Questions to ask a Successful Person

Questions to ask a Successful Person

A Step Towards Becoming Successful

Before we discuss this topic in detail, we need to identify who a successful person is and what category of success we are trying to identify the questions to ask. Is it generic (Successful at life)? Is it about business (A Successful Entrepreneur)? Is it about a job, marriage, school? Success is a relative concept and is differently defined for each person you encounter. Therefore, before you go out there to ask a Successful Person any questions, it is a good idea to ask: “do they consider themselves successful? How? In what?” and tailor the questions based on their most likely answer. 

Another notable importance is that the best questions to ask a successful person can only come when you admire that person. This is because it is personal for you. While you can ask questions to successful people in any category of your choice, the best always stems from having some form of connection with the person. This makes the answers you get to the questions asked more ingrained in your mind for immediate practice. The main reason for asking these questions to successful people is that you hope to be successful yourself, so these questions must come out of sincere curiosity and intentionality.

Questions to ask a Successful Person

That being said, here are fifteen thoughtful questions you can ask a successful person within any category:

  • How did you become successful? 

This is more like asking: What is the root of your success? Asking this question may seem a bit vague to the successful person, but still, they would be able to answer the question by highlighting several factors in their lives that led them to where they are. Those factors could be considered as the root of their success. This also helps you understand what factors led to their success and learn a bit about the person.

  • At what point did you consider yourself successful? 

This question is crucial to ask because it serves to measure or determine success. The successful person would be able to share the metrics they used to measure their success. These metrics usually come from preset goals or objectives that would be regarded as successful when accomplished. This question, when answered, can help you understand and outline what form or metric you would like to use to measure your success.

  • How can one become successful? 

This might seem similar to the first question, but one could ask a successful person to gain clarity on their unique journey. This is more like a personal question, but asking this to a successful person helps them highlight key factors that helped them become successful. While they might have answered the first question, a successful person wouldn’t advise you to do the same thing as them but would offer advice based on information from your journey. This allows them to learn about your own story.

  • In your opinion, what are the keys to success? 

This question is really thoughtful because not only is the person successful, but they can identify key strategies or actions in their lives that they took to become successful. These key strategies would hold ground and can be applied in any category of interest that you want to be successful in. Most successful persons can only share this information based on their personal experience, which is a strong factor in success.

  • What habits made you successful? 

Even when dealing with professional success, it’s important to get some insight into people’s personal lives. People don’t just stumble on success. They strive for it, and habits are the backbone of any work we do.  They are responsible for generating intentional action and focus on supporting their goals and dreams. Asking a successful person this question is important because it provides insights into their personality, character, and traits they adopted to get them to the level they are at. While this may be unique to their own experience, it also helps you identify the habits to adopt if you want to become successful.

  • Who is someone you consider successful? 

The people we consider successful are pretty much like us. They have other people they admire who inspire them on their journey. One can even say that those people were the anchor to their success, so asking this question can provide insightful details into the life of the person you consider successful. From their response, you would be able to identify who they look up to, which would also clarify their approach or life based on the person they admire. Be sure to listen attentively to how this question is answered, as it will also provide clarity into who you should identify as your role model or mentor in your journey towards success.

  • What do you plan to do to remain successful? 

Put in another way, “What does success look like for you in the future?” This question puts the successful person into a mode where they understand that not only have they not reached a destination, but there are several other destinations to journey on, which would maintain the success they already know to have. That makes them aware that it is not over, and they need not be complacent because of their current or previous accomplishments. This question, I would reckon, is something even a successful person should ask themselves. This is because there is nothing worse than being regarded as a “one-hit wonder” or peaking early. These are what we have seen in some celebrities and people who the world deemed to be successful. By asking this question to a successful person, it keeps you in check to understand what is required to achieve your success.

  • What did your definition of success change along your journey? 

This is also another good question to ask a successful person. This is because as we progress in life, what we thought we wanted before begins to change. This is because we have more insights into what is going on in our lives which we didn’t consider before. We gain clarity with time, and our priorities change. This is why it is important to be more flexible with life to adapt to any drastic changes in time easily. By asking this question to a successful person, you would be able to identify from their response what success meant to them at a previous timeline, what success is to them at the current moment, and what they anticipate success to be in the future. 

  • Have you ever experienced failure? 

This is also an important question to ask because it is only a successful person that can understand the meaning of failure. Take it from Thomas Edison when a reporter asked, “How did it feel to fail 1,000 times?” Edison replied, “I didn’t fail 1,000 times. The light bulb was an invention with 1,000 steps.” From this example, we can see that Thomas Edison could value his success in creating a light bulb due to his major familiarity with failure. By asking them this question, they get to share their personal experiences with failure, which removes the facade that successful people are perfect people and see the truth that they are just like you – everyday normal people. 

  • How do you approach failures or setbacks?

This brings deeper clarity into the question asked above. Thomas Edison once said, “Great success is built on failure, frustration, even catastrophe.” and “Many of life’s failures are people who did not realize how close they were to success when they gave up.” For him to have kept going, he must have had some level of tenacity within him or his instinct telling him to keep going. This is because he kept going after several failures. These failures were built upon previous failures, which provided the clarity he needed and ultimately led to success. And sometimes, in life, the destination makes the journey worth it. A successful person would be able to answer these questions after sharing their experiences with setbacks and failures and how they could navigate them and eventually end up successful. When answered, this question helps you understand how such an approach could be adopted into your journey of interests. 

  • What is your biggest motivation? 

This is basically like asking, “what gets you out of bed every day?” A successful person must have a reason for getting out of bed each day. By asking this question, they can articulate that reason, inspiring you in your journey towards success.

  • What are you most grateful for in your success journey? 

This question is pretty much like asking, “what or who would you credit your success to?” “Who do you owe for your success today?” This question provides key insights into the major factor that played a huge role in their success. It could be a person, a piece of advice that they got when they were young, or a seminar they attended that changed their lives forever. Whatever it is, make sure you take note of that significant factor to understand better how you would approach your success journey and what you would consider your potential biggest success factor.

  • What would you do differently if you could go back in time? 

It is important to ask similar questions differently because they provide quality answers. Asking this question is simply taking them back in time to a situation or moment where they decided or took an approach that did not provide the best outcome. If Thomas Edison knew that the first 999 steps he took would be wrong, he would do the right thing the first time, saving a lot of time and resources. While this is an ideal question, it is also a learning opportunity for you and them to understand better what could have been done previously to get the right action, which opens you up towards careful consideration of the several possible factors that can contribute to your success.

  • What is the best advice you can give? 

When this question is asked to a successful person, they share in detail something they either strive to live by daily or something that they think was a huge factor in their success. This question might be seen as connecting more deeply with the person and getting to know and understand the principles, beliefs, and standards they choose to live by each day. 

  • What advice would you give your younger self? 

After living a well-experienced life, a successful person would be able to identify several moments in their lives where they dropped the ball or made the wrong decision. Would they be willing to change that? And if they would, what would that change look like? When this question is asked, it gives you insights into the kind of life they lived when they were much younger, the mistake they made, as well as the possible solutions they would have adopted to ensure those mistakes never happened in the first place.

While there are many questions to ask a successful person, these listed above give you a start if you have no idea what to ask. It also serves as a foundation for the more specific questions you would like to ask them. This specificity would be centered on the different categories you find them to be successful in and strive to succeed in. The best opportunities to ask these questions would be at schools, conferences, seminars, a networking session, etc. They are also an ideal conversation starter, and who knows, you might find yourself making a friend. Now that you have this information, how best would you apply them? Wherever you find yourself and whoever it is that you find successful, get into a deep and thoughtful conversation with them by asking these questions.

Also read 25+ Question to Ask a CEO in a Job Interview

Questions to ask a Successful Person

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