Business Leadership Today

The 5 Toughest Challenges of Leadership Today (and How To Overcome Them)

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Matt Tenney, Author of Inspire Greatness: How to Motivate Employees with a Simple, Repeatable, Scalable Process

The primary role of all leaders is to inspire greatness in their followers. 

Indeed, leaders profoundly impact the employee experience, exerting tremendous influence on everything from how engaged employees are at work and how likely they are to stay in their jobs to the quality of employees’ performance and the organization’s long-term profitability. 

Leaders are responsible for creating an environment in which their team members can flourish and consistently deliver exceptional work. 

However, creating and maintaining this kind of work environment can be a daunting task in a constantly evolving landscape where workers’ priorities are shifting, and it is becoming more challenging to meet the needs that help them fully engage and reach peak performance. 

While many of the challenges leaders face aren’t new, they are becoming more difficult to surmount and require better strategies than those they relied on in the past.

The toughest challenges of leadership today are setting achievable goals, delegating effectively, building trust, maintaining transparent communication, and managing change. When leaders overcome these challenges, they are better able to meet the challenges of employee engagement and retention. 

In this article, I’ll look at the main challenges today’s leaders face and some methods for overcoming these challenges. 

Setting Achievable Goals

One of the common causes of underperformance and unmet objectives among employees is the setting of unrealistic goals. It’s hard for employees to build confidence in their abilities and engage with their work when they can’t reach the goals that are set for them. 

To guarantee that the goals established for teams and individual members are attainable and aligned with the vision, it’s crucial for leaders and team members to collaborate in setting S.M.A.R.T. goals.

S.M.A.R.T. goals are specific, measurable, achievable, relevant, and time-bound.

Setting a specific goal helps employees narrow their focus and ensures there is no ambiguity around what is expected of them. Making the goal measurable connects it to a single performance result and helps employees chart their progress. 

Setting achievable goals ensures that expectations are reasonable and possible to meet, and setting goals that are relevant to the larger purpose or vision can keep employees intrinsically motivated. Making the goal time-bound can help employees avoid procrastination. 

This goal-setting approach offers the transparency employees require to understand what is expected of them, and it aids them in self-accountability by formulating a strategy to reach their objectives and a method to monitor their advancement.

It can also support leaders in addressing two other tough challenges: delegating effectively and maintaining transparent communication.

Delegating Effectively

Delegation aids leaders in strategic thinking to pinpoint the optimal route ahead and offer their employees the right level of direction and independence for self-motivation.

Effective delegation necessitates a high level of trust and a comprehensive understanding of your team members’ abilities and limitations. Steering the employees’ tasks to ensure a seamless flow and confirming they are prepared for the work lays the groundwork needed for employees to remain driven to excel.

The essence of successful delegation lies in asking the right questions and doing a lot of listening, thereby guiding team members and enabling them to execute the work instead of commanding them.

I recently sat down with Dr. Wanda T. Wallace, author of You Can’t Know It All: Leading in the Age of Deep Expertise, to discuss the important role delegation plays in motivating employees. 

According to Dr. Wallace, too often, leaders take the wrong approach: 

“Instead of simply telling your team members the ‘why’ and ‘how’ of a task, it is better to direct them to learn the how and why themselves because they are much more likely to absorb and retain that information. Way too many deep experts default to ‘Never mind, I’ll do it myself,’ because that’s faster. Which leaves your team members feeling demotivated.”

Transparent Communication

Effective leaders set the example and pave the way for robust communication by being accessible and receptive to ideas. They provide clarity to all team members by articulating goals, objectives, and expectations, enabling them to perform their roles confidently and efficiently. 

Communication is always important, but it becomes even more important for motivating employees in remote and hybrid work environments. Transparent, respectful communication can promote trust and create a culture of improvement through frequent feedback between employees and leadership.

Leaders ought to be proficient at acknowledging communications from their team, responding promptly, and ensuring that their responses make the employees feel genuinely acknowledged. They should be easy to reach and maintain transparency, promptly addressing any obstacles to communication.

Leaders should also regularly and consistently communicate values to team members to build cultural buy-in. It helps employees align with core values and see the deeper purpose in their work when they see leadership modeling those values. 

According to author and thought leader Dave Gordon, communication, particularly communicating values, is the key to a strong culture and strong leadership: 

“I’ve seen cultures fail because of a lack of communication. Cultures thrive because organizations get communication right. And we are more likely to follow people who are like us, who have the same values as us.”

Building Trust

In trusting work environments, effective communication, teamwork, and a sense of belonging among employees are standard. Trust also enhances employees’ engagement with their tasks and boosts individual performance.

A lack of trust in the workplace can trigger a chain reaction. Employee morale may plummet, harmful behaviors may surface, and employees might start seeking other, more positive work environments.

Workplaces that foster high levels of trust experience a high level of employee motivation and positively influence productivity, well-being, and various other factors. 

Compared to those in low-trust companies, employees in high-trust companies report 74% less stress, 106% more energy at work, 50% higher productivity, 13% fewer sick days, 76% more engagement, 29% more life satisfaction, and 40% less burnout.

Dr. Paul Marciano, author and strategic advisor, says establishing trust with your employees is crucial to effective leadership:

“Building trust can be like a piggy bank. We have a relationship where I put a nickel in, you put a dime in, and so on and so forth. And if one of us does something to break that trust, it’s like the piggy bank has been shattered. We can try to put it back together, but it will more than likely never be the same again.”

Managing Change

Managing change can be one of the toughest challenges of leadership. Why is this?

According to Business Leadership Today contributors Mark S. Babbit and S. Chris Edmonds, the reason is simple: leaders lack the experience to successfully navigate change and avoid the common mistakes that cause our efforts to fail. 

When leaders don’t fully invest in the process, when they let fear of change prevent progress, or when they don’t support a culture that values respect over results, their efforts won’t be successful. To stay up for the challenge, leaders must be adaptable. 

Adaptable leaders are flexible, creative, and adept at problem-solving, and they know how to develop these qualities in their team members. 

They are able to maintain a consistent work environment to make employees feel psychologically safe, and they can guide employees as they adapt, making them less fearful of the future and more positive and motivated in the face of challenges. 

Adaptable leaders know that change is inevitable. They know they need to be able to adapt if they expect their employees to adapt, and they make adaptability a part of the organizational culture. 

Adaptable employees are more self-motivated and develop an improvement mindset as a result. Leaders can help their employees be more adaptable by helping them grow in their roles, develop new skills, and seek out better ways of doing things. 

How To Overcome These Challenges

The secret to effective leadership and surmounting these obstacles lies in consistently meeting the needs of employees and providing a work environment in which all employees can thrive. When leaders do these two very important things, they will also be better able to address two other challenges: engagement and retention. 

However, to ensure these needs are being met and identify areas for improvement, it’s crucial to consistently measure how effectively these needs are being addressed and implement necessary adjustments.

There are two highly effective methods leaders can utilize to ensure they are meeting their team members’ needs and helping them thrive in their roles so that the organization retains talented, highly engaged employees. 

Pulse Surveys

Pulse surveys are short surveys that can be sent out frequently to gather feedback about employees’ perceptions. These frequent check-ins assess the employee’s perception of how well their needs are being fulfilled and their attitudes about the organization and its culture.

Unlike large annual surveys, which can sometimes be misleading and even hurt engagement, pulse surveys can gather feedback in small, digestible bits on how well direct supervisors are meeting the universal needs people have for being engaged at work. This allows direct supervisors to quickly respond to the feedback. 

1:1 Meetings 

1:1 meetings can be structured or casual discussions with employees that help us understand how they are feeling about their jobs and identify ways we can support them in excelling at their tasks.

Putting time on the calendar to invest in 1:1 meetings with team members and doing whatever we can to make sure we meet at the scheduled time sends a very strong message that we truly care about them. 

While the initial time commitment might seem hard to manage, well-executed 1:1 meetings can ultimately be time-saving in the long term. Moreover, they can enhance your effectiveness as a leader and make your leadership role not only more productive but also significantly more enjoyable and gratifying.


Matt Tenney has been working to help organizations develop leaders who improve employee engagement and performance since 2012. He is the author of three leadership books, including the groundbreaking, highly acclaimed book Inspire Greatness: How to Motivate Employees with a Simple, Repeatable, Scalable Process.

Matt’s ideas have been featured in major media outlets and his clients include numerous national associations and Fortune 500 companies.

He is often invited to deliver keynote speeches at conferences and leadership meetings, and is known for delivering valuable, actionable insights in a way that is memorable and deeply inspiring.

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