9 Leadership Challenges and How to Overcome Them

9 Leadership Challenges and How to Overcome Them

John Eades 02/04/2022
9 Leadership Challenges and How to Overcome Them

Overcoming complex challenges can be tough.

You'll have moments when you feel your only option is to give up. Doubt, stress, and obstacles can come in intense waves. Challenges, especially as a leader, are a journey with many steep mountains. 

But if you want to be a successful leader- the sort you were created to be, it requires looking at challenges as opportunities. Because the best leaders know challenges are opportunities wrapped in ugly wrapping paper. 

The best leaders know challenges are opportunities wrapped in ugly wrapping paper. 

To take this idea even a step further, approach challenges not as something you have to deal with, not even as something you get to deal with, but as something you choose to solve. 

In research by LearnLoft, we have found that there are a set of common challenges that leaders face regardless of industry. While they are typically described differently with varying symptoms and players, the root of the issues remains the same. These eight challenges are faced by middle to upper managers pretty uniformly. 

So what are these opportunities wrapped up as challenges in ugly wrapping paper?


1. Inspiring Others

This challenge is number one because inspiration is the core difference between managers and leaders. Managers use authority and titles to demand behavior while leaders inspire action. 

2. Redefining Culture 

Another challenge facing leaders today is redefining their culture amidst remote & hybrid work. Redefining and maintaining an elite culture is difficult but ultimately attainable. 

3. Meeting the Needs of Team Members

The challenge of consistently trying to meet every team member's needs and expectations is wildly complicated. If that weren't enough, the number of direct reports leaders now are responsible for has increased by 25% or more on average. This means devoting adequate time to more people is hard. 

4. Enabling Change

The challenge of opening people's hearts and minds to different ways of thinking and behaving than they are previously accustomed to is difficult because we are wired to resist change. However, every industry is in a state of transformation, so change is required to stay ahead or advance past the competition. 

5. Developing Skills

Whitney Johnson, Author of Smart Growth, highlighted developing people as a significant leadership challenge. She told me, "People want to grow. They want more because the Great Resignation is really the Great Aspiration. Leaders have the humility to grow themselves to grow their people." There is nothing easy about coaching skills and creating new opportunities for people to develop. If this is a struggle for you, check out the upcoming Coaching for Excellence workshop. 

6. Recruiting Talent

The challenge of recruiting talented people is evergreen. However, there isn't a leader I have coached or trained in the last twelve months that isn't concerned with recruiting more than they used to be. The labor shortage has hit nearly every industry.

7. Creating an Excellent Team 

A challenge for any leader is to bond people together to accomplish more than they can on their own. A team, by definition, is a group of people that come together to achieve a common goal. While it might sound simple, it's anything but, especially in remote work and mental health crises. 

8. Unlocking Elite Execution 

A significant opportunity for any leader is improving daily execution. Monte Peterson, Principle of CDA Group and expert in all things execution said it well, "For as much as people talk about execution and claim it as the reason their organization's plan was met with failure for yet another year, it just proves that not many really understand it." 

9. Avoiding Burnout 

The most emerging challenge facing leaders today is avoiding burnout in themselves and their team. There is immense pressure from the C-Suite to increase results faster. While speed is essential, it also causes burnout. 

When leaders solve these nine challenges they will have more fulfilled, engaged, and productive team members. 

How to Begin to Solve These Leadership Challenges

Solving some or all of these will require ongoing effort, strategy, and modifications. Here are a few solid ideas to help you in the short term. 

Earn Trust and Strengthen Relationships

Leadership has always been about relationships, but trust-based relationships are more important than ever. Remote and hybrid work has made it increasingly difficult to have authentic and genuine relationships built on the bond of mutual trust.  

Great leaders build authentic and genuine relationships built on the bond of mutual trust. 

In Building the Best, I wrote about a way to build trust called "The Trust Compound Theory." This means you get the opportunity to develop stronger bonds of mutual trust by sharing your competence, showing you care, and exposing your character. 

Empower Others to Solve Problems

You will solve more problems and overcome challenges faster and more effectively if you empower others to make decisions. The word empower means "to give control over another's life and the authority to do something." So often, managers do the opposite of empowering. They micromanage when challenges arise. 

Suppose you want to get better at empowering your people and inviting them into the problem-solving process. In that case, it starts with making them aware that solving problems is a part of their job responsibility regardless of their title. 

Make team members aware that solving problems is a part of their job responsibility regardless of their title. 

Come up with a Maximizing Mantra for the Year

There will always be priorities and market changes that grasp your people's attention. With as fast as the business world is moving, we are past the point of being able to have a one-item execution list. 

However, you can create a maximizing mantra to create consistent energy on a team or company. A Maximizing Manta is a short and simple phrase that provides clarity, is action-oriented, and is fun. A few of my favorite examples include:

  • Let's Go

  • Move the Needle

  • Row the Boat

When you or your team come up with a Mantra for the rest of this year, please put it on walls, T-shirts, or slack channels. Use it to keep it in the forefront of your people's eyes and hearts. 

Recommit to Core Values 

Take a lesson from Meta's CEO, Mark Zuckerburg. After two decades of running one of the largest tech companies in the world, they have reset and added new core values to help prepare for a more distributed, more honest, and faster future. 

On a recent episode of the Tim Ferris Podcast, Zuckerberg said, "One of the things that I've always found is you can … get an organization and a team through almost any challenge as long as you can maintain good cohesion."

He outlined five refreshed core values and precisely what they meant to him and his team at Meta. 

Reward and Recognize Effort

One of the biggest reasons teams consistently face the same challenges is because leaders are too critical of their team. Instead of encouraging them to persevere and looking for new and better ways to solve problems, they judge.  

People tend to shut down and give less than their maximum effort when this happens. While there are places for critical feedback and tough conversations, more leaders must start rewarding and recognizing the positive effort team members demonstrate daily. 

Leaders must start rewarding and recognizing the positive effort team members demonstrate daily. 

A great trick for this is to give at least three positive comments to every critical one.  


If there has ever been a time to turn challenges into opportunities, it's right now.  

It's my hope these strategies will help you turn your team or organization run toward these opportunities because that's precisely what the best do.  

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John Eades

Leadership Expert

John is the CEO of LearnLoft, author of, F.M.L. Standing Out & Being a Leader and host of the 'Follow My Lead' Podcast. He writes or has been featured on Inc.com, LinkedIn Pulse, TrainingIndustry.com, eLearningIndustry.com, CNBC Money, and more. John completed his education at the University of Maryland College. 

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