Tag Leadership Challenges

Leading Difficult People

Steve Keating Leave a comment

If leadership was easy then everybody would be doing it. The fact is, leadership is not easy. It’s not easy because leadership is about people. People come in all shapes and sizes. They bring with them all kinds of backgrounds and upbringings. They carry with them past experiences, good and bad. Sometimes they even bring with them a chip, one they carry on their shoulder. Those “chips” can make them a unique challenge to lead.

But leading difficult people is part of the package a leader accepts. Leading difficult people can be a challenging but essential skill for effective leadership. Whether you’re leading a team or working on a project, dealing with difficult individuals is a not an uncommon occurrence.

But nearly everyone can be led to success if the leader is willing to hang in there with them. Here are some ideas to help you hang.

• Start by trying to understand the difficult person’s point of view. Ask questions and actively listen to their concerns and motivations. Often, people become difficult when they feel unheard or undervalued. Empathy is a powerful tool for building rapport.

• When dealing with difficult people, it’s important to maintain your composure. Don’t let their behavior provoke you into a reaction that you might regret. Take a deep breath, stay patient, and remain level-headed.

• Clearly communicate your expectations for their behavior and performance. Make sure they understand their role and responsibilities, as well as the consequences of not meeting those expectations.

• Consistency in your actions and responses is key. Make sure you treat all team members fairly and equally. This helps prevent any perceived favoritism or bias that can lead to conflict.

• If a difficult person’s behavior is disruptive or problematic, address the issues in private rather than in a public setting. This allows them to save face and reduces the chances of escalation.

• Provide feedback that is specific, objective, and focused on behavior or actions rather than personal characteristics. Use the “I” statements approach to express your feelings and concerns. For example, say, “I felt frustrated when you missed the deadline” rather than, “You’re always late.”

• Clearly define the boundaries for acceptable behavior within the team or organization. Enforce those boundaries consistently and fairly.

• Look for areas of common interest or shared goals and use them to build rapport. Finding common ground can help bridge gaps between difficult individuals and the team.

• Encourage difficult individuals to develop their skills and work on self-improvement. Offer training, coaching, or resources to help them grow and address their problem areas. Make their faults seem easy to correct.

• If necessary, involve HR or a higher-level manager to help mediate or address more serious issues. They can provide guidance, support, or disciplinary action if required.

• Keep records of problematic behavior and interactions, including dates, times, and descriptions. This documentation can be helpful if you need to escalate the issue or if it becomes a pattern of behavior.

• Sometimes, a person may be difficult due to external factors such as personal problems, stress, or health issues. Consider the context and be open to offering support or accommodations when appropriate.

• Changing behavior or attitudes can take time. Be patient, but also be persistent in your efforts to lead and difficult individuals effectively.

The sad reality is that not all difficult people can be transformed, and some may need to be led differently. In extreme cases, they may need to be removed from the team or organization to maintain a healthy working environment. Your approach should depend on the specific situation and the impact of the individual’s behavior on the team’s overall performance and well-being.

Redirecting someone to another organization or another role is not the most rewarding part of leadership but it is a mighty important one. Ignoring a difficult team member and hoping they will improve or simply “go away” is not leading.

If you’ve accepted a leadership position then it is imperative that you Lead…Today!

Your Leadership Journey

Steve Keating 8 Comments

I am always a little surprised when someone refers to me as an “authority” or “expert” on leadership. While I certainly appreciate the respect they are showing me by describing me with those words I know otherwise. 

 

I know some stuff about leadership but I also know that I know a tiny percentage of what it’s possible to know. I know too that neither I nor anyone else can ever come close to knowing more than that small percentage. 

 

Since leadership is about people and only people it’s impossible to truly be an “expert on leadership.” People will always surprise you. You can predict with some accuracy what people will do based on their past performance but never with enough accuracy to be a true expert. 

 

People are unique, they are actually even unique from themselves depending on the circumstances in their life at any given time. 

 

That’s what makes leadership so fascinating. It is what makes leadership so rewarding and it’s what makes leading so challenging. 

 

When someone else tells me that they are a leadership expert I am more than skeptical. I have only heard a couple of people describe themselves as an Authentic Leader. The moment the words came out of their mouth I was pretty certain they were anything but authentic. 

 

It’s kinda like when someone offers a class on humility taught by an “expert” on the subject. As soon as someone accepts the description of themselves as an expert on humility they are no longer humble enough to speak about it. So it is with leadership!

 

Authentic Leaders know that their journey to leadership excellence will never end. Authentic Servant Leaders know that helping the people they lead must always be the purpose of that journey. 

 

If you’re not constantly working on your knowledge of leadership then you run the risk of falling behind other leaders. If you’re not always developing your leadership skills then you run the risk of losing the people you would lead. 


Learning about all things leadership never stops for the best leaders. If you didn’t learn something new about leading others yesterday then you had best double your efforts today because if you’re not learning then you’re not leading.

Leading from the Front

Steve Keating 3 Comments

Most commonly leaders lead from the front. There is nothing wrong with that, usually. But, if you’re only leading from the front you run the danger of getting too far out in front of your people and when you turn around there’s actually no one there anymore. 

 

Authentic Servant Leaders never outrun their people in their rush to succeed. 

 

Hopefully you’ve found yourself in a leadership position because in some way, or perhaps many ways, you have outrun your competition for the position. If that’s the case then one of the first things you need to do upon becoming a leader is slow your roll. Stop trying to outrun everyone else, the race is over. 

 

If you consistently outrun the people you’re supposed to be leading it won’t be long before you’re leading no one. You may have incredibly high expectations for yourself but it is a mistake to transfer the expectations you have for yourself to everyone else in your organization. 

 

They may not be as committed as you are, they may not have the same skill level as you, they may value “life balance” more than you and there are a hundred other things that could cause them to not keep up with your pace.

 

As a leader it’s your job to help them exceed their expectations for themselves and overcome any artificial limitations they may have. But…. and this is big, setting unrealistic and unreasonable expectations for your people will cause them to fail as surely as having no expectations at all. 

 

Authentic Servant Leaders lead from the front and pull their people to success, they occasionally lead from the rear and push their people further than they thought they could go. Most often however, Authentic Servant Leaders lead from the middle. It’s leading from the middle that allows a leader to come along side of their people and coach them to success. 

 

When a leader coaches their people to success they ensure that their leadership legacy outlasts their leadership. When a leader leads from the front or rear they tend to make more and frankly, better followers. But Authentic Servant Leaders know that true leadership success means making more than just followers, it means making more leaders.

 

That requires being close to your people. It requires that you never get so far out in front of them that they lose sight of you. It would be simple to say that if your people can’t see you then they can’t follow you. But the fact is if they can’t see you, hear you, and even feel you then they can’t learn from you. 

 

You can’t grow your organization without growing your people. You can’t grow your people by separating yourself from them. One of the fastest ways to separate yourself from your people is to outrun them.


Stay close to your people, never think of them as slowing you down. Think of yourself as the leader who helps them move forward as fast, but never faster, than they possible can. 

The Challenge of Frustration

Steve Keating 26 Comments

Recently I had the opportunity to discuss leadership with a group of mid-level managers. At the end of my presentation I was approached by a significant number of the attendees who all had the same question.

 

The questions, while asked differently all had the same theme: what do I do when my “leader” isn’t a real leader at all?

 

The answer to that question is simple and complicated all at once. I’m assuming (I know that’s dangerous) that the people asking the question are truly leaders. That means they care about the people they lead, they understand that their own success is completely dependent upon the success of the people they lead and that they get as much pleasure from their people’s success as they do their own. 

 

If that is the case then the answer to the question is this: Lead Up.

 

Lead your leader the same way you lead your followers. Realize that your leader is a person too, realize that they, like every other human being on the planet, have their faults and limitations. 

 

The most Authentic Leaders lead in every direction, down, across and up. That means that instead of criticizing the person above you, which accomplishes nothing, you should be trying to help them overcome their faults and limitations. You can coach them the same way you coach others, you can demonstrate that you care about them the same way you demonstrate that you care about others. You can invest yourself in their success as if their success was your own…because for an Authentic Leader it is.

 

But…and this is what makes it complicated, before you can do any of that you must earn the right to lead up. 

 

Earning the right to lead up requires that you lead yourself exceptionally well. You must have the trust of the person above you to lead up. You earn that trust by being completely transparent with your leader. You don’t say one thing to them and then something else to your followers. You do what you say you will do 100% of the time. You display the same integrity upwards as you do across and down. (just an aside here, you either have integrity all the time or you don’t have integrity any time)

 

You must lead yourself in such a way that the person above you does not feel as if you require much help from them. You control your own attitude and keep it positive as much as humanly possible. You choose your words well and seldom just spout off the first thing that comes to mind. 

 

And then there’s this…you let them devour your ego food!

 

You allow them to sometimes, often, or even frequently take your success as their own. (I told you this was complicated) You take on assignments that your leader may receive credit for doing, you do more than you are required to do knowing full well that “others” may never know it was you who accomplished so much. 

 

I know from personal experience how truly challenging and frustrating that can be but here’s a question for you: are you leading to lead or are you leading for some type of personal glory?

 

If you’re leading to lead that means you lead because you want to make a difference; your motives are not selfish they are selfless. That’s a huge difference that allows you to feed your own ego even after giving much of your ego food to someone else. 

 

YOU know what you did and if you’re truly leading to lead, if you’re truly leading for the benefit of others and not yourself, then that is enough. More than enough actually. 


Leadership comes from many levels within an organization, it also goes in many directions. If you’re experiencing the frustration that comes with following a leader who doesn’t lead then do what real leaders do, stop complaining and start leading…today.


The One True Prerequisite of Leading

Steve Keating 1 Comment

You must have a follower!

 

No matter what your title happens to be, no matter how lofty your position may be within your organization if no one is following you then you are not leading. Period!

 

It’s probably the number one leadership mistake I see and I see it often, very very often. People believe that it’s their title or position that makes them a leader. This misnomer is especially common with people new to a position of leadership. 

 

But here is the absolute fact: titles and positions on an organizational chart do not make you a leader. The people following you make you a leader. 

 

You can be promoted to a position with a fancy title that makes it sound like you are a leader but you must earn the right to truly lead. No one, absolutely no one can promote you to the position of Leader, that can only come from the people you would lead and you must constantly demonstrate that you’re worthy of it.

 

The fastest way to demonstrate that is by showing your people that you care about them. Bringing donuts to the meeting is nice but a drone could do that. 

 

Showing you care requires that you connect with your people in a meaningful way. If you’re in a leadership position then I have some questions for you… How much do you REALLY know about the people you claim to lead? Do you know their goals, their needs, their hopes and desires for their future?

 

Do you know what their life struggles are outside of work? Did you ever consider those struggles may affect their work performance? Did you ever consider that maybe, just maybe you could help them, coach them or perhaps just offer them someone to talk to?

 

Leadership is about people and to earn the right to lead you’re going to have to be willing to SHOW you care. You must be willing to invest a piece of yourself in someone else’s life. You see, when you make a difference in your business you’re a manager and that’s great but when you make a difference in the life of someone else you’re a leader and that’s better, much much better.


If you’re in a leadership position it’s a good idea to turn around once in a while to see if anyone is really following. If they are not then it’s possible, actually likely that the people who could be following you have decided that you simply don’t care enough to truly lead.


Mind Your Gaps

Steve Keating 5 Comments

I had the opportunity several years ago to sit in on a presentation to a group of senior leaders. The presentation was from a speaker who uses Civil War history to teach leadership lessons. 

As someone who was required to take Military History as part of my high school curriculum I can tell you that military battles offer great insights into leadership successes and failures. I was excited to hear the presentation. 

The presentation focused on The Battle of Gettysburg which began on July 1st, 1863. During the first hours of battle, Union General John Reynolds was killed while leading his troops from the front. Outnumbered, the union forces were stymied for a time and it took awhile for them to regroup.

After sharing the story of the early hours of that famous battle the presenter asked the assembled group of senior leaders whether or not General Reynolds made the right decision in leading from the front. He had exposed himself to enemy fire and left his troops without his leadership as a result.

The leadership team in the room had differing opinions as to the wisdom of General Reynolds decision. Some thought it better if he had “lead from the rear” thus protecting himself from direct conflict. They felt that he jeopardized the mission by putting himself in harms way. You could see their point considering that his death did seem to slow down the union forces for a time. 

Others thought he showed true leadership by putting himself out front. Their point was that a leader shouldn’t ask their people to do something that they as a leader were unwilling to do. They also pointed out that since the Union forces eventually won his decision was proven correct. Also a good point. 

But here’s what I truly found fascinating; most had an opinion. They had this opinion in spite of having very little actual information about how the battle unfolded. There were a lot of “gaps” in the story of the battle as presented. (I’m sure the presenter did that mostly in the interest of time)

So how did this room full of top leaders come to an opinion with so little information? How did they know if General Reynolds had made the right decision despite the “gaps” in the story?

They did what all leaders, all people actually, do when they need to make a decision without all available information….they filled in the gaps with information from their own experiences. 

As I observed these key leaders offer their opinions I knew immediately which ones would accept risk in a decision and which ones would be more cautious…perhaps too cautious to lead in difficult circumstances. 

Those who believed that Reynolds had made the right call were willing to accept some level of risk and those who thought he had made the wrong call likely were not willing to accept that same level of risk. 

If time had permitted and the presenter had filled in the gaps himself then the audience wouldn’t have needed to supplant the story with their own experiences. In that case I really would not have been able to assess their appetite for risk. 

That same scenario plays out in business all the time. Leaders and their people make decisions even when they don’t have all the information that they wish they had. They simply use information from their own life history to fill in the gaps. 

That’s why two smart people, presented with identical, if incomplete information, can reach such differing conclusions. 

As a leader it is imperative that you know you’re people well. The better you know them and especially the better you understand them, the better you’ll understand the information they use to fill in their gaps. 

It’s also vital that you understand where your own “gap filling” information comes from. 

Understanding how both you and your people mind their gaps will help you see how two very different conclusions could both seem correct. 

Now, as to General Reynolds…the only mistake we can actually confirm he made was getting himself shot. As a good military leader he knew full well that his ultimate goal was not dying for the North, his ultimate goal was making as many Confederate troops as possibly die for the South. 

In that effort he failed completely.

The Evolution of Leadership

Steve Keating 8 Comments

Geez, I’ve seen a bunch of posts and articles lately on the “evolution of leadership.” It seems a fair number of people are falling into the trap of believing that leadership needs to “adapt” to the “times.” 

Well, that just ain’t so!

Certainly some, just some, of the tactics of leadership change through the years. The well documented generational differences dictate that change. Generally speaking, very generally speaking, the motivational triggers of the different generations vary, but not as much as many  people think. 

Given those variances good leaders adjust. But they don’t adjust to trick or manipulate, they adjust to deliver motivation, discipline, and vision in the manor in which it is best received. 

While some leadership tactics change the core leadership principles and strategies do not. 

They don’t change because leadership is about people and people haven’t really changed….ever.

The basic human needs, as described by Maslow’s hierarchy of needs have never really changed. Humans as it turns out are human. It doesn’t make a difference when they were born, where they where born, what sex they are, what color they are, or if they are rich or poor, humans are human. Every single one of them.

Leaders don’t lead businesses, (businesses are managed) leaders don’t lead countries, (countries are governed) leaders lead people, nothing more and nothing less. Those people also happen to be human.

Leaders get in trouble when they forget that very basic fact. 

One of the biggest reasons that people dislike change is because they see change as a threat to one or more of their basic human needs. A leader understands that just because it might not make sense to the leader doesn’t mean it isn’t very real to the person they are leading. 

Here’s another thing that can cause challenges for a leader. While human beings basic needs are much the same no two people are exactly identical. Even identical twins would be better described as “more similar” than most people. Understanding the differences of the people you lead is what makes leading so interesting and a constant learning experience.

Great leaders understand the sameness of their people’s basic needs to develop leadership strategies and learn the unique aspects of their people’s personalities to develop the tactics of successful leadership. In both cases they never forget that they are leading people not things.

That’s why the most important skills for a leader to have are people skills. They always have been most important and they will always be most important. Because leadership is about people! 

That’s never changed and it never will.