Q: I have a friend who has taken his business as far as he is willing to go without investing more money into it. I believe the business has great prospects. What's a win-win way to propose the idea of our entering into a working relationship to expand the business?
A: The next step depends on how well you know your friend and how well he knows you. If you feel your friend knows and trusts you, then asking whether he would welcome a written proposal for how you might work together would be the next step.
If you think there isn't enough rapport to feel confident you'll get a yes answer, then take time to get acquainted. Propose doing something you know he likes to do, then find a time when it's appropriate to share your interest in taking his business to the next level.
When you do this, notice whether your friend is picking up on what you're expressing and if he's returning your interest. If you're not sure, you might test his interest by asking a few questions like "What do you think?" and "How does this sound to you?"
Be sensitive to the way he makes decisions. Some people need time to let an idea percolate; others need to hear something more than once. Still others decide on the spot, in which case you risk losing a relationship if you press further. If you're not sure how your friend prefers to make decisions, one way to find out is to ask how he's decided something in the past.