Asking someone who you admire career questions could truly be a once in a lifetime opportunity. Therefore, it is essential that you ask the right questions.

The responses to any questions that you ask someone you admire can be transformational. Your career could evolve and go to the next level. So make valuable use of this opportunity.

Below are 19 career questions that you can consider asking in case you meet someone that you professionally admire.

Let’s take a look at each of these.

What challenges did you overcome along your journey?

We all have obstacles and challenges that we face throughout our career. It could be beneficial for you to understand how this individual manages adversity. What strategies that are used in their lives to manage various challenges.

What fears did you have to push pass in your career?

Again, we all have areas of weaknesses that we need to work on. Great leaders such as Mahatma Gandhi had a fear of public speaking which he had to overcome. Champion boxer Muhammad Ali had a fear of flying which he had to face in his career.

Understanding how the person you admire deals with their fears could provide useful tools that you can use to conquer your own adversities.

What career mistake taught you the greatest lesson?

The greatest lessons that we learn often occurs in the midst of mistakes. It will be beneficial to understand what career mistake that individual made.

Also, how the mistake improved or impacted the person’s career. This can truly be a learning moment for you.

What soft skills added the maximum value to your career?

Soft skills are those extra skills such as personality or how you deal with people, circumstances, setbacks that have allowed one to excel.

It will be advantageous to know what soft skill has added the most value to your admirer’s career.

Looking back, is there anything professionally that you would have done differently?

This is an interesting question as in life everything happens for a reason even the detours and disappointments.

However, it will be useful to know if there was a role that he/she regretting not taking as an example.

Also, if there was a business opportunity that was not pursued. This can really be a golden nugget to remember. What were the lessons learned through this process.

Is there a favourite saying/ quotation that you say that keeps you going?

We all have down days. There are days when we feel unmotivated or as I like to call it “blah”. It will be interesting to know what motivates him/her.

Is there a favourite saying or quotation that pushes him/her through on those rough days? If it’s a great one, you can possibly adopt it.

What habits have you nurtured that has benefitted your career?

This is a big one! One’s habit and routine are often a source of their success. Try to find out how they approach their jobs/ roles. Understand how time management is approached. Identify what tools are used to achieve efficiency.

Does he/she keep a rigid sleep and wake up time. Is reading a habit? How many books do they read in 12 months? These are a few of the habits that you should try to glean from the conversation.

One habit that has remained with me from reading the autobiography of Muhammad Ali is that he practiced exactly as his fights. His rest period in practice was exactly one minute. No shorter or longer. Just as if he was fighting for the world championship.

Understanding what routines and habits that the individual maintains could be a great learning lesson for you in building your career.

If there is one thing that you will want me to remember along my career journey, what would it be?

This question forces your admirer to really reflect and identify the single most important factor for you to remember. This response could be what they consider a career make or break.

What is the current global trend that as a professional (insert your field here), I should not ignore?

This question gives you the opportunity to tap into that person’s perspective on current global topics. You should understand what the individual believes is ground breaking or career impacting in the current marketplace.

Answers to this can be used to strengthen your career plan. From the responses seek to identify any skills that you need to consider updating or courses that you need to take.

It may be wise to prepare for what they consider to be the next hot trend.

Who are you inspirations/ mentors?

Every great person has someone that they look up to. It will be interesting to know who that person is.

This could give you the opportunity to check out their mentors yourself. Maybe you can consider creating a reading list around his/her mentor.

What book have you read that has had the biggest impact on your life?

Reading is truly transformational. It will be beneficial to know if there was one book that changed that individual’s life.

What tools/strategies so you use to maintain productivity?

Time is a limited resource. It will be helpful to gain a deeper insight into how that individual maintains productivity.

Does he/she maintain a calendar or daily to do list? What strategies do they use to manage time.

What are your hobbies?

Are the hobbies that the individual maintains related to their profession/ career?

What does the individual enjoy doing in their spare time? Does this activity have any impact on his/her career?

Is there anything that happened in your career that was life changing?

This question will give the opportunity to hear about a highlight moment of the individual. You may be able to learn something new as well as learn more about the individual.

What strategies/approaches do you use when you are making tough career decision?

Making wise career decisions can be tough. This question can give you insight into techniques that you may be able to employ when challenging career choices.

What is your greatest weakness?

We all have weaknesses. At times, some of our weaknesses we try to overcome them.

On the other hand, one may choose to avoid them. It will be helpful to understand how the person you admire deals with professional weaknesses.

How do you handle disappointments in your career?

We all face disappointments at one time or another. Understanding how the individual deals with these moments could provide you with techniques that you can use in your tough seasons.

What strategies do you use to manage your overall career growth and development?

Getting an overview of how the individual manages career growth. What techniques do they employ to manage growth and development? Do they attend conferences and seminars every year?

Is there someone in their field that they follow? Do they maintain a career plan? Do they try to change jobs every 5 years? Understand strategies that they use to ensure growth.

Looking back, what career detour/disappointment/ setback do you now view as a blessing?

Listening to stories of career detours and this individual’s perspective looking back at their career experience can be enriching.

If you enjoyed this article, you may find the following posts on this blog useful. Feel free to click on any of the links below to explore:-

Why Hobbies Are Essential To Your Career

11 Top Strategies To Advance Your Career

10 Top Career Planning Advice For Success

How To Develop Skills At Work

How To Ask Someone To Mentor You

How To Find A Mentor For Your Career

6 Valuable Benefits of Mentoring To Advance Your Career

Final Thoughts

Sir Richard Branson has been someone who I have professionally admired for several years. I truly hope that one day I would get an opportunity to ask him some of these questions above.

Solomon, the wisest man that ever lived said in Ecclesiastes chapter 1 vs.9 “and there is no new thing under the son.” Having the opportunity to draw from the experiences and stories from someone you admire can be career advancing.

It could save you a lot of time as you could avoid mistakes. You can also immediately implement the learnings from his/her life story.

Hope these career questions help prepare you for having a discussion with someone you admire. It is always good to have a few of these rehearsed as your meeting could be unexpected.

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19 Top Career Questions To Ask Someone You Admire

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