When companies begin to grow, most CEOs focus on revenue, hiring, and new opportunities. Those matter. But they are not usually the first thing that breaks.
What breaks first is often much more personal.
The founder still tries to do too much. Decisions pile up. Communication gets uneven. Processes stay informal for too long. The team waits for direction that should no longer need to come from one person.
Michael Cherney has lived that shift from the inside. After spending more than 13 years rising from account executive to vice president, he co-founded Cooler Logistics and stepped into the hardest kind of role there is: building from zero after years inside an established organization. He understands both sides of the journey. He knows what it takes to scale inside an existing company, and he knows what it feels like to start over and build the machine yourself.
One of the clearest lessons he shared is also one of the most important. “You can’t do it by yourself.”
That sounds obvious. It is not.
A surprising number of founders and early-stage CEOs still operate as if they are the exception.
The First Trap
Michael described his early leadership experience with refreshing honesty. When he moved to Los Angeles to open an office, he did not have much guidance. He tried to do everything himself. His words were direct: “I honestly was probably a terrible manager, but I tried to do everything by myself.”
That is the first trap.
A lot of smart, driven people become leaders because they are used to being the one who gets things done. That instinct helps in the beginning. It becomes a liability later. The very habits that make you effective as an individual contributor can slow the company down when you are supposed to be building through others.
Michael learned that the greatest opportunities for success came when he stopped pretending he had to carry everything alone and started asking for help.
That shift matters because scaling is not a test of endurance. It is a test of design. Can you build a company where strong people know what to do, trust each other, and move without waiting on you?
That is the real work.
Why Communication Breaks
One of the smartest parts of my conversation with Michael was his explanation of why communication breaks down as companies grow.
Most people assume communication problems are about personality. Someone is too blunt. Someone else is too passive. A third person is not paying attention. Sometimes that is true.
More often, communication breaks because the company has not been intentional enough.
Michael said it well. If there are no clearly defined avenues of communication, people naturally retreat into silos. And once silos form, communication becomes narrower, slower, and more defensive.
He tied that directly to trust. You cannot have healthy conflict without trust. You cannot challenge one another productively if people do not feel safe being candid. And if your leadership team only says polite things in meetings while frustration builds underneath, your culture may look calm, but it is not strong.
That is one reason I talk so often with CEOs about the difference between harmony and health. A healthy team can disagree openly and still move together. An unhealthy team protects itself, avoids conflict, and lets bad assumptions survive.
Michael and his team were intentional about avoiding that trap. They built around clear values: collaboration, leadership, integrity, metrics, and balance. That gave them a framework for how to operate, not just what to accomplish.
Culture is not what you write on the wall. It is what your people trust enough to do when you are not in the room.
The Role Of Process
Michael also brings something many CEOs do not naturally love: a real appreciation for process.
That matters.
Most founders light up when they talk about vision, product, customers, or growth. They do not get energized by standard operating procedures. Yet the company eventually depends on them.
Michael’s view is practical. He is not advocating bureaucracy. He is advocating preparation.
At Cooler, they spent real time building processes early, even before every process was urgently needed. In his view, it was better to be overprepared than to find out during growth that the business had weak foundations.
That is exactly right.
I often tell CEOs that process is not there to slow you down. It is there to prevent you from breaking under success. When you are small, people can compensate for poor systems. Once you begin to grow, they cannot. Customer experience suffers. Employee experience suffers. Mistakes multiply. Leaders get pulled back into work they should have left behind.
Michael had seen that before. In an earlier environment, as the company scaled quickly, corners got cut. The cracks showed up in the customer experience and the employee experience. He did not want to repeat that mistake.
There is a lesson here for every CEO. You do not need maximal process at the beginning. You do need enough process to support the next stage of growth. If you wait until the strain is obvious, you are already behind.
Process Without Rigidity
What I also liked was Michael’s balance. He values process, but he does not confuse process with rigidity.
He was clear that CEOs cannot be so rigid that they stop evolving. Change is necessary. Improvement is necessary. You need structure, but you also need the willingness to revisit that structure when the business changes.
That is where many leaders get it wrong. Some resist process because they are afraid it will slow innovation. Others create process and then cling to it long after it stops serving the company.
The real skill is knowing that both things are true.
You need process so people know how to execute. You need flexibility so the company can improve.
That is what mature leadership looks like.
The CEO Must Scale Too
Every scaling company eventually reaches the same truth. The business cannot outgrow the CEO for long.
Michael spoke powerfully about this. He said he is a completely different person and leader now than he was on day one. That is exactly what should happen.
One reason he has been able to make that shift is that he has worked with an executive coach on a weekly basis. That outside perspective helped him navigate startup challenges before they became company-threatening problems.
I believe strongly in that kind of support because it changes the time horizon of your leadership. Instead of reacting after the damage is visible, you start seeing patterns earlier. Problems become manageable while they are still small.
Michael also brought up another quality that matters just as much: humility.
He said there is still so much he does not know and so much he needs to learn. That openness makes him more effective, not less. It allows him to learn from coaches, executives, and frontline employees alike.
The CEOs who improve fastest are usually not the ones who think they already know. They are the ones who are secure enough to keep learning.
AI As A Force Multiplier
Michael’s approach to AI was disciplined and useful. He does not see it as magic. He sees it as leverage.
His phrase was strong: AI is a “force multiplier.”
That is a far better way to think about it than either extreme. It is not a gimmick. It is not a replacement for everything human. It is a tool that can remove low-value work so talented people can spend more time on what actually matters.
In his business, that means using AI to eliminate operational bottlenecks. One tool helps the purchasing side decide which carrier partner should be assigned to a load. Another handles order entry and appointment scheduling. A third manages paperwork, auditing, pricing, and documentation on the finance side.
These are not flashy use cases. They are better than flashy. They are useful.
And that is the point.
The goal is not to say you use AI. The goal is to use it where it creates measurable gains in speed, capacity, and service quality.
Michael was also clear about the limit. In a service business, especially one built on relationships, the human element cannot disappear. Clients still want trust, responsiveness, judgment, and accountability. AI should reduce the time spent on minutiae so people can focus more on revenue-generating work and relationship building.
That is exactly the right priority.
What CEOs Should Take From This
Michael’s story reinforces something I see again and again.
Founders often believe scaling will come from more hustle. It usually comes from better design.
You need the right people. You need a culture that can handle honest communication. You need process before the strain becomes destructive. You need enough humility to ask for help. And you need to stop treating yourself as the only one who can solve the problem.
The company grows when the CEO stops being the hero of every scene.
Michael captured that lesson in the simplest and strongest way: “You can’t do it by yourself.”
That is not a limitation. It is the unlock.
I am Glenn Gow. I coach CEOs.
If you feel like the bottleneck in your company, do not start by working longer. Start by asking a better question. Where am I still acting like the business depends on me personally instead of on the system we are building together?
That answer will tell you a lot about your next stage of growth.
