Introduction
Many business owners build something meaningful on instinct, determination, and speed. They make the calls, carry the key customer relationships, and solve the problems nobody else can seem to handle. Their personal involvement helps the business survive and, eventually, succeed.
Then the business grows, and the same approach starts creating problems. Every important decision still comes back to the owner. Capable managers wait for permission. The owner becomes frustrated that nobody takes initiative, while employees become frustrated that they have little room to lead. Everyone is working hard, but the organization is not becoming more capable.
In my work with CEOs and business owners, I see how difficult this transition can be. What made you successful feels right because you have years of experience proving that it worked. Recognizing when you need to change requires a level of honesty that success does not always encourage.
While doing my research for a leadership experience that I will be conducting in Belgium referencing The Battle of Waterloo, in August 2027, I have been thinking about these challenges through the experiences of Napoleon Bonaparte, The Duke of Wellington, and the commanders around them. Their decisions raise important questions about judgment, preparation, coordination, and trust—questions that remain relevant to business owners today.
Business is not warfare, and the human cost of these battles should never become a casual metaphor. However, studying how these leaders responded to the circumstances they faced offers a useful starting point for examining how we lead, especially when our greatest strengths begin working against us.
1. Focus Your Business Priorities Before Moving Faster
At Waterloo, Napoleon’s strategy depended on keeping Wellington’s and Blücher’s armies apart so he could defeat them separately. Together, their forces outnumbered his own. Their eventual cooperation helped bring about his defeat. He had a plan, but its success depended on preventing his opponents from doing exactly what they ultimately accomplished. For business owners, there is a useful question here: do you understand the conditions that must hold for your plan to work? National Army Museum
Most business owners understand the value of moving quickly. A smaller company can often respond to a customer, solve a problem, or pursue an opportunity faster than a larger competitor. That responsiveness can become an important advantage.
However, moving quickly becomes a liability when everything receives the same sense of urgency. Owners rarely lack ideas. The challenge is deciding which ideas deserve the organization’s limited time and resources, and which ones need to wait.
If you keep adding priorities without removing anything, you eventually undermine your own ability to execute. People shift between assignments, important work remains unfinished, and your strongest performers absorb the consequences. What looks like an execution problem may have started with your unwillingness to make a choice.
A new opportunity also deserves more scrutiny than your enthusiasm alone can provide. Do you have the capacity to deliver? What existing commitment will receive less attention? Who will carry the additional responsibility? These questions help you determine whether the opportunity makes sense now.
Before asking your team to move faster, make sure you have given them a clear place to concentrate their effort. Name what matters most, explain why, and take responsibility for deciding what will come off the list.
Where would fewer commitments allow your business to make more meaningful progress?
2. Prepare Before You Make the Next Bold Move
Wellington gets less attention than Napoleon in popular discussions of leadership, but his approach at Waterloo deserves consideration. He positioned much of his army behind a ridge, providing protection from French artillery, and held his position while awaiting Prussian support. His preparations did not make the outcome certain, but they gave his forces important advantages. Preparation and coordination were essential to the outcome, and both depended on work done before the decisive moment arrived.
Business owners often admire decisive action. There is satisfaction in making the big move, pursuing the opportunity, and being willing to take a risk. However, some of your most important leadership work happens before the moment when a decision becomes visible.
A bank renewal, a major customer negotiation, or a difficult conversation with a partner requires preparation. You need to understand the facts, anticipate concerns, consider alternatives, and know what you can reasonably commit to. Confidence is more useful when you have done the work to support it.
The same is true of managing the business through uncertainty. Protecting cash, strengthening operations, and developing your management team may receive less attention than announcing another growth initiative. They still require judgment and discipline, and they may be exactly what the business needs.
Preparation also includes deciding how you will respond if events unfold differently than expected. What would cause you to reconsider? What options would remain available? Thinking through these questions beforehand helps you avoid making every difficult decision under pressure.
Your people also watch how you respond under pressure. If every challenge becomes an emergency, you make it harder for them to think clearly. When you arrive prepared and maintain your composure, you give others a better chance to contribute.
Where does your business need better preparation from you right now?
3. Build a Leadership Team With Complementary Strengths
The commanders at Waterloo illustrate how differently capable people can respond to pressure. Ney’s cavalry attacks, Grouchy’s detached pursuit of the Prussians, and Blücher’s arrival offer examples for considering initiative, coordination, and dependable support. Their decisions involved circumstances that a simple leadership label cannot fully capture, but the questions they raise are useful. How much freedom should someone have to act? When do instructions need to be reconsidered? Who can you depend on when a commitment becomes difficult to keep?
Most owners have someone on their team who moves faster than the rest of the organization can comfortably follow. This person makes commitments, pushes through obstacles, and expects everyone else to catch up. Their energy produces results, but it can also create problems for the people responsible for delivering what they promised.
You may also have someone who follows instructions carefully but hesitates when circumstances change. They are conscientious and dependable, yet reluctant to make a decision without checking with you. When an unexpected problem arises, they may wait precisely when you need them to act.
These people need different things from you. The first needs clear boundaries and accountability for the consequences of their decisions. The second needs a clear understanding of the desired outcome, explicit authority, and support as they develop their judgment.
You also need people who will follow through when doing so becomes inconvenient. Dependable partners matter inside and outside the company. You learn a great deal about a relationship when keeping a commitment requires additional effort or sacrifice.
Look honestly at the team you have built. Have you surrounded yourself with people whose strengths complement yours? Do you listen to the person who raises concerns as carefully as you listen to the person who shares your enthusiasm? If everyone approaches problems the same way, important questions may never get asked.
Who needs clearer boundaries, who needs more authority, and whose perspective is missing?
4. Recognize When Your Leadership Approach Needs to Change
Two days before Waterloo, Napoleon defeated the Prussians at Ligny. However, that victory did not remove them from the campaign. They regrouped, maintained contact with Wellington, and arrived at Waterloo to help defeat the French. For business owners, there is a useful lesson here: an encouraging result can reinforce your confidence even while the larger situation remains dangerous. You still need to question your assumptions and understand what has changed.
It is tempting to explain a disappointing result by pointing to circumstances: the economy, a competitor, an employee, or a customer who changed direction. Sometimes those explanations are valid. They still leave an important question unanswered: what was within your responsibility to recognize, prepare for, or address?
Owners can become attached to how they built their companies. That is understandable. You remember the risks you took, the sacrifices you made, and the decisions that kept the business alive. Those experiences shape how you think.
However, a company with 75 employees cannot rely on the same informal communication that worked with 10. A management team cannot develop if you routinely take back difficult decisions. Customer service cannot remain consistent if fulfilling your promises depends on a few people repeatedly saving the day.
The warning signs are usually worth examining before you feel ready to change. The same problems keep returning. Decisions sit on your desk. Strong employees stop offering ideas. Revenue grows, but profitability or service suffers. You work longer hours and wonder why the business still requires so much of you.
If every important decision requires your approval, you need to examine how you have helped create that dependency. If managers hesitate to act, consider what happens when they make a reasonable decision you would have made differently. Your behavior teaches people what is actually expected, regardless of what you say in a meeting.
What evidence would convince you that your current approach is holding the business back, and who has permission to tell you?
5. Reduce Founder Dependency and Develop Your People
Napoleon’s legacy offers another useful lesson. His military defeat did not erase everything developed under his leadership. The Civil Code, adopted in 1804 through the work of legal experts and extensive deliberation, had a lasting influence on France and other countries. Despite its serious limitations, including restrictions on women’s rights, it demonstrates how formal institutions can endure beyond an individual leader. For a business owner, that raises an important question: what are you building that will continue to function when you are no longer there to direct it? Fondation Napoléon
Being needed can feel rewarding. Customers ask for you, employees trust you, and difficult situations land on your desk because people believe you can resolve them. There is real satisfaction in knowing that you make a difference.
There is also a cost when too much depends on your availability. Your people have limited room to grow. The business becomes more vulnerable. Taking time away becomes difficult because your absence exposes responsibilities that nobody else is prepared or authorized to handle.
Ask yourself what would happen if you were unreachable for 30 days. Who would manage your most important customer relationships? Who would make financial decisions? Who would respond to an operational crisis? Would people know their authority, or would they spend their time trying to find you?
The answers need to include names, responsibilities, and processes that people understand. “My team would figure it out” leaves too much to chance. If you have not prepared them, it is unfair to assume they will suddenly operate effectively without you.
Developing that capability takes patience. Someone else may approach a responsibility differently. They may need coaching and experience before their judgment becomes consistent. Your job is to provide that support while giving them enough room to learn.
What responsibility could you begin transferring now that would make both your team and your business stronger?
Do This This Week: Turn Leadership Lessons Into Action
A leadership article has limited value if it produces agreement without action. You may recognize yourself in several of these examples, but trying to address everything at once will only add to the competing priorities already on your plate.
Research by Peter Gollwitzer and Paschal Sheeran supports the value of making specific plans for when, where, and how you will act. Their review of 94 independent tests found that these plans helped people translate intentions into goal achievement. For a business owner, the practical application is simple: give your commitment a place on the calendar and a clearly defined first step. Gollwitzer and Sheeran, 2006
Start with three commitments and one person who will hold you accountable:
- Change one leadership behavior. Identify something you do that limits another person’s effectiveness. Decide what you will do differently and when you will begin.
- Advance one business priority. Choose an improvement that deserves concentrated attention over the next 90 days. Define who owns it and what progress should look like.
- Stop doing one thing. Create capacity by eliminating, postponing, or transferring work that should no longer require your attention.
- Schedule an accountability conversation. Share these commitments with a peer you respect. Set a date to review progress and give that person permission to challenge your explanations.
Conclusion
The leadership your business needs will change as the organization grows. There will be times for bold action, times for careful preparation, and times when your most useful contribution is allowing someone else to take responsibility. Good judgment includes recognizing which situation you are in.
Napoleon’s experience is a reminder that past success does not guarantee sound judgment in the next challenge. His talent and determination could not ensure victory at Waterloo, while some of the institutions developed under his leadership endured beyond his rule. For business owners, that raises two questions worth revisiting: are you willing to adapt when circumstances demand it, and are you building something that can function without you?
You deserve credit for what you have built. Your next responsibility is to help others become capable of carrying it forward. Over time, the strength of your leadership should show up in the judgment people exercise, the commitments they keep, and the results they can deliver when you are not in the room.