The key to business success is good preparation. The same philosophy applies to difficult money conversations such as asking for a raise, collecting an overdue account, or negotiating royalties with the publisher of your new book. The preparation stage requires you to look inward and self-reflect. It also warrants looking outward and anticipating the possible thoughts and feelings of the other party.

Here are 10 questions to ask yourself as you prepare for a difficult money conversation.

1. Who do you want to engage in this money talk and for what purpose?
2. What, if anything, triggered your desire to have this conversation?
3. What specifically do you want to discuss with this person?
4. What would you consider a good outcome if this conversation went well?
5. What do you anticipate would be a good outcome for the other party?
6. What is the best way to invite this person to engage in a money talk?
7. When and where might you have this conversation?
8. What feelings might this conversation trigger for you? For the other person?
9. How might you handle these feelings if they arise?
10. If you put yourself in your money talk partner’s shoes, what else should you consider as you prepare for this conversation?

Answering these questions may not be easy, especially when you are anticipating what your conversational partner may be thinking and feeling. But doing this exercise is a great way to get in the right mindset, think about your priorities and ensure a better outcome. Don’t wing it! Prepare!

Do you have an upcoming money talk that is stressing you out? I would be happy to guide you on how to break money silence and negotiate the outcome you want. Click here to set up a free 30-minute discovery call. You don’t have to face a difficult financial conversation alone.