65 Questions to Ask a Leader | Effective Leadership Questions | Drill it Down

Questions to ask a leader

Questions to Ask a Leader: Hello Readers! Welcome to Drill It Down. This article presents you with answers that were previously unanswered and probably unknown to you. With regard to life and its confusing complications, all of us humans dream in majestic and deep magnitudes where we want to or at least try to fulfil our ambitions as far as possible.

Dreaming is a positive action. It is sub-conscious in nature and will always differ on the basis of your thoughts which are always different from each other. The more motivated you are, the dreams turn more grave in terms of intent and will try to influence you. Chasing a dream is like chasing a star but that does not mean you should give your dreams up. Dreams also equate to your ambitions. An ambitious person will stop at nothing to pursue his or her dreams and make it a reality.

It is not enough to just chase ambitions without a planned path or knowing previously acquired skills by already established people. These people might be businessmen, investors, developers, coders and what not. What differs you from them is their experience and knowledge about certain things in life, things to look forward to, things to be avoided, things to be kept in mind, things that might be helpful or beneficial, things that will be of constant help, things that will help you keep you calm, things that will help you control you anger, things that will help you get back after failure and much more.

Since the professionals have faced troubles, obstructions and had multiple difficulties in their paths which stood as barriers therefore their take on these ‘challenges’ or ‘challenging situations’ is nothing short of very useful knowledge which if imbibed by a person can turn him successful in his area of interest or field of work. But it takes a lot of courage and determination to overcome these ‘challenges’. With prior knowledge of these challenges, work becomes easier and successive people can pursue their ambitions to the fullest and turn their dreams into reality.

Before you meet a successful person, you should keep in mind that he or she expects humility. Humility is nothing but a mark of a learning person. You might be excited before meeting your role model or someone important but it is very necessary that you contain your cool and pay respect, veneration in the most formal fashion possible.

Do not delve into the personal side of the conversation and put the other person in an uncomfortable position. Keep in mind that the other person has gone through lot more than you so it is best to ask him or her about the scope of his or her work, challenges faced and similar questions. So, make sure you are down to learning and taking experiences.

This article will provide you with a set of questions to ask a leader and the need behind every question, explained in a very lucid and simple form.

13 Survey Questions to ask a successful entrepreneur | Questions to ask a leader

An entrepreneur is someone who implements unique notions and ideas about the contemporary worldly situations and establishes a space of his or her own in the society. When it comes to success, entrepreneurs have witness failure like none before and therefore an entrepreneur is probably the best person who can offer you guidance on life and let you have his perspective to it.

Entrepreneurs have a ton of sacrifices to make and are always on the go. Time for them is a precious commodity. After all, ideas need time and brains need motivation but what is most important here is dedication to the work. Entrepreneurs do not stop until they reach the goal. They are voracious readers and observers. They grasp opportunities like a hunter and use them to the fullest. From greatest technology companies like Microsoft to Apple, Google to YouTube; watchmakers like Rolex; utensil companies like Tupperware and Borosil; automobile makers like Ferrari to Lamborghini; all of these companies have aced their test of struggle and left behind a legacy which was once a dream to every single one of these founders.

This list of 13 questions should cover almost everything you want to know from an entrepreneur.

“Getting to know you” questions to ask a leader of this field

  1. What was your mission before launching your company into the market?
  2. Do you think sharing your idea with people will be a good choice?
  3. How long do you think it took your company to generate profit?

“Deep and thoughtful” questions to ask a leader of this field

  1. What were the things that you feel you could have avoided?
  2. What were the failures you faced, before turning your idea successful?
  3. Do you think that you could have performed better in any other profession?
  4. Suppose in the coming days, your company experiences downfall, what would be your approach be to the failure?

Conversation starters

  1. How long did it take you to turn your idea into reality?
  2. What have you sacrificed from your life for your company ?

Confidence boosters

  1. What impact did your company create in the society?
  2. To what extent should a person risk before launching a particular company?
  3. How did you react to competition in the market, or rather how did you face competition in the market ?
  4. How did you get the right company of people to work along with you?


13 Questions to Ask an App Developer | Questions to ask a leader

In the recent times, technology has seen multiple advancements and has brought computers and smart phones to every home, to every person. You can observe how people have changed over these years and are technology dependent.

Previously shops used to be crowded, restaurants packed, takeaway joints beaming with people. People flocked to visit the malls, window shop clothes, shoes, jewelry and what not. Even theatres and cinema halls were full; there used to be a huge crowd outside these places waiting for the next show. It was all humbug and chatter in the air. After the introduction of smart phones, things started to change.

A new form of business started to thrive and people started to go online, which is now the very norm of life. No more did people have to go to crowded stores and wait for hours in order to buy a certain thing. No more did people fear the ‘Out-of-Stock’ sign boards outside popular garment shops. No more did people have to wait for copious amounts of time for their favorite snack. The advent of applications and their use changed the mode of life. People started to buy online using these applications popularly known as ‘apps’. Now ‘online’ businesses earn many more times than ‘offline’ mode of business.

In the current times, large companies offer jobs to people with a good knowledge of ‘app’ making skills. Getting involved with these huge companies and bragging high-profile jobs are dreams of every young person.

This list of questions will clear your mind of doubts about approaching this subject of ‘apps’ and will also help you obtain the needed information and knowledge from the creators of these apps.

“Getting to know you” questions to ask a leader of this field

  1. Does community matter when you are a developer?
  2. What do you actually do when it comes to the field of data science?
  3. What tools do you use when it comes to protecting codes from piracy?

“Deep and thoughtful” questions to ask a leader of this field

  1. What would you recommend as ‘key tips’ when it comes to learning new languages?
  2. How do I enhance productivity while I debug?

Conversation starters

  1. What language should a beginner start programming in?
  2. What are some efficient sources or tools to start programming with?
  3. How does developing themes for Hackathons work?
  4. Is it recommended to use Scikit Learn and TensorFlow in jobs?
  5. Should code be commented for production too?

Confidence starters

  1. Is it a good choice to freelance with the skills an app developer has or should he join a company to work?
  2. How much should I expect to make an average application ?
  3. Should I jump into Machine Learning without prior knowledge of application development?


Also read: 15 Amazing Growth Mindset Activities


13 Questions to Ask Mentors about Career Development | Questions to ask a leader

A good mentor will always guide you in the long run. Mentors can be anyone. Parents are probably the first teachers and mentors to a child. But as he or she grows up to be an individual, the person looks forward to meeting new people, learning new trades, acquiring new forms of knowledge. But as the person grows he or she experiences difference in opinion, perspectives and all of this results in a lot of strife, gives is to problems. Due to lack of experience, these young people fall out and often rebel against others and even their own selves.

A mentor clears out life and its problems, clears out and provides knowledge and change in direction; and provides a path to follow. Mentors have been instrumental in creating the biggest of people, very successful in life. Ambition is a good attribute but ambition without a direction proves to be a lethal choice.

Mentors provide direction and qualities which help their students or rather disciples to grow as a person and realize their own capacity. A good mentor can be anyone. From your college senior to your college professor, from your uncle to your grandfather, from your neighborhood writer to your acquainted news reporter; any one can be your mentor. But it is a great challenge to find a mentor in these days because time and space are two great things that a mentor has to sacrifice.

Only on sacrificing, will a great person be born and people these days hardly have time or want to do something for someone. Therefore, it is very important to identify a person and give him or her the right amount of respect, not sugar coated words and maybe you will find a good mentor in that very person, who in turn will change you and your life.

These are a few questions that you can ask your mentor about progressing forward in your life. These questions cover almost everything one can ask about developing one’s career.

“Getting to know you” questions to ask a leader of this field

  1. How did you acknowledge failure in life?
  2. How do you think can a person set up a disciplined schedule in life?

“Deep and thoughtful” questions to ask a leader of this field

  1. Is it very difficult to follow one’s passion in life?
  2. How can one obtain one’s perspective on any idea?
  3. Does one need to develop plans or define a particular set of strategies in life?
  4. How can one manage time efficiently?

Conversation starters

  1. What skills do you think are difficult to develop when it comes to leadership?
  2. How can one develop his or her communication skills?
  3. Does one need to upgrade skills with the passage of time?
  4. How can one engage with their audience while delivering a talk?

 Confidence starters

  1. How should one be proficient enough in a particular domain?
  2. Is there any strategy to obtain success in life?
  3. What do you think can boost confidence?


13 Questions to Ask Investors in the first meeting | Questions to ask a leader

Investing is the act of putting resources especially money to either support a growing company, organization or to passively earn from the profits of an established company or an organization.

Investing has been in play or rather has been active since a long time. Even in the earlier times when civilization had a different definition to the present one, investing was always a very profitable job. But again investing on the right thing is a challenge. With experience and prior knowledge investing is often a good experience.

Investing from an early stage in life, investing in things can take a person long way. From earning profits off well performing companies to investing in larger stocks in established conglomerates, a person can turn his fate and thank his lucky stars to obtain a good amount of money. Investing in the right things also boosts a person’s mindset and success definitely knocks on a happy and intelligent person’s door.

Understanding the power of investment right from now is a golden opportunity one can thrive in.

This is a list of questions that you can ask a successful investor and acquire required knowledge, tips and hacks about investing.

“Getting to know you” questions to ask a leader of this field

  1. What metrics do you keep in your mind when you invest in something?
  2. What basic fund size do you keep in mind when you invest in something?
  3. Do you follow Warren Buffet?
  4. Do you focus on any specific industry during the time of your investment?

“Deep and thoughtful” questions to ask a leader of this field

  1. Who do you look up to when it comes to guidance in terms of investing in something?
  2. Do you consider any life opportunities that you wish to explore further in investment sector?
  3. How has investment changed your life?
  4. Do you think investing in the right things change one’s life?

Conversation starters

  1. How can one invest their money wisely?
  2. What tips will you offer to a budding investor in order to be successful?
  3. Can you provide us with any tip on sectors that could be booming in future which might be good for investment?
  4. What do you think is the best online platform to invest in funds and stocks?

Confidence starters

  1. Can investment be regarded as one of the best sources of passive income?


Also read: Why is Creativity Important? and How to Develop an Creative Environment?


13 Survey Questions to ask a Freelancer | Questions to ask a leader

Freelancing as it suggests is an independent venture where people, referred to as freelancers, work with multiple bodies in shapes of emerging organizations, companies, conglomerates, ventures where they work under a short duration and carry the right to move on from one body to another.

Freelancing may sound like an interesting and easy job but it is not really as it sounds. It is definitely interesting but demands a lot of attention with a highly focused mind. Along with focus and attention, freelancing also requires the ability to identify people. There will always be instances where after the completion of a certain piece of work or assignment the promised remuneration is not received. Freelancing involves a lot of reputation to build.

Freelancers often suffer from blocks in terms of work and opportunities. Therefore, they must be ready to face the world in its bitter and realest form. Freelancing is not everyone’s cup of tea but again with the right amount of motivation and determination. Every one likes to be their own boss but it comes with a price; the price of responsibility and the foresight to complete work, assignments within the stipulated period of time.

Here’s the list of questions you can ask a successful freelancer:

“Getting to know you” questions to ask a leader of this field

  1. What was your first project on when you got into a freelancing career?
  2. What skills do you have in your current skill set?
  3. How did you get your first client?

“Deep and thoughtful” questions to ask a leader of this field

  1. How do you approach your clients to respect your work?
  2. If you get a full time offer from any company with a decent pay, will you accept the offer?
  3. What do you think about your future goal as a freelancer; do you want to settle down with your own business or are you happy with your current setting?
  4. Being your own boss is a difficult task, so how do you manage your affairs?

Conversation starters

  1. Which skills, according to you, help you get maximum pay for your work?
  2. What are the best freelancing platforms that you want to recommend to people looking forward to freelance?
  3. With an ever increasing competition how do you manage to stay ahead of competition?

Confidence starters

  1. Do you recommend freelancing as a career to people?
  2. Can you provide any piece of advice for the uprising freelancers?
  3. Have you ever been cheated in terms of completion of a certain job and you did not get paid?


People have suffered from losses and have emerged victorious. But again in the current times reaching successful people and asking them for tips and guidance is not as difficult as it was during the previous years. This article should be a good one when it comes to asking questions. With these lists of 65 amazing open-ended questions to ask a leader, we sign off from today’s article.

If you have any query or want some quick fix questions, you can reach us at [email protected]. Our team is always ready to clear you doubts and will drill it down for you.

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