10 Questions Leaders Should Ask Themselves

Tyler Reagin

If you’ve raised children (or been around them for any length of time), then you know their impressive ability to come up with a question for every scenario.

“Dad, are we there yet?”

“Why can’t I have cake for breakfast?”

“Where does Santa go in the summer?”

“How do squirrels clean their teeth?”

“Does God have a belly button?”

The never-ending bombardment of questions bounces between endearing and aggravating, but they afford us a few insights we should note as leaders. Children enter this immense, daunting world with absolutely no context for anything. For years, their survival depends strictly on other people.

It’s no coincidence that those who teach children how to walk and talk are then viewed as their own personal Google. Where else are kids supposed to go to get answers about the vast world around them? All of these questions, as silly as they may seem, make complete sense.

We’re wired with a desire to understand, and questions are a tool to help us satisfy that craving. Questions are the vehicle for learning and understanding. They open us up to new realities and break down boxes to offer new alternatives.

Andy Stanley says, “Great leaders ask great questions.”

This should be of no surprise. Leaders are learners, and they need to understand their environment - an impossible task for the man with no questions. But one of the most dynamic aspects of questions is their ability to help you become more aware of you.

To lead others well, you must lead yourself well. And to lead yourself well, you must routinely ask yourself hard, heart-checking questions. Questions that pinpoint your motivations and fears, and help you align your heart with your purpose.

Great leaders, like children, should practice a lifestyle of infinite questions, and here are ten that I think are empowering for every leader, every day.

1) What would make today great?

This question will reveal your heart’s priorities quicker than any other question I know. How do you define a great day for yourself? You have to know your desired end goal in order to take the right first step.

2) What are two things I’m grateful for today?

There are endless gifts to be thankful for in this life. Research upon research links gratitude with happiness. Get specific by writing down a couple of things you’re grateful for each day.

I love what Ann Voskamp has to say about practicing a life of thankfulness: “A life contemplating the blessings of Christ becomes a life acting the love of Christ.”

3) What are three things I want to accomplish today?

Too many leaders are distracted by the urgent rather than focused on the important. Focus yourself each morning by starting your day with this question.

4) If someone replaced me right now, what would they do differently?

I first heard this question from my good friend, Craig Groeschel. It challenges you to think differently about your current role and to plant new seeds for new fruit.

5) Who do I need to listen to?

Leaders are flooded with countless voices throughout their days. While every voice matters, not every voice should carry the same weight in your life. There are people  whose voices play too loudly in your head, and people you need to hear more from. Good leaders practice discernment with the voices they allow to speak into their lives.

6) What is holding me back?

The enemy would love to stunt your leadership growth, and the main way he does so is through fear fueled by lies. Identify the lies that are producing unnecessary fears.

7) What do I need to quit today?

Bob Goff quits something new every Thursday. How awesome is that? What would your life look like if you slowly started to cut out things that drain you of life rather than give it?

8) How can I make this fun?

This might be my favorite question on the list. As leaders who love the Church, we should be the most joy-filled people on the planet. There are seasons where our work won’t be the most fun, and that’s okay, but what’s not okay is to make no attempt to create a joyful space for yourself and your team. Get creative and make an enjoyable environment.  

9) How can I help someone else succeed?

Your work is not your stepping stone for building a greater name for yourself. Leadership is about creating stepping stones for other people to experience life to the full.  

10) What would a great leader do?

When I heard Andy Stanley give his talk about great leaders asking great questions, he delivered this as the cornerstone question every leader should carry with them. As a leader, you’ll face numerous scenarios where you don’t know what to do. But you know what? You’ll have an idea about what a great leader would do. If you get in a habit of asking yourself this question, then you’ll begin to develop the habits of a great leader.

Tyler Reagin is the President of Catalyst and author of Life-Giving Leader: Learning to Lead from Your Truest Self

Learn more about Tyler and his upcoming book here

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