By Alex Damske | Mastery Logistics Systems
I've spent a lot of time onboarding freight brokerage employees, including nearly two years training new hires across multiple offices. Some had transportation experience. Others had never worked in logistics.
And one thing became very clear: Teaching someone how to use a transportation management system (TMS) isn't the same as teaching them how to be a successful freight broker.
You can show someone how to enter a load, search for capacity, or update a shipment. But that doesn't prepare them for a missed pickup, an unhappy customer, or a carrier that backs out at the last minute.
Freight brokerage is a business where things change constantly. The people who thrive are the ones who understand why they're doing something, can think on their feet, and aren't afraid to approach a problem differently.
That's why I believe successful onboarding starts well before anyone logs into a TMS. And it certainly doesn't end when formal training is over.
Hire for Adaptability, Not Just Experience
At one brokerage where I worked, we recruited heavily from the restaurant industry, particularly bartenders. That might sound like an unusual place to find freight brokers, but think about the skills a good bartender or server develops.
They interact with all kinds of personalities, manage competing demands, handle difficult situations, and make decisions under pressure. They know how to adjust their communication depending on who's standing in front of them.
That's freight brokerage.
One minute you're talking to a director of pricing about a customer opportunity. The next, you're speaking with a truck driver who's been on the road for weeks and needs help resolving a problem.
The conversation, the priorities, and the way you communicate can change completely.
Of course, not every bartender makes a great broker. What matters is whether that person is adaptable, curious, and willing to keep learning.
Someone working in a busy restaurant with constantly changing menus and customer expectations may already be comfortable operating in an environment where no two days look alike.
Industry experience can be valuable, but it isn't always the best predictor of success. When hiring new brokerage employees, I'd look just as closely at their ability to adapt, solve problems, and keep learning.
You can teach someone how freight brokerage works. What's harder to teach is the willingness to grow as the business changes.
Teach the Why Before You Teach the How
When I was training new hires, I wanted them to understand more than the mechanics of moving freight.
I wanted them to understand why their work mattered.
If someone sees brokerage as nothing more than entering information into a computer, they're missing the bigger picture. They're coordinating the movement of goods, solving problems for customers, working with carriers, and making decisions that affect the profitability of the business.
Once people understand that purpose, the individual tasks begin to make more sense.
Instead of simply learning where to click to cover a load, they can begin understanding why carrier selection matters, what happens when an appointment is missed, or how a service failure affects a customer relationship.
That understanding becomes especially valuable when something unexpected happens, which, in brokerage, is pretty much guaranteed.
My approach was to give new employees that foundation first. Then we could teach the processes, systems, and specific responsibilities they needed to perform.
It's the difference between training someone to follow instructions and preparing them to solve problems.
The Real Test Begins When Training Ends
One of the biggest lessons I learned came from watching what happened after employees completed their initial onboarding.
We could bring 20 or 25 new hires together, teach them the business, get them excited about their opportunities, and send them back to their respective offices.
But the results weren't always the same.
I remember one office in Raleigh that consistently did a great job supporting new employees. We had two strong internal champions who genuinely cared about helping people succeed. They reinforced what we'd taught, answered questions, and encouraged employees to keep developing their skills.
Just as importantly, management was engaged and held people accountable.
Compare that with other offices where employees returned from training and found little support. Their coworkers were busy. Managers weren't reinforcing what they'd learned. Sometimes the attitude was essentially, "You already went through training. Why do I need to show you again?"
The difference was significant.
And it taught me that you can have an excellent training program, but without ongoing support, its effectiveness quickly fades.
For brokerage leaders, I'd recommend making three things part of every onboarding plan:
- Identify internal champions. Give new employees experienced coworkers who can answer questions and reinforce good habits.
- Make managers accountable. Training should continue through coaching, feedback, and regular conversations about performance.
- Create opportunities to apply what they've learned. Move beyond demonstrations and let employees work through real brokerage situations with support.
Formal onboarding builds the foundation. What happens afterward determines how effectively people put it to work.
Don't Confuse Learning the System With Learning the Business
I've trained employees on older transportation systems and on MasterMind®, and there's an analogy I used to explain the difference.
Imagine handing someone a hammer versus a jackhammer.
Most people can figure out how to swing a hammer. A jackhammer can accomplish much more, but you need to understand how to use it effectively.
That's how I think about the difference between basic transactional systems and modern transportation technology.
When software is largely a place to enter and retrieve information, training tends to focus on where to find things and which steps to follow.
A more advanced TMS creates opportunities to automate repetitive work, connect different parts of the business, and give employees better information for making decisions.
But employees need to understand those capabilities and how they relate to their responsibilities.
For example, if technology can reduce the time a broker spends making routine tracking calls, that creates an opportunity to spend more time developing customer relationships, sourcing capacity, or pursuing new business.
The goal isn't simply to do the same work faster. It's to help employees spend more time on the work that creates value.
That requires teaching people how to think differently about their jobs, not just how to operate new software.
Technology Adoption Is a Leadership Responsibility
Now that I'm on the technology side of the industry at Mastery, I've seen how many of the same challenges appear during TMS implementations.
Organizations invest in better technology, but employees don't always understand why. Some worry that automation will replace their jobs. Others return to familiar processes because that's what they've always done.
That's why a successful implementation requires more than configuration and technical training.
At Mastery, our implementation approach starts with understanding how customers operate and identifying opportunities to improve workflows rather than simply recreating old processes in new software.
We use a phased approach, often described as crawl, walk, run, along with role-based training and internal champions who help employees become comfortable with change.
One example is Trailer Bridge, where I previously worked. The company invested in a continuing education program and internal champions to reinforce learning across its brokerage operations. In a published Mastery customer story, Trailer Bridge reported a 33% year-over-year increase in loads booked per person per day alongside those initiatives.
That kind of example reinforces something I learned long before joining Mastery: People need more than access to capable technology. They need to understand how it helps them succeed, and they need support as they learn to use it.
Onboarding Is the Starting Line, Not the Finish Line
If I could give brokerage leaders one piece of advice about onboarding, it would be this: Don't measure success by whether someone can complete a checklist of tasks in their first few weeks.
Ask whether they're developing the judgment, confidence, and adaptability to handle what comes next.
Can they communicate effectively with a customer and a driver? Do they understand the business impact of their decisions? Are they comfortable asking questions, learning something new, and changing their approach when circumstances demand it?
And perhaps most importantly, have you created an environment where they can continue growing?
Freight brokerage is constantly evolving. Customer expectations change. Technology advances. New opportunities emerge. The skills employees need today won't necessarily be enough tomorrow.
The most successful brokerage teams I've worked with understand that employee development is an ongoing responsibility, not an event on someone's calendar.
Teach people why the work matters. Give them the tools to do it well. And build a culture that helps them keep getting better.
Developing freight brokers who can do more than manage loads is cultural. You prepare them to help grow tomorrow's business.
Give Your Brokers More Time to Build the Business
MasterMind® brings brokerage workflows, automation, and connected data together in one transportation management platform. With an implementation approach focused on training, adoption, and continuous improvement, Mastery helps brokerage teams spend less time on repetitive tasks and more time building customer relationships, securing capacity, and growing revenue.
