Our team of consultants has advised many business leaders over the years. The companies these owners run are very diverse. Construction. Manufacturing. Medical. Insurance. Agriculture. Retail. Law. Just to name a few. It is our goal to add value and deliver results to every owner we serve.
One of the ways we do this is to ensure business owners are asking themselves important questions – questions whose answers can have a long-term positive or negative impact on the future of the enterprise. Some owners are already wrestling with these questions, which led them to us. Others are busy running their business and have not been able to catch their breath long enough to think about them. Here are seven questions every business owner should be asking themselves regularly.
1. What predator is stalking my business right now?
A predator is not inherently bad, but it can be deadly if you are not aware of how it may impact your business. For example, predators may include competitors who are looking to snatch your top managers. Or a technological innovation such as Artificial Intelligence that can either reduce the need for your services or reduce what people are willing to pay for your services. For example, streaming was a predator that swooped into the music and broadcast television space and redefined how we receive content. Every business has a predator close by or on its way, and it is vital for owners to consider what the predator is and where it may come from.
2. Are my kids or other family members the best ones to take over the business?
Many owners would love to see the business they worked hard to build stay in the family. But sometimes they do not have any family members who want to run the business. Other times, a family member wants to run it, but how can the owner be sure this person is the best one to do it? Northeastern University professor Kimberly Eddleston says that in one out of three family businesses, “unprepared family members, who have little to no idea what they’re doing, often brought businesses to the brink of bankruptcy.” There is sometimes a gap between well-meaning and wisdom. An owner is doing no favors to themselves, their children, their employees, or their customers when they are not sure if the person to whom they are passing the leadership baton will lead successfully.
3. Which part of my business is not generating the profit that it should?
Most businesses with multiple products or services know that they do not all generate the same profitability. For example, a landscape company may have lawn care, snow removal, hardscaping, landscape design, and even a retail nursery. The owner could discover that hardscaping generates far more profit than cutting lawns. This doesn’t mean the owner should eliminate lawn cutting since 1) it may serve as a feeder to more profitable work from a customer in the future, and 2) it provides diversification of revenue. But an owner should know what it costs to offer a product or service and what profit they are making from that service. They may even discover that they are losing money every time they provide a particular service or sell a particular product.
4. Why am I still running this business?
“Why” questions have a bit of a philosophical feel to them, don’t they? For example, why do some very bad people live longer than others who are doing amazingly good things? Or, why do people deeply in love end up in a bitter split? Some “why” questions are deep and hard - I will leave those for someone much smarter than me to attempt to answer. But I have heard several business owners over the years ask the question, “Why am I still doing this?” For some, it may be that they love the work. For others, they feel a deep sense of moral and spiritual calling and responsibility to both God and their employees. Some continue because they still need the money or are too young to step out of it. Others do it because of family legacy. And there are those who do it because they just aren’t sure what else they would be doing. It is important for every owner to think about “why” they are still running the business because the answer can shape the future of the business as well as their life.
5. Who on my team can I not afford to lose?
The 2026 Olympics concluded with the USA men’s and women’s ice hockey teams both taking home the Gold Medal. While the success of any team seldom rests with only one person, there are team members who would change the outcome of the game if they were not there. This is true of Team USA goalie Connor Hellebuyck, who stopped 40 shots from Canada. Truly remarkable! As a business owner, you likely have at least a few people like Hellebuyck. Which employees, if you lose them, could have serious short-term and long-term consequences? Wise owners not only know who they are, but they work to ensure that they do not lose them.
6. Do I know what my customers really think of my business?
Having an accurate perception is difficult when looking at both ourselves and our business. For example, I may see myself as 6’4”, 230 pounds, and able to bench press 380 pounds. But that would not match how others see me: 5’8”, 179 pounds, and barely able to lift a case of Diet Coke out of the trunk. Sometimes owners may have an unclear picture of how their clients and customers see their business. Without some form of anonymous and honest customer feedback, it leaves us to guesswork. Research and life experience show that customers may leave a business, even if they are relatively satisfied, because a competitor offers a higher level of satisfaction. To know your customers, you need to proactively seek honest feedback – far beyond the symbolic Google review.
7. Which customers or clients are most vital and valuable to your business?
We often hear stories from business owners about customers or clients who have high expectations or are consistently rude to the staff, but they spend the least. When an owner understands which customers and clients matter most to their business, they can ensure those customers get the attention they deserve. Running a business can be hectic, so it is easy to see why an owner may not have a clear understanding of their customers and revenue per customer. But a failure to understand this can result in misplaced focus, misguided decisions, and missed opportunities.
Most owners know which question on this list they have been avoiding. You do not have to work through it alone. Contact us to learn how our experienced consultants can help you find the answer.
Jay Desko is the President & CEO of The Center Consulting Group and brings experience in the areas of organizational assessment, leadership coaching, decision-making, and strategic questioning. Jay’s degrees include an M.Ed. in Instructional Systems Design from Pennsylvania State University and a Ph.D. in Organizational Behavior and Leadership from The Union Institute.
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