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What are the Most Common Leadership Challenges?

By Sheri Cyprus
Updated May 16, 2024
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Leadership challenges vary by organization, but many of the most common have to do with motivating, encouraging, and effectively managing people. This is particularly true in business settings, where employees must learn to work together in order for a company to be profitable. Any situation in which there are both leaders and supporters can have leadership challenges, however, including a number of volunteer organizations and community movements. So-called “good” leadership is often a lot easier to describe than to actually implement. Many of the most common leadership challenges arise when leaders are either unaware of common pitfalls, or are inattentive to developing problems.

Motivating Employees

No organization, be it formal or casual, will get far if its workers are not motivated. Workers who lack focus or are uninterested in the end goal are not usually very productive, and can often undermine a leader’s efforts and authority. Sometimes, the fix is as easy as clearly communicating the mission. In other instances, leaders must work with employees individually to figure out an effective incentive structure.

A lot of worker motivation has to do with workplace psychology. The happier and more valued employees feel, the more likely it is that they will give the company their best efforts. Investing in employee happiness sometimes seems counterintuitive, but ignoring corporate culture is often seen as a serious misstep.

Cultivating Leadership Experience

One of the hardest parts of running any sort of organization is ensuring that those in superior positions are actually capable of leading effectively. The skills needed to head up a cause or execute specific goals are not usually intuitive, and they cannot always be learned in a classroom. Leadership students and scholars are often able to describe leadership styles and techniques quite well — but in order to actually execute them, some experience is usually required. Executives and others looking to hire or appoint leaders are usually wise to consider much more than what is on a paper resume.

Creating Team Unity

Leaders are often responsible for helping build unity between staff members. Teams that do not work well together often take a lot longer to complete even routine tasks. It can take a bit of time for workers to develop trusting relationships with one another, and the role of a supervisor or managers is to set the proper framework to encourage these relationships to grow. Employees do not need to become each others’ best friends, but they do need to be able to work effectively with each other. This does not always come as naturally as some might assume.

Facilitating Open Communication

One of the hardest things many leaders face is finding ways to be approachable without losing authority. Effective teamwork depends on a culture of open communication, where superiors and subordinates can freely discuss progress and problems. Employees who feel that their bosses are distant or somehow “off limits” have a tendency to make mistakes that could have been avoided had parties felt more comfortable talking to each other.

Encouraging Action and Innovation

Particularly in larger organizations, encouraging employees to be creative with their ideas and to take risks in their work is one of the more difficult leadership challenges. While it is important for workers to have boundaries and parameters in order to stay focused, some latitude is essential to growth. Organizations that do not ever generate new ideas are often surpassed by more innovative competitors.

Leaders must find a balance between keeping employees focused and giving them space to think creatively. The amount of freedom workers should have necessarily depends on the setting and the sort of work being done, but is important in nearly all disciplines.

Information Management, Consistency, and Other Details Challenges

Leaders are often overwhelmed by the sheer number of things that must be done to keep a business or organization going apart from staff management. Being a good leader usually requires a strong attention to detail, and an ability to manage a lot of competing demands at once.

Most of the time, those in more senior positions must learn how to stay on top of enormous amounts of data, information, and paperwork. Organizational work like this is often only tangentially related to managing staff — but it must be done just the same. Adjusting to different roles is, for many, one of the most surprising challenges that comes with assuming a leadership position.

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Discussion Comments
By anon284400 — On Aug 09, 2012

@anon223602: Do not try and make small talk with them that is meaningless, don't offer help with things unless they are obviously having trouble doing something. This will aggravate a one-word response.

What you can do is become friends with them by letting them desire your friendship. Make them "jealous" with how the other employees like you more than them.

By anon223602 — On Oct 19, 2011

I just started a new job and my supervisor does not want to be at this job and makes it clear. I am trying to make the best of the situation obviously. I offer my help with whatever tasks she needs done to make it easier for her but she is unresponsive. I offer my suggestions on tasks that she assigns me and it is the same thing, she either knocks it down or just does not respond. I am really trying to just smile and grin and get through the day but it is difficult because I really do like this job and want it to last for a long time. I can't go over her head because I just started and do not want to step on her toes and make enemies. Please any suggestions.

It is especially frustrating because I work with children and it is disheartening, to say the least, that she does not have passion for the job.

By cafe41 — On Oct 13, 2010

BrickBack-Sometimes the new leadership challenge involves a young leader with an older group of employees.

This leader will be constantly challenged by the group as not savvy or experienced enough to know what they are doing.

It is essential that this type of situational leadership issue be nipped in the bud immediately because if not the young manager will be undermined every step of the way and not be effective.

It is of the utmost importance that this type of manager treats everyone with respect as all managers should do and outline the expectations that he or she expects from each employee.

At the same time, it would be a great idea to ask them what they expect from you. This way they feel that they their feelings are being heard and that they matter.

This might also make the group eventually cooperate with the manager. The worst thing to do is to form an authoritative demeanor with this group because instead of cooperation, you will have a war. You really need them on your side because you can’t accomplish your department goals on your own.

By BrickBack — On Oct 13, 2010

Comfyshoes-Leadership challenges today usually involve the lack of motivation. Many employees start jobs especially out of college with very high expectations.

Some expect very high income right off the bat without proving themselves. This faulty thinking creates a leadership challenge because motivating these employees takes a special skill.

That is where the effective leader will always be one that can inspire people and particularly show these employees how far he or she has come so they can understand their potential.

Developing employees and working with her strengths is also important to get them motivated. Noticing what the employees do especially when they do something well is important to recognize. Most people love recognition and sometimes evaluate that higher than money.

By comfyshoes — On Oct 13, 2010

Sneakers41- This is why a leadership challenge model shows ways to layout the expectations for the employee and ask the employee what he or she expects from the manager as well as documents all performance issues.

This is really important because although most states are at will states in which you can be fired for any reason for which the company does not have to disclose, there are exceptions to this measure and if the employee can prove that the environment was hostile or discriminatory they may win in a challenge.

This can be very costly for a company which is why most leaders have to document all of these exchanges.

In addition, when terminating an employee it is best to have a member of HR in the room as a witness to the proceedings.

When a person is terminated they tend to get very emotional and having another person there can help you in case the person files a legal challenge.

By sneakers41 — On Oct 13, 2010

Challenges in leadership really result because not all employees have the same level of motivation and work ethic.

Effective leadership really pays attention to all employees and trys to develop them to the best of their ability.

Having employees that are easily promotable really demonstrates effective leadership because the leader developed his people to the point that they were able to take on additional responsibilities at work.

The challenges of leadership involve coaching an underperforming employee as well as terminating an underperforming employee. Both situations are difficult because not everyone accepts constructive criticism well and terminations are unpredictable.

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