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In over 13 years of recruiting top talent in Rail and Transportation—from supervisors to C-suite— I’ve heard one question time and again: ‘Why would I take that role? It’s a lateral move.’ This mindset, that careers should only move upward in title and scope, is one of the biggest barriers to long-term success. True leadership is built by broadening skills across functions, not just climbing a single silo

Here’s the truth—especially in transportation and logistics: Real careers don’t go straight up.

In fact, the smartest, most successful leaders I know didn’t just climb. They took intentional side steps—lateral moves that shaped who they became.

And I’ll say this as clearly as I can: If you’re aiming for executive leadership, lateral moves are not a detour. Lateral moves that broaden one’s experiences are key differentiators in those who make it to the executive suite and those who do not.  Without lateral moves our experiences stay in siloed functions, companies and responsibilities.  We are currently seeing the negative impacts of people who have had very loyal careers to one company, one leader or one profession come to an end.  The pivot to something new is very difficult, at best.

The Real Talk We All Need to Hear

At the MARS Winter Meeting, Jean Savage (CEO of Trinity Industries) said something that really stuck with me:

“Accept lateral moves. You learn so much in those roles—not just what you like, but what you don’t. Where you thrive, and where you don’t.”

She’s right.

Across rail, maritime, logistics, and intermodal, the most successful leaders I’ve worked with all share one thing: they made smart, intentional lateral moves. These weren’t sidesteps—they were strategic decisions to broaden their skills and grow into well-rounded leaders.

Why?

Because they weren’t just chasing titles or raises. They were chasing perspective. Depth. Range.

Every Role Should Be a Learning Opportunity

If a new role feels easy from day one, you’re aiming too low. When there’s no challenge, there’s no growth—and boredom sets in fast. I’ve seen high performers burn out quickly simply because they weren’t stretched. The most effective leaders don’t chase comfort—they seek out roles that push them.

They’ve learned what they don’t want by stepping into unfamiliar functions, environments, or scopes of responsibility. That discomfort? It’s where real skill development happens. And yes, lateral moves often bring those very challenges that build stronger, more adaptable leaders.

Here’s why we often recommend lateral moves….they are good for your career!

• Discover where you bring your A-game and create the most impact
• Gain exposure to new ways of thinking and operating
• Learn to adapt your leadership style to different teams and situations
• Build skills in cross-functional and cross-cultural collaboration
• Identify the team dynamics and cultures that help you thrive
• Uncover strategic blind spots you didn’t know you had

If a role is challenging you, that’s a sign you’re in the right place—even if the paycheck looks familiar.

When Money is the Only Motive, It Backfires

Often people don’t take lateral moves because it is lateral in money as well.  Let’s face it, everyone hopes for a pay increase. But, taking a new role just for money almost never works.

At least, not long-term.

Yes, compensation matters. But if a role doesn’t align with your strengths or values—or the company culture is off—you won’t be able to bring your A-game. You get bored. Frustrated. Disconnected from the work. Eventually, you burn out or move on—sometimes by choice, sometimes not.

I’ve seen executives leave high-paying roles within two years—not because they couldn’t do the job, but because the learning stopped, or they were simply miserable.

The truth? Money can’t compensate for a lack of challenge or a poor fit.

So before you chase the bump in title or salary, ask yourself:

• What will I learn here?
• Who will I become in this role?
• Will this move set me up for long-term growth—or just a bigger paycheck?

If you can’t answer those questions with clarity and confidence, it’s probably not the right move.

Lateral Moves = Executive Readiness

Executives aren’t made by sticking to one function and waiting to be promoted. They’re built through broad exposure and cross-functional depth.

I’m talking about:

• Ops leaders who spend time in finance
• Sales directors who rotate through supply chain
• HR leaders who sit with tech teams
• Anyone who moves across markets, regions or business units

Those lateral experiences pay off big time when you’re asked to lead diverse, complex teams. You understand how the pieces fit. You lead with empathy because you’ve been in their shoes. And you make better decisions because you’ve seen how functions interact.

It’s the difference between leading from theory… and leading from real-world knowledge.

Questions to Ask Before Making a Lateral Move

Not every lateral move is created equal. The best ones are intentional and strategic.

Here’s how to assess a sideways move:

1. What will I learn? Will this stretch a skill set I need to grow? Will it deepen my industry knowledge or expand my leadership range?
2. Will I gain exposure to new people and perspectives? Lateral moves are a chance to build new networks and prove yourself in a different light. That matters when executive roles open up.
3.  Is there a clear development opportunity? Even if the title is flat, is there a coach, mentor or path that gets me closer to where I want to go?
4. Will this move strengthen my story? Recruiters and hiring leaders love candidates with range. A lateral move should make your resume more compelling, not just longer.

If the answer is “yes” to most of these—it’s likely a smart play.

What This Looks Like in Transportation

 Here are just a few examples I’ve seen recently:

• A senior ops leader at a trucking company moved into customer experience. Six months later, she cut customer churn by 18 percent—and gained exposure to the board.
• A rail executive took a lateral step into compliance to get closer to federal regulators. Two years later, he was tapped for a C-suite role because he had built credibility across functions.
• A warehouse manager switched to transportation planning. Same level, same pay—but it gave him visibility into upstream challenges. That knowledge fast-tracked his promotion into network leadership.

None of them took these moves because of salary. They took them because of strategy.

Stop Thinking Like an Employee—Start Thinking Like a Leader

Employees chase promotions. Leaders build careers.

If your only definition of growth is vertical, you’re going to miss half the opportunities available to you.

Smart leaders ask:

• Where can I develop the skills I’ll need five years from now?
• How can I become more well-rounded?
• Where’s the next gap I can fill—even if it’s not glamorous?

It’s not always sexy. But it’s always smart.

Final Thought

If you’re in a season of asking, “What’s next for me?”—this might be your sign to stop looking up… and look sideways.

That next great opportunity might not be more money or a bigger title. It might be a role that teaches you something new, introduces you to new stakeholders or stretches you in the best way possible.

And if you’re not sure which move is the right one? That’s where we come in.

At TTSG, we help transportation and logistics professionals map out real career paths—not just job changes. If you’re ready to think strategically, grow intentionally and build the kind of leadership story that lasts—we’d love to connect.