Leadership looks simple from the outside, but ask anyone who’s been in charge of a team, project, or organization, and they’ll tell you it’s anything but easy. After working with leaders across industries for over two decades, I’ve discovered that the biggest challenge—and greatest asset—is always the people.
The team that delivers on the promise of an initiative or project is simultaneously your toughest challenge and your most valuable resource. Let’s dive into five critical leadership challenges and explore practical strategies to tackle them head-on.
1. Building Meaningful Connections With Your Team
The most valuable asset in any organization isn’t the technology, the intellectual property, or even the business strategy—it’s the people. Yet connecting authentically with team members remains one of leadership’s greatest challenges.
As I mentioned in my book, 10 Leading Tools, learning the “language” of your team isn’t about learning Spanish or Mandarin (though that wouldn’t hurt!). It means understanding what motivates your people, how they communicate best, and what matters to them personally and professionally.
I once spoke with a father who started playing video games with his teenage sons just to understand their world better. “By playing with them, I get it,” he told me. “I’m not just skating on the surface or watching from the sidelines.”
The same principle applies to leadership. When you take time to learn the language of your team—whether they’re engineers, marketers, or customer service reps—you create a foundation of trust and understanding that transforms performance.
Try this: Set aside time each week for non-work conversations with team members. Ask about their interests, listen to their stories, and find common ground. These small moments build the relationship capital you’ll need when challenges arise.
2. Reducing Employee Turnover
Have you ever walked into your favorite café only to find all new faces behind the counter? That constant turnover doesn’t just disrupt your coffee routine—it signals deeper problems in the organization’s leadership.
High turnover is more than an inconvenience; it’s financially devastating. According to a report from The Center for American Progress, replacing an employee can cost anywhere from 16% to 213% of their annual salary, depending on their role and seniority.
But the real cost goes beyond dollars. When employees leave, they take institutional knowledge, customer relationships, and team cohesion with them.
In my consulting experience with organizations facing retention challenges, I’ve found that people rarely leave companies—they leave managers. People don’t quit jobs; they quit toxic cultures and poor leadership.
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Try this: Conduct “stay interviews” instead of exit interviews. Ask your best people: “What keeps you here?” and “What would make you leave?” Then actually address what you hear.
3. Developing Emotional Intelligence
I once worked with a brilliant tech executive who could solve any technical problem but couldn’t understand why his team was disengaging. His technical IQ was off the charts, but his emotional intelligence needed serious work.
Emotional intelligence—the ability to recognize and manage emotions in yourself and others—is no longer optional for leaders. Research published in Forbes shows that 90% of top performers score high in emotional intelligence, while just 20% of bottom performers do.
Developing emotional intelligence requires three key capabilities:
- Self-awareness (understanding your own emotions)
- Self-regulation (managing your reactions)
- Empathy (understanding others’ perspectives)
Authentic leadership starts with vulnerability—showing your team that you’re human too. I learned this lesson the hard way early in my career when I tried to maintain a perfect facade. Only when I started being more transparent about challenges and even failures did my team begin to truly connect with me.
Try this: The next time your team faces a setback, resist the urge to gloss over it. Instead, acknowledge the disappointment, share what you’re feeling, and then guide the conversation toward solutions. This authenticity builds trust and psychological safety.
4. Executing an Effective Business Strategy
Having a brilliant strategy on paper means nothing if you can’t execute it. According to Ernst & Young’s Global Leadership Forecast, very few CEOs have the leadership talent needed to successfully implement their business strategy.
The report highlights three specific challenges modern leaders face:
- Acting decisively in uncertain conditions
- Operating effectively in digital environments
- Using data to drive decision-making
These challenges require agility—a mindset that embraces change rather than fearing it. The most successful leaders I’ve worked with develop this capability by constantly testing their assumptions and adjusting their approach based on real-world feedback.
Take Olympic gold medalist Simone Biles, who demonstrated remarkable agility when she turned an ankle injury into an opportunity to create an innovative new gymnastics move. Rather than withdrawing, she and her coach developed what became known as “The Biles”—a signature move that worked around her limitation.
Business leaders need this same adaptability when executing strategy in today’s rapidly changing environment.
Try this: After establishing your strategy, identify three potential disruptions that could derail it. For each disruption, develop a contingency plan. This “pre-mortem” exercise builds agility into your strategic thinking.
5. Inspiring Your Team Through Purpose
In a world where people increasingly seek meaning in their work, being an inspirational leader isn’t just nice—it’s necessary. Yet many leaders struggle to move beyond management to true inspiration.
The key difference? Purpose.
Great leaders help people see beyond their daily tasks to the larger purpose they serve. I learned this principle during a leadership training at the Disney Institute. They shared a story about a maintenance worker named Jenny who spotted a little girl who had dropped her ice cream cone. Rather than simply cleaning up the mess, Jenny recognized her real purpose wasn’t just cleanliness—it was creating magic. She led the disappointed girl and her friends in an impromptu parade to get a replacement ice cream.
This simple shift—from task-focused to purpose-focused—transforms ordinary work into meaningful contribution. In my leadership workshops, I often challenge participants to reconnect with their purpose by asking: “If your team achieved perfect execution but lost sight of why they were doing it, would you consider that success?”
Try this: At your next team meeting, ask each person to share how their work impacts others positively. Help them connect their daily tasks to the organization’s purpose and the difference they make for customers or colleagues.
The Leadership Challenge That Matters Most
After working with countless leaders across industries, I’ve found that the most fundamental challenge is also the most rewarding to overcome: creating authentic connections with your team.
The modern leader understands that technical expertise and strategic thinking are important, but the ability to connect with people is what truly transforms good leaders into great ones.
Leading isn’t about having all the answers. It’s about creating an environment where people feel valued, understood, and inspired to bring their best selves to work. When you focus on this human element of leadership, many other challenges become easier to navigate.
A leader I worked with at a global technology company summed it up perfectly: “I thought leadership was about making perfect decisions. Now I realize it’s about creating the conditions where others can make good decisions, even when I’m not in the room.”
That’s the essence of addressing all these leadership challenges—developing yourself so you can develop others, creating an environment where people want to stay and contribute, and building teams that can navigate change and complexity together.
Remember that leadership isn’t a destination but a journey of continuous learning and growth. As you face these challenges, see them not as obstacles but as opportunities to develop your leadership capacity and create positive momentum that lifts everyone around you.
What leadership challenges have you faced in your career? Share your experiences in the comments below, or connect with me to continue the conversation.
