Business Leadership Today

10 Reasons Why Leaders Fail


Jeff Skipper, Contributor

“Hey, if you’re looking for Phil, don’t bother. He’s been assigned to a ‘special project.’ No one knows what he’s working on. He must have had a major screw-up.”

Executives regularly tell me they can’t figure out what a peer could have been thinking when they went off the rails. So they say goodbye or relegate them to a far-off corner of the organization where they can’t do any major damage. 

In over thirty years of consulting with leaders in every industry, I’ve seen pretty much everything—leaders who’ve failed to adapt, leaders who’ve chosen to be reactive instead of proactive, and leaders who’ve lost sight of the vision, leaving their team members without a clear path forward. 

Leader failures are never about just one thing but result from an accumulation of missteps, all of which are completely avoidable. To understand how to succeed as a leader and build teams that are equipped to succeed, we have to gain an understanding of how these failures occur. 

When leaders fail, it’s usually because they:

  1. Failed to define success
  2. Received feeble feedback
  3. Neglected to communicate with others
  4. Forgot to say “sorry”
  5. Hired last year’s skills
  6. Underutilized the team
  7. Created a disconnect
  8. Lost touch with the frontline
  9. Ran inefficient meetings
  10. Ignored the environment

Here are my insights into the top 10 reasons leaders end up failing and what they can do to avoid these common mistakes.

1. Failed To Define Success

When I’m asked to help a leader out with a project, my first question is, “What’s the objective?” Half of the time it’s vague or undefined: “We just need to do this!” 

For some, that is intentional to avoid being held accountable for the results. If there’s no target, they can’t fail, right? Wrong. It just means you will be accountable to everyone else’s definition of success.

Most people simply haven’t thought through exactly what success looks and feels like. 

To help them clarify the goal, I ask: What will people be doing differently when success is achieved? What does the future look and feel like? What are the stats? What will customers be saying? And, most importantly, how will progress fulfill the organization’s strategy?

Employees want to follow leaders with an objective and a plan. Clear goals make it easy to create a roadmap, declare success upon arrival, and determine when a leader is headed for failure.

2. Received Feeble Feedback

Even when goals have been made clear, without feedback, it’s difficult to know when you are getting off course. Quality feedback improves communication and decision-making and is essential for continuous improvement and strong, trust-based relationships.

Wise leaders regularly check in with their superiors to see how they are doing. Because some are hesitant to give feedback, it’s important to invite constructive criticism; it demonstrates that you are focused on contributing. 

If you’ve created positive, trusting relationships with your team, they should be a good source of feedback for leaders as well. Ask them, “If you could change one thing about the way we work together, what would it be?” 

If they hesitate to give feedback, or if the feedback is all positive, there is likely fear in the team. This is why you should use an anonymous survey. Thank everyone for their honesty, and let them know what you are putting into practice. 

3. They Communicated With Themselves, Not Their Audience

Read the last request you sent out. Now put yourself in the shoes of one of your team members. Are they getting everything they need to act? Could they misinterpret your request and do the wrong thing? Have you provided an explanation that they really don’t need to get the point? 

When leaders don’t communicate effectively with team members, it can lead to potentially serious organizational issues. The workplace culture can become dysfunctional, leading to a decline in trust and commitment.

A lack of access to reliable and up-to-date communications can cause team members to become increasingly frustrated. This can end up hurting performance because team members aren’t being equipped with the tools they need to perform their jobs effectively and efficiently. 

When this happens, team morale can take a nosedive. This can lead to a decrease in morale and motivation, potentially turn cultures toxic, increase conflict, stress, and absenteeism, and ultimately hurt productivity and retention. 

To avoid the snowball effect of poor communication, leaders should develop their communication abilities and dedicate part of their daily routine to interacting with their team members and providing them with current information so they have the clarity they need to do their jobs effectively and with confidence. 

Clear, concise communication that highlights action items, available resources, and expected outcomes helps the team help you.

4. Forgot To Say Sorry

We all make mistakes. Sometimes we get upset and angry with people. We lose our heads or check out for a while. People expect more of their leaders, and while we can’t meet everyone’s expectations all of the time, we can apologize when we’ve stepped out of bounds. 

Interestingly, loyalty increases when leaders admit mistakes and ask for forgiveness after an incident. When leaders admit their mistakes and ask for forgiveness after an incident, it improves trust and respect among team members. 

This kind of openness, vulnerability, and humility can significantly enhance loyalty within the team and throughout the organization. It demonstrates the leader’s integrity and commitment to learning and growth, which can inspire similar values and behaviors in team members.

We can all relate to people who make mistakes. A bit of vulnerability can generate a ton of goodwill. It makes people more willing to help leaders be and stay successful.

5. Hired Last Year’s Skills

The best leaders hire people who are smarter than themselves. It sounds like a good way to lose your job, doesn’t it? Top performers can be threatening to leaders who are insecure about the value they deliver to the organization.

The truth is that leaders can only deliver at high levels by leaning on the skills of the team. They recognize that loading the deck with the best possible performers pushes the whole team—including the leader—to learn, adapt, and perform at increasing levels. 

Leaders should not stack their teams with people who aren’t going to move the needle; they should hire people with the talent to take the organization to the next level—and beyond. Hiring people who bring diverse skills and perspectives to the team can make collaborative efforts more productive, increase innovation, and bring organizations closer to achieving their vision. 

Of course, hiring the best skills means having an understanding of what will be required in the future. It means having clear goals and a definition of success. Sound familiar?

6. Underutilized the Team

Let’s assume you’ve been hiring good people with strong skills. Time to relax and let them make you look good! If only. 

A wise person once told me to “Shine your stars.” Those who have the capability to excel should be given the opportunity to grow and acquire more responsibility. Top performers will not stick around if they don’t feel they are being used well. 

Sure, Sam may be the best report developer you’ve ever met, but what if Sam has seven other hot skills that she never gets to apply? She learned them for a reason. She wants to shine. When a job opportunity comes her way that uses more of her skills, she’s going to give it serious consideration. Departures do not spell success. 

Do you know all of the skills your team members have? Have you asked them if they would like to contribute more? 

Involving your team in increasing levels of planning, decision-making, and responsibility is an easy way to motivate and develop people. It reinforces your capability as a high-performing developer. The flipside is failure. A lack of opportunity is the number one reason people leave their jobs.

7. Disconnected Measures, Actions, and Consequences

What gets measured gets done. Measures direct attention. Rewards and consequences are tools for shaping behavior. When leaders fail to apply them, employees are left to guess where to focus their efforts and how to deliver. 

Worse yet, when leaders fail to sanction unprofessional behavior—dishonesty, negligence, personal attacks, insubordination—it sends a message that those behaviors are acceptable. 

Coaches of the best teams tell their players what they are doing right and help them improve by keeping a careful eye on performance. Immediate rewards and consequences drive the right behaviors.

8. Lost Touch With the Frontline

People don’t follow leaders they don’t believe in. Credibility matters. The CEO of Starbucks committed to working as a barista once a month. I work with a CEO who goes on rides with his delivery team. They know what their people are experiencing.

Getting to know the challenges customer-facing employees face can improve engagement, performance, recruitment, retention, and decision-making.

Leaders are better able to understand the needs of both employees and customers when they spend time with frontline workers. Interactions with frontline employees provide leaders with much-needed feedback and insights into where pressure points are in the organization and where improvements need to be made.

Credibility accumulates when leaders deliver on their promises and demonstrate they understand what life is like for those on the front lines. They’ve witnessed the joy of happy customers and felt the pain of frustrating systems and processes. Consider how powerfully your strategy will inspire action when you can illustrate how it works by drawing upon real-life stories. 

Start small. Begin by taking members of the frontline for coffee and begin building relationships. Then join them on the job. 

9. Ran Inefficient Meetings

Do your meetings always utilize the entire time scheduled? If so, it’s a sign that you are not using the time effectively. In the process, you may be wasting the time of employees.

Well-run meetings have a higher probability of accomplishing goals quickly. Unfortunately, most meetings are horribly inefficient. 

At the beginning of 2023, Shopify wiped out the majority of meetings from people’s calendars and gave strict rules for booking any new ones, backed by a calculator that demonstrates the cost of each new meeting. The radical change sparked a renewed focus on booking meetings for the right reasons, including only those needed to make decisions. 

Earlier advice for defining success applies to meetings, too. Set meeting objectives and an agenda that is focused on action, getting you to the results you want. 

Beware of FOMO: those who fear missing out can be informed of meeting outcomes by email, so you can include only those whose input is required to help make decisions. And when the meeting objectives are met, wrap it up. Your team will thank you.

10. Ignored the Environment

The pace of change is increasing rapidly. Everyone knows that. And yet, because our brains love stability and predictability, it’s easy to ignore change and hope it passes us by. 

The pandemic was a great example. Black Swan events have been predicted for years, a pandemic among them, and yet most leaders stood still while the world shut down around them. 

Those who took action profited. Small businesses that quickly transitioned to online sales and curbside pickup captured market share with a public desperate for easy meals and socially-distanced purchases. 

Failure happens when leaders assume that the status quo will continue forever. Success comes to those who keep their heads up, constantly watching for shifts in politics, investments, technology, and social norms. They are always alert for the changes that signal opportunity and the need to adapt.

It may seem like the leader’s path is littered with pitfalls and landmines. That’s not true. Those traps exist just off the trail to success. It’s a well-marked trail. 

Great leaders stay on track and avoid failures by constantly listening to their managers, their people, and the world around them. With their heads up, they’re sure to keep their feet on the trail to success. 

Jeff Skipper is an expert in accelerating change. For more than 25 years, clients such as IBM, Suncor, Goldman Sachs, and The Salvation Army have engaged him to achieve dramatic results during strategic transformation by wrapping complex change in motivating missions. Jeff holds a Master’s degree in Organizational Psychology and is a Certified Change Management Professional. His book, Dancing with Disruption, was published in 2023.

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