7 Important Questions to Ask People You Admire  

What if you suddenly found yourself sharing an elevator or seated at an event with somebody you admire, someone like, Warren Buffett, Elon Musk or Bill Gates? Would you stammer an introduction and look awkwardly at your feet, or would you be able to make the most of the encounter with a set of smart, concise questions?

It’s unlikely you’ll ever meet any of those people, but you probably encounter other admirable people on a regular basis. Whether it’s a national leader in your field or the senior manager who works down the hall, here are some questions you can ask from the leaders you admire to learn from their success:

1. What’s the biggest factor that has helped you be successful?
Success is different for everyone, but it’s always interesting to learn how people arrived where they are. Their stories may point you in a new direction, give you an answer you’ve been looking for, or motivate you to push through the tough times. Responses also give you insight into their values and priorities.

2. What are your success habits?
Asking successful people about their daily habits can give you ideas for your own routines. The answers are rarely esoteric; generally, they’re actions anyone can take. As the old saying goes, we are what we repeatedly do.  Excellence, then, is not a quality but a habit, and successful people are simply those with successful habits.

3. What mistakes have you made along the way?
This question is one of the most important things you can ask anyone, because it allows you to learn from their experience. If you ask it often and listen carefully to the answers you hear, you will make fewer mistakes yourself. You’ll have insight into how to do things in a way that doesn’t lead to miscalculations or blunders.

4. What was the hardest decision you ever had to make?
Most successful people have had to make at least a few genuinely difficult between-a-rock-and-a-hard-place decisions. Learning what they chose, and why, gives you a close look at their thought processes and priorities, helping you prepare for the tough decisions that lie down the road for you. At the end of the day, it’s in your moments of decisions that your success is shaped.

5. What is the best advice you can give?
Some people respond better than others to such an open-ended question, but when it connects, it can cut right to the important stuff. Compile the responses you get to this question and keep them where you can read through them all from time to time.

6. If you could start all over again, what would you do differently?
Successful people tend to be self-aware, and it’s likely that they’ve already given this question some thought. You might expect to hear about preventing some mistake or failure, but successful people know that mistakes and failure are among our greatest teachers. Many focus instead on wishing they had taken more chances and been bolder.

7. What’s one change I should make right now to help me get closer to my success?
This question is appropriate to ask of someone who’s already familiar with you and your work. Improvement requires change, and sometimes the hardest part is knowing what needs to change.

Most successful people are grateful for what they’ve achieved, and many are happy to share their knowledge and experience. It’s too good a resource to waste, so be prepared to make the most out of every encounter, especially with those you admire.

Lead From Within: Just remember, we tend to become those we admire.



N A T I O N A L   B E S T S E L L E R
The Leadership Gap: What Gets Between You and Your Greatness

After decades of coaching powerful executives around the world, Lolly Daskal has observed that leaders rise to their positions relying on a specific set of values and traits. But in time, every executive reaches a point when their performance suffers and failure persists. Very few understand why or how to prevent it.

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Photo Credit: Getty Images

Lolly Daskal is one of the most sought-after executive leadership coaches in the world. Her extensive cross-cultural expertise spans 14 countries, six languages and hundreds of companies. As founder and CEO of Lead From Within, her proprietary leadership program is engineered to be a catalyst for leaders who want to enhance performance and make a meaningful difference in their companies, their lives, and the world.

Of Lolly’s many awards and accolades, Lolly was designated a Top-50 Leadership and Management Expert by Inc. magazine. Huffington Post honored Lolly with the title of The Most Inspiring Woman in the World. Her writing has appeared in HBR, Inc.com, Fast Company (Ask The Expert), Huffington Post, and Psychology Today, and others. Her newest book, The Leadership Gap: What Gets Between You and Your Greatness has become a national bestseller.

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