5 Simple Questions the Best Leaders Always Ask

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“Dream more than others think practical. Expect more than others think possible. Care more than others think wise.” Howard Schultz How do you measure a great leader? What differentiates them from mere leaders? Of course they inspire and motivate others, they lead by example, they are creative, and constantly seeking ways to improve their performance. They never stop learning because their minds are not closed to new ideas. They build new teams, encourage others to aspire to leadership without feeling threatened, and have a strong vision.

What makes great leaders stand out and what kind of questions do they ask of themselves and others?

1. What do you think?

Great leaders know they haven’t got all the answers and are confident enough in their own abilities to ask other team members to share their thoughts. They are not afraid to hear ideas that may be superior to their own – in fact, they encourage it. They want their teams to flourish in a creative environment, so they ask them to speak openly and with candor. They see ideas not as a challenge to their authority, but a reflection of their own inclusive leadership.

2. How can I be better?

In his book Good Leaders Ask Great Questions, author and leadership speaker  John C Maxwell outlines  the kind of questions he asked himself in his quest to become a better leader. They cover everything from how to get the most out of a team, his own leadership style and how he could help potential leaders.

One of the key lessons is that great leaders should always ask how they can improve. They never stop learning, constantly ask themselves how they can enhance their performance. The day you stop asking honest questions about your leadership is the day you stop growing.

“Become the kind of leader that people would follow voluntarily, even if you had no title or position.” Brian Tracy

3. What is your biggest problem and how can I solve it?

When Lori Goler applied for a job at Facebook she asked Sheryl Sandberg, “What is your biggest problem and how can I solve it?” Surprised, Sandberg said recruiting was her biggest problem, and hired Golder, who repaid the show of faith by going on to become Vice President of Human Resources and Recruiting at Facebook. Have the belief and self-confidence in yourself to stand out from the crowd.

4. What do we need to fix? or What is our biggest problem? In a variant of this question great leaders also wonder aloud, “What is our biggest problem?” The beauty of asking that question is that it forces the team to articulate what is holding them or the company back.

It may be that this is a problem no one wants to talk about because it may appear insurmountable, or too intimidating to confront. By posing the question it will take center stage, be discussed openly, and be one step closer to solution. Great leaders are always looking to clear logjams.

5. What have I learned today?

The question is one all great leaders ask. They do it regularly – some do it daily –  because their growth is ongoing, and their learning curve steep. They are happy to hone their skills, profit from mistakes, and never assume they know it all. They never rest on their laurels, or bask in past achievements. Instead, they analyze their mistakes and decisions, and strategize how they can avoid a repetition.


Great leaders are not afraid to ask tough questions of themselves or others. They know the value of openness with their teams and how asking the right question will elicit a positive response and reveal impediments to company growth. They also know that they must always be looking forward and not backwards to past achievements.

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