Bridging the Gap: Why Great CEOs Struggle with Leadership and How to Fix It

CEOs are some of the bravest, boldest, and hardest-working individuals you’ll ever meet. They’ve climbed mountains of risk, stared failure in the face, and carved a niche in their industries with sheer determination. Their expertise is unmatched, their willpower unstoppable, and their success stories inspiring. Yet, even the best CEOs often find themselves hitting an invisible wall when it comes to managing their teams.

The Disconnect Between the Corner Office and the Team

From the CEO’s perspective, they’ve earned their spot. They’ve fought tooth and nail to build their business, taken risks others wouldn’t dare, and, frankly, they feel they shouldn’t have to answer to their employees. After all, they’re the ones providing jobs, salaries, and benefits. Isn’t that enough?

But here’s the issue: while their hard work and vision have built a thriving business, their employees are burning out. Complaints are piling up, staff are quitting, and the office feels like a revolving door. It’s chaos, and the CEO doesn’t understand why.

In their frustration, they react impulsively, bending over backward to please employees, only to resent it later when things still don’t improve. Then the cycle repeats: generosity turns to frustration, frustration turns to demands, and the demands lead back to burnout.

Sound familiar?

The Hard Truth About Leadership

Leadership isn’t just about being the best in your industry. It’s about building relationships, fostering trust, and creating an environment where people feel valued, motivated, and aligned with the mission. The skills that make someone a brilliant entrepreneur or industry expert don’t automatically make them a great leader.

That’s a tough pill to swallow, especially for someone who’s spent years perfecting their craft. But here’s the good news: leadership skills can be learned.

Let’s dive into why these disconnects happen and how CEOs can bridge the gap between their vision and their team’s needs.

Why CEOs Struggle With Leadership

1. Experience Gaps Between CEO and Team
   CEOs have years (or decades) of experience that their team doesn’t. Concepts that seem like common sense to the CEO are often brand-new to employees. Assuming that everyone shares the same knowledge base creates a communication breakdown.

2. The Burden of Perfectionism
   Many CEOs feel an overwhelming pressure to excel in everything, including leadership. This can lead to micromanagement or belittling team members who don’t meet expectations.

3. Misaligned Expectations
   CEOs often expect employees to match their level of dedication and mindset. But employees are not owners—they won’t work 80-hour weeks or sacrifice their mental health for the business, and that’s okay.

4. Reactive Management
   Instead of addressing systemic issues, some CEOs make impulsive decisions to keep the peace. This only creates confusion and inconsistency for the team.

5. A Lack of Leadership Training
   Leadership isn’t an innate skill; it’s a learned one. Yet, many CEOs enter their roles with little to no training in managing people.

How CEOs Can Improve Their Leadership Skills

1. Be Honest With Your Employees
   Transparency is everything. When issues arise, address them directly and professionally. Let your team know you’re aware of the challenges and that you’re committed to finding solutions.

2. Practice Delivering Feedback
   Negative feedback doesn’t have to be destructive. Here’s a prompt you can use to craft supportive, constructive feedback:

   Prompt for Feedback:
   "I need to deliver constructive feedback to [team member's name] about [specific issue]. I want to highlight the mistake, explain why it’s important to address, and frame it as a learning opportunity. Please make the message professional, supportive, and focused on improvement."

   Example Output:
   “Hi [Name], I wanted to discuss [specific issue] from [specific situation]. I understand mistakes happen, and I see this as an opportunity for growth. Here’s what went wrong: [specific example]. It’s important because [reason]. I’m confident you can improve, and I’m here to support you. Let’s work together to prevent this in the future by [specific action or plan].”

3. Align Actions With Words
   Employees notice when leaders don’t practice what they preach. If you want your team to prioritize mental health, set the example by taking breaks and respecting boundaries.

4. Stop Assuming "Common Sense" Is Universal
   What’s obvious to you may not be to others. Take the time to explain processes, expectations, and goals in detail.

5. Ask, Don’t Accuse
   Instead of saying, “Why didn’t you do this correctly?” try, “Can you walk me through what happened here?” This opens a dialogue and prevents defensiveness.

6. Invest in Leadership Training
   Just as employees benefit from professional development, so do CEOs. Enroll in workshops, hire a coach, or join peer groups to refine your leadership skills.

7. Foster Psychological Safety
   Employees perform best when they feel safe to share ideas, voice concerns, and admit mistakes without fear of punishment. Build this culture by listening more than you speak.

8. Set Clear, Consistent Expectations
   Inconsistency breeds confusion. Make sure your team understands what’s expected of them and what they can expect from you in return.

9. Recognize and Celebrate Successes
   A little acknowledgment goes a long way. Celebrate milestones, praise good work, and show your team you value their contributions.

10. Learn the Art of Delegation
    Trust your team to handle tasks without micromanaging. Delegation not only lightens your load but also empowers employees.

The CEO’s Journey to Better Leadership

It’s not easy to admit that you have room to grow, especially when you’ve already achieved so much. But the best leaders are those who never stop learning.

Improving your leadership skills isn’t about giving up control; it’s about gaining alignment. It’s about understanding that while your expertise got you to the top, it’s your team that will keep you there.

Remember, great leadership isn’t about being perfect. It’s about being human—honest, empathetic, and willing to grow. And when you lead with those values, you’ll not only build a stronger team but a stronger business too.