50 Questions for Your Next Coffee Date
We thought we’d share 50 conversation starters for you to pick and choose from on your next coffee date. These are curated for you and your fellow female-entrepreneur. Steal a few, skip the ones that don't fit, and let the rest come naturally.
Don’t have a coffee meet-up on the books? I bet you can add three to your schedule for when you return to the office post holiday weekend.
What's the real story behind how you started your business?
What were you doing before this?
Was there a specific moment you knew you had to go all in?
What's something people assume about your business that's totally wrong?
If you had to describe your business in one sentence to a stranger, what would you say?
What does a normal Wednesday actually look like for you?
What part of running your business do you secretly love that most people would hate?
What's the task you keep putting off?
Do you work better alone or with people around you?
What's one tool or system that's saved your sanity?
What was the first year like financially?
When did it start to feel sustainable?
What's a pricing lesson you learned the hard way?
How do you think about reinvesting versus paying yourself?
What's the smartest money decision you've made for your business?
What's the hardest season your business has been through?
What almost made you quit?
How do you know the difference between pushing through and needing to pivot?
What's something you got wrong that ended up teaching you the most?
Who or what do you lean on when things get hard?
Who's someone in this community you'd love to work with?
Have you ever partnered with another local business? How did that go?
What does support actually look like for you, practically speaking?
Is there a business you refer people to constantly?
What's a collaboration you're dreaming up but haven't started yet?
Do you feel like your business reflects who you are, or is it separate?
What part of your personality shows up most in how you run things?
Has owning a business changed how you see yourself?
What's a value you refuse to compromise on, even if it costs you?
What would you do differently if you started over today?
Where do you want this to be in five years?
Is bigger always the goal, or do you want something else?
What would "made it" actually feel like for you?
Is there a version of your business you haven't tried yet?
What scares you about growth?
How do you protect time for yourself outside of work?
What does rest look like for you these days?
Who are the people who keep you grounded?
What's something you do just for you, with no business angle at all?
How has this work shaped your relationships?
What's your coffee order say about you?
If your business had a favorite color, what would it be and why?
What's the best piece of advice a mentor or customer ever gave you?
What's a small win from this week you haven't told anyone about?
What's something in your industry that everyone gets wrong?
What do you need more of right now: time, money, clarity, or connection?
Is there anything I can help with or connect you to?
What's one thing I could introduce you to someone about?
What would make this feel like time well spent for you?
When can we do this again?