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September 29, 2026

Small business team collaborating around a table, with the title Winners, Wonderers, and the Wise: Six Traits That Make or Break Your Team

Part 1 of the series: The Wacky World of Workplace Workers

While alliteration is wonderful in waging winsome whimsy, let’s get down to what really makes the workplace work — and what doesn’t. After 25 years of leadership and hundreds of employees, you develop a knack for getting to the root of what makes people tick: why one person succeeds where you least expected it, and why another struggles where you were sure they’d shine.

Early in my career, I was told that social workers could never become CEOs. Fortunately, I didn’t believe it. I went on to become CEO and owner of a successful multi-million-dollar company that I grew from almost nothing. That experience taught me something I’ve seen confirmed again and again: our assumptions about who will succeed are often wrong.

We have spent decades trying to predict success with personality tests and behavioral assessments. They aren’t bad tools, and they have their place. But what they mostly measure is a person’s natural style, and the learned style they use to get things done. They can’t look into someone’s soul and measure their will, their desire, or their capacity to grow. We can see tendencies in groups of people — and then we’re dumbfounded when an individual defies them.

Too often, we decide that a certain type of person can’t succeed in a role based on beliefs that say more about us than about them. What actually drives success is harder to test for: a person’s ability to be introspective, to learn, and to develop.

So rather than a test, I want to offer a lens. Below are six behavioral traits — three that tend to lead to success and three that can signal trouble. They aren’t labels or predictions. People are messy, surprising, and driven by motivations we’ll never fully see. But these traits give leaders a practical way to understand what’s happening on their teams and, more importantly, what they can do about it.

I’ll go deeper into each pair in future articles. For now, here’s a starting point.

Winners & Whiners

You’re probably thinking, “Obviously winners are good and whiners are bad.” But hold on for just a second. What makes a winner a winner? Why is a whiner a whiner? Can a winner become a whiner? Can a whiner actually be helpful?

As with most things in life, the answer is “yes and no.” There’s no absolute predictor of behavior, and many factors shape the outcome. But one thing is clear: you, as their leader, can absolutely turn a winner into a whiner. Shocked? You shouldn’t be. Leaders have enormous influence over their people, and we can drain even our best performers until they’re unproductive shells of who they were.

We don’t like to admit it, but our power cuts both ways. Are you turning your whiners into winners — or your winners into whiners?

Wonderers & Wanderers

Most people have a natural curiosity about the things that reward them. Think of the car guy, the football nut, or the knitter. Fueled by the emotional, psychological, and sometimes spiritual reward they get from it, they’ll spend a lifetime learning and improving. Entrepreneurs are a great example: their passion drives them to conceive, build, and grow something new.

In your organization, the difference between a wonderer and a wanderer is significant. The wonderer is engaged — at times even obsessed — with some part of their work. They do mental gymnastics to develop new processes, improve quality, grow the business, or just make their own little corner better.

Wanderers, on the other hand, are engaged — just not in anything happening at your company. They may not be bad employees, but they’re running at 50% capacity at best, while the wonderer is at 110%. If they stay disengaged, wanderers eventually leave for more money or something that gives them a deeper sense of connection. That isn’t always a bad thing. But if you can turn a wanderer into a wonderer, everyone wins.

Wise & Warring

Finally, the wise versus the warring. This may be tough for some to hear, but the culture wars playing out in the world don’t belong in your place of business. The only culture you should be focused on at work is the one that makes your business run like a finely tuned machine.

Wise employees hold their personal values firmly and live by them. They also recognize there’s a difference between living your values and debating them at every turn. As an organization, we should encourage people to be true to their values, while keeping the workplace focused on the shared work and the respect we owe one another.

Warring employees bring every outside fight through the front door. Whatever side they’re on, the result is the same: time, energy, and trust consumed by battles the business can’t win and shouldn’t be fighting.

Families have stopped speaking to one another. Civility and respect have eroded in public life. Protect your workplace from that. Model wise decision-making, treat everyone with respect, and hold true to the culture that makes your business successful.

What’s next

In future articles, I’ll dig into each of these traits with practical tips for managing, growing, and developing your people, wherever they fall today. No one is incapable of change, and no one is locked into their current tendency — no matter how good or bad it is.


At D41 Consulting, we help founders and leadership teams build cultures where people do their best work. If you’re wondering which of these traits are shaping your team — and what to do about it — thirty minutes is usually enough to know if we’re a fit. Start a conversation at d41consulting.com.

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