Workforce Development

10 Leadership Challenges

Being the leader can be incredibly rewarding. It can also be difficult and feel impossible to do well.


Being the leader can be incredibly rewarding. It can also be difficult and feel impossible to do well. It’s sometimes easy to look at your boss or team leader and become critical of their actions, choices and decisions. 

Employees often look at their bosses with jealousy, resentment and envy. They might think they could do the job better or they might feel their assigned leadership doesn’t understand them. Whatever the case is, being a leader is a lot tougher than it sounds.

Leadership is a skill which can be honed through mentorship and practice. This process can take time and the road to successful leadership is often bumpy. As an employee, it can help to understand the challenges a leader faces so resentment doesn’t build up. Also, all leaders were once employees so understanding the pitfalls and challenges a leader faces can help one to rise up the ladder as smoothly as possible.

Here are 10 major challenges leaders are faced with:

  1. To establish boundaries and build professionalism they may need to distance themselves from other employees. Sometimes leaders have to make difficult choices and oftentimes those choices can be colored by friendships and personal relationships as opposed to what is best for the company. This means leaders often have to sacrifice personal relationships to maintain a non-biased view.
  2. The stakes are higher. The higher up in an organization a leader is, the more weight his choices carry. Being at the bottom of the totem pole may come with less pay, but it also comes with less responsibility. A top flight leader’s simple decisions can trickly down the organization and affect multitudes of people. This can be a heavy burden.
  3. No one is perfect. Even the most seasoned and professional leaders make mistakes. Owning up to mistakes and learning from them is something great leaders have to do on their way up to the top. Leaders have to acknowledge when they mess up, own up to it and try to do better.
  4. Leaders have to put the organization first. Leaders often have to fire employees and make tough choices in times of downsizing. They may also have to call employees in to work over the weekend or not allow them to take certain vacation days. To be a good leader, you need to have thick skin as you will be forced to make hard choices that not everyone will be happy about no matter what you do.
  5. Leaders have to get over being friendly and often show tough love. When a friend or fellow employee isn’t performing at their job, it’s up to the leader to tell them so. It can be socially awkward and uncomfortable, but ultimately it falls on the leaders shoulders to let people know when their work is subpar. 
  6. Enforcing rules can be tough, especially if you don’t agree with them. Leaders often get subjected to the same rules from higher management that employees lower on the corporate ladder do. It doesn’t matter if leaders agree with some of these rules or policies, they still have to enforce them for the greater good of the organization.
  7. Getting compliance and making sure things get done is not easy. Perhaps the key difference between the mediocre and great leader is can he or she get others to get the work done. It’s one thing to clearly and calmly lay out a plan or project...it is something else entirely to get a team of people to actually do it. Oftentimes, a leader has to get angry or more serious to get things moving and this can be tough. 
  8. Leaders have to deal with everyone’s complaints. It is virtually impossible to get every single person within an organization to get along everyday. When there are petty clashes, the leader is the one who has to sort it out and oftentimes listen to ridiculous or silly complaints. These complaints can vary from the position of an employees desks to the distaste an employee might have of a colleague’s deodorant. A leader has to take all the complaints in and somehow keep his team focused on the job and happy.
  9. Leaders are under a microscope. Everything they say or do is dissected and closely watched not only by the employees underneath them, but also their superiors. Leaders are usually sandwiched between the pressure of their own bosses and the stresses of running the team below them. This level of pressure and attention can be a lot to tolerate for some people.
  10. When a team performs well, the leader may get praised. Conversely, if a team falters the leader usually takes the brunt of the blame. A leader often has more responsibility and power. With these two things comes benefits, but also more potential penalties. A leader has got to be able to stand up to failure and take the blame when several people may be at fault.

When grooming future leaders in a mentoring program these are 10 points to focus and work on. By identifying these challenges, mentors and mentees can develop skills to make leadership easier and smoother.

Mentor Resources can help any company to leverage technology to create tailored career development programs that are cost-effective. Our mentoring software - Wisdom Share is a cloud-based program that is simple and comes with guided workflows. Included are tools for administrators to attract, enroll, connect, and guide participants. We also provide analytics to ensure you can monitor your employee development program and easily see ROI metrics. 

Reach out to us today for a Free Demonstration of our software. 

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