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3 Questions Every Leader Should Answer

April 25, 20235 min read

As a coach, I typically start a relationship by digging into how a leader started his organization.

I try to understand the leader’s history and role in the organization. I seek to grasp some of the organization’s strengths and challenges.

Once I connect with him sufficiently and discover some key insights into what he does, I normally ask 3 key questions. The leader’s answers to these questions help to chart a path forward.

What are those 3 questions? Read them below.

3 Questions Every Leader Should Answer

Question #1 – How much do you want to make?

Although money is only one part of an organization, it is an important part. Knowing how much money you want to make is critical for moving your organization forward. Occasionally, I find a leader that does not have an immediate answer to that question.

Not long ago, I asked a medical doctor how much she needed to make in order to practice medicine the way she desired, to pay her overhead for the business, and to take care of her family. She responded by staring at me and saying “I don’t know. I’ve never thought about it like that.”  

Most people have an idea of what they want to make. They usually will give me an immediate number. I like to know what their goal is. As a coach, if I can help them reach their goal, they will be happy and feel successful.

I also find that naming a specific amount provides them with a clear target. It’s very difficult to hit a target, if you don’t really know what it is. By naming a specific amount of income, it helps both the client and the coach to work together towards an income goal.  

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Question #2 – How much do you want to work?

Leaders work a lot! Sometimes they don’t even think about how much they work. They just do what they have to do to keep their company functioning. I always smile when people tell me that one of the reasons they started their company was so they could control their schedule.

While controlling your schedule sounds good, working for yourself often means you have little control over your schedule. It’s not that you do not have authority to make decisions about what you do, but there is so much to do that it takes a great deal of time to get it all done.

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Many people have a specific amount of time they want to work. A common answer will be 40-50 hours per week. Often staying within desired work hours requires changes in the organization. Leaders need to rethink their role and responsibilities.

Many times, leaders are not really aware of how much they truly work. They just work.  I find that leaders simply try to do too much. They are the bookkeeper, the scheduler, the manager, etc. They run from job to job and often feel overwhelmed.

Asking leaders how much they want to work forces them to pause and give thought to what they are currently doing. From there, we begin to work to reduce their workload so that they can reduce their work hours. If I can help them find better work/life balance, they are happier and the joy of working in their organization returns.

Question #3 – Where are you most profitable?

Question 3 is one many people have never thought of before.  Whether they distribute a product or provide a service, there will be at least one product or service in which they are most profitable.  Yet, many leaders do not think about this concept. They are just moving products or providing services.

I remember asking a leader this question to which he responded, “I honestly don’t know. I have never thought of this question.” Not knowing where you are most profitable means you might be working hard, but you are not likely working smart.

A number of months ago I asked a tradesman about his services. He is a handyman and does a variety of work. When I asked him this question, he paused for a moment and said, “I suppose if I think about it, I make the most money doing ceramic work. If I do ceramic work, I can make a thousand dollars a day.” I continued by asking him if he liked doing ceramic work and if he was good at it. He said, “Absolutely.” I then asked the obvious question: “And why are you not doing more ceramic work?” He could work the same number of hours and make $300 per day or $1,000 per day. Which one would you choose?

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Most leaders are simply working. They don’t take the time to stop and think that certain products or services are more profitable than others. By pushing a certain product or providing a certain service they can make more money in less time.  Simple mindset adjustments can make huge differences. 

These 3 questions help align a leader towards his or her target. Leaders get lost in the details of owning and/or running their companies.  They run from task to task and fail to stop and think about how much they’re really making, how much they’re really working and where they are most profitable.  A coach can help them take a “time-out” to give deep thought to what they are doing, why they are doing it, and how they can do it better.

As leaders get better alignment, they are happier, more productive, and more effective. When a leader reaches these goals, his fire will return and his success will increase, without having to work harder.  

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Dave Pennington PhD

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Mike Kanty

Dave is a calm and thoughtful leader. His focus on Pastoral Leadership is ideally suited to his skills and life experience. Dave helps pastoral leaders develop and implement a church growth system that reaches and impacts their communities. If your vision for your Church is getting fuzzy or you are challenged with not just retaining but inspiring and growing an active congregation reach out to Dave at Penn Coaching and Consulting.


Kristin Sherry

Dave has been consulting with me for about half a year and helps me stay focused on what's important for YouMap LLC to scale and grow. The YouMap® Coaches and Facilitators love his quick start coaching process and everyone finds his insight to be extremely beneficial. He is a trusted partner and a blessing.


Bob Sager

Dave is one of those people who, upon meeting him for the first time, you feel like you've known for years. Easy to talk with, he takes a non-judgmental approach to helping business owners become more successful and have more fun.

As a member of one of the Mastermind Groups I run, Dave has always applied his knowledge, experience and imagination to helping others solve their biggest challenges. I am so pleased to know him and recommend him highly.


Mike Chirveno

I had the pleasure of working with Dave on an executive team for a couple of years. His ability to identify the "big rocks" in a situation, fashion the best "next steps" and marshal the efforts of a team to execute are the best I have seen. Dave is a gifted executive coach who makes his clients more productive, helps them stay focused on their highest priority tasks and probably most importantly, gives them a good sounding board for the important decisions they must make. There is no one I could recommend more heartily than David Pennington.


Heidi Chapnik

I have known Dave for several years. It has been an honor to know him and engage with him at his best. Dave is a heartfelt salt of the earth man of integrity, which belie his talents. Dave is super focused, organized and effective in decision making, problem solving and team building. His approach as an executive coach is open door, empathetic, yet firm and strong. Dave is able to build teams after on target analysis of challenge areas. His wide range of knowledge spans to all levels of management and his effectiveness knows no bounds.


Mark Burdette

Dr. David Pennington provided insightful, strategic business coaching that enabled my commercial firm to grow from 1 to 13 brokers and expand from 1 to 4 different geographical locations. He assisted with hiring & developing brokers, putting processes in place to manage and grow my firm. He is wise, encouraging, and a good personal friend. If you want someone who will help you grow as a leader, you cannot do better than hiring him!


Anthony Totta

Doc Dave has been a very positive influence by challenging me to become more focused and thereby more effective. He showed me effective ways to prioritize. His "spin less plates and spin the remainder well" approach for me has been just what I needed. I am thankful Dave is now offering himself full time as a coach mentor. I am sure he will help many folks from many walks of life as he did me.


PJ Petrillo

He is an excellent instructional leader who remains cool in a crisis, and responds well with clients and employees alike. David is a diverse individual who will be successful on whatever path he chooses to work within. He is a team player and mentors others well too.

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