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4 Leadership Development Challenges & How to Overcome Them

Friday August 30, 2024

A business leader wearing glasses engaging in a conversation with coworkers around a table in an office building

Developing competent leaders in the workplace is important. In the U.S. alone, organizations spent over $100B on training initiatives in 2023.

Unfortunately, many of these initiatives aren’t as successful as leaders might have hoped.

There are many obstacles to effective leadership development. Organizational leaders hoping to get the most out of their training initiatives need to ensure they’re prepared to deal with these challenges as they arise and overcome them.

Here are four key challenges many leaders face when attempting to develop future leaders in their organizations as well as steps they can take to combat these challenges.

The Importance of Leadership Development

Leaders have a significant impact on organizational success.

Research from Gallup reveals that managers account for approximately 70% of the variance in team engagement and performance. This underscores the crucial role effective leadership plays in driving success.

The influence of managers extends far beyond productivity, reaching into the well-being of their teams.

A study by the Workforce Institute at UKG revealed that managers have a greater impact on employees’ mental health than doctors and therapists, and the same impact as spouses.

These statistics demonstrate that investing in leadership development isn’t just nice to have, it’s a necessity.

 

By nurturing leaders’ skills, knowledge, and emotional intelligence, companies can cultivate high-performing teams, foster a positive work environment, and drive lasting success.

Unfortunately, many leadership development initiatives don’t have the hoped-for return on investment.

4 Leadership Development Challenges

1. Lack of Psychological Safety

According to Harvard Business Review (HBR), a lack of psychological safety is one of the top reasons leadership training fails.

When employees feel safe to speak up, they’re more likely to improve and develop the necessary competencies to lead.

That’s because psychological safety promotes learning. If people don’t feel comfortable taking interpersonal risks, they’re likely to stagnate, only doing what’s comfortable and familiar.

For this reason, the HBR article suggests that psychological safety is the “fertile soil” leadership training needs to thrive.

2. Employee Cynicism

Cynicism is inherently a hindrance to leadership development.

According to HBR, cynical employees are:

  • Less likely to advance their salaries
  • Less likely to advance to leadership positions
  • Less likely to get along with coworkers

Unfortunately, even if employees aren’t cynical about most things, they can easily become skeptical of leadership training initiatives—especially following a negative experience.

This can hinder its effectiveness, since your team might have preconceived biases against leadership training based on past experiences.

3. Poor Organizational Design

According to HBR, poor organizational design can result in barriers to coordination across business functions or regions.

It can also lead to:

  • Uncertainty and confusion within roles
  • Barriers to sharing ideas and information
  • Slower decision-making
  • Added stress, complexity, and conflict

These challenges can make learning and training incredibly difficult.

To combat this, it’s important to ensure that your organizational structure is the right fit for your company’s size and industry. Clarity regarding roles and responsibilities is also vital, as is a strong mission and vision.

Once there’s a strong structure in place, leadership training can take place without unnecessary friction.

4. Executive Buy-In

Because of the poor return on investment many companies experience, getting executive buy-in to training initiatives can be tricky.

Making the business case for leadership development is one thing, but getting approval for specific tools and strategies is another.

Ultimately, organizational leaders don’t want to waste money on training endeavors that don’t work—or worse, end up frustrating employees.

This means in addition to making the business case for leadership development in general, leaders need sufficient evidence that their specific strategy will result in positive outcomes rather than frustration and wasted resources.

Overcoming Leadership Development Obstacles

To address the above challenges, it’s important for leaders to consider the following before designing a training program:

1. Determine the Purpose of the Training

As important as cultivating “better leaders” is, clarity regarding the purpose of the training is vital to its success.

Simply advocating for leadership training to develop better leaders isn’t likely to gain executive buy-in.

According to Forbes, most barriers to learning can be connected to whether or not there’s clarity regarding its purpose. This means that before training your team, you need clarity on the business outcomes you want to achieve.

It’s a good idea to conduct an audit and solicit employee feedback to determine what leadership competencies they feel are lacking.

For example, do you need to focus on skills like emotional intelligence and trust? Or are there communication issues that need to be resolved?

Determining what areas you want to focus on ahead of time can help you make the business case for leadership development.

2. Examine Your Organizational Culture

Because organizational obstacles can prevent leadership training’s success before it even begins, it’s important to consider your culture before any money is spent on training programs.

Consider your current organizational culture. Determine whether your company has sufficient levels of the following:

  • Psychological safety
  • Trust
  • Communication
  • Engagement
  • Openness to change

If any of these factors are struggling, you might encounter difficulties training your team.

The good news is that if there’s a lack of psychological safety, trust, or any other factor, it can give you an idea of where to focus your training efforts—particularly for your organization’s current leaders.

3. Leverage Team-Based Learning

It’s easy for leaders to take a very individualistic approach to training and leadership development.

It’s important to keep in mind that leaders need to learn how to work with and effectively lead their teams.

This means that team training is an incredibly important component of effective leadership development.

In addition to equipping current and future leaders with skills that will benefit them personally, team learning initiatives can have the added benefit of helping them engage and learn with their team.

4. Learn From Experts

According to an article from Forbes, it’s important for leaders to learn from someone who has experience and expertise in their field.

Obtaining practical, tailored training from experts is an excellent way to develop leaders. While asynchronous learning such as training videos or recordings of keynotes can be helpful, synchronous learning takes training to another level.

For example, Teamraderie’s live, virtual experiences are expert-led and allow your team to engage and interact with the experts they’re learning from on a real-time basis.

How Teamraderie Can Help

If you’re searching for an effective method of developing leaders in your organization, Teamraderie’s experiences can be an effective tool to leverage.

Our live, virtual experiences are outcome-oriented and research-backed. These 45-minute workshops are designed to help your team connect, learn together, and improve business outcomes.

If you’re interested in learning more about how Teamraderie’s experiences can help develop leaders in your organization, check out our experience finder.

From Olympian-led workshops to help your team learn how to set and achieve goals, to experiences led by authors, Stanford professors, and more, Teamraderie has something for every team.

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