We all know someone who has worked hard and reached a position where you want to be someday. Every time you look at them, you must have a plethora of questions popping up on your mind, but you have been hesitant to ask all these years. What if someone told you exactly what to ask without upsetting the person you look up to? Wouldn’t it be great?

Asking questions is not a bad thing, but sometimes, they unintentionally dig on personal information, and you are unaware of it. Hence, it is better to keep it simple and formal, which makes the conversation easy-going and much enjoyable. Awkward questions may stimulate a bad mood, or the person might get offended, especially when it is concerned with someone you don’t know personally. To avoid that, let’s prep you up for a super easy, smooth, and helpful conversation that both you and the person you ask will enjoy because a formal discourse is way better than being unprepared and asking random stuff.

Here are some important questions that you should keep in mind:

1. Why Have You Chosen This Career Path?

The first question and the most important one that must come to your mind, why that particular person has chosen this career path and the industry he/she is working in. There must be many reasons for this answer, and these reasons will serve as your guide if you too are willing to get established in that particular industry.

The more the person unfolds the reasons for choosing a particular career path, the more insights you get and, you might also get motivated even more after listening to this answer.

2. What Has Driven You to This Industry?

The reason for choosing a particular industry is a question of interest. While considering a particular industry as a career path, all of us consider many factors in terms of job opportunities, career growth options, salary, types of works, and many more. When you ask this question, you will discover why that particular industry can be right for you, what you can expect from it, and so on.

This question can also help in opening up a deeper conversation between the two of you.

3. What Is Your Current Position and What Would You Be Doing by Now If You Were Me?

Asking about their current positions may sometimes take the conversation to a further level where you can strike up another important question such as “how do you think you have come this long way?”, “what were your main obstacles?” “how many years did it take to reach this position?” and so on. But the most important of them all will be asking that person what he or she would have done at the present stage you are in. This answer may be a little complicated, but in this way, you will get a glimpse of their past work life to suppose, the person might say, “when I was of your age, I was working as an ABC under an ABC company” so and so… this answer will help you in establishing an idea what you should be doing by now, or are you any closer to your aim.

4. What Are Your Career Aspirations?

A person who is already working in a high position may not have much career aspiration; he or she might want to upgrade their positions to the highest level in the company, such as becoming the “CEO” or “Director.” But with this question, you may ask some serious questions about life consecutively like, “what do you plan to do next?”, “ how do you plan to spend the rest of your life?” and some other questions like these that will give you more wisdom.

5. Do You Enjoy Your Job Position?

Now, a person who is working in the highest position is not all free and ordering things to be done to their employees. It is not that easy to have hundreds and thousands of people work under you, where you are responsible for taking all the biggest decisions on which the future of a company depends. So, the person might not say that he is all happy and contented with their position, but it is always good to ask this particular question because they get a chance to share what particular responsibilities they love the most, or what is the favorite part of their job role. It might also turn out that no one has ever asked them this question before, and it will, in a way, impress them.

6. Do You Think You Are Making a Difference in Your Industry?

You may directly ask this question, or better mold it in your way by being more formal, and perhaps asking, “how much do you think are you important for your company?”, “how much do your employees depend on your important decisions?” and questions like that. These questions will provide a deeper insight into their daily work life and the kind of work they have to do on a day-to-day basis.

7. What Skills You Think Are Required for This Industry?

This is one of those important questions that you cannot miss. Skills are very important in every job role, but they cannot be acquired within a day. It requires years of experience to obtain that level of skills suitable for higher positions. But, asking this question will always be appreciated, and you will get to know some key skills you must begin to work on in order to reach that level someday.

8. What’s the Worst Career Decision You’ve Ever Made?

Asking about all good things and ignoring bad ones is not a good idea. It is failures that teach life lessons, and you should listen to their failures too to avoid making the same mistake on your career path. This question can be followed with “how did you cope up with a bad situation like this?” “How did this decision affect your life then?”, “what was your biggest motivation at that time?” and stuff like that. Worst career decisions can sometimes be devastating, but the lesson you learn from them are surely long-lasting, or you can say, stay lifelong.

9. What Do You Think Is Your Greatest Strength?

Knowing about the greatest strengths of the person you admire is going to be your biggest guide. When you get to know their strengths, you know a lot about their character and personality. Such as, if the person says he is “punctual and hardworking,” you can predict how perfect that person is at work and how much pressure his employees have to go through for submitting works on time. Knowing strengths will also help you in understanding what things you need to rectify or focus on to reach that level of perfection.

10. What Books Do You Read?

Asking about what books they read is always helpful. Powerful and successful people always read motivational books, and behind every successful person, there is a book that has guided them through the path. Jotting down a list of books that they have always admired will help you a lot in following the same path.

11. How Do You Take Those Important Decisions at Work?

One of the most important questions that cannot be ignored, it is not easy for anyone to make decisions on which the future of the employees and the company depends. The person might say, a lot of factor plays on the mind while making these decisions. One cannot take these important decisions hastily, and for that, you need to be calm and have the ability to envision what these decisions may lead to tomorrow. You may also get to know, what keeps them calm during these decisions, what do they do, like do they depend on discussions and give opportunities to other employees to present their thoughts or take decisions solely, you will get to know a lot of important things from this question.

12. Do You Have an Advice for Someone Looking Up to Your Position?

Last but not the least, a person who has come this long way must have a lot to tell when it comes to guiding the younger generation, who look up to them. It is always wise to ask for advice on what you should be doing to reach that position someday.

Final Thoughts

These were a few questions that you can ask someone whom you look up to without any hesitation. And to be honest, the answers you get in return are going to be a lot helpful to youngsters like you, who aim high, and want to become successful in their professional life. These questions will not only help in taking the biggest career decisions but also will provide a lot of information about that person’s work life, which will, in a way, serve as a motivation. The wisdom you get from asking these questions will guide you in the best way.