my company one day when they’re no longer working for me?

34. What example am I setting everyday for my employees and my peers in how I live my life and run my business?

35. What am I out to prove and to who?

36. What else could I be doing right now that would be more interesting and fulfilling?

37. Who are my mentors? Who do I wish were my mentors? Why aren’t they?

38. How comfortable am I at talking about money? What impact does this have on my business? 

39. What excuses do I most often make for not doing something?

40. When will that stop?

41. What do you feel guilty for?

42. Is it ok to quit? Why or why not?

43. In what circumstance would it be ok to quit?

44. If I could move my office anywhere in the world for a month, where would I go? Where would my meetings take place?

45. What are my goals for my personal success?

46. Are they as high as other people I admire? Why or why not? 

47. Where/what do I have to do to consider myself successful?

48. How often do I promote my company's wins? How does this impact my business?

49. What or who am I grateful for? 

50. What is the most important lesson I will teach my employees, co-founders, customers, clients, and peers? 

Bonus: What do I already know that others do not? 

If these were helpful or you have more questions you think we should add, let us know via Twitter