A Guide to Common CEO Challenges That You Might Face in 2024

CEO Looking Out the Window Thinking About Business Challenges in 2023

From the unique obstacles facing new CEOs to avoiding pain points as an experienced leader – below are the steps you should take now to prepare yourself for success. Enlist the aid of a coach and get ready to face the biggest CEO challenges with confidence in 2024.

Table of Contents:

  • What are some of the biggest challenges as a CEO?
    • Resistance to Change
    • Lack of Commitment
    • Inadequate Communication
    • Limited Resources
    • Lack of Follow-Through
  • 3 of the Biggest Obstacles New CEOs Face
  • How to Avoid these Pain Points as the CEO
  • How a CEO Coach Can Help
  • What are CEOs worried about in 2024?
    • Globalization
    • Talent Acquisition & Retention
    • Automation & Artificial Intelligence (AI)
    • Data Governance & Privacy Protection
  • Final Thoughts on The Biggest Challenges Facing CEOs in 2024

What are Some of the Biggest Challenges for Any CEO?

Resistance to Change

Change is a necessary part of running any successful business, yet many CEOs struggle with implementing it. Employees are hesitant to accept change due to fears of job safety or new and uncertain work conditions, or whether or not they will succeed in the new environment. 

As a CEO, it’s important to recognize this resistance and find ways to address it head-on to ensure the success of your change initiatives. This could include offering rewards for those who embrace change and providing training and support for those who are struggling with it. It’s also essential that you remain open-minded and flexible when responding to feedback from staff members so that everyone feels heard and respected during the process.

Lack of Commitment

It’s not uncommon for CEOs to have difficulty getting their team members fully committed to projects or initiatives due either to a lack of motivation or unclear expectations on what needs to be done. To combat this issue, try breaking down tasks into smaller chunks which makes them easier for people to understand and complete in a timely manner while still achieving the desired outcome. 

Additionally, setting measurable goals within a 90-day timeframe helps create accountability among team members and encourages commitment since there is an end goal they need to reach together as a team. Finally, celebrating successes along the way will help keep morale high which should result in better commitment levels overall within your company.

Inadequate Communication

To avoid communication issues, ensure everyone has access to up-to-date information regarding all aspects of any given project and hold regular check-ins with key players throughout its duration. Establishing clear lines of communication between different groups involved helps maintain transparency, ensuring nothing slips through the cracks. Utilizing visual tools like Gantt charts can also show progress against timelines, allowing stakeholders to easily track where things stand and hone their time management skills so deadlines are met properly.

Limited Resources

Understanding what assets you truly have and maximizing those assets is key to achieving desired results. Brainstorming outside-the-box solutions, such as forming alliances with other organizations of similar interests, can open up additional resources and help get the job done right the first time around; a win-win situation for both short-term success and long-term benefits for your company.

Lack of Follow-Through

The last common issue is failing to follow through. Without consistency in implementation, plans fall flat and lose traction quickly. Keeping a close eye on new developments and measuring results continually shows commitment to the plan, providing much needed stability during growth spurts and helping ensure the success of the project. If anything does happen to derail momentum, taking quick and decisive action to rectify the matter as soon as it’s noticed can prevent further damage.

The biggest challenge as a CEO is to effectively lead and manage your team while still achieving the desired results. To gain a deeper insight into these difficulties, let’s take a gander at three of the most frequent issues new CEOs confront.

Key Takeaway: CEOs must address resistance to change, lack of commitment, inadequate communication, and limited resources in order to ensure their initiatives succeed. To do this they should incentivize employees to embrace change, set measurable goals with the team, foster open lines of communication between groups, and maximize existing assets. Additionally, staying consistent with plans will help keep the momentum going toward achieving your desired outcomes.

3 of the Biggest Obstacles Unique to New CEOs

In addition to the challenges discussed above, new CEOs face their own obstacles to success:

Time Management

As a new CEO, one of your most critical areas of focus is managing time. New CEOs find it difficult to manage their time while they are still acclimatizing themselves to the company and adjusting to their new duties. Moreover, it can be simple for inexperienced CEOs to slip into unfavorable practices like delaying important decisions or overexerting their influence in the wrong areas due to the feeling of being inundated by everything that must be accomplished.

Understanding Your Departments

Another obstacle that many new CEOs face is understanding how different departments work together and how decisions affect each other across teams. Having the capacity to rapidly comprehend intricate frameworks and procedures so as to make educated choices quickly is fundamental for CEOs. It also means having a very deep understanding of your culture so you know what kind of approach works best in each situation.

Establishing Trustful Connections with Stakeholders

Establishing trustful connections with stakeholders both within and outside the company, is often one of the most challenging obstacles for new CEOs. Constructing trust is a lengthy process, yet it’s essential if you want your stakeholders to be aligned with your vision for the company as well as obtaining support from influential individuals who may not always concur with your strategies or approaches.

Navigating the unfamiliar terrain of a new CEO role can be daunting, but with careful planning and preparation, you will overcome these obstacles. By understanding the potential pitfalls ahead of time, new CEOs can take steps to avoid them in order to ensure success as they move forward into their roles.

Key Takeaway: As a new CEO, it’s essential to manage your time effectively and understand how different departments work together. In addition, forging connections with both internal and external stakeholders is essential to win support for your ideas.

How to Avoid these Pain Points as the CEO

A challenge I see with all CEOs is knowing how and where to focus your energy and effort. To address this pain point, you will need a management system (like OKRs or EOS) to enable you to prioritize and allocate resources. Using this system, you will also have your team create plans on how to address these priorities.

Additionally, having a system in place that allows for tracking progress on projects is key – without this visibility into performance metrics, it can be hard to determine which areas need more attention or if any changes need to be made along the way.

CEOs, swamped with their everyday duties, may forget to stay abreast of industry trends – a crucial factor for success. Failing to do so can mean falling behind competitors quickly due to technological advances or shifts in customer preferences that you weren’t aware of until too late. As such, CEOs must find ways to set aside some time each week (or month) dedicated towards reading trade publications and networking with your peers. Doing this ensures they remain ahead of the curve while also helping drive innovation within the company itself, making sure it remains competitive in the marketplace for long term success.

As a CEO, it is essential to anticipate potential issues and take preemptive measures to address them. A professional coach can help identify these potential pain points and provide guidance on how best to navigate them.

Key Takeaway: CEOs should use a system for managing their time and resources, clearly articulate objectives and key results, and remain current with the changing landscape. They should use a management system that enables them to track progress on projects while also taking the time each week or month dedicated towards reading trade publications and networking so they can remain ahead of the competition.

How a CEO Coach Can Help

As a CEO, you will encounter numerous complex challenges and impediments on your journey to success. From building the right team, to navigating financial and business decisions, to understanding customer needs and trends, to staying ahead of competitors – it can feel overwhelming. That’s why having an experienced coach on your side is so valuable.

A CEO Coach provides guidance for new CEOs as they take on their first executive role or for more experienced CEOs facing fresh challenges. A great CEO coach will provide feedback on your decision-making processes and offer constructive criticism to help you grow.

A CEO Coach will provide an objective, impartial perspective on any problem or opportunity. They will use their expertise to provide tailored strategies for growth and constructive feedback on decision-making processes. A coach’s outside view will lead to more creative solutions than those derived from internal teams with vested interests, so don’t hesitate to enlist a coach’s help. 

Veteran CEOs who have been at the helm of companies for years can benefit from enlisting a coach to review existing practices and procedures. Coaches are well-equipped to help leaders navigate complex situations such as mergers & acquisitions or other major strategic initiatives, offering expert guidance that is based on both business operations and human dynamics. 

Their insights (including psychology and data analysis) into potential pitfalls along any path allows you to make informed decisions quickly yet thoughtfully. 

Key Takeaway: Executives face a turbulent journey as they traverse the terrain of 2024, but having an experienced coach to assist them in plotting out their course and making wise decisions is invaluable. A CEO Coach provides impartial perspectives to foster growth while offering tailored strategies and constructive feedback – so don’t hesitate to enlist their expertise.

What are CEOs Worried About in 2024?

In 2024, CEOs will be worried about how to keep up with the rapid changes in technology and financial markets. CEOs must remain cognizant of the newest approaches and techniques that can assist their company in staying ahead of the competition. Additionally, they must find ways to manage increasingly complex financial markets, changing workforces, and continued pressure to manage costs. Finally, CEOs have a responsibility to ensure their businesses are following ethical practices and staying compliant with changing regulations.

Financial Markets

CEOs are faced with significant questions related to Fed policy, banking regulations, banking policies, cash management and fundraising.

Talent Acquisition & Retention

Attracting and retaining the right talent will be a challenge as competition for top workers intensifies in many industries.


CEOs must protect their data from malicious actors and invest in reliable cybersecurity solutions.

Automation & Artificial Intelligence (AI)

CEOs must embrace automation and AI technologies while managing potential risks such as job displacement or ethical concerns around decision-making algorithms.

Data Governance & Privacy Protection

Companies should develop policies that address how they collect, store, use, analyze, share, and delete customer data responsibly and in compliance with data privacy laws.

Final Thoughts on The Biggest Challenges Facing CEOs in 2024

The biggest challenges facing CEOs are staying on top of the ever-changing business landscape, managing their teams effectively, and making strategic decisions that drive growth. They must be able to adapt quickly to changes in technology and customer needs while balancing long-term goals with short-term gains. Furthermore, CEOs must guarantee their organizations have the vital assets to be successful while staying focused in a vigorously competitive market. Finally, CEOs must be able to lead with integrity and inspire their teams.

As a CEO, there will inevitably be difficulties to overcome; yet, with assistance from an experienced CEO Coach, those hurdles will be much more manageable. CEOs should take proactive steps now in order to ensure they’re prepared for any challenges 2024 may bring their way. A coach who understands you and your goals and objectives will help you achieve them while guiding you on the path toward success as a CEO.

Contact an Experienced CEO Coach Today 

My name is Glenn Gow, CEO Coach. I love coaching CEOs and want to help make you an even better CEO. Let’s decide if we are a fit for each other. Schedule a time to talk with me at calendly.com/glenngow. I look forward to speaking with you soon.


Take Their Word For It

What Glenn’s Clients are Saying…


Janice Raises Over $100M for Her Company

Janice Raises Over $100M for Her Company

As one of the founders, Janice had created the perfect solution in an exploding market. As her CEO Coach, we worked very hard to create a scalable business model that significantly accelerated revenue growth. This model included geographic expansion, the addition of new product offerings, and stickiness to create repeat business.

This triple revenue-acceleration model not only worked but it attracted the interest of growth investors.

But a growth model wasn't enough. We needed to help Janice become a better CEO. Specifically, we worked on how to manage her board, so their faith in her as the CEO grew as time went on.

For some CEOs, the board can be intimidating. At first, it was for Janice as well. We worked on how to manage the board and get the most out of the board. Ultimately, we turned the board into a strong set of advisors and advocates for Janice as the CEO.

The support and confidence of the existing board was a critical factor in enabling her to raise well over $100M in the next round, increasing the valuation by more than $600M.

Darren Raises His First $3 Million

Darren Raises His First $3 Million

My CEO client (Darren) was starting a company in a new category. He was focused on raising capital for his business and wanted help crafting his story. Darren is a brilliant CEO, yet he realized he could produce a better story with help from someone who has created successful fundraising stories many times.

When we started working together, his story was overly complex, difficult for investors to understand, and not as strong as it could have been. Together we built a story about the tremendous value the company was creating. We used historical precedent to bolster the vision and mission. We gave investors confidence in the founders. We proved that the company could scale.

Investors are pattern-matchers. They look for the patterns that tell them this opportunity is like other opportunities they’ve seen, giving them a strong belief in the potential ROI. Together, Darren and I constructed a winning story that helped key investors see the patterns of success.

According to Darren, “Glenn gave me the perspective and confidence I needed to succeed.” Darren raised $3 million for his startup company in his first round. Darren has continued to successfully raise money in later rounds as well.

Meilin Creates A Scaling Organization

Meilin Creates A Scaling Organization

Meilin was always asking, "How can I help my company grow faster?" She was successful by most measures but had higher growth ambitions.

As her CEO Coach, I helped focus her efforts and energies on an often-overlooked area for many CEOs. This area enables scaling and enables the CEO to manage their team more effectively -- values.

Most CEOs have corporate values but don't use them as the ultimate way to install a belief system - a way for every employee to focus on the most critical issues for the company.

Meilin and I worked on making the values core to the thinking and speaking of the management team. Once the management team adopted these values and started speaking about them in their regular communications, we knew that we were on our way to ensuring that every employee “lived” the values.

While values are not the only thing a company needs to grow fast, they are critical to its success. Meilin's company is now growing over 100%.

Sean Gets It All Done

Sean Gets It All Done

As CEO, Sean had no work-life balance, and he was struggling with the overwhelming responsibilities of being a CEO. One of the biggest challenges of any CEO is to get everything done. The list of critical items seems to grow every day.

As his CEO coach (and as a former CEO), I recognized the stress he was under. That level of stress is no fun. To help Sean become a better CEO, I focused him on delegation, talent development, and balance.

First, we focused on developing Sean's delegation skills. Delegation is the "8th wonder of the world." When you make it work, your workload diminishes, and the company performs at a higher level. As Sean became better at delegating, he also began to see strengths and weaknesses in his leadership team from a different perspective.

The next step was to refresh his leadership team. We created a plan to either develop the ones that could step it up and perform better or find new leadership team members for those that couldn't help the company grow.

Finally, we worked on creating a way of living for Sean that provided him some balance. I tell my CEOs to "put their oxygen mask on first." If a CEO wants to perform at the highest level, they need to take care of themselves first.

Now that Sean has a much better leadership team, he has become a master delegator. By delegating many of the activities he had taken on before, he now has much more time to take care of himself.

Sean's company has now entered a new growth phase. More importantly, he is enjoying his work a lot more and his life a lot more.

Viraj Fires His “Best” Employee

Viraj Fires His “Best” Employee

As a CEO, Viraj was focused on employee retention. He recognized the value of keeping high-performing employees and the high cost of turnover.

One of Viraj's direct reports was one of his "best" employees. This person consistently out-performed against their targets. Within their function, they were a rock star.

However, this same person was toxic to the rest of the organization. They constantly argued with others, and they made most others feel bad about themselves. Viraj found he was spending a great deal of time managing around the toxicity created by this employee.

Viraj valued this person's contributions within their function, and he also really hated the idea of employee turnover. As a result, Viraj put up with this person and continued to work around the toxicity issue.

As Viraj's CEO Coach, I helped him understand that team alignment and team cohesion are critical factors to help the company grow. We agreed that preventing employee turnover is a good goal, but not at the expense of creating a well-functioning team.

Viraj wanted to become a better CEO, and he knew what he had to do. While it was difficult, he decided to fire the person he once thought was his "best" employee.

The first thing he heard from the rest of his direct reports was, "What took you so long?"

Olivia Finds Product-Market Fit

Olivia Finds Product-Market Fit

Olivia, my CEO client, is a product genius. She is highly creative, an excellent problem-solver, and knows how to get products out the door on time.

Olivia raised a great deal of money based on her product ideas and some early successes. The challenge was that her company wasn't growing fast enough. The pressure from the investors was building, and she was worried.

Raising a lot of money early is a blessing and a curse. The curse is that Olivia delivered her product too quickly. She delivered it, making too many assumptions about the market she was serving. When the product was released, it was a good fit but not a great fit.

Olivia was concerned about the time and dollars it would take to conduct research and test product-market fit in multiple market segments. We created a partnering strategy that enabled us to test multiple new market segments in a short time.

Olivia has found multiple market segments that are a fit for the product. Now that she has achieved product-market fit, the strategy is to "go big" on the go-to-market. And her company is taking off.

Wilson Turns the Board Around

Wilson Turns the Board Around

Wilson was a first-time CEO. The company was doing well, but not quite as well as the board had hoped. Wilson found himself uncomfortable as a minority shareholder working with a board that could fire him if he didn't perform.

Wilson wanted to know how to manage a Board of Directors. The first step was to acknowledge that a board has different measures of success than the CEO. That means there will naturally be tension. The second step was to dig in to deeply understand what the key drivers are for each board member.

Based on this information, Wilson can now address his needs, the company's needs, and the board's needs. That was the first breakthrough.

Once he knew how to address the needs of the board, we turned to address his needs. As Wilson's CEO Coach, I helped him realize that the board is an incredible asset to leverage.

Wilson began to build relationships with the board members individually to understand better how they could be of service to him and the company.

When Wilson works with the board, he is fully aware of their needs and addresses them appropriately. More importantly, he now tells the board what he is doing and relies on their insight and experience for feedback on how to help the company perform at a higher level.

Wilson is no longer concerned about the board and now gets more out of them than ever before.

Darius Solved His Crisis

Darius Solved His Crisis

I got the call at 10 PM on a Thursday. Darius, a CEO client, reached out to me just as I was about to end the day. "Glenn, my Chief Revenue Officer, just resigned, and I'm not sure what to do."

Darius was running a rapidly-growing business that was highly dependent on a well-run sales organization. He had delegated sales responsibility to his Chief Revenue Officer so Darius could focus on engineering and product.

The good news is that Darius didn't relinquish oversight or reporting of sales, just sales execution. It's also true that Darius wasn't in a panic, and we had worked on a plan for the departure of each of his direct reports.

At the moment, though, Darius and I needed to review that plan to ensure it was our best option. We checked whether or not the interim head of sales could genuinely step into the role. We discussed which accounts Darius should immediately nurture relationships with. We agreed that the recruiter we would need was still the right recruiter.

We quickly put together a communication plan on how to bring this news to the leadership team and the rest of the company. We worked on the exact next steps to interact with the interim head of sales, the director of sales operations, and HR.

Darius felt he didn't know what to do, but in actuality, he did. We had prepared for this, and he just needed to talk it through in the heat of the moment so he could execute against the plan immediately.

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