Career Development

Best Questions to Ask a Leader About Career Development

Career development includes aspects beyond higher education, natural talent and technical skills. You can gain insight from leaders in your own company by asking in-depth questions about their professional, real-life experiences. This article shares some thoughtful questions you can ask a leader when you are seeking advice about your career development.

Tips for meeting with a leader about career development

When you have scheduled an informational interview with a leader or mentor, be sure to arrive at your meeting prepared. Bring paper and pens, a laptop or a voice recording app on your smartphone to record the answers. Make sure to thank your mentor for taking the time to sit down and talk with you. Their wisdom and life lessons can be priceless to someone who is enthusiastic about their own career path.

Best questions to ask a leader about career development

If you have an opportunity to interview a leader within your own company, consider asking some of these questions:

What do you think makes someone a good leader?

A leader is someone who successfully directs a group of people, an organization or a company. In career development, a great leader is able to motivate people to work together to accomplish a common goal. Those who follow this type of leader can inspire others to follow their values, attitudes, goals and beliefs. They are often very aware of how their actions and behaviors affect those they work with and guide on a daily basis.

Who are your role models?

The choice of a role model can indicate the traits and qualities an individual hopes to achieve in their own life. Role models carry a lot of influence, whether the person knows them personally or simply admires their work. Whoever a leader admires usually has the same morals and values that they want in their own life. For example, if the role model is known to be honest, sincere and trustworthy, you can most likely surmise that honesty is very important to the admirer.

What would you do differently at the start of your career?

When asked this question, many leaders would say there are many decisions they would change throughout their past. People tend to learn by making mistakes and using that experience to mold their future choices. Discovering what a leader would change about their past career decisions will offer insight into how they believe their past choices have affected their future professional life.

Tell me how you got started in the company.

Learning about how someone got started in their field offers a lot of valuable information for new professionals. When you ask a leader this question, you can get a glimpse into the work ethic, determination and perseverance they needed to practice in order to be where they are right now. 

Share a past failure and what you learned from it.

Asking a leader to share past experiences, even negative ones, can be very helpful as you make your own career decisions. Understanding the decisions they made and the consequences they led to can help you avoid making the same mistakes in the future. It may also help you learn how to make decisions that lead to more positive results.

How do you balance family time with work time?

Many people have had to learn how to balance family and work. It can be one of the hardest parts of being in the workforce. You may want to ask more pointed questions, such as how they schedule family time, if they take particular days off from work and how they handle a work emergency when it interferes with a scheduled family event.

Are you actively involved in any self-improvement methods?

Part of growing as a leader means looking for opportunities to grow as a person. Improving yourself is usually a life-long endeavor. It’s something that needs to be done consistently. Good leaders are often very quick to recognize that there is always room for individual growth, self-discovery and personal improvement.

What books have helped you in your leadership journey?

Reading is one of many methods leaders use for self-improvement. Many leaders create goals for themselves and often, for their own teams, with techniques learned from personal development books. You may also want to find out if there are any other methods they use to learn more about effective leadership.

What characteristics do you believe every leader should have?

Being in a leadership position requires characteristics and traits such as good communication, respect for others and a positive attitude. Discovering the characteristics your role model believes are the most important will give you an advantage when choosing which attributes you should focus on.

Share an experience when you had to make a tough decision, even when you knew it was the right decision.

Every leader has had to make tough decisions at some point in their career. The lesson lies in how they made that difficult choice. Did they weigh all of the available options? Did they consider the consequences if they were to choose a different path? How did they handle those who were negatively affected by the choice they made? Gaining insight into their thought process can help you learn how to approach difficult decisions of your own.

How do you communicate the importance of the company’s vision with your staff?

As someone who wishes to improve their own leadership skills, it’s important to know how to encourage, motivate and inspire those around you. The leader you’re interviewing has had to learn how to inspire people through years of experience. They know what works and what doesn’t in their own circle of influence. This is a great opportunity to learn from the experiences of your role model.