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The Top 10 Leadership Challenges

For every Richard Branson or Elon Musk, there are hundreds of ineffective CEOs. A great leader runs more than a successful business, they are charismatic examples of their company’s culture and vision.

Our team of CEO coaches at CEO Coaching International recently weighed in on the top 25 mistakes CEOs make and how to fix them. In this blog post, I narrow down the top 10 reasons that educated and talented leaders fail. In my work with the world’s top CEOs, I encounter a variety of leadership challenges. From effective communication to executive alignment, here are the top ten challenges business leaders face today below:

1.Effective Communication

The complexity of today’s business world requires CEOs to communicate on multiple levels. For example, you have to create the company vision and persuade your team to make it their vision, too. You have to connect on an individual level and inspire people to move from “I” to “we.” And you have to build trust by ensuring your verbal communication and your non-verbal actions reinforce each other.

Effective communication is so hard because it takes commitment. You have to make effective communication a priority and that takes discipline, consistency, clarity of message, and a willingness to keep at it day after day.

By putting a structured communication system in place that connects with all of your stakeholders at the right level, you can dramatically improve your effectiveness as a leader and drive faster top and bottom-line growth. Keeping employees and stakeholders on the same page is also essential, especially in the fast-paced business environment. Communicating with key players about schedule changes, meetings, product performance, and obstacles will ensure everyone involved with your organization is current on what’s going on.

To address this leadership issue, start by being more transparent and honest with yourself and your employees. Transparency is essential for running a successful business, as transparent leaders can build a company culture based on trust and respect.

The last thing employees want is to be left in the dark regarding how their organization is performing. By being honest with your employees and communicating both good and bad news, you’ll be able to motivate them and boost productivity.

Additionally, successful CEOs need to be receptive to feedback. Everyone has blindspots; as a leader of your organization, this can be a hard pill to swallow. However, the only way for you to grow as a leader is by communicating with your staff and learning from them. Being open to feedback will allow you to gain better self-awareness and change your behaviors for the better. While this may be difficult at first, it can lead to massive benefits.

Lastly, make sure to communicate wins. While a common leadership problem is difficulty communicating bad news, many executives and leaders also ignore delivering the good news. Communicating positive developments is an excellent way to boost morale and celebrate success.

2. Accountability

If you notice that the big things are not getting done and good ideas are falling through the cracks, you lack accountability within your organization. We all need scoreboards that track the results we want. Most CEOs know this, but putting this system into place requires self-discipline and focus. Build the systems you need to support accountability and don’t get distracted until they are part of your operations.

To address a lack of accountability, it’s important to invest in the right resources to hold yourself responsible. At CEO Coaching International, our executive coaches can teach you skills and best practices that make an effective leader, including how to hold yourself accountable. As a leader, the way you conduct yourself directly impacts your bottom line. If you’re an ineffective leader, you can decrease your workforce’s productivity, increase employee turnover, and reduce profits.

Holding yourself accountable, whether it’s for a company setback or poor planning, will help you better understand some of your weaknesses. In turn, you’ll be able to address them and create an action plan to improve for the future.

3. Terminations

Even the best leaders worry about firing a member of their team if the team has become a close-knit family. When was the last time you fired someone who has been with you so long you know their family?

Unfortunately, we often find that the people who got you here will not get you any further because the company has outgrown the person’s ability to keep up. As the company grows, so must your team members, and as a leader, you have to make the tough decisions to continually upgrade your talent. People want to work for winning organizations, and keeping a team member around who’s not pulling their weight just drags everybody else down with them.

Who was the last person you fired too soon? As CEO, you need to make tough decisions almost daily. But some choices are more difficult than others, and one of those choices is terminating an employee.

When it comes to this leadership problem, it’s essential to address this issue with respect and grace. While firing someone is never an ideal situation, remain composed and handle the situation in a respectful manner. This means being clear and straightforward with your reasons for termination to ensure there’s no confusion. Being professional in moments like these goes a long way and shows your true character.

4. Executive Alignment

Imagine being a fish trying to swim upstream. It’s tough to make progress. That’s what happens when your key players are not all on the same page. Sure, you’ll have disagreements, but as the leader, you have to make sure that when the decision is made, your team is behind it, and they move forward in unity to make it happen. Simple things like making sure your compensation systems are lined up to reward the desired behavior are critical. Once you align your team’s incentives to those of the company, magic starts to happen.

Being a leader means guiding a team of people from a wide range of backgrounds, opinions, and experiences—and taking all that into account can make moving forward a challenge. To address the leadership issue of a lack of alignment, you need to find common ground. You can accomplish this through communication, accepting feedback, and being transparent.

5. Clear Vision

What is your company’s vision? If I walk into your building and ask three people, can they articulate it? Can they describe what the vision means to them and how the work they do supports the vision and brings meaning to their jobs?

Your vision can’t just be a fluff statement that sounds like a bunch of corporate speak. Real leaders create a compelling vision for the future that ignites a fire under their team and keeps them working hard and doing the right thing even when nobody’s looking. Millennials, in particular, want to believe that the work they do goes beyond just a paycheck and contributes to the greater good. Does your vision inspire this greatness?

To keep employees engaged, you need a vision you wholeheartedly believe in to get everyone on board. First, start out by going back to the reason you started your business:

With these questions answered, you’ll be able to create a vision statement that can act as the soundboard for all the decisions you make going forward.

Once you have your vision defined, you’ll need to define a set of clear and measurable activities that put you on the path to achieving your vision. These activities will be accomplished day by day, week by week, quarter after quarter, to help you accomplish your annual goals.

However, it’s crucial you take the time to pause and review the actions you’re taking to move you closer to your vision. If an action is pushing you in a different direction, it’s time to reevaluate and either pivot or abandon the action altogether. Being flexible and adaptable is essential to strong leadership.

Check out our FREE Crystal Ball Exercise to help you with your vision
This is the key exercise our client CEOs use to determine what they want to accomplish and helps provide clarity on what needs to get done to make your BIG goals a reality.

6. Successful Execution

There are three reasons leaders fail to execute. First, they don’t follow their own plan with discipline. Second, they fail to keep score on what matters. Third, they don’t have the right people in the right jobs to make it happen. If you can assemble these three puzzle pieces, you can put your company on track to win.

How do you execute in a way that ensures you reach your goals? A key component is using data. Tracking progress allows you to use metrics to guide your decisions. This way, you’ll be able to make choices backed by evidence.

Consider this leadership challenge example:
You’re launching a new product in an effort to reach a new audience. You task your marketing team with creating a campaign that aligns with the target audience and the product you’re trying to sell. But you fail to conduct any market research and you’re not hitting the numbers you projected.

This example shows poor execution. Failing to do your due diligence before spending time and resources on a new product can set your organization backward.

With every decision you make, both big and small, make sure to execute. This means creating a plan, doing your research, and getting the right team together to make your plan a success.

Start with a Plan – Get our FREE Annual Planning E-Book
Effective annual planning provides the surest, straightest path through these kinds of obstacles. It’s the most significant differentiator between companies that stay small and companies that get BIG.

7. Company Culture

We all envy Google, Facebook, and Zappos for their dazzling company cultures. But what we forget is that the creator of culture is the CEO, not HR or anyone else. Did you create your culture by design or did it just happen by default? When you consciously think about and design your culture to foster your desired behavior, your culture becomes a competitive advantage that attracts top talent and drives massive results.

First and foremost, you need to make a safe and positive work environment. If employees don’t feel safe at work, whether it’s due to a hostile environment or toxic employees, they won’t be able to focus on the tasks at hand. If you notice key indicators of an unsafe working environment, such as constant drama, tension, or unproductivity, it’s time to make some changes. This means addressing issues head-on, such as terminating employees that might be contributing to a hostile working environment.

Once you have a company culture where employees feel safe enough to have meaningful conversations without fear of retribution, you’ll see immediate results. As a CEO, you want team leaders who listen and respect those they manage. This is where progress is made and ideas are shared.

8. Driving Inspiration and Motivation

One of the driving forces behind company growth is a team that’s inspired and motivated to show up to work every day and accomplish goals. With that said, one of the top leadership challenges is inspiring and motivating your team to be the best they can be. When employees show up to work every day, they want to know why they’re there.

“What are we trying to accomplish?” “Where are we headed?” These are just some of the questions employees ask themselves every day in their careers. And if they don’t have answers to these questions, they won’t have the drive to continue pushing forward.

To rekindle the flame, you’re going to have to be creative. There are several ways you can get your team excited to show up every day. To get started, consider these tips:

These are just some of the useful tactics you can implement in your workplace to motivate and inspire your team. Another leadership problem many executives struggle with is staying motivated. While having a bad day is normal, it shouldn’t be commonplace. As the CEO, you need to show up every day for both you and your team. To stay motivated, make sure to reward your accomplishments and create a healthy work-life balance. You should also learn how to delegate tasks when needed, and even find someone who inspires you.

Check out our FREE E-Book on Mobilizing Your Team
Whether you’re a seasoned pro or a newly-minted chief executive, the job remains the same: You need to lead the company ship by charting the course, mobilizing your crew, and making tough calls through choppy seas to reach the shores of extraordinary success.

9. Decision-Making

As the CEO, you’re the captain of the ship. This means you need to be a strong decision-maker. Unfortunately, a familiar leadership issue for most CEOs is knowing how to be good at making decisions. Each day, you’ll be faced with decisions like terminating an employee or making key financial choices. Some of these decisions will not be as hard to make as others.

What makes decision-making so challenging is that someone might be upset in the end. But you have to think about your company’s long-term growth and future, and what might be difficult at the moment can prove resourceful in the future.

Take this leadership challenge example: Let’s say you run a relatively new startup and are in need of top-tier talent. You hire an experienced recruiter. Over the next few months, your team grows and your company is in a good place. But you’re only growing at a steady state, and there’s not much work to do for the full-time recruiter you hired.

While they’re a great employee, their salary is cutting into your bottom line. A tough decision you’ll have to make is whether to continue them full-time and accept the cost, reduce their hours to part-time, or terminate them altogether and outsource recruiting to a third-party company.

No matter what, each decision comes with a set of pros and cons. As CEO, you’re going to have to make a decision in the best interest of your company.

10. Inclusive Company Culture

If your company is lacking inclusivity, there are several changes you can make. Don’t let a fixed mindset hold you and your company back from expanding in a positive direction. As CEO, there are several changes you can make to promote inclusivity, such as:

Creating an inclusive workplace doesn’t have to be a leadership challenge. Above are just some of the ways you can honor and accept all of your employees and become a more effective and respected CEO.

The Bottom Line

Leadership is a skill you can learn. By avoiding these ten common leadership problems, you can lead your team—and your company—to greatness. If you’d like to schedule a call with one of our CEO coaches, contact us today. We offer CEO coaching that can help you become a more effective leader, along with a variety of executive coaching events, so you can interact with like-minded peers looking to grow alongside you.

Dedicated One-On-One Executive Coaching for CEOs

CEO coaching is designed specifically for CEOs and business owners to gain clarity on goals and keep score on the specific and measurable activities it will take to turn vision and planning into reality.


About Mark Moses

Mark Moses is the Founding Partner of CEO Coaching International and the Amazon Bestselling author of Make BIG Happen. Mark has won Ernst & Young’s Entrepreneur of the Year award and the Blue Chip Enterprise award for overcoming adversity. His last company ranked #1 Fastest-Growing Company in Los Angeles as well as #10 on the Inc. 500 of fastest-growing private companies in the U.S. He has completed 12 full distance Ironman Triathlons including the Hawaii Ironman World Championship 5 times.

Mark Moses
FOUNDING PARTNER & CEO

About CEO Coaching International

CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 1,000 CEOs and entrepreneurs in more than 60 countries and 45 industries. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have made BIG happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $10 billion, and many are founders that have led their companies through successful eight, nine, and ten-figure exits. Companies working with CEO Coaching International for two years or more have experienced an average EBITDA CAGR of 67.8% during their time as a client, nearly four times the U.S. average and a revenue CAGR of 25.5%, more than twice the U.S. average.

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