The fifth question on my list of things to talk about before going into business or starting a project together is: 

What is your risk tolerance? 

(See post #1 in this series here: https://leighchandler.com/questions-to-ask-before-you-work-together)

So many great partnerships have a risk taker and a risk averse person who balance each other but also drive each other crazy.  Assessing your comfort with risk ahead of time will help you appreciate what each person’s perspective brings to your project, instead of always feeling like your partner is trying to drag you off a cliff or hold you back.  And it will also help you get a feel for each other’s boundaries and come up with ways to protect your project from going too far in either direction.

And if you discover that you have the exact same risk tolerance?  Talk about that, too!  If you both hate taking risks, talk about how that can be an advantage – you won’t rush into anything stupid – and a disadvantage – you might miss a great opportunity.  See if you can create a system for assessing opportunities that allows you to make smart, not just safe, decisions.  If you both love taking risks, have the same conversation in reverse.  What can you do to build some caution into your decision making?