You learn: Are they doing well or going through a difficult time? If they are doing well, they might have funds that need a home.

3. How did you start your business? They love telling this story! It's more fun if they built it from scratch, but they might have inherited it from their parents. When they tell this story, you will learn how the business grew and evolved. It's rare to hear: "I started it 25 years ago and have been doing the exact same thing ever since.

You learn: What was their motivation? Did they see a need in the marketplace? Were they tired of the corporate world? Do they have the same motivation and enthusiasm now? Would they encourage someone to do the same?

4. Where do you see your business going? It's often their major asset. Many see their business as a family dynasty. Sometimes their children don't want to get involved in the business. Then selling the business becomes the logical course of action.

You learn: What's their endgame? If they have partners, this might involve key person insurance. It may mean they need to take the long view towards getting their business ready for sale.

5. What keeps you awake at night? Presumably their snoring dog isn't the answer. They have concerns about the future. Expenses rising faster than income. Health insurance might be a big concern. We were out for dinner with another couple when one of them introduced this topic into the conversation. He explained how he addressed the issue.

You learn: All sorts of things! As an insurance provider, you might be able to find them equivalent coverage at a better price.

6. Who are your competitors? This can be a very interesting question! They might be the traditional ones you expected them to name. They might be a brick-and-mortar operation that's losing business to online competitors. They might have new competitors who have opened stores nearby. What are they doing to address these challenges?

You learn: New entrants to the local market might be business prospects for you. You learn how they are coping with staying competitive.

7. How do you find new employees when you need them? This is one of the biggest post pandemic news stories. Businesses can't find people to hire! What happened to their former employees? Don't they want to come back? What types of skills are they looking to hire?

You learn: What are their needs? You might know the right people.

8. How has the pandemic affected your business? You are wondering what has changed pre-pandemic vs. post-pandemic. It's a good question because they might be worried about it, but they don't have anyone to talk with about the problem. You expressed a sincere interest. You are friends.

You learn: The pandemic was an unexpected challenge. Some businesses folded. Others thrived. Many adapted. You learn their story.

9. Do you sell to the government? This could be the Federal government. The question also includes state and local government. The logic here is the evening news is filled with talk about how much the government will be spending on infrastructure and other projects. Regardless how the economy is doing, the government is always spending. They may not have given serious thought how they could get some of that business.

You learn: Now you've got them thinking. They see a big customer seeking to buy goods and services. Can they provide them?

These conversations, held over time have given you a good understanding of your friend's triumphs and setbacks running their own business. It can also get them curious about how you could help. It might be in doing direct business with you. You might be able to make some connections for them.

Bryce Sanders is president of Perceptive Business Solutions Inc. He provides HNW client acquisition training for the financial services industry. His book, "Captivating the Wealthy Investor" can be found on Amazon.

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