7 Questions for Agency Leaders

The quality of your answers is determined by the quality of your questions.  

While asking great questions to our team members, clients, and other influencers is critical, the most important questions we can ask are the ones that we ask ourselves.

As a leader, you have undoubtedly learned that experience is an effective teacher. However, is experience the BEST teacher?

Have you ever met someone who said they have 20 years of real world experience, only to realize that what they really have is 1 year of experience doing the same thing for 20 years?

Experience is indeed a good teacher, but only evaluated experience creates greater awareness and positive change.

I am a natural risk taker and eternal optimist. In many ways, these tendencies serve me well. However, they can also cause me to forget to stop, reflect, and make necessary improvements. That’s why asking great questions is so important.

Recently I read a terrific leadership book based around asking great questions from John Maxwell titled, “Good Leaders Ask Great Questions.

One of the sections focused on asking yourself great questions to allow you to think deeper, gain greater self-awareness, and serve others more effectively. There were seven questions mentioned and I want to share these seven questions with you from the lens of an insurance agency leader.

You can use them all, use a few, or maybe you can add some of your own, but the most important point is that you begin to ask questions to position yourself as a stronger leader.

1) Am I investing in myself?

Have you ever tried to pour an empty glass into another glass to fill it up? Of course not, that’s silly.

However, I see it happen too often with agency leaders. They try to “pour” into their team, their carriers, and their clients without first “pouring” into themselves. 

In 2003, I heard a quote that caused a huge shift in my mindset from the late great Jim Rohn. He said, “Work hard on your job, make a living; Work hard on yourself, make a fortune.”

You can’t give what you don’t have

Personal development isn’t a fad or something you should think about when you have time. Your personal and professional growth will be the difference in you reaching your potential or wondering why you didn’t accomplish more.

In what areas do you want to grow personally and professionally?

How are you investing in your personal growth and development?

2) Am I Genuinely Interested in Others?

True leadership is not how far we advance ourselves, but how far we advance others.

People (team members, clients, influencers, carriers) are your most important asset. Yet sometimes in our day to day lives, it can be easy to take these precious assets for granted.   

One of common questions from agency leaders is, “How can we add more value to others?” The first and most simple answer is to genuinely value them.

What are your true motives? I have learned that when I focus on chasing dollars I become frustrated and exhausted, but when I focus on serving others, the dollars seem to begin to follow me.

The greatest purpose of leadership is to serve others. That starts by genuinely valuing others.

To serve is to lead. How are your serving others?

3) Am I Practicing Humility?

In 7th grade I thought I was good at basketball. I lived in a small town and I was the best player in my grade. Then I played in a tournament in a larger city. As I went up to shoot a three-point shot, an 8th grader jumped up out of nowhere, blocked my shot, and then dribbled to the other end of the floor and dunked it! With my eyes open wide, I realized very quickly that there were many bigger, faster, and better basketball players than me.

It was a lesson in humility.

The same is true in business. There will always be a person or business that is bigger, faster, and stronger than you. Just when you feel you have the tiger by its tail another one comes out of nowhere to bite you.

Rick Warren says, “Humility is not denying your strengths. Humility is being honest about your weaknesses.”

While you should leverage and be proud of your strengths, you must also be aware and humble of your weaknesses.

Where do you need to practice humility?

4) Am I Consistently Adding Value to Others?

You are either making emotional deposits or emotional withdrawals from those around you every day.  Make enough deposits and you become rich in your relationships, make too many withdrawals and you will soon become relationally bankrupt. 

They key phrase to challenge yourself every day is, “Who can I add value to today?” At the end of the day, ask, “Who did I add value to today?”

As Zig Ziglar said, “If you help enough people get what they want, you can have everything you want.”

Who are you adding value to today?

5) Am I Staying in My Strength Zone?

A couple years ago I spent an entire day working on formatting a landing page for a new program I was offering. For about 8 hours I tried and toiled to do something that I wasn’t very good at. At the end of the day, I was irritated, emotionally drained, and had accomplished little. Bad choice.

Instead, I could have had someone help me for little cost and focused my time on the content creation and delivery which is in my strength zone. 

Too many leaders spend too much time in the weaknesses, which leads to frustration and inefficiency instead of focusing on their strengths. 

You have been equipped with natural God-given talents that are hardwired into your DNA. 

Where are you spending your time? Are you focused on the activities that provide you the greatest return and reward?

How are you leveraging your strengths? 

6) Am I Taking Care of Today?

There is an old proverb that states, “When is the best time to plant a tree?  20 years ago. When is the next best time? Today”

Have you ever been so focused on what happened yesterday or what might happen tomorrow that you lose sight of the day right in front of you? I know I sure have. That’s why this question is so valuable.

While your past may be filled with problems and your future may be filled with possibilities, today is the only day that counts.

John Wooded famously said, “Make every day your masterpiece.”

Today is truly all that matters. What is the most important thing you need to accomplish today?

How are you taking care of today?

7) Am I Investing Time with the Right People?

Charlie “Tremendous” Jones famously said, “You will be the same person in five years except for the books you read and the people you meet.”

Who are you spending most of your time with? Are you investing time with people who inspire you, make you think, and raise your level of effectiveness?

This includes the content you put into your mind as well. What books are you reading? What podcasts are you listening to? What videos are you watching?

Just like what you feed your body determines your physical health, what you feed your mind determines your professional health. It’s bread for the head.  

As the saying goes, “Garbage in, garbage out.”

Who are your greatest influencers?  

The Bottom Line

Remember, the quality of your answers is determined by the quality of your questions. 

What questions are you asking yourself to be a better leader?

These are just a few of the questions that every leader should ask themselves. I challenge you to answer them or come up with your own that help you maximize your potential as a leader.

Brent Kelly is the Vice President of Sitkins Group. He helps agency leaders become “Professionally Fit” so that they can sell more, retain more, and earn more. Learn more at   


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