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3 Leadership Mistakes That Could Be Holding Your Team Back

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Most of us remember the moment—or at least the phase—when we realized our parents were people. People with their own fears, doubts, and mistakes. Not flawless sources of authority, but works in progress.

Before I started my own company, I thought about leadership the way kids think about their parents. I imagined that once I became a leader, I’d eventually “arrive”—earn my stripes, develop my style, and then lead more or less on cruise control.

Of course, that’s not the case. Technology and business are evolving at an increasingly rapid pace. Leaders must stay vigilant against economic volatility and global health crises. New generations of employees arrive with fresh expectations. Tools like AI agents are becoming integral parts of teams. The work of becoming a strong leader is never finished.

For me, the most valuable lesson has been keeping a beginner’s mind—staying open, curious, and willing to course-correct. With that in mind, here are three common mistakes leaders continue to make, and how to get back on track.

They Underrate Humility

In an era when new paradigms are constantly shaking up workplace expectations, it’s surprising that certain leadership stereotypes persist. For example, many still believe that traditionally “masculine” traits, like assertiveness and competitiveness, are requisites for success. Confidence—sometimes even overconfidence—is still seen as a leadership trademark, even if it comes at the expense of admitting mistakes or acknowledging limitations.

But I’ve found that humility brings tangible advantages. When leaders openly acknowledge mistakes and share credit for accomplishments, they model those behaviors for their teams. This builds a culture of trust and respect, fostering collaboration over competition. New research also shows that humble leaders inspire employees to step into leadership roles themselves. In other words, humility doesn’t weaken authority—it just creates space (and motivation) for others to grow. What’s more, the initial research focused on employees in China, but researchers found the same results emerged in Western cultures, where professionals tend to be less collectivist and more individualistic.

It’s worth considering what those findings mean for companies. If you’re a leader who wants to build a leadership pipeline, a bit of humility can go a long way. I try to make a habit of recognizing others’ achievements and sharing my challenges at our weekly demo days. I notice that it opens up the floor for others to do the same, while setting the standard for the type of leadership we value.

They Forget To Reward Employees For Consistent Results

Many of today’s social media platforms operate on a similar reward loop: share content, get feedback, feel motivated to share again. Snapchat added a wrinkle to the formula that turned out to be remarkably effective: streaks—rewarding users with emojis for Snapping back and forth with friends at least once a day. It essentially gamified frequent usage.

As it turns out, rewarding employees’ streaks in the workplace can be just as powerful. It’s natural, even intuitive, to recognize major achievements, but consistent results on ongoing tasks sometimes go overlooked. New research has found that offering employees streak incentives—like payments that increase for consecutive work tasks—boosts motivation. In fact, this kind of reward motivates people even more than larger, one-off incentives.

By framing continual progress as a streak, organizations can strengthen employees’ commitment to long-term goals and sustained effort. And incentives don’t have to be financial; they can take the form of perks like extra time off, public recognition, or other personally meaningful rewards.

They Approach Learning With No Playbook

It’s no secret that continuous learning is essential for staying competitive in today’s market. Leaders are tasked with encouraging and facilitating upskilling, and AI tools are making those efforts more effective than ever. AI agents, for example, can train a higher volume of employees than traditional teaching methods, all while tailoring lessons to the individual. Employees gain skills and confidence faster, and managers spend less time overseeing training.

All too often, however, leaders implement learning efforts without really considering the process. Recent research shows that the most innovative teams engage in learning in a specific order. Writing for Harvard Business Review, the researchers explain, “Just as music relies on rhythm and harmony, effective team learning requires structured, harmonious sequencing.” They go on to describe a cycle that alternates between exploration (specifically, experimenting, learning alongside others, and applying that learning) and structured reflection.

You might be wondering: What can I do to ensure that my team learns in the right order? The answer is to guide them through the various stages and encourage them to build in time for reflection. This will help drive home lessons and ultimately, fuel innovation.

Here’s an example of how to put it into practice. Let’s say your company is releasing a new AI-powered customer support tool. Instead of diving straight into technical training, let your team start with exploring—tinker around with the new tool and share the benefits and challenges with one another. Then, they can dive into more structured lessons (powered by AI agents if you’re so inspired) to answer any questions and make sure each employee has the know-how for their role. Finally, you can pencil in a meeting at the end of the week where the team discusses what worked, what didn’t, and how to improve. I’m sure you can imagine how this cycle would lead to true mastery, much more so than a simple video tutorial, and help employees to quickly and efficiently incorporate new skills and tools into their daily work.

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