Monday, Sep 23, 2019
HomePeople, Passion and ProfitFive tough questions every leader should ask

Five tough questions every leader should ask

Being a leader is not easy and in today’s context it is even more complex because of the varied dynamics that have crept into the workplace. Some leaders feel that some of the things they are required to do and be to be great leaders are too much and quite frankly not necessary for the workplace. Some of those things are: questioning their purpose for being in leadership, their response to change, to leaving a leadership footprint, to mentoring and grooming the people on their team. This is all in addition to being an expert at what they do, managing administrative tasks, financial responsibility, as well as almost parenting today’s professional.

To be an effective leader, one must self-reflect and ask some powerful yet tough questions to challenge their performance.

  1. Why do I do what I do? Honestly, every human being should ask themselves this question. Why is it important for leaders to do this? Leadership is already tough enough. If you are in leadership for the wrong reasons, it will almost feel impossible. Why do you want to lead? Sadly, weak leadership is predominantly seen throughout many organizations in all aspects of society. What makes them weak? When leaders focus on trivial, shallow aspects of the perception of what leadership is: being able to boss people around, have special privileges, more benefits and status.

Higher question of purpose should center on: why am I in this profession? What do I hope to contribute by being in this role?

  1. Am I willing to make changes for the better of my organization, no matter what? Change is a requirement. In today’s world, if you cannot embrace change, you will face being obsolete and irrelevant. One of the areas of improvement for leaders – and it is a human trait – is to be able to release the things we are attached to. We get entangled in our last idea or our original idea, strategy, concept, partner, supplier, team member. We get emotionally invested, making it very difficult to make changes for the better. We hold on to our detriment and that of the organization. What am I prepared to let go to improve my organization?
  2. If I left my organization today, what would be the legacy I left behind? This is one of the scariest questions of all. What is your footprint as a leader? What would your organization say of you if you left? Would there be a collective sigh of relief that you’re gone? Rejoicing and celebration? Disappointment that you left and worry that who remains will not care? Satisfaction that what was invested would be used to continue the good work begun? What will they say about you when you’re gone?
  3. Who am I preparing to take my job? Here is another toughie. Have you identified your successor? One of the things that I do automatically is find the people I can invest my time, knowledge and experience in to prepare them to do what I do. I’ve been criticized that this is foolish. And I do believe I have been taken advantage of because few people ever give credit to the ideas, strategies, counsel, or coaching that you give them behind the scenes. Or that it is you pushing them from backstage while they are on the platform. Regardless, it is incumbent upon leaders to prepare the next in line and to generally help to develop the people around them – whether they aspire to leadership or not. People around you can learn from your experiences. Share your stories. Be transparent. Be honest. Be willing to share what you know, knowing it won’t take away from you but only multiply your worth.
  4. What were the mistakes I learned from the most? A valuable question for leaders to ask is this – how can I learn from my mistakes? What did this apparent failure come to teach me? How will I grow from this experience? Oftentimes we ask ourselves the opposite: why did this happen to me? Why am I so stupid? Won’t I ever learn?

Mistakes are life’s lessons that come to shape us and help us to graduate from one stage to the next. I remember my first leadership mistake. It was thinking that all people would want to be led the way I like to be led – lots of autonomy and freedom with support as needed. I quickly learned that not everyone appreciates, wants or needs that type of leadership for various reasons. One is skill level. The higher the skill level the less supervision someone needs. The lower the skill level, the lower the confidence and proficiency and thus the increased need for more guidance, direction, and feedback until they reach a level of mastery. This is a mistake that some leaders make: they revert consciously or unconsciously to their default methods – how they have been managed in the past or how they want to be managed, not how their employee needs to be managed.

It is critical for leaders to face what could be painful truths about themselves or harsh realities about their practices, methods, way of thinking and habits. It is a worthwhile effort that will reap the greatest rewards for the leader, their team, and the organization.


  • Simmone L. Bowe, MSc, SPHRi, is a seasoned human resource and organization development consultant & trainer, speaker, author, mentor, and activist who focuses on helping business owners, leaders and professionals diagnose their people and performance problems and implement strategic solutions. For comments, queries and bookings, email



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