The Top Challenges You’ll Face at Each Stage of Your Leadership Journey

"If only I had known then what I know now.”

If you’ve been a people leader for any length of time, I’ll bet you agree with that statement. Every stage of the leadership journey—from frontline supervisor to middle manager to senior leader—is accompanied by its own challenges and pitfalls.

Whether you’re an individual contributor considering getting into management or you’re well established in your leadership journey, it’s important to be aware of common challenges you’ll face along the way. Knowing the terrain ahead will help you be prepared to successfully navigate whatever comes along.

The Problem

Before we explore these common leadership challenges, we need to acknowledge the elephant in the room: most people promoted into first-time leadership roles don’t have a clue what they’re doing.

The common practice for most organizations is to promote top individual performers into leadership positions. Unfortunately, companies typically don't do a good job of preparing these people for these roles. In fact, 87% of leaders wish they had received more training before assuming their new roles.

Being a high-performing individual contributor often doesn’t translate into being a great manager. The skill sets are completely different. Excellence as an individual contributor is being proficient at certain tasks and the corresponding skills; excellence as a leader is knowing how to help other people be their best. Being a great manager is tough work and it’s not for everyone. Recent research bears this out: only one in ten people have the qualities to be excellent managers.

Companies would do better if they proactively helped people explore whether they wanted to be leaders. Most workers figure the only way they can earn more money or achieve greater responsibility is to move into management—but that is exactly the wrong reason to start leading people.

So, what are some of the challenges frontline leaders, midlevel managers, and senior leaders can expect as they transition to their new roles? Here’s a closer look.

Challenges of a New Frontline Leader

Buddy to Boss

One of the first challenges for frontline leaders is the move from buddy to boss. It’s likely you will be supervising people who were once your friends. That means the dynamics of your relationships will change as soon as you get the promotion.

You're no longer going to be participating in the scuttlebutt. You're not going to hear the same kinds of conversations you heard before. You're going to be viewed differently. All these things change the tone of your relationships—and you need to be prepared for that.

You'll have to cultivate trust in this new role just by virtue of moving from buddy to boss. Your former peers aren't going to have the same level of trust in you simply because you’re no longer part of their group.

A New Type of Work

New frontline leaders must adjust to the nature of managerial work. Your calendar will no longer be your own and your work will become much more fragmented. Your days will be a little more chaotic because you’ll be dealing with the issues of the moment.

In comparison, individual contributors have much more control over their time. They typically manage their own calendar and their primary worries are about themselves.

Being a supervisor will bring a different mix of tasks and duties to your calendar. You'll be constantly ping-ponging from one issue to another. As a frontline leader, you’ll need to become much more diligent about how you use your time.

New Skills to Master

A different skill set is needed to supervise people. What made you a top individual contributor will not be terribly relevant to your new goals as a frontline leader.

If your organization doesn't provide leadership training, you should proactively seek out approaches to help you meet the demands of your new position. Exploring educational opportunities, reading books, or connecting with an experienced leader for mentorship are all viable strategies for building your competence as a new people leader.  

Challenges of a New Middle Manager

Cultivating Emotional Intelligence

Developing emotional intelligence is one of the first skills a new middle manager must cultivate. Your span of control will be greater than it was when you were a supervisor. You're probably going to manage both individual contributors and supervisors—and that means you must have a better understanding of yourself and your people.

Empathy is an important part of emotional intelligence. Some consider it the most important leadership skill. Good leaders try to understand and help their people. The pandemic has made this even more important. Everyone has struggled and suffered, and leaders need to show they understand and care by demonstrating empathy.

Developing Your Leadership Point of View (LPOV)

As a middle manager, you will have survived the supervisory phase. Now is the time for you to put a stake in the ground and say, “This is what I want to do with my career.”

Great leaders know what they stand for and share it with their people. They need to be clear about what motivates them, what they expect from themselves, and what they expect from others. Getting clear on your leadership point of view is essential to expressing your full potential as a leader and building a high-performing team.

Trust Dilemmas

There inevitably will be times as a middle manager when you are caught in the messy middle: having to uphold the trust of the organization while also advocating for the interests of your people. No matter what you do, you will likely be building trust with one party and eroding trust with the other.

You need to be prepared to handle these situations with integrity, transparency, and trustworthiness. You’ll have to turn these challenges into opportunities to build trust with both parties. It's difficult, but it's possible.

A helpful thought is to remember that great leadership is about relationships and results. The two must work in harmony. It is a dynamic equilibrium. Organizations go through different seasons. Sometimes there is a higher priority on results and sometimes there is a higher priority on relationships.

Challenges of a New Senior Leader

Role Modeling

Once you've transitioned into a senior leadership role, one of the biggest challenges will be becoming a role model for how people should behave in the organization. Senior leaders set the tone for what is acceptable and unacceptable behavior.

When you assume this senior position, you must be mindful of the behaviors you are role modeling because people in more junior positions will follow you. In fact, people in more junior positions may even subconsciously imitate your body language and speech patterns. When you are a senior leader, remember not to get so involved in the business of the organization that you forget the importance of relationships. People will be looking up to you.

Senior leaders are often viewed one-dimensionally. Many people will see you only on a stage or at an all-company meeting. They may form lasting impressions of you through this perspective. Senior leaders can become almost like cartoon cutouts to some employees. This places even more importance on developing personal connections with those you lead.

If you developed and presented your leadership point of view when you were a middle manager, it will really pay off when you become a senior leader. Ideally, you will have been sharing your story with people for quite some time, so most people will already know you as a person with hopes, dreams, and fears—just like them.

Shifting Mindsets

A change in mindset is necessary when you become a senior leader—the shift from a managerial approach to a feeling of being a leader of others. You will no longer manage individual contributors on their tasks—you will now lead people who lead people. The nature of your thinking will become more holistic, more strategic, and less tactical.

Culture Creators

Senior leaders are the standard bearers for an organization's culture. If we define culture as “the way things are done around here”—what's acceptable and what's not—it's easy to see how a senior leader’s behavior will set the tone. They cultivate the attitudes that people are going to bring to work.

Leadership is a Journey, Not a Destination

These are a few of the challenges leaders face as they climb the leadership ladder. But forewarned is forearmed. Now that you know the evolutionary progression of leadership, you can be prepared for the journey!