top of page

21 Leadership Challenges & How to Overcome Them

Updated: Jan 24, 2023


Every day, leadership challenges are going to come for you. From all sides, around every corner, even from within. Leadership—true leadership based on honesty, authenticity and meaningful relationships—takes guts. The kind of leadership that inspires others, serves others, and points them toward a greater purpose and vision … it’s hard work. There are many bumps on the path of leadership. Sometimes they’re roadblocks. Sometimes the bridge is out entirely. But every challenge is an opportunity. It’s a chance to learn about yourself, improve your skills and strengthen the emotional intelligence that’s so critical to effective leadership.


Business Woman In A Comfortable Chair With A Coffee

The first and probably most persistent source of leadership challenges? It’s you. The leader yourself. Yes, there are plenty of external forces that can throw obstacles in your path. But most often, it’s our own thoughts, feelings and ways of reacting to situations that can create some of the biggest hurdles in leadership. So that’s where we need to start, with the internal leadership challenges we’re all likely to face.


When you’re in a position of leadership, it can be easy to start believing your own press. Maybe things are going great. You’re hearing accolades. It’s easy to start believing that all this success is your doing. That maybe, just maybe, it’s you who deserves the credit for your organization’s greatest accomplishments. But you don’t need us to tell you that the arrogant leader is not someone we want to follow. That’s a leader who alienates their team, causes conflict and incites drama. None of which is healthy for an organization. The best leaders are humble leaders. They know that leadership is about influence and impact, not authority. They recognize the value of the team around them. And they reap the rewards of a team that respects their character and willingly works alongside them to reach a common goal. It can be a challenge to stay humble as a leader, but it’s an essential leadership quality that’s worth fighting for.


Business Man In Front Of A Conference Table

It’s funny. We just said you have to fight to stay humble, and this sounds a little like the opposite. But having self-confidence isn’t the opposite of humility. It’s healthy. The problem is, most leaders, if we’re honest about it, struggle with self-doubt. And the more you succeed, the more you’re likely to wrestle with those feelings that you’re not really who people think you are. That’s known as imposter syndrome, and it can be a particularly painful challenge for many leaders, because it creates so much self-doubt. It can cripple your ability to inspire, motivate and serve your team. That’s why healthy self-confidence is an essential characteristic of leadership. Whereas humility is all about knowing you’re not the center of the universe, self-confidence means understanding that you bring value to that universe. It’s about quieting the internal voice that tells you you’re failing, you’re not good enough, you’re a fraud. When self-doubt says you are not enough, self-confidence says, “I am enough.”


Not much can get in the way of leading well, making good decisions and moving your organization forward like fear. Fear of the changes that are bound to happen, how you’ll handle them and how your team will react. The fear of making the wrong decision. All the risks and “what ifs” that can stop you in your tracks—from economic changes or market shifts, to the specter of job cuts or restructuring, to global crises. Fear is a basic human instinct, and no leader is immune to it. What you can do is recognize it, own it and deal with it effectively. More on that later.


Business Meeting Or Conference Taking Place

Leaders are busy. There’s always too much to do and never enough time to do it. Distractions, emergencies and new opportunities pull you in a lot of different directions. Which is why it isn’t surprising that one leadership challenge you might face is having a tough time following through on the plans, ideas and strategies you put in place. In fact, some studies suggest that 90% of strategic plans fail to meet expectations. Yes, there’s a lot to get done. There are changes and surprises. But taking on so much that you’re unable to finish what you started has hamstrung the effectiveness of many leaders before you.


With all of these leadership challenges staring you in the face, you’d be well within your rights to feel a bit stressed out. It’s natural. But the anxiety these leadership challenges create can itself be a significant challenge to your leadership. The fear, the self-doubt, the cascade of problems and expectations that leaders often face—it can all add up to a level of stress that puts your ability to lead in danger. Because we act differently in times of stress. It’s harder to be patient. It’s tough to stay focused. We can become angry and fall back on defensiveness—it’s the old fight-or-flight response that can effectively turn off our rational brain. That’s why it can be so valuable for leaders to learn more about how they react to stress, understand their behaviors, and better avoid the pitfalls to leadership that happen when anxiety goes unchecked.


Everyone has bad days. Blah days. The times when progress is slow or an effort fails, and you fall into a funk. It’s easy to dwell on what isn’t working and let it sap your energy. And that can be especially tough for a leader to work through, because everyone’s looking to you to be a cheerleader. A champion of forward momentum, enthusiasm and the “get it done” attitude. Sometimes just the expectation of you to be the chief motivating officer can be one of the most demotivating factors you deal with. But your team is looking to you to lead, guide and inspire. Even if you’re not your best or most enthusiastic self.


Work Burnout

Maybe it’s a progression. You lose motivation, then your will to lead fizzles out entirely. We’ve already gone through a long list of leadership challenges, and we’re just getting started—with all of this against you, how do you NOT burn yourself out as a leader? It’s a real challenge. And to be perfectly frank, burnout gets the best of a lot of leaders. They push too hard, never rest, and wear insane hours as a red-eyed badge of courage. But if you burn yourself out, you’re not leading anyone. We see a lot of this working with high-performing leaders in all kinds of industries. It’s tempting to try to be the superhero, but if you’re not taking care of yourself, if you’re not stepping back to fill your own well, how can you lead and inspire others?


Let’s bring this back full circle, because vulnerability is closely tied to humility. And it’s equally important to good leadership. It takes a lot of intestinal fortitude to say, “I was wrong.” It takes high emotional intelligence to admit your mistakes, ask for feedback and learn from criticism. If you’re not able to ask for help, it can be a major hurdle to effective leadership. Perhaps being vulnerable even encompasses all of the internal challenges we’ve talked about so far. Because vulnerability is about authenticity. It means having an accurate picture of yourself. Knowing what gets you down and what keeps you going. Being real about what you’re feeling. Engaging in honest conversations with your team. Being willing to show your humanity. It’s hard to do, which is why many leaders prefer to project invulnerability. But that’s a trap. Great leaders take the challenge to be vulnerable, own it and live it.


A Man And Woman Discussing Challenges

It’s not only internal challenges you face as a leader. Some leadership challenges come down to the variety of skills it takes to lead effectively. The strengths you need to build and the approaches you need to learn if you’re going to make the kind of impact great leaders make on their teams. All skills can be learned, honed and improved. Some take more work than others. But every challenge to your skills and abilities as a leader is an opportunity to take yourself and your team to the next level.


We touched on the challenges of keeping yourself motivated. It can be just as challenging to keep your team motivated. Maybe even more. Every day, the people you lead are asking, “Why?” What’s the vision? Where are we going? Every one of us is looking for purpose in our work. As a leader, it goes with the territory to keep your team focused on that purpose. To inspire them with a shared vision and encourage them as you accomplish your goals together. But it isn’t always easy. When you’re not feeling very inspired yourself, or you’re unsure how things are going to turn out. When a team is struggling and you’re grasping at some way to rekindle the fire. People are people—we’re emotional beings with highs and lows. And it’s up to the leader to inspire and motivate their team through all of those times.


People want to grow in their careers, and it’s the leader’s job to make sure they can. To give them the opportunities they need, push them, guide them. It means looking for strengths and recognizing potential. Setting a high bar for them to clear, but assuring them that you know they can do it and giving the direction and support to believe it. All of it takes time and commitment. Another important part of the equation of developing and mentoring employees is giving recognition. We all need to know we matter. Everyone wants to feel seen, heard and appreciated. It’s your job as a leader to make sure your people know that you appreciate them. And not in a generic, “thanks for everything you do” sort of way. In a specific, “I see what you did in this moment and sincerely appreciate the great work” sort of way. That means paying attention, listening actively and making a genuine effort to help your team value their own strengths, find fulfillment and grow toward their potential.


Multicolored Sticky Notes On The Wall

Managing. Not micromanaging. That distinction in and of itself could have been another leadership challenge.

But for our purposes, we’re talking about the constant problem-solving. Arranging the chessboard. Navigating the complexities of interpersonal relationships and handling team dynamics. It’s the daily pressures of good decision-making as a steward of your organization’s resources. All of that wrapped up into a bundle of challenges that can tie the leader into knots if you let it.

And don’t forget about delegation. Delegating is easy. Delegating well is not. When you do it right, delegating isn’t about simply “handing things off” or “clearing your plate.” It’s about empowering others to do the work you’ve brought them on board to do.

Taken together, all the demands of managing resources well can present a deep challenge for you as a leader.


The more you spend your time and energy helping your team grow and develop their skills, the harder it can be to intentionally develop your own. At the risk of sounding a little anti-servant-leadership (we’re not, promise), you can’t only do for others and not take care of your own growth and development. Actually, it’s related in a way to the challenge of avoiding burnout. Just as you want to make sure you’re filling your own well in terms of emotional rest and self-care, you want to make sure you’re able to provide for your own intellectual and professional well-being.


Change is the only constant. That’s a cliché these days, but a long time ago it was profound philosophy. And it’s true. If there’s one thing we can count on, especially in this day and age, it’s that things will always change. For the leader, that means facing the challenges that come along with change in our organizations. Understanding how things are going to be different, planning for it and accounting for the fallout. Reassuring teams when things are uncertain and bringing people along for the ride when they’re resistant to change. Sometimes change is predictable. More often, it’s not. The challenge for the leader is to provide consistency and clarity through it all.


There’s always an easy way out. And it’s almost never the right choice. Leadership is full of tough decisions. Some gut-wrenching. It’s the leader’s job to stare those tough decisions down. That can be hard. But even harder can be the idea of living with the decisions you’ve made. There will be consequences. Physics tells us that for every action there is an equal and opposite reaction. And tough decisions aren’t too different. You might get blowback. The decision may turn out to be a bad call. But you’ve got to make the decision—often with very little time to think through all the eventualities. Some decisions you can easily walk back if you need to. But there’s a good chance the toughest decisions come with no takebacks. You make your bed, you lie in it. Great leaders can make those difficult decisions … and sleep through the night afterwards.


You have internal leadership challenges. There are challenges that stretch your skills and abilities. But you could argue that the challenges that stem from communication top them all. So much can get skipped, jumbled or misinterpreted. And when there’s faulty communication, people will fill in the gaps with their own assumptions.

Communication presents plenty of leadership challenges. We’ve boiled it down to three.

A Business Meeting


Every time you gather a group of people and they bring their different backgrounds, experiences and feelings to the table, it’s a challenge to get them all moving in the same direction. That’s the life of a leader. And it’s one of the chief challenges in any organization. How do you make sure there’s common understanding of what you do and why you do it? How do you get everyone rowing the same direction, rather than following their own agendas? It’s critical for the success of your organization to have alignment with a common vision, purpose and understanding of what it means to win. And it takes continuous attention and communication to make it happen.


Finally, the elephant in the room. Any room. The drama that spills over when under-the-table agendas that drive so many unhealthy behaviors in our organizations meet each other in battle. When differences of opinion get personal. Or the healthy side of conflict, when what needs to be said finally gets said—even if it’s no less painful. Conflict is part of life. And it’s most definitely part of business. It’s also yet another chance for the limbic system to pull the ripcord on our fight-or-flight response—with the result that we either avoid conflict (which leads to problems) or dig in our heels for a good, old-fashioned brawl (which leads to problems). Effective leadership means embracing the fact that conflict has to happen—but that there’s a way for conflict to be constructive. It means tough conversations. Sometimes it hurts. But conflict can be incredibly healthy for an organization that’s willing to grow out of it. It’s up to you as the leader to steer conflict toward productive resolution.


Life isn’t all sunshine and rainbows. We all know this. But that doesn’t make it any easier to be the bearer of bad news. Things don’t always go as planned. Mistakes happen. Problems need to be addressed. Sometimes leadership means having to deliver the bad news about what went wrong or what needs to change. Sometimes it means being “the bad guy.” It can be challenging to be in that position. But it’s the leader’s calling to be clear and decisive. Empathy is important, but so is clarity and understanding. It’s hard work to be honest. To deliver information clearly. Bad news can be dramatic—it’s your job to deliver it and manage it in a way that stifles drama before it contaminates your culture.


Speaking of bad news.… Sometimes the biggest challenges come when the unexpected happens. A natural disaster. Economic upheaval. A failed product launch, catastrophic mistake or a losing season. Even a global pandemic. Those are the times when we most need to step up as leaders. And they’re the pressure-cooker moments that expose just how hard effective leadership can be. Crisis leadership can challenge you like nothing else. But it can also bring out the best in great leaders. Let’s unpack just a handful of the leadership challenges that rear their heads during tough times.

Business Members Collaborating At A Conference Table


It’s far too tempting to go negative. In a time of crisis, negative is probably how you’re feeling. But your team needs to see hope. Not false hope or foolish optimism—but it’s never hurt anyone to find the opportunities in challenges or the light in dark times. Exhibiting leadership in tough times takes an extra measure of patience and empathy. It means working more diligently to rally the team, find the lessons you can learn from adversity, and celebrate your wins. It takes vigilance against placing blame or finger-pointing. It’s a time to lean into sharing your purpose and vision even more. Teams look to their leaders as a beacon in difficult circumstances. As hard as it can be, you need to model the positivity they’re looking for.


It’s also tempting to sugarcoat things or withhold information. To take “staying positive” a step too far. Maybe there’s real danger to the organization, and you’d rather insulate your team from it. But far and away the best way to lead through a crisis is to prioritize clarity over comfort. Be real. Be transparent. It’s not the path of least resistance, by any means. But making the effort to shoot straight with your team, even if it’s not easy to hear, can only strengthen your organization.


Remember the fight-or-flight response? That’s where your amygdala—part of the limbic system, where we process emotions—goes on red alert in the face of danger, whether it’s physical or psychological. Times of crisis can be an absolute playground for your amygdala. So it can be an incredible challenge to stay calm—let alone model and encourage calm for all those in your care—when it feels like the wheels are falling off. But that’s exactly what your people need to see from you when the going gets tough. They need to see a leader who stays levelheaded during a crisis.


On the other hand, you are not a machine. You’re human. Your people understand that, and they need to see it. It can be simpler to turn off the person part of you and just deal with the challenges you’re facing as rationally and methodically as possible. There’s nothing wrong with that, really. But you are a person and the people you lead are people too. As difficult as it can be to admit, being human—and allowing yourself to be vulnerable, to be seen as human—can be one of the greatest examples you set for your team.


We’ve spent a lot of time talking about leadership challenges. All the fears, stresses and worries you face as a leader. How do you overcome them? Can you? Of course you can. And since the challenges start with you, overcoming them has to start with you, too.

A Woman Planning A Project On A Dry Erase Board


The better you are at making decisions, the better you can overcome the leadership challenges you’ll face. And how do you get better at making decisions? You have to start by understanding your own attitudes and beliefs, distilling them into a clear purpose for yourself and your organization, and making that the measuring stick for your decision-making. At InitiativeOne, we teach a Decision Frame that provides clear guidance for even your toughest decisions. It’s powerful because it starts at the very heart of who you are and why you do what you do. And it gives you a recipe for dealing with challenges in a way that’s consistent with your values, purpose and goals—as a person and as an organization. Here’s the basic framework:

  1. Get clear on your purpose. Define why you exist as an organization, and what it means to be at your best as a leader.

  2. Clarify your vision. Make sure you and your team understand what winning looks like.

  3. Define your values. What are the nonnegotiable, deeply held values that will lead to doing your best work, in the way you believe in doing it?

  4. Use your purpose, vision and values to guide your decision-making.

When you’re facing leadership challenges, it can be easy to become reactive. To just put out fires as you see them. But if you give yourself a clear framework for how you make decisions, in good times and in tough times, you’ll be able to handle challenges from a position of clarity and choice. You’ll stay aligned with the bigger purpose you’re aiming for. And you’ll be able to proactively deal with leadership challenges because you’ve already determined how you’ll approach them.


What’s the opposite of fear? The obvious answer would be the absence of fear. Or you might say it’s courage. But the opposite of fear isn’t courage … it’s action. Fear isn’t unhealthy until you let it run the show. That’s when our old friend the amygdala takes a little too much control and rational thought goes out the window. Fear-based leadership isn’t leadership at all—it’s where bad decisions happen. And fear isn’t always the same as being afraid. Many of us will likely say we’re not fearful. We’re courageous leaders, willing to take on anything. But here’s the secret … no matter who we are, how much authority we have, what position we’re in, deep down inside every one of us is really a scared little kid. We’re stressed out, unsure of ourselves, looking for approval, fearing failure. When we get honest about that, that’s when we can decide not to let it control how we act or how we lead. So, understand who you are. Acknowledge the fears and insecurities we all face. Then tell them to be quiet so you can get to work. Make a plan. Base it on your decision frame. Take action. The fear will have no choice but to get in the back seat.

Walking A Tightrope


Make a plan. Take action. That’s good advice. But sometimes there’s just too much to do. That’s where you need to take stock and set some priorities. There’s a concept called the Pareto principle, or the 80/20 rule. It’s a principle that says 80% of the effects come from only 20% of the causes. It translates into leadership, too. As a leader, 80% of your impact comes from 20% of what you do. That means you need to find that 20% that’s going to make the majority of the impact and put those efforts at the very top of your list. Think of everything that needs to get done. Everything on your plate. Now (mentally or on paper) rank them all on a scale from 1-10, where 1 is highest priority and 10 is lowest. Look at that list. There’s a lot there, but the Pareto principle tells us that only what’s in the 1 and 2 spots will really make the majority of the impact. Your 3s through 7s are worthwhile, and 8-10s probably don’t deserve much time at all—but those 1s and 2s are where the real difference can be made. The problem is, when we don’t assess our efforts in that way, we often end up spending far too much time on the tasks, projects or decisions that simply won’t have the impact to solve our leadership challenges. But when you prioritize your efforts to get the 1s and 2s done, that’s where you can really start moving the needle. Follow the Pareto principle. Don’t focus on just doing more. Focus on what you can do that will make the biggest impact.


If there’s one bit of wisdom you take with you from this article, make it this: your best work happens when you and your people feel safe enough to have the conversations that matter.

But that kind of psychological safety is a rare thing to find in most organizations. It takes work to create it. It takes commitment. It takes a willingness on everyone’s part to engage in authentic conversations. Building an environment of safety requires honesty and transparency. People will only feel that kind of safety in an environment of high trust.

How do you build that?

A good place to start is to get great at listening. You want to make sure your people are heard. They need to know they have a voice. They need to know they matter.

When your team knows that you’re listening, when they know their voice matters, great things can happen. They’ll be more engaged. They’ll care more, serve better and work harder. Not out of fear or compulsion, but because they know they’re part of something the whole team is working toward. Because they know you care about them and value them. You’ll all be pulling in the same direction—which means leadership won’t be about trying to push people harder to meet goals, but pulling them along by offering a vision and mission they can get behind.

When you’re all working toward the same goal, everyone knows their voice matters, and they see the support of leaders who believe in raising up those around them, that’s where you build trust. And trust creates a psychologically safe environment where your best people are happy to speak up, eager to push the ball forward and excited to take on any challenge together.


Leaders are learners.

Great leaders know that leadership isn’t about arriving at a destination or achieving a position. Leadership is about influence and impact, and that means it’s a journey that doesn’t end. The best leaders, the ones who are best able to overcome the leadership challenges that come their way, are the leaders who can adapt. They’re the leaders who never stop learning and always look for ways to improve themselves.

Great leaders are humble, hungry and smart. Great leaders have a mindset of continual growth. And when a growth-minded leader faces challenges, they can adapt, learn from them and come out on the other side even better equipped to tackle the next one.


I think you already know the answer to that question. We’ve identified some of the biggest hurdles any leader faces. We’ve talked through how to overcome them.

So much of being ready for the leadership challenges waiting for you is simply having a proper understanding of what leadership really is.

It’s not a position that makes you a leader. It’s not authority. Leadership is about impact—how you’re able to make rain in the lives of others. When that’s your starting point, you can create an environment where people are engaged. Where they care about each other, have real conversations and tackle challenges together.

“Leadership is a choice. It is not a rank.” —Simon Sinek

We began by talking about internal leadership challenges. You could make the case that almost everything we’ve talked about is a kind of internal challenge. Because great leadership always has to start inside your own heart and mind. It’s about choosing to look to the needs of others. Building up your team. Being the torchbearer for your organization’s purpose.

With leadership like that, no challenge can stop you.

A Woman Calmly Thinking


We know you have gained new insights and leadership questions to ask others on your leadership journey. If you are looking to take your team’s leadership to the next level, InitiativeOne can come alongside to help increase the effectiveness of your team.

There are several parts to this leadership transformation process provided by InitiativeOne, including a personal profile assessment, cognitive learning, group sessions with real-world challenges, personal discovery, and a toolkit to empower leaders to perform at their best.

There are really only two things stopping good teams from being great. One is how they make decisions and the second is how they solve problems. Contact us today to grow your team’s leadership performance by making decisions and solving problems more swiftly than ever before!


Recent Posts

See All


bottom of page