Driven for Success
Driven for Success is a podcast for trucking company owners and executives running 20–80 truck fleets who want to scale without chaos.
Hosted by Mike Ritzema, founder of Superior Trucking Payroll Service, the show focuses on what actually breaks as fleets grow—and how strong operators fix it before constant firefighting takes over.
This isn’t a motivational show and it’s not theory-heavy. Each episode is grounded in real patterns seen across hundreds of trucking companies, covering topics like:
- Where complexity quietly creeps in as you scale
- What to standardize—and what not to
- Why payroll, pay clarity, and systems become retention issues
- How to build infrastructure that supports growth instead of relying on heroics
The goal is simple: give you practical ideas you can apply immediately to run a calmer, more profitable operation.
If you’re building a trucking company that needs to work without you carrying everything on your shoulders, this show is for you.
Driven for Success
S1 E31 The Escalation Habit That Turns Trucking Owners Into Bottlenecks
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As trucking companies grow, something subtle begins to happen inside the business.
Dispatch escalates decisions.
Payroll escalates questions.
Safety escalates problems.
Operations escalates anything uncertain.
Eventually, everything ends up in the same place: the owner’s desk.
In this episode of Driven for Success, Mike Ritzema explains the escalation habit that forms inside growing trucking companies and why it quietly turns owners into the bottleneck.
You’ll learn:
• Why escalation becomes the safest behavior inside companies
• How good leaders accidentally train teams to escalate decisions
• The moment when growth stops increasing decision capacity
• A simple framework to start fixing the problem this week
If your trucking company has grown to 20–80 trucks and it feels like every decision still comes back to you, this episode will help you understand why.
And more importantly, how to start fixing it.
You're trying to finish something important. Maybe you're reviewing numbers. Maybe you're working on an important customer issue. Maybe you're finally catching up on something you've been putting off all week. And someone walks in with a question. Hey, Bill, quick question. A few minutes later, someone else asks something. Dispatch calls. Payroll needs clarification on something. Safety needs an answer right now about a driver's situation. And by the end of the day, you realize something. Nothing actually moves in this company without going through you. Last week I talked about the system many trucking company owners are still afraid to build. The system where people inside the company make decisions without checking with the owner. Today, I want to zoom in on the habit that quietly prevents that system from ever forming. And it's called escalation. And escalation can be realized in a number of different ways. It can be the dispatch rate decisions or the payroll exceptions or driver discipline. It can be customer service. It can be all those little things that become big things. And they're all there and they all happen all the time. Welcome to Driven for Success, the podcast where we talk about the systems and decisions that keep trucking companies growing without the owner becoming the bottleneck. I'm Mike Ritzimo, your host. If you've run a trucking company between 20 and 80 trucks, you've probably experienced this stage where the business is growing, but it still feels like every single decision somehow finds its way back to you. Today, we're going to talk about one of the biggest reasons that that keeps happening. So the escalation habit, and that's what this is, this is an escalation habit, starts with good intentions. Early in the trucking company, the owner is the person who knows everything. They know all the customers, they know all the lanes, they know each driver on a personal level, and they've handled almost every situation before. So when someone asks a question, the owner answers it because they know and they've been in all of those jobs. And that works perfectly fine when the company is small, but as the company grows, something subtle begins to happen. The pattern stays the same. Ask the owner, wait for the answer, and then move forward. The only difference is that the number of decisions happening every day has exploded. It goes up exponentially. It's always little things. It's things like what should we do with this driver, or should we take this load, or can I accept this rate on this backhaul? Or, you know, when should we replace the tires on that truck? Should we do it before or after it goes out on this load? It can be things like a safety question. It can be, do we pay detention? And that's the example I use in a lot of these episodes. But it's just those little decisions that keep coming up. And so the owner is involved in every single one of them. And it's just hard. And it just adds so much decision fatigue. You know, here's the part that most owners never notice. Every time someone asks a question and the owner answers it immediately, the company learns something. They learn that the very safest thing, the thing that keeps them out of trouble the most, is escalation. Not deciding for themselves, but escalating. And sometimes the reinforcement becomes even stronger because when someone does have the courage to make a decision and the owner, the owner goes and overrides it. The lesson becomes really clear when that happens. And it's next time, just ask. Over time, the company doesn't build decision makers, it builds escalators. People who pass decisions upwards instead of owning them. And you'll see this happen because nobody wants to get in trouble and nobody wants to do it wrong. Nobody wants to be the one who goofed it up. And so the safest way to do it is to just ask. Well, that way, if I got permission, then I'm okay. And that's really not what you want for your employees. Let me give you a quick example of how this actually plays out. I once talked to a fleet owner who told me his dispatcher asked about almost every single rate, every load, every day. And man, he was frustrated. He thought the dispatcher lacked confidence, but when they talked about it, the dispatcher said something that was really interesting. He said, Every time I pick a rate, you ask me why I chose it. So it's just easier if I ask you first. And that's not a confidence problem. That's a learned behavior. You know, how many employees, if this employee has to do this, you know, how many other employees with every other decision have the same thing? If they felt like their decisions were being questioned, and all the owner might have really just wondered was how'd you get to that number? Maybe for the owner to learn, or maybe just to see what the number would be, make sure they thought it through. I know I've done that a lot with people. I'll just ask it, I want to learn their thinking about how did you get to that decision? But the employee heard it as, well, I need to run it by you. And so, and once that starts to happen, it can spread like a virus. We don't want that. Eventually, a company hits what I call an escalation ceiling. The business may have more trucks, more drivers, more office staff, but the decision capacity of the company has not grown at all. Because the decisions all still route to the exact same place. The owner. This is where owners start feeling buried. Questions all day. Interruptions all day. And even though the company is bigger than it used to be, it still feels like everything depends on you. You know, just imagine you know, your family's like, look, you work hard all the time, let's go take a vacation. And so you're going to some tropical resort and you're spending the whole day in the room on the laptop or on the phone, even if you're by the pool, you know, you're on the phone with your people because you're constantly getting calls, because no one's willing and able to act without your blessing. It's a hard way to live. So let me ask you a question. If you disappeared for two days or three days, what decisions inside your company would completely stop? Would it be dispatch pricing? Would it be pricing loads? Would it be driver discipline issues or driver hiring issues for that matter? Would it be payroll exceptions? You know, can we do this? Can we do that? Would it be customer things? You know, this question, what things would completely stop, reveals exactly where escalation has become the default method of operation for your company. So think about it for a minute. Just look listen to your own company, listen to your head right now. Which of these things hit home with you? And you should just that is the thing that is where everybody escalates. And sometimes they do have to escalate for sure, but not nearly to the extent that they do. Fixing this doesn't start by telling people to stop asking questions. That never works and it confuses them. The real starting point is identifying where the escalation happens most often. Ask yourself what category of decisions end up with me all the time. Then just pick one category. Sit down with the person responsible for that area and define three things what decisions they own, what decisions they make but notify you about, and what decisions truly require escalation. Once those boundaries become clear, something is interesting, it starts to happen. The questions stop coming to you because people finally understand where their authority actually begins. And even in this, the worst case scenario is they make a mistake on a decision. Let's use driver rating as an example. Or I'm sorry, load rating. So how much we're going to charge for a load as an example. If you wanted them to charge$2,000 for this load and they charged$1,900 or$1,800, yeah, that's$100 or$200 out the door that's not coming back. But you can see that later and just say, hey, next time, let's let's let's change our instructions to maybe make sure we get$2,000. It's just going to happen once or twice. Uh, but the autonomy that you're going to build among your people and the ability to make their own decisions and the ability to scale is well worth it. And who knows, maybe instead of 2,000, they charge$2,100 and they got it. So you're going to win on some of those too. Some of these decisions that your employees are going to make are going to be better than the decisions you make, which I know sounds crazy, but I'm telling you, it's true. They will be like, oh no, I think I can do better. You said 2,000, I think I can get 2,100, I can get 2,200. And maybe they can. So you never know. Them going off on their own might actually benefit you. Let me give you one thing to try this week. Pay attention to the next five questions that get escalated to you. Just write them down. Don't fix anything yet, but just notice that pattern that starts to develop. Because the owners discover that it's the same category decisions all the time. And that category is usually the first system that needs clarity. And often it's one of the easiest ones to do. So just even think back to the last five questions you've gotten. Or the last the questions you've got today, you know, was there a theme to them? Was it the similar questions, just different loads or different drivers? But it was in different people asking the questions, that's a really good sign, too. If it's multiple people asking you questions on the same topic, that really just means that they haven't been given clear instructions on where their boundaries are. Escalation itself isn't the problem. Every company needs escalation sometimes, of course. That's why you're there. The real problem is when escalation becomes the default response to every single decision because that habit quietly turns the owner into the bottleneck. The companies that grow past this stage don't eliminate escalation. They just make sure escalation happens only where it belongs. And that happens, the team begins to gain confidence and decisions move so much faster. The company finally starts operating like a real organization instead of a group of people waiting for the owner. And isn't that what you had in mind when you started your company and you had three or four or five trucks, and now you have 25 or 30 or 50 trucks? You thought it was going to be a lot easier. You thought these people you would empower people to make decisions and they would go make them. Well, they're just waiting for you to empower them and you can do it. So if this feels like you, you know, just know you can fix it. You did the hard part. Getting from three trucks to 23 trucks, 33 trucks is the hard part. You can do this. There's another layer to this that most owners don't realize. The escalation habit doesn't usually start with the team, it starts with the owner. And in the next episode, I want to talk about why that happens. Because one of the biggest hidden costs in a growing trucking company is when the owner stays as the smartest person in the room. Thanks for listening to Driven for Success, and I'll see you next week.