What Is the Biggest Challenge Facing Leaders Today? (In 2024 & Beyond)

Leaders face all sorts of challenges, on a yearly, monthly, and daily basis. It’s a part of work and life. In this post, I’d like to address the biggest challenge facing leaders today: difficult people. We’ll address who difficult people are, why they’re so difficult, and what leaders can do to more effectively deal with them. I’ll also provide a practical real-life example.

Who Are Difficult People?

To help us better identify this pervasive challenge that leaders face, let’s more specifically define who difficult people are.

Difficult people are those who act in dysfunctional, unhelpful, and uncalled for ways. While there are all different types of difficult people, they all share something in common: they aren’t team players, and they don’t have the best interests of their colleagues and/or the organization at heart.

Here are some of the activities of difficult people in the workplace and other arenas of life:

• Excessive criticism (not constructive feedback, but someone who knocks you down and insults you because they like doing it)
• Backstabbing
• Sabotage
• Lying and manipulation
• Saying one thing and doing another (lack of integrity)
• Stealing the credit for others hard work
• Bullying

This is only the tip of the iceberg, as there are countless ways that dysfunctional behavior will manifest in difficult people.

It may be painful to see and admit, but you may be working with a lot of difficult people right now. The first step is to be aware of people like this and know them for who they really are.

Why Are They So Difficult?

The biggest reason why difficult people are so dangerous is because they prevent team members from reaching their potential and the organization from reaching its goals.

Particularly nasty people will sometimes say when confronted, “But I’m getting my job done!”

Yeah, you’re getting your job done, alright…but you’re making the lives of everyone around you harder, and preventing the organization from succeeding at a higher level!

With difficult people, their cons outweigh the pros. But leaders will often keep difficult people in their roles because they don’t truly understand how much damage these dysfunctional people are truly dong.

The negative effects of difficult people are not always immediately apparently because the effects are often invisible. Difficult people create stress and anxiety in others. They ruin people’s careers by causing people to quit their jobs. And they sabotage people’s success by doing their best to make other people look bad.

These effects are very real, and they ending up causing organizations to lose money in the medium and long-run.

What Can Leaders Do To More Effectively Deal With Difficult People?

Now that we have a grasp on who difficult people are and why they’re so difficult, let’s discuss ways and strategies for leaders to more effectively deal with difficult people:

1. Talk to them directly: Provide them feedback to help them improve their self-awareness. If they don’t know how they are coming across to others, this may help. If it’s someone who is known to lie and manipulate, I’d suggest having a third person with you when you speak to them – otherwise they may lie about what was said behind closed doors. The goal in talking to them directly is not to try and change them; the goal is to simply make them aware of how they’re coming across to others.
2. Set up a reward system: Difficult people are the way they are because in some kind of warped way, they think their behavior works. When you see their behavior improving for the better, make it a point to both privately and publicly praise them. What gets praised and rewarded gets repeated.
3. Consult trusted colleagues, friends, and advisors on how to deal with this person or group of people: We can all use input and insights into our blind spots to provide us with useful ideas. You may feel alone at times, but you’re not in it alone.
4. Treat each situation as a unique case: As you work on providing feedback and setting up reward structures, remember to take each circumstance as it comes. Not everything can be prevented, and sometimes stuff happens. Do your best to dig deep into each person’s life by asking questions and showing interest: why are they the way they are? What are they struggling with both at work and in their private life? When you meet difficult people where they’re at, you just might be able to get through to them.
5. Consider taking legal action: There are varying levels of difficult people. In more extreme cases, with people who are severely difficult, the above tips may not work. Consider involving lawyers and suing them. Last year, in 2020, I faced two absurdly dysfunctional and difficult people who were literally hurting my health with their discrimination, demands, and threats. I involved lawyers and had a lawyer speak with them, and it worked like a charm: the difficult people backed right off.
6. Kill them with kindness: This is a controversial approach in that not everyone resonates with it. Before you say, “Nice people finish last”, please consider the words and research of author Adam Grant when he says that both kind and mean people are at the top. The approach of being kind works for me, as being mean to people never got me very far. But only do this if it works for you. When people’s true colors come out, this approach does not mean that you’re oblivious to their deceitful ways (as we said above, we need to be aware of who these people are). Instead, killing them with kindness is about disarming them and seeing the best in them, even when they don’t see the best in themselves. They may not deserve your kindness, but this is about the person you are choosing to be, not how they are showing up. Some practical comments and responses with this approach are:
   • “I know you’re a good person and wouldn’t be acting like this without a reason.”
   • “You’re smart and have a lot of potential. Let’s work together to solve this, as I value your input.”
   • “You’ve been through a lot in life and have every right to feel the way you feel. I’d love to see you succeed at an even higher level by putting your energy and efforts in the right places.”
7. If people refuse to adjust or meet you halfway after a couple of feedback sessions and nothing else seems to work, fire them: Both you and your organization will be way better off in the long run without a person like this draining people. If you are not in a position to fire them, involve others leaders in the company (worst case scenario – if it means protecting your sanity and mental health – find somewhere else to work. But first take action where you’re working).

Dealing With a Difficult Person in the Workplace: A Practical Example

In the first half of 2021, I contracted with a multi-billion-euro company. I’m happy to say that my boss’s boss, the Director, told me that I succeeded in the role and was very pleased with all the value I added to the company.

While in this contract, one of my colleagues was the quintessential difficult person to work with. Many others I spoke with shared this feeling. This particular difficult person was a bully. She worked by insulting and excessively criticizing others. Her specialty was in lying and manipulation, as she would say one thing in a video call and then later deny what she said.

I started sending written emails to her confirming what we spoke about after our calls, so that she couldn’t deny her words anymore and so I had written confirmation of what we discussed.

Another one of our colleagues left the company to advance his career, and a lot of that guy’s work came onto my plate because the company leaders trusted me. I was doing two jobs in one because a lot of people didn’t realize how much activity was buried in this one man’s role.

Now, back to the difficult coworker: she ended up harassing me on more than one occasion saying that I wasn’t doing enough to cover all of the guy’s work who left the company. I understood that she wanted the work done, but she wasn’t my manager and she wasn’t aware of all the other projects I was working on.

Things came to a culmination when one Friday afternoon, after an especially long and difficult week of reports, projects, and other fires to put out, she sent me an email demanding I do more work in an area that wasn’t really my main focus – with my true focus agreed on with my managers (I was reporting into the Senior Manager as well as the Director; this difficult person was Supervisor-level but not someone I reported into).

Up until then, I handled her antics quite well and maturely. This emotionally unintelligent, unempathetic, and fairly nasty email rubbed me the wrong way. I felt genuinely frustrated: this person was not only trying to dictate my work activities, but she was making my life harder and not acknowledging all the work I was doing.

I proceeded by emailing her, my boss, and my boss’s boss, explaining the context around how I was doing two jobs in one and working on all sorts of projects. I also asked that we resolve this, as it wasn’t the first time I experienced this rude and disrespectful behavior from my colleague.

In essence, I was providing her with feedback, while also encouraging her to align with my managers so that everyone could get on the same page.

She may not have been particularly pleased with my response, as she didn’t respond to me directly, but she did end up liaising with my boss and they discussed things further. I’m also proud of myself for involving the Director of the team, so he could see some of the challenges happening on the front lines.

From that point on, things improved in some ways. Thankfully, my manager took my side and acknowledged all the work I was doing in addition to the additional responsibilities I was asked to take on. I also improved communication with my difficult colleague, keeping her in the loop with all the things I was working on so that she would have a better understanding of the complexities of my role.

When I left the company after six months of insanely hard work, I left on a positive note with my difficult colleague and she was even sad to see me go.

Here are some things that may work when dealing with difficult people:

• Confront them honestly, and do so in a respectful way. Don’t stoop to their level by being rude and disrespectful like them, if you can help it.
• Communicate, communicate, communicate. I took a positive, life-affirming risk by taking this blunt, uncalled for email from my difficult coworker and involving my two bosses. I did that not to blow the situation out of proportion in any way whatsoever, but rather to identify root causes and seek to find solutions. The situation, while annoying and painful at first, led to better communication between me and my difficult colleague, between my difficult colleague and my boss, and between our team as a whole and our Director.
• Being kind doesn’t mean taking crap from people: I mentioned earlier how I’m a big advocate of the “be kind” approach. I stand by that completely. At the same time, please notice how I’m NOT advocating for you to be a pushover and take people’s crap. Be kind, but don’t fawn in front of bullies. It’s possible to be respectful and stand up for yourself at the same time. I’ve been working at finding this balance for years, and I’ve come up short many times, but the balance IS possible and you will find it if you keep on practicing.

I’d like to also point out in a humble way that there are times when respectfully confronting others and communicating with them will not work. While this colleague I told you about was indeed extremely difficult, I’ve encountered worse.

Some people are impossible to reason with. Some people don’t want to find a solution and they just want to fight with you for the sake of fighting. I’ll even say that some people in the workplace are mentally ill, taking their problems out on other people, without seeking the help they need. In cases like those, strongly consider involving Human Resources, legal help, and other third party resources.

Stay Strong, Fellow Leaders: There’s Hope for a Better Workplace and World

What we discussed here in this article is the beginning of the conversation. There’s so much here in terms of different kinds of difficult people and varieties of approaches and solutions.

What’s your take on this? How can leaders approach this huge challenge of dealing with difficult people? I’d love to hear in the comments below.

Jeff Davis is an award-winning author, most recently publishing The Power of Authentic Leadership: Activating the 13 Keys to Achieving Prosperity Through Authenticity. He’s an authentic leadership keynote speaker and Executive Coach to leaders and CEOs, offering individualized coaching. Follow him on Twitter. For three free books (The Power of Authentic Leadership, Reach Your Mountaintop, and Traveling Triumphs) in exchange for being added to his email list, email his Executive Assistant at meg@jeffdspeaks.com. This post is the tip of the iceberg when it comes to dealing with leadership challenges in the workplace – consider taking the next step by working with Jeff as your trusted advisor.