Six Tough Questions Leaders Need to Ask Themselves

Being a leader is not always as glamorous as it might first appear. Leadership isn’t only about decision making and being in charge. The leader’s role is to guide and support the team so that all will be successful, as the leader is the shepherd to their flock. People know that a leader is the one responsible for making the difficult choices. To improve the capability in making the hard decisions, the leader needs to gauge their own perspective on a number of key issues. Although these questions require hard, reflection and internal dialogue they will aid in the successfulness of the leader’s approach.

Is what I am doing working?

Leaders need to make tough decisions each and every day. No matter how great a leader they are, they do not always make the right decision. A leader needs to be able to look objectively at the decisions they have made and determine if the decisions are leading to positive results. Depending on how the leader perceives the team’s success should lead to two different approaches. If a leader’s approach is working, nothing changes. If the leader does not feel their leadership is getting the desired result, they need to go through a secondary reflection process to refine or change their approach. There is no cookie cutter approach for leading. Each situation is different because each team is different. All team members come from different backgrounds with different strengths. A leader needs to tailor their approach to make the team successful. The team’s success (personally, professionally and developmentally) should be the gauge to determine if a leader’s approach is working.   

Do I rule my emotions, or do my emotions rule me?

When you think of a leader, you probably think of a stoic individual. A person who is always cool, calm and collected. A leader needs to understand that being calm through the storm shows their team that they have a plan, even during the most stressful of times. If a leader slams their door when they are mad, what message is this relaying to the team? If a leader ignores a team member at the water cooler because their wife was up all night sick, what message is that relaying? A leader needs to be the foundation of their team and demonstrate that they are in control of their emotion and the situation. This doesn’t mean that the leader ignores and disassociates with everything happening around them. Regardless of what life hands you, the leader needs to be consistent and grounded in their behaviour. Don’t let emotions lead. Lead your emotions.

If I am gone tomorrow, will my team thrive?

The strength of a leader is demonstrated by how their team carries on when they are gone. The term gone, may mean many things. The leader may be gone to a meeting, gone for the afternoon, away on vacation, or maybe retired. Each time the leader is absent, there is additional stresses on the team. Planning needs to be proactive to ensure that when the leader is away, the team will not fall apart. A successful leader needs to understand that they should not be controlling their team, rather equipping them with the skills and resources to be self-sufficient. If the leader is able to give their team additional responsibilities, it prepares them for when they need to take over some of the leader’s function. By thinking ahead on whether or not your team will thrive in your absence, you are developing a proactive development plan for your team.

If my organization is going bankrupt, would you pay yourself or your employees first?

I was having a conversation with a leader and business owner recently, who let’s call John (not his real name). John was telling me that in his nearly 40 years as a business owner, there have been multiple times where the creditors came calling and he had to make a hard decision. Does he pay himself, or does he pay his employees? In the case of John, he chose to pay his employees first and ensure they didn’t know anything about the financial stress the company was under. John reinforced to me that if he was to have withheld payment to his employees, their trust in him would have be compromised. Without trust, a leader is on unsteady ground with their team. This is an ethical question, and ultimately everyone will have their own unique answers. I am not about to tell you how to answer this question. As Atticus Finch says in To Kill a Mockingbird, “before I can live with other folks I’ve got to live with myself. The one thing that doesn’t abide by majority rule is a person’s conscience.”

What weaknesses do I have that my competitor can use to destroy me?

No one is perfect. Great leaders know this and turn their weaknesses into strengths. How does a leader turn their weaknesses into a strength? How do we keep our weaknesses from being exploited by competition? Leaders need to understand what areas they are strong in and what areas need improvement. If they are unsure, they should ask their team for feedback; make sure not to condemn or refute the answers they have provided as this will stop the open dialogue. Receive the suggestions from the team and work to improve your weak areas. Bring people onto your team that complement your weaknesses and then learn from them. Through dedication and perseverance, your weaknesses can become a strength.

What am I doing to prevent getting burnt out?

A leader dedicates a large portion of their time to ensuring their teams is taken care of. They are making decisions and motivating their team to perform at a peak level, regardless of at work or home. Unfortunately, leaders sometimes forget to take care of themselves. It is essential that a leader takes a moment to ensure they are adequately equipping themselves to be successful. If this crucial step is ignored, burnout can occur, causing damage to the team. If you don’t want to care for yourself, for your own sake, do it for your team.

Leaders need to consistently ask themselves a number of crucial questions. Leadership is not easy, but with reflection and positive growth, a good leader can become a great leader.