10 Questions We Ask Millionaires And Other People Worth Interviewing

One of the most important realizations I’ve had in my life is that all of the content we consume, is made and written by people. The internet, books, blogs, podcasts, articles, TV Shows, art, businesses, products etc.

This may sound pretty straightforward and like a dumb realization, but it has changed our lives.

Consuming the creating content is wonderful, and we should do it. But what if we went directly to the sources? The people who created them?

When Kay and I started building our Personal Finance Course, we wanted to talk to people who had already “made it”. Whatever that meant.

So this is what we did:

1. We asked our friends who the most successful person/people they knew were. It seems like everybody knows at least 1 successful person. We then asked if they thought if that person would be open to us interviewing them.

50-60% of the time, the answer was yes, and we got a phone call or in person meeting set up.

2. We came with a list of questions. To be honest, we asked a lot of the same questions in our interviews, and still to do today. Because every person we interview is so different, the answers are too. Here are the questions and the preparation we did:

Preparation

1. Look up the person on LinkedIn and other social media channels. Find things they’ve done in the past (previous Businesses, hobbies, where they went to college etc.) If they’re big enough, find articles etc. Look at the social media of their organizations or businesses. This helps build a good background.

2. Be on time for the call. Since graduating, I sometimes have students reach out and ask if they can ask me some questions, interview me, etc. The worst thing in the world is when I block off time on my calendar to help them, and then they forget or don’t show up. Don’t be that person. Call on time, and end on time.

3. Be in a quiet, organized space. Sometimes if I was driving somewhere I’d just pull over and take the call in my car. Don’t be distracted and focus on the person you’re interviewing.

Questions to Ask

Start by explaining that you like to learn from successful people, and mention that this person has been recommended to you as someone worth talking to about their life. Tell them the time expectation (30-60 minutes depending on what they can do), ask if they’re okay with that and begin!

You don’t have to ask all of these questions, these are just some good starting points. Typically these questions lead to other topics and tangents you can follow up about. Sometimes you’ll only get to 1 or 2 questions!

Question #1

“Why do you do what you do today?”

This question is a good one to start with because it’s easy. They’re just talking about their current projects and focuses. But it’s deeper than just “What do you do.” It’s likely they’ll say something interesting that you can ask a follow up question off of.

Question #2

“Can you tell me a little bit about how you got where you are today?”

People love sharing their history and talking about themselves. Surprisingly, they don’t often get asked about their careers on this level. Just let them talk. Ask follow up questions. This is often the funnest part of the interview, and gives you a lot to talk/ask about.

Question #3

Are there any specific books that have impacted you that you would recommend?

I love books, so this is a question I always ask.

Question #4

Are there any specific routines or habits you have developed that you would recommend? (This could be morning routines, a weekly date with their spouse etc.)

This is an interesting question because it shows what they’ve found is important to be disciplined in.

Question #5

How do you define success?

Question #6

What is the biggest problem you’re facing right now in your work?

Question #7

Without getting too personal, what personal financial decisions do you feel have made the biggest difference in your life?

Prepare to be wowed. Either good or bad.

Question #8

I don’t know your exact family situation, but what practices, habits or traditions in your family have had an overall positive effect?

I ask about family because sometimes “successful” people have actually neglected or lost their family. Sometimes they have really strong families. Either way, they often share an insight of either what not to do, or what to do. It’s a personal question, so handle it with respect.

Question #9

If you could tell yourself anything at the age of (your age here, or if you’re older than them, use 22 or 25) what would you say.

This is a deeper question that often makes the the person being interviewed pause and think. The answers are always meaningful, and I always come away learning something new.

Question #10 (Conclusion)

1. Thank Them
2. Ask if there is anything you can help them with as you continue to interview other people. (For example, they want to join a board and you find a successful Entrepreneur)
3. Ask if you can reach out (not very often if you have a question)
4. Ask them if they know anybody you could conduct a similar type of interview with (successful/interesting people know other successful/interesting people)

Take the time to interview someone new once a week. Your life will change for the better for it. We promise!

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