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September 30, 2026

Three colleagues in conversation around a table in a bright office, beside the title How Leaders Turn Winners Into Whiners

Series: The Wacky World of Workplace Workers | Part 2: Winners & Whiners

Your exceptional employee has stopped asking for your direction and feedback. The independent overachiever hasn’t checked in for weeks. The person who used to champion the company has lost interest. Something has changed in your organization, and you may be the last to know.

In Part 1 we looked at winners, wonderers, and the wise. This time we look at how leaders turn winners into whiners. I know how it happens because I’ve done every single one of the five things on this list.

What makes a winner a winner

What made these employees special to begin with? They’re high performers. They work independently, use good judgment, and seek your input at the right times. Those are the traits of a good employee. They aren’t what made them great. A winner was a winner before they ever met you.

You may think you brought them in, coached them up, and gave them opportunities. You didn’t make them winners. That was already inside them. What you did is just as important: you gave them room to excel.

I’ve coached many employees over the years, and many of them were fantastic at their work and wonderful people. I would never say I made them the success they are now. I recognized their potential and cultivated it. It was a team effort.

Winners want feedback, honest discussion, and reasonable criticism. They want to excel personally and professionally. That doesn’t mean they all want to be leaders. It means they take pride in what they do and how they perform.

Unfortunately, leaders can also turn winners into whiners. Even the best employees are susceptible to the whining around them. Winners are still human, and we can’t take our relationships with them lightly.

Five ways leaders create whiners

1. Ignoring input

Every winner has a vested interest in the company’s success. They depend on it for their salary, benefits, stability, and a rewarding place to work. Winners will spot challenges and bring them to you. That’s a good thing. Build a culture where it happens.

Sometimes we brush off their input because we see “the big picture.” Don’t fool yourself. The big picture is a collection of smaller brush strokes. You may not agree with the employee’s assessment, but never ignore it. They can handle hearing why an idea will or won’t work. What they need to know is that you value their input. Make the effort.

2. Limiting communication between them and you

We’re all busy. I get it. But to run a successful organization you have to communicate with your people, whether the news is good or bad. They need to hear it, and they need to hear it from you. Good news travels fast, bad news travels faster, and rumors seem to be wired into people from day one.

You are their source of truth. You’ll never stamp out every rumor, but you can take them head on. When you go quiet, employees nominate their own leader, and trust me, it won’t be one of your winners. Eventually the winners give in to the negativity around them because they haven’t heard the truth from you. Communicate regularly and often, even if the whole meeting is you saying there’s no new update and you’d like to hear from them.

3. Rewarding the squeaky wheel

Every organization has a whiner who is never happy but always gets attention. They complain until they get what they want, even when it isn’t good for the organization. They wear you down.

Don’t fall into the trap. Whiners usually have a few faithful followers who repeat the same talking points. Set the standard for professional communication in your business, coach them to it, and hold them to it. If they can’t get on board, show them the door. Your winners will thank you.

4. Taking credit, assigning blame

I’ve never taken credit from my employees and claimed it as my own. That was never my style. But when things go sideways, we all go straight to assigning blame. It’s human nature. We need to run from it.

Every person in your company, especially you, is going to make mistakes. We all screw up. Blaming people, whether fairly or unfairly, is wrong. That doesn’t mean you don’t hold people accountable. Accountability is a different conversation. As the leader of winners, you can lose your best people fast in a blaming culture, because it’s only a matter of time until they’re the target.

5. Tolerating toxic behavior

I saved this one for last because it’s the most important. Remember it. A toxic employee is a ticking time bomb. It’s not a matter of if it will explode, only when. Toxic employees are worse than whiners. They infect and erode everyone and everything around them.

I’ve had my share, and I wish I had addressed them much earlier than I did. The worst damage isn’t to your whiners and poor performers. It’s to your winners. Winners want the barriers cleared so they can do their best work. They want clear communication, and they want to know you support them. Toxic employees plant landmines and wait for the boom. Winners will go somewhere else rather than deal with that regularly.

Turning whiners back into winners

Listen to your winners. Get to know them. What drives them? What are they passionate about? If you don’t know that while they’re winning, it’s hard to get them back from whining. Your culture should be built for winners to excel. If it isn’t, take a serious look at it.

Winners will tell you what they love, what they hate, and how they work best, but it takes time for them to feel safe saying so. Winners don’t like changing jobs and they hate being whiners, so don’t give them a reason for either. Spend time with them. Let them know they matter to you and to the company.

Give ownership and celebrate visible wins. No, I’m not saying make winners partners in your business. But they need to feel like owners, with some control and say over parts of their jobs. Winning should come with a reward. Invite them into certain meetings and some of the company’s important decisions because you value their input. To them, that matters as much as a check.

Celebrating wins doesn’t mean cake and pizza every time. When a winner has a win, tell them how much you appreciate them, not just what they accomplished. Relationships aren’t built on completed tasks. They’re built on trust and respect. Even small acknowledgment goes a long way.

Follow through. Say what you mean and mean what you say, then do what you said you would do. I’ve taken this to heart. Sometimes I may even interrupt the meeting I’m in to do what I just promised. When a critical decision is made, your winners see how much it matters to you when it gets done that minute. Keep your commitments and keep your people informed.

One of my own whiners

One employee worked for me for about ten years. She whined about everything, but not to me or to other leaders. She whined to the other employees and sowed discontent. Ironically, she would then come to me and report that the staff were upset, as a concerned employee.

I knew what she was doing, so I made a plan to understand her better and find what would turn her into a winner. I met with her one-on-one over a long period and concluded she wanted attention and accolades. So I gave her that. I looked for things she did that matched how I wanted her to act, and I recognized them.

It worked. It took a while, but she became the most committed employee I have ever had, and our biggest cheerleader in rough times. Turning a whiner around takes time and energy. It’s hard, and it’s worth it. The question is whether you’re committed to doing it.

Build a plan

If you study organizational development or group dynamics, or you’re simply aware of human nature, you know someone will always fill the role of whiner. The larger the company, the more of them. In my experience it’s about one for every 10 to 12 people. Your leadership team needs to know who the winners are and who the whiners are, because both need to be managed with intention. Work with your HR leadership, and with the leaders who work closest to these employees, to build a deliberate plan for each.

Start the conversation

Want a clear-eyed look at what’s driving your team’s energy? Thirty minutes is usually enough to know if we’re a fit. Start a conversation at d41consulting.com.

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