People talk a lot about what makes someone a “natural leader,” but the truth is, there’s nothing natural about it. Even the best leaders must learn skills and mindsets that are different from—sometimes even contrary to—the behaviors that come naturally to most.  

For example, leadership requires decentering your own success to promote the success of others. And it necessitates quickly adapting to and advocating for new paradigms when most prefer the comfortably familiar. 

Overcoming these and other leadership challenges requires actively learning new habits and ways of thinking. To do this, most people—even those who appear to be natural leaders—first need outside help.

The Problem of Uneven Leadership 

When someone does their job well and is promoted into a senior or executive role, they’re suddenly thrust into a position where they must make bigger, more impactful decisions. They may manage individuals or a team—often taking on more direct reports or their very first ones. This can be a particular challenge for leader development, given that 85% of new managers have no formal management training, according to Gartner.  

Some leaders embrace their new challenges proactively, seeking out opportunities for professional and personal development. Others are more passive and treat their new role as another task to check off. Most fall somewhere in the middle, relying on a mix of basic leadership training and their own instincts to perform their duties.  

The result is uneven leadership and management quality across the organization, which can lead to uneven productivity and employee satisfaction.  

To overcome this, organizations need to move beyond their mostly hands-off approach to leadership development. Instead, they must confront the many leadership challenges their senior leaders and managers face and begin exploring ways to address them.  

Leadership Challenges Facing Modern Executives and Managers

Today’s business leaders are met by an especially high number of leadership challenges, including:  

1. More disengaged employees 

A recent Gallup poll found that a higher-than-usual percentage of U.S. employees are actively disengaged with their work. Perhaps unsurprisingly, a lower percentage than usual claim they are thriving.  

Disengaged employees are less creative, less productive, and less responsive to leadership. Now that the ratio of disengaged employees has grown, leaders must strive even harder to reach, empower, and inspire them to own their roles and be accountable for producing their best work, which helps create a more positive workforce and culture. 

2. Conflicting personality types 

A great leader should understand how to make strong decisions by collaborating effectively with other leaders from different backgrounds, and they need a firm handle on how to meet their subordinates’ unique professional and personal development needs. But this is a tall order, especially for those who lack emotional intelligence and the ability to navigate a variety of work relationships.  

Often, a new manager will lead in a way that disappoints or upsets some reports, or an executive won’t get along with their peers solely because their personality and leadership style doesn’t mesh with their colleagues’ goals or working styles. Simple misunderstandings can spiral into conflicts that could have been avoided with a better understanding of different personality types. 

3. Communication difficulties 

Gallup also found that there is a wide gap between leaders’ and employees’ perceptions of the quality of manager communications. Many employees feel their managers don’t communicate often enough or provide enough feedback, but managers think they do.  

A number of factors could explain this disparity, but key among them is the fact that regular communication is a skill that even experienced leaders struggle to master. Leaders need support to learn how to provide it.  

4. Hybrid work 

Most offices today allow at least some level of remote or hybrid work. Leaders in hybrid environments need to be even more proactive about how and when they communicate to remain connected with their team.  

When employees are in the office, leaders need to find opportunities for plenty of in-person interactions; when employees are home, they need to work harder to maintain relationships and ensure alignment on expectations and outcomes.  

5. Balancing day-to-day work with leadership 

Most business leaders have work of their own to get through. They can’t get sidetracked by endless meetings and disruptions, get overly involved in unexpected problems or crisis management, or spend too much of their time managing the people under them.  

These competing priorities often cause senior leaders to feel pulled in too many directions. On the one hand, they need to make sure the trains are running on time and that those reporting to them get the support and attention they need to do their best work. On the other hand, they need time and space to do their own best work. Most people need guidance to learn how to strike this delicate balance. 

6. Time management 

Time management is difficult for all professionals, but especially hard to master for those in leadership roles.  

This is partly because of the challenges already discussed, in which leaders have to balance daily operations, management, and distractions with deep work. On top of that, they also must have one eye on their business’s long-term vision, so their time may be further eaten into by higher-level discussions and strategic planning sessions that lead to more responsibilities. All of this necessitates assistance in making room for what’s most important. 

7. Learning to delegate 

A key aspect of successful time management is delegation, but it is a skill that must be learned. Delegate too little, and the leader is overwhelmed with work. But delegate too much, and there’s a chance certain tasks won’t be completed adequately. Often, learning the correct way to approach this skill comes through experience rather than dedicated training. 

8. The need for heightened self-awareness 

Leaders have to be aware of aspects of their work styles that lower-level employees take for granted. They need to recognize how their tone sounds, what their body language communicates, and how they tend to react when faced with conflict. 

This level of self-awareness often becomes necessary overnight when one is promoted into a leadership role. But soft skills take time to cultivate and, often, require outside training from experts like an executive leadership coach.  

9. Navigating organization-wide issues 

Employees will often bring grievances to their managers, even when they’re aware that the manager isn’t at fault. Managers then become responsible for explaining complicated situations with broader implications across the company, like organizational restructures, or advocating for tools that improve operations but are outside their budget, like skill development classes or new software applications. Doing so with grace can be an immense challenge for leaders who haven’t cultivated a strong mindset.  

10. Adapting to new technologies 

Technologies are always changing, and many business leaders are eager to try new ones out. Yet often, they’re left to figure out how these technologies fit in with their team’s workflows.  

Leaders need to be adaptable and ready to embrace new innovations. At the same time, they’re best positioned to advocate for their team if certain technologies aren’t appropriate for them. This duality can put them in a tight spot.

When It’s Time to Ask for Help

Most executives and managers will face these leadership challenges and likely even more. Leadership is a muti-faceted, demanding undertaking, and no one is naturally perfect at it.  

Some support should come from the organization, but it would be too burdensome to expect the organization to address every one of these challenges for each of their leaders. Internal resources can get you started, but help from an executive leadership coach or other external expert can help all your leaders maximize their potential.  

Contact us to learn how every leader in your organization can overcome their most pressing leadership challenges.