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Notes From the Window Seat

Life is full of extraordinary moments hiding inside ordinary days—if we're willing to slow down and notice them.

Join photographer, traveler, author, and storyteller Marty Pearson for conversations that explore travel, photography, pets, and the stories that change the way we see the world. From quiet beaches before sunrise and coffee shops filled with new friends to adventures in Antarctica, Africa, and beyond, every episode is an invitation to look a little closer and discover what's been there all along.

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Notes From the Window Seat

The Most Frustrating Employee on Your Team Might Be Right

March 23, 2026 • Marty Pearson

0:00 | 13:01

Do you have an employee who challenges how things are done?

They’re not rude. They’re not underperforming. In fact—they might be one of your best people.

But they don’t follow the script. They question processes. They push back. They sometimes bend the rules—especially when they believe it’s in the best interest of the customer.

In this episode, we unpack a powerful leadership question: Are they the problem… or are your rules?

You’ll learn how to distinguish between problematic behavior and valuable disruption—and how great leaders use these moments to improve their business instead of shutting people down.

What You’ll Learn:

The difference between a problem employee and a nonconforming high performer Why rule-breaking sometimes signals broken systems
How outdated or “comfort” rules hold businesses back
The connection between process, efficiency, and customer experience
A simple framework to evaluate when to enforce rules—and when to rethink them

Key Takeaways:

Not all rule-breaking is bad—sometimes it’s innovation
High performers often prioritize outcomes over rigid processes
If your systems don’t serve the customer, your best employees will challenge them
Leaders must learn to get curious before correcting behavior

Reflection Questions:

Do I have someone on my team who challenges how things are done?
Have I labeled them as difficult instead of valuable?
Are my processes designed for outcomes—or just for control?
If my team followed every rule perfectly… would we actually be better?

If this episode hit close to home, it might be time to take a deeper look at your systems and leadership approach. I offer a 90-minute Leadership & Operations Audit where we: Evaluate what’s working (and what’s not) Identify blind spots Build a clear path forward. Because sometimes the problem isn’t your people—it’s the way the business is built.

Learn more about the window seat here: Notes From The Window Seat

SPEAKER_00 0:32

And it actually works for you and your team. So whether you're in the office, on the job site, or just grabbing your first cup of coffee, let's just start your week so you can lead better, work smarter, and build a better business. Welcome back to the podcast. In the next few weeks, we're going to talk about what your people are revealing about your business. And today we're starting with the employee that probably frustrates you the most. Have you ever had an employee who just doesn't quite fit? Not in a bad way. They're not rude, they're not disrespectful, they're not causing drama, but they show up, they do their job, they get great results. In fact, they might even be one of your best employees. But they don't quite follow the script. They question things. They do things a little differently. They might push back every now and then. Maybe they bring an hourglass to a meeting because they think they drag on too long. Or they crack a joke or make a balloon animal just to lighten the room. Maybe they skip steps in a process because they think they're unnecessary. And if you're being honest, they annoy you just a little because they don't conform. So here's the question I want you to sit with today. Are they the problem or are your rules the problem? Now before anyone gets defensive, let's be clear about who we're talking about. This is not the toxic employee, the one who refuses to listen, or the one who creates conflict or undermines others. This is the person who delivers results, they think independently, they challenge the norm, and they don't just blindly follow the process. They're not breaking your business, they're breaking into your comfort zone. Let's be honest about something. Most leaders say they want innovation, ownership, accountability, and people who think for themselves. But what they actually feel comfortable with is predictability, control, consistency, and this type of employee, they disrupt that. They ask, why do we do it this way? They say things like, this doesn't make sense. They try something different, and suddenly it feels like a threat. Not because it is, but because it challenges the system you're used to. And sometimes it challenges you. Now here's where most leaders go wrong. They jump straight into they're not following the rules. But there's a better question. Why not ask why are they not following the rules? Is it because they're careless? Or is it because the rule doesn't make sense? Now not all rules are created equal, and not all rules deserve to be followed. There are three types of rules I see in business. First, they're the outdated rules. These are the rules that were created five years ago, ten years ago for a version of the business that no longer exists, but nobody's ever revisited them. Second, there are comfort rules. These are the rules that exist because that's how we've always done it. Or it keeps things under control. These rules aren't about outcomes. They're about making leadership feel comfortable. Lastly, there are the clarity gaps. These aren't even really rules. These are the habits that turn into expectations, and nobody ever explained why it matters, what the outcome should be, and what success looks like. So people either follow it blindly or ignore it completely. Here's what most leaders miss. Your high performers, they see things differently. They'll spot inefficiencies faster. They get frustrated with wasted time. They care more about outcomes than processes. And very often they care deeply about the customer. They're the ones thinking, why are we making this harder than it needs to be? Why does the customer have to jump through all of these hoops? Why are we doing it this way if it slows everything down? So the employee who brought the hourglass into your meeting? That might not be disrespect. It might be feedback about wasted time. The employee who skipped steps in your process, that might not be laziness. It might be them trying to serve the customer better. And this is where this is going to get uncomfortable. Because sometimes your roles are protecting the process, not the customer. And your employee is choosing the customer over the process. If your best employees are working around the process, that's data. It's not random, it's not rebellion, it's a signal. Something in your system isn't working the way you think it is. So let me ask you this. If your best employee has to choose between following your process and doing what's right for your customer, which one do you want them to choose? Because how you answer that question tells you everything about how your business is actually run. And this is where it can get expensive. Because when you shut down this type of employee, they learned don't ask questions, don't make suggestions, don't think too much, just comply. And for a little while that might feel good. Things get quieter, things get more predictable, there's less friction. But here's the trade-off. You lose innovation, you lose engagement, and you lose ownership. And then eventually you lose them. Because high performers don't stay where they're told just follow the rules. They go somewhere where they can think, contribute, and make things better. So what do you do with this employee? First, you don't ignore them. You also don't shut them down. You should get curious. Instead of why aren't you following the process? Try asking, help me understand why you're doing it this way. Every rule should have a purpose. Ask, is this about quality? Is it about safety? Is this rule about efficiency? If it's not protecting something meaningful, why does it exist? If the outcome this employee is providing is solid, do they have to follow the exact same steps? If your team can't question how things are done, your business will stop evolving. So ask yourself, does this process make things better for the customer? Or is it just easier for us internally? Because if your systems are built for internal comfort, your best employees will fight for them. And honestly, they should. Ask yourself, is their outcome acceptable? Is anyone being negatively impacted? Is there a better way hiding in what they're doing? If your answers are yes, no, and maybe, that's not a problem. It's an opportunity. Now keep in mind, not all rule breakers are the same. There are three types of rule breakers. One, the problem, two, the shortcut taker, and lastly, the innovator. And we're talking about the innovator. Now let me leave you with this. Do you have someone on your team right now who doesn't quite fit the mold? Who pushes back? Who questions your processes? Who tries to do the right thing by the customer, even when it bends the rules? And have you labeled them as difficult, disruptive, a problem? Instead of asking, what are they trying to show me? Because sometimes your most frustrating employee is the one closest to the truth about your business. And here's an even bigger question. If your best people followed every rule without question, would your business actually be better? Or would it just be quieter? The next time you feel yourself frustrated with someone who doesn't follow the rules, pause and ask yourself, is this a problem or is this potential? Until next time, lead with confidence, focus on your people, and let's build a better business.