The 23 Most Difficult Parts of Being A Team Leader

Leading a team is an exciting but challenging task. It requires the ability to conduct a diverse group of individuals in the same direction as one. Yet, it can be even more challenging if one is not aware of the difficulties that they may encounter. 

For that reason, I’ve looked into The 23 Most Difficult Parts Of Being a Team Leader. From overcoming personal challenges to guiding everyone through team challenges or their dilemmas.

We will be explaining how each of these twenty three parts of being a leader make it so challenging, keep on scrolling.

Why Is Being a Leader Difficult? 

Being a leader is incredibly challenging for many reasons. Amongst them: 

Knowing And Overcoming Yourself

Perhaps the first challenge you’ll have to deal with as a leader is not standing in your own way by getting to know your strengths and weaknesses and making a conscious effort to work with them. You don’t need to get over all your weaknesses. As a human being, that is almost impossible. Yet, you need to be aware of them. That way, when they threaten to get in your way, you can work to counter them or use them in your favor. 

Let’s say you’re leading a team in a foreign country. Being a foreigner is a disadvantage for many reasons in your leadership. By recognizing that, you can put extra effort into getting to know the country and its business culture. 

Staying Confident Yet Humble

A good leader has confidence in himself without the need to feel better than his team. Humble confidence is a challenge to many leaders because it’s easy to get carried away by the power that comes with leadership. Yet an arrogant and difficult-to-deal-with leader will most probably discourage the team and harm, rather than help the work. 

Being a Source of Positive Energy 

As a leader, your team will look up to you for positive reinforcement. That can be exceptionally challenging when facing adverse situations in which the resolution is still uncertain. Regardless, it’s your job to pull it together and search for the strength within you to keep your team motivated. 

Managing A Group Of Individuals

Probably one of the most challenging parts of leadership. People are complex, and each individual has their personality, background, and way of dealing with things. Managing a group of diverse individuals is challenging as it requires you to have the ability to understand all these individuals with different backgrounds.  

Yet, that is one of the primary and most important parts of leadership. 

Giving Confidence To Your Team Members 

Besides building your confidence, as a leader, you should build your team’s confidence, in you, in your goal, in your method, and, most importantly, in themselves. That’s where the challenge begins, as convincing people of their capacity to achieve something or to thrive in difficult situations is even more difficult than convincing yourself of it. 

As we said, people are complex, and each person deals with circumstances in their way. Most of us have preset attitudes, crafted in childhood , that are difficult to let go of as adults (read Robert Greene’s “The Laws of Human Nature” ). As a leader, you’re expected to guide people to overcome those for the team’s benefit. 

Delegating Effectively 

It’s not enough to delegate and give out tasks to your team members. As a leader, you should have discernment and the ability to delegate to further help the team achieve the common goal. 

Managing what needs to get done and figuring out who should be doing it is hard, as it will determine how smooth the ride to the goal is (or even if the goal is achieved or not). 

Connecting Different Team Members As One 

A good leader is only good as long as it can unite people and motivate them to work as one for one purpose. As I said, people are complex. They have different ways of interacting with others based on their values. 

Even so, a leader shouldn’t be taken aback by such a challenge. 

Dealing with Stress from Work 

Dealing with any stress is challenging in itself. Leaders feel this heavily since almost all the pressure from work ultimately falls on them as the head of the team. And they have the weight of setting an example for their team, so where a regular person could react poorly, they are expected to respond appropriately. 

Human interactions are obviously not so black and white. Leaders make mistakes. Yet, in those moments, they are expected to humble themselves and redeem. The pressure to act right in stressful situations is never really lifted from their shoulders. 

Managing Your Own Stress, Fears, and Anxiety

Fear is a part of human nature, an instinct to help us stay away from danger. Still, it can have a destructive effect, especially in a business setting. Therefore, you want to deal with your fears, whether related to your self-doubt or attached to an actual external situation. 

Managing anxiety and stress is something most of us are still trying to master. As a leader, you don’t have the space to let your concerns stay in your way of doing a good job. You must overcome this challenge. 

Managing Your Team’s Stress, Fears, and Anxiety  

Besides managing your stress, as a leader, you must also manage the stresses and tensions of those in your team. After figuring out how to deal with your anxiety, you should prioritize working on your team, as the team’s balance is essential for an effective team environment and teamwork. 

Letting Go of Control Sometimes 

Although a leader has the responsibility to be inside everything that happens within the team, a good leader knows when to surrender control and trust their team to do what they are good at doing. 

Having the ability to recognize when the moment for letting go of control has come may not be easy for you when you’re used to taking control yet, it’s key in leadership. 


Leadership comes with a lot of decision-making. You are expected to guide your team with your decisions effectively, and when that doesn’t happen, you need to live with your choices. 

We all know that decision-making, regardless of the context, is never an easy task. Despite that, most of the team’s hard decisions ultimately fall on the leader, as the head of the team. It’s not just any decision that is handed to the leader, but those that will determine the course of the group. That’s a big responsibility. 

Dealing With Your Team’s Expectations 

If it wasn’t evident in the previous points, I should say that a lot is expected from a leader. No matter the context, whether as an individual, as a leader, or for the team, you’ll have the heavy responsibility of meeting the expectations. 

It is certainly not easy, but it’s part of the role of a leader. You might fail to meet some of the expectations, which can cause some discontent within the team, yet you should be prepared to deal with those situations in the best way possible, always with the collective in mind. 

Managing Unexpected Situations or Circumstances

The unexpected is an expected factor in leadership. When you’re managing a team and implementing something new, many unplanned events and circumstances can arise. It comes down to the leader to figure a way of working them out. 

Though most times, with the team’s help, it still is a lot of pressure on the leader. 

Staying Focused 

Being a leader comes with a lot of responsibilities and tasks. With so much going on, it can be tough to keep focus in your leadership role or on the tasks that you’re assigned. 

You can’t allow that to happen. Your ability to focus can be crucial for your team’s work, being that the team relies on you for guidance. 

Managing Conflict 

No matter the context, conflict is an intrinsic area of any business. Whether it’s stemmed from differences between team members or challenges in work, it will often be your responsibility as a team leader to manage them. 

Developing the ability to navigate through conflict and conflicting situations smoothly is a must for good leadership. Yet, it’s good to recognize that it might take some time to develop it. 

Splitting Yourself In Many Tasks 

If there was a machine to multiply human beings, many leaders would probably be in line to try it. In your role as a leader, you’ll be expected to multitask and divide your time and attention. 

We all know that multitasking is hard. It will certainly demand a lot of you, and you need to be up for the challenge.  

Being Practical Yet Human 

Finding the sweet spot between our practical instincts and our emotional side is a considerable challenge. Too much of either can make you seem too robotic and cold or too emotionally unstable to lead. 

Balancing both traits is necessary to create an effective yet safe team dynamic. Your team must feel the drive to do their job correctly while knowing they have an understanding leader.  

Keeping Yourself from a Burnout 

With so much going on and so much to do, you might feel tempted to overwork. Perhaps you’re working on something you really love, and initially, overworking doesn’t seem so bad. Or maybe you feel the pressure to do it. 

Either way, you must remember that you can’t successfully guide your team from a place of instability. You can only ever have a clear vision from a clear place. That to say, even if it seems impossible, finding space to check in with yourself is necessary. 

Staying Transparent 

Not letting your position influence the level of transparency you keep with your team is essential. Although there may be situations where being transparent is the last thing you want to do, because of the fear it might steam in your team, you must have it in yourself to be honest and real with them. That will influence trust-building. 

Staying a member of The Team

Leading a team can separate you from your team members. It’s easy for them to feel like you’re above them or somehow better than them. You can also easily let your ego drive you into the same mistake. 

Staying grounded or making your teammates feel comfortable around you enough to see you as part of the team is therefore challenging. You’ll need to make an extra effort to bond with your team if you want to overcome that. 

Delivering Bad News 

The “bad guy” role is usually left to the leaders, as the ones who need to show up when work is not going so well or when a team member isn’t aligned with the team or the mission. It’s not an easy role, especially when you are left with the task of terminating people. Yet, a true leader needs to be ready to handle that. 

Leading Effectively

Taking the position of the leader isn’t enough. You should be able to fill in that role and direct your team towards the mission effectively. You should be able to navigate all the difficulties and, in the end, fulfill the team’s objectives, keeping in mind the team’s wellbeing. 

Knowing what challenges you may encounter is a great start if you want to become a good leader. It prepares you for your task. But there are other things behind a good leader.

What Makes A Good Leader 

After deep research, I’ve gathered a few traits commonly brought up when discussing what makes someone a good leader. Many leaders have suggested these traits in interviews for Forbes or in business and personal growth Handbooks. 

Highly Recommended Article: 15 Places to Learn leadership Skills for Free or on a Budget


Only a confident leader can transmit to the team the confidence that they need. People are likely to follow someone who exhales confidence, even if false because we all want to feel safe. Learning key communication skills for leaders is paramount here.

A good leader makes self-confidence a crucial step of his growth and personal building. 


One can’t control a team dynamic and effectively lead without the ability first to control himself. 

A leader with self-control sets the example for his team of what it is like to prioritize the right things in the place of instant gratification. 

The Ability to Make Decisions 

Decision-making is one of the main tasks of a leader. An indecisive leader transmits insecurity and generates mistrust from the team towards him. 

From another perspective, a good leader not only makes decisions (good or bad). He makes them quickly and rarely backs off, unless in the right timing. 

A Definite Vision and Plan 

To lead people without a vision and a plan is to blindly lead people to failure. Strong leaders know where they are going and where they are taking their team. They combine their’s and their team’s creativity into the craft of a plan that will take them there. 

Any leader who underestimates the importance of having a clear vision and plan risks having all the team’s efforts wasted. And that may cause dissatisfaction in all those who have worked hard in it. 


A good leader knows that his own beliefs communicate to the team, so he chooses to express faith in himself, the team, and their vision. 

When things get tough, and the team has nowhere and no one else to turn to, the good leader is always the last man standing. He is there for reassurance, inspiration, and motivation. He isn’t easily broken by temporary defeat, no matter how long it has been around. 


Empathy is essential in human relationships. Lack of empathy can be disastrous and harmful for a team dynamic. Empathy is the only way different individuals can work together from a place of understanding and without consciously harming each other. 

A leader should have this trait to inspire other team members to develop it too. 

Charisma or a Charismatic Personality 

A charismatic personality is key for anyone who wants to be successful in today’s society. A leader who is easy to be around and makes their followers feel good about themselves and their work will probably have more success than an arrogant or rude leader. 

Charisma is a seductive quality. In leadership, it’s about seducing your team into giving their best in the job, willingly and while genuinely feeling good about it. 


An intelligent leader knows that his power lies in his team and in his ability to connect with them. Like the saying “there’s no I in team”, a leader knows that he wouldn’t be there if it wasn’t for the team. For that reason, he values cooperation and working with his team, as one, above all.

This is the best dynamic as team members will be more satisfied with work if they feel valued by their leader. 


We can’t stress enough the importance of taking responsibility in leadership. A true leader takes their team’s mistakes as their own. He shows up when it’s most necessary, and he is not against doing and giving more than what’s asked of him. 

A team will respect a leader who shows up for them and doesn’t abandon the ship when times get hard. 


A good leader tries to be just and fair in all his decisions. Above anything, he recognizes the importance of honesty and justice. He takes it beyond just a moral code. He makes it a part of his character. 

This character trait builds trust in his team. And it makes the team more likely to follow their lead. 

A Great Sense of Ikigai

A great sense of what the Japanese call Ikigai is one important step that can make a good leader. Ikigai is a Japanese word and concept that stands for having a reason for being, a personal purpose, a reason for waking up every day. 

It can be confused with a definite vision and plan, but it’s different as it’s linked with the leader’s internal motivation. It’s not attached to the job that the leader needs to perform or the team’s goal. It has to do with his general drive and passion for living and serving. 

It seems like a lot, but with the internet and so many self-help groups out there for personal and team development, you can make it through the challenges and develop the character of a true leader. Here’s a small list of a few books that might help you: 

Good Books About Leadership 

Think and Grow Rich

This book, from Napoleon Hill, is on the top recommendation list from most great team leaders.

The book dedicates a small part in chapter 7 to enumerate the 11 traits of a good leader. 

Although the book is not centered in building leadership skills, it’s a great help for developing the character and the mindset of a successful person, in whatever area, including leadership.

The Laws of Human Nature

A book by Robert Greene. It’s a great way to learn about people and their motivations based on psychological analysis. It’s precious for anyone working in a team, especially for the leader. 

The book also touches on many subjects that can be valuable for the leader’s self-development, things like developing empathy and overcoming fear, crucial for leadership. It also contains clear examples of bad leadership and what not to do as a leader. 


Ikigai, a book by Francesc Miralles and Hector Garcia, is the ultimate guide to the Japanese concept. It is a concise book, a quick read for anybody wanting to learn from people’s stories and examples. 

It’s great for personal growth and life and labor motivation.

Summing It Up !

Leadership is an arduous and demanding task. Being the head of a team and guiding different people takes a lot of someone and their time and resources. Yet, when done correctly, it can be beyond fulfilling. 

Not many tasks and roles can make you grow as an individual and professional, as much as a leadership role. For that reason, you shouldn’t be discouraged by the challenges and difficulties you may encounter. 

Your job can change people and their lives in the most remarkable ways. To be a leader is a one-in-a-lifetime experience. Make the most of it! 

Further Reading

The Hardest Part Of Being A Leader That Is Rarely Discussed. MEDIUM

10 Unique Perspectives On What Makes A Great Leader. FORBES  

45 Quotes from Thought Leaders for Inspiration

Emidio Amadebai

For the past 2 years, I have been working as the head of Customer Experience, Sales, Marketing, and Customer Finance at an international pay as you go solar home system company working in rural areas in Africa. After my previous 7 years working in B2B, IT&Telecoms industry, as a Service Delivery and Project Manager, having worked with Vodacom, Huawei, and other multinational companies. My job is to make sure we improve the lives of thousands of families, with access to electricity, utilities (radio, TV, lights), doing our very best so that they get the best-in-class customer experience, and succeed in acquiring the products for themselves.

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