If you’re a business advisor, it’s an essential part of the job to create a list of unique questions to ask leaders and can help drive clients’ internal reflection. Mentors, whether in a formal position or a casual advisory role, can also leverage strategic questions to ask senior leaders to encourage introspection and improvement. Regardless of the relationship, any leader can use questioning techniques to invite exploration, professional development and personal growth.
Leaders are exceptional individuals who have the skills, values, and knowledge to direct the affairs of an organization or group. A leader’s vast experience and expertise often mean they have valuable insights into a variety of topics. One needs to prepare to ask the right question to maximize the relationship with a leader.
Unique questions to ask leaders
Are you looking to elicit meaningful conversations from your executive peers or individuals you lead, coach and mentor? If so, here are a few inquisitional directions you may want to try.
Introspect from personal inspiration
Try looking to a leader one considers an inspiration for a leadership career path. This shows the behaviors and ethics a person believes in. It is very telling of how a leader will conduct themselves during times of stress and uncertainty, by following the same behaviors as their mentor.
To think about ones mentor can help a leader focus on areas where they aspire to better themselves.
Importance of motivation
Understanding the motivation to pursue leadership as a career path is critical as “If their ‘why” isn’t strong enough, they will stumble when faced with large obstacles.
Explore goals and challenges
Two leadership questions to ask your team by looking towards the past and then toward the future:
- What was the biggest challenge you were faced with last year and how did you overcome it?
- What’s the biggest decision you must make this year and what’s keeping you from making it?
Self-awareness
Self-awareness is the hallmark of a great leader, enumerate the leaders strengths and weaknesses.
The best leaders know what they are good at and where they need to surround themselves with others who can augment their talents.
Decision-making process
Questions should center on a leader’s decision-making process. Ask them to share a decision that did not go well. Talk about the result, what they would do differently, and the impact it had on others, the organization and themselves.
Also probe about recent decisions the leader regrets and always asks why.
Ready for risk
Closely tied to failure is the concept of risk. Two insightful questions:
- What is a risk you have taken in your career that has paid off?
- What risk have you taken that has failed?
Great leaders know how to take calculated risks, so using right questions can help in assessing and enhancing the leaders risk tolerance and resilience.
Reading material of leaders
Asking what reading material shaped a leader into who they are today is important as If a person is reading, it shows they are continuing to learn and grow. What they read indicates areas they’re curious about and seek to improve themselves.
Lifelong learning is critical. There is no constant. If you are not growing, you are falling behind in your craft.
Differentiate leadership from manager
Asking leaders how do they encourage great ideas from their workforce? Why is it important? As the answer can help separate true leaders from mere managers. As leaders inspire new ideas and stimulate curiosity. Managers simply tell people what to do and can suffocate creativity. This question will indicate if a person has the heart of a leader.
Focus on the big picture
There are many ways to zoom out and get a “10,000-foot view” of leadership. If the leaders are able to summarize their life stories in a single sentence. Making him focus on the one accomplishment about which the leader is most proud.
No matter which questions feel most natural and what phrasing works best for you, the keys to a thought-provoking leadership conversation are these: Have the courage to ask and the wisdom to sit back and listen.
