Just as leadership roles offer perks like higher pay and more room for delegation, they also come with bigger responsibilities—and risks.
One of the biggest pitfalls of being in a leadership position is that if a team crashes or botches a project, everyone turns to the leader for answers and often blames them for the damage. Where did they go wrong? Were they even ever right for the job? And if given the chance, what can they or their successors do differently?
To answer these questions and more, we’ll explore 10 common reasons why leaders fail, how to curb issues before they escalate, and real-life examples to learn from.
1. Leaders refuse to adapt
As your work and company evolve, you also need to change how you lead. If your company is headed in a new direction or has new team members, adapt your leadership style to that new environment.
If you make the necessary changes to how you lead your team, aligning their day-to-day activities to the company's new goals will be easier.
How leaders can adapt quickly and move with changing times
The key to mastering adaptability is to have an innovative mindset. Depending on the situation, this mindset could reflect in many ways, from being comfortable with ambiguity to staying curious, creative, and open to new ideas.
If an issue arises or you believe a task can be performed better or faster, develop a strategy and identify team members to help implement it. Don’t be so connected to a plan that you can’t let it go if it’s not working. Be honest enough to admit when something needs to change and work with your team to chart a new path forward.
2. Leaders stop navigating the team
When a leader is satisfied with the current state of the company and group, they stop directing people forward.
Leaders must share clear visions and goals to ensure everyone constantly delivers high-quality results for the company. Leaders have to set expectations, keep track of everyone’s progress, and hold themselves accountable.
How leaders can navigate their teams better
The most effective leaders are never satisfied with past glory or “just enough” effort. Instead, they plan meticulously for the future and prioritize teamwork.
This approach involves consistently updating individual and team-wide objectives and key results (OKRs) that are directly tied to business goals and will help move the needle. It also means encouraging your direct reports to ask for the support they need and holding one-on-one and general meetings with them to track their progress.
Take responsibility when things go wrong, share your OKRs with the team so they can hold you accountable, and be open to their feedback so you can get better.
3. Leaders are too reactive
Leaders need to be proactive, not just reactive. If you spend all your time putting out fires, you aren't using your time effectively. Proactive leaders influence the future and form the right alliances to advance their causes.
Of course, you should ensure your team gets all the answers and resources they need in the present, but don’t ignore the future.
How leaders can be more proactive
Proactive management is all about planning for the future so new developments don’t catch you unaware. It also involves anticipating challenges to minimize risks, exploring new opportunities, and looking for ways to reduce tension within your team before situations get a chance to escalate.
At the same time, proactiveness shows up in your commitment to gaining team members’ trust, identifying and solving problems, and preparing for emergencies like revenue loss or product glitches.
4. Leaders try to do everything themselves
Good leaders delegate tasks and ensure everyone on their team is learning and growing.
When leaders start to do the work they should be passing down to their employees or micromanaging their team members, they end up hurting themselves. They become stressed out because they are overloaded with work, and their employees get bored and want to leave.
How leaders can improve their delegation skills
The best way to delegate work is to trust your team members and give them a chance to prove their capabilities or fail fast (at the very least). Other key tips for getting better at delegation include:
Identify low-lift tasks you can delegate to avoid burnout, like taking notes, doing preliminary research, creating presentation slides, and more.
Avoid delegating high-level tasks that require your extensive input or unique expertise. If you want to create a critical report or conduct a performance assessment, it’s better to handle those types of tasks yourself.
Give clear instructions for the delegated task so you don’t end up with results completely different from what you expected.
The better your team members perform at delegated tasks, the more responsibility and compensation you can give them, creating a ripple effect of happy, satisfied direct reports.
5. Leaders stop prioritizing learning
Even the best leaders can lose their way if they stop learning. Leaders must be continuous learners to keep up with the challenging demands of today’s economy.
Your employees and those you meet outside of the office can help you make better decisions, and you listening to them is key. Ignoring what others say will make your job harder because people may oppose your decisions, and you might be left stranded.
How leaders can maintain humility
Many leaders become arrogant because they believe it is necessary to show confidence and ambition. Instead, it does the opposite. To prevent arrogance from getting the best of them, leaders need to understand that humility and ambition are not mutually exclusive—so they can take on a unique blend of both.
In the words of Bill Taylor:
“Indeed, humility in the service of ambition is the most effective and sustainable mindset for leaders who aspire to do big things in a world filled with huge unknowns.”
Want to earn your team’s support and get them to perform at their best? Adopt the servant leadership style. Focus on the work and people who help you get it done, not yourself. Stay ambitious and seek success, but when it comes, remain humble. Be grateful for everything you accomplish, and never entertain thoughts that glorify your personal efforts over teamwork.
6. Leaders focus too much on politics
Leaders have to play politics all the time at the office. They must do the right thing at the right time and make the right allies without angering too many people.
But this politicking tends to get in the way of productivity and makes them lose focus. Leaders should instead focus more on doing excellent work and managing their teams.
How leaders can prioritize their work over office politics
Great leaders curb office politics by re-evaluating their hiring processes and creating a company culture that rewards merit and de-emphasizes favoritism. This process involves cultivating values like transparency, communication, collaboration, and impartiality. Outline and reiterate these values on the company website, during the hiring process, and in team meetings.
By providing the right tools and support, leaders can also help employees enjoy their job and perform optimally—without worrying that they need to play politics to get ahead.
For instance, custom project management software will help you outline team goals and create automated workflows to achieve them.
You can also support team members by setting up monthly or quarterly anonymous surveys to discover what they like or dislike about their jobs and the work environment. Since the collection process is anonymous, respondents will be more willing to share their honest opinions, which you can use to improve internal operations and overall outcomes.
7. Leaders become selfish
Old, young, or new, all leaders are at risk of growing selfish. But unlike younger or new leaders who are usually energetic and enthusiastic, older or previously successful leaders tend to forget they are there to support their team, not themselves.
They become power-hungry and seek more control instead of giving advice, mentoring, and ensuring the team benefits from their leadership.
How leaders can avoid becoming selfish
Avoid the trap of selfishness by focusing on employee engagement, training, and collaboration. Meet with your team members regularly to outline goals, identify their needs and challenges, discuss potential solutions, and help implement them.
Also, operate an open-door policy or run weekly office hours to collect feedback, answer questions, and plan accordingly. You’ll win your team’s trust and foster a work environment conducive to productivity.
8. Leaders don’t give or accept enough criticism
It’s very easy for leaders to try to please everyone and befriend coworkers, but that’s not always effective. You have to take a step back and look at the weaknesses of your team and talk to them about what they can improve. If all you do is compliment everyone, you are doing them a disservice.
At the same time, you should accept criticism from them. Some of your leadership tactics might not be best for the group. It’s your call to create an environment where your colleagues can give you feedback without fearing that it will backfire on them.
How leaders can use criticism as a tool for growth
When team members or direct reports perform poorly, don’t ignore the signs to avoid conflict or speak to them abrasively. Instead, take a holistic look at the situation to identify what caused the problem, what role you may have played in it, and how other colleagues influenced the situation.
Once you have a solid hypothesis, approach the erring team member and have an open, non-judgmental discussion with them to discuss the challenge and ways to improve going forward.
And if you’re the one who’s on the receiving end of criticism, accept it with grace. Don’t see yourself as a victim or react hastily to avoid the feeling of inadequacy that comes with getting negative feedback. Review the criticism, own your mistakes, and respond respectfully and thoughtfully. That way, you can assess the situation and plan for better outcomes next time.
9. Leaders don’t understand self-leadership
You have to know yourself, control yourself, and communicate your core values, expectations, and beliefs. You need to understand your strengths, weaknesses, and goals to give your best self to your team and find fulfillment.
How leaders can lead themselves effectively
Self-awareness is key to leading yourself effectively. Once you’ve identified your values, strengths, weaknesses, and goals, it’s time to use them to your advantage and that of your team. Ask yourself the right questions:
How can I improve myself?
What areas can I apply my current expertise to?
Who do I know (internally or externally) that can help us achieve our current team goals?
Answering these questions honestly is a great first step to building yourself up and sharpening your leadership skills to foster a more productive, growth-oriented team. Conduct this self-assessment continually instead of on a one-time basis, so you can keep improving yourself.
10. Leaders don’t communicate well
If you want to lead a team, you must constantly communicate with them and ensure they are all in the know. You can use Zoom, instant messaging, email, and team meetings to get your message across, but the important part is that it gets there.
If you don’t communicate effectively, people won’t know what to do next or where the group is heading.
How leaders can improve their communication skills
No matter how knowledgeable a leader is, poor communication skills can bring them down if left unchecked. Key tips for communicating effectively and sharing information include:
Asking questions and listening attentively
Acting on feedback from your team members or customers
Illustrating your points through stories, videos, or presentations
Collecting different points of view before making team-wide decisions like restructuring, expansion, tool migration, and more
Picking your battles—determining whether you need to add to a conversation or delegate to someone else
3 examples of leadership failures to learn from
One main reason why leaders fail is that not everyone is meant to be a leader or a good fit for the role. Some people are just more effective as individual contributors—and trying to fit a square peg into a round hole becomes their undoing.
To illustrate the importance of good leadership and what happens when leaders err, consider these three leadership failure examples.
Ron Johnson and the JCPenney saga
JCPenney is one of the oldest retail chains in the United States at over 100 years old. In 2011, the company hired Ron Johnson as its CEO, banking on his past successes at Apple and Target to turn around its dwindling fortunes. Unfortunately, Johnson did, however unintentionally, the opposite of that.
One of Johnson's most notable and crippling changes at JCPenney was to cancel all sales and discount prices, replacing them with everyday low pricing. He allegedly implemented this strategy without testing it on a small sample size or performing customer research to gauge the potential consequences.
The result? Customers didn't appreciate losing their special deals, and the company's sales dipped significantly. Yet, Johnson insisted that coupons were like drugs that customers needed to be weaned off. By the time JCPenney fired him in early 2013, the company had recorded (and continued to record) millions of dollars in net losses.
While some believe the changes could have worked if he had rolled them out gradually instead of all at once, we may never know. What we know, though, are his mistakes and what he could have done differently with the benefit of hindsight.
The mistake(s): Overconfidence and refusal to adapt
The lesson for leaders: Before implementing a new strategy, study your audience, test it out with a small group of customers, and get input from experts who’ve been in the industry longer than you. Also, be honest with yourself if a plan is not working and go back to the drawing board to re-strategize while you still have the chance.
Martin Winterkorn and Volkswagen’s Dieselgate scandal
In 2015, Volkswagen faced backlash from the United States Environmental Protection Agency when it found that the car manufacturer was cheating on US pollution emission tests.
As a result, many questioned what could have led to such an oversight or intentional misconduct, surfacing the conversation on company culture at Volkswagen. Some executives under the then-Volkswagen CEO Martin Winterkorn claim that he created a culture of fear and respect, making him hard to approach or disagree with.
About five years after the scandal (in 2021), an investigation also found Winterkorn guilty of responding poorly to signs that the brand was using illegal diesel engine technology. Volkswagen also reported that he didn't answer quickly and truthfully to questions about the scandal in 2015, suing Winterkorn and securing a $14 million settlement from the former CEO.
The mistake(s): Arrogance, lack of proactiveness, and poor communication
The lesson for leaders: Don't enable ethical breaches or illegal activity to boost sales numbers; it backfires woefully. Also, create a safe environment for your team to disagree with you and be willing to accept feedback and criticism. And finally, be proactive by having a crisis management plan and being as transparent as possible to avoid current and future liability.
Jørn Utzon, the Australian government, and how the famous Sydney Opera House came to be
In 1954, the Australian government decided to build an opera house in Sydney, South Wales. It held a competition in 1956 to choose the best design for the project, and 38-year-old architect Jørn Utzon won the contest.
The original plan was to complete the project with an AUD $7 million budget within a four-year timeline. What the judges and government didn't consider was Utzon's inexperience, their own lack of engineering knowledge, and the need for a cooperative, well-versed project management team.
After much back and forth, with Utzon himself leaving the project after a few years, the Sydney Opera House was finally completed—14 years later and having swallowed up a whopping AUD $102 million. The building itself is a masterpiece, and the Australian government made its initial investment within two years of opening it for business. Still, there are many leadership lessons to be learned.
The mistake(s): Poor communication, weak project management, and arrogance (in the form of not acknowledging shortcomings/lack of expertise)
The lesson for leaders: When starting a new project, look at the big picture from all angles before zooming in on the details. Identify everything you need to succeed, including the qualifications of your team members, your own knowledge gaps, the necessary tools, and the step-by-step process you’ll take. This approach will also help you set a realistic timeline and budget from the get-go.
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