The Top Issues CEOs Face: What CEOs Want to Know Now

Top Issues CEOs Face by Glenn Gow

I coach CEOs every day. They ask me questions about their challenges and struggles. They ask about how to manage the enormous pressure they feel every day. When we address these issues together, we learn how to become better versions of ourselves.

In this article, I’ll share the most common questions and challenges CEOs face and provide practical advice to help you overcome these challenges and become a more effective leader.

Whether you’re a seasoned CEO or a newly appointed executive, this post will offer valuable insights and strategies you can implement in your organization. Let’s dive in and explore how you can navigate the path to success.

Leadership and Management

One of the most frequent questions CEOs have is how to create a leadership development program. To ensure the long-term success of your company, you must identify the critical leadership competencies required for your organization, such as communication, strategic thinking, and emotional intelligence. Develop a curriculum that includes workshops, mentoring, and on-the-job learning opportunities. Encourage leaders to take ownership of their development and provide resources and support to help them grow.

Effective delegation is another critical aspect of leadership. Many CEOs struggle with delegating tasks and responsibilities due to a lack of trust or a desire to maintain control (see: “How Your Ego Might Harm Your Business”). However, delegation is essential to scale your organization and empower your team. Start by identifying tasks that can be delegated and then provide clear expectations and guidelines. Trust your team to deliver results, but be available for support and guidance when needed. Remember, delegation is not about relinquishing control but empowering your team to take ownership and grow.

Leading through change is another common challenge for CEOs. Change is a constant in any business environment. As a leader, you must be able to navigate uncertainty and guide your team through transitions. Communicate the vision and rationale behind the change, involve your team in the process, and provide support and resources to help them adapt. Be transparent about the challenges and celebrate the successes along the way.

Company Culture and Employee Engagement

Building team spirit and organizational culture (see: “Importance of Building Positive Workplace Culture as the CEO”) is another common challenge, especially in remote work situations. To create a strong company culture, you must encourage cross-departmental projects, celebrate achievements, empower employees, provide growth opportunities, and prioritize employee well-being. Create a safe space for employees to speak freely and fail, but address poor performance when necessary. As a CEO, you must also manage self-doubt by acknowledging your strengths and accomplishments, surrounding yourself with a supportive network of mentors, coaches, and peers, and practicing self-care by prioritizing your physical and mental health.

To further strengthen employee engagement, consider implementing regular employee satisfaction surveys and acting on the feedback received. Recognize and reward employees for their contributions and provide opportunities for professional development and career growth. Foster a culture of transparency and open communication where employees feel heard and valued.

Sales, Business Development, and Fundraising

CEOs often seek guidance on increasing sales, networking for business development opportunities, and raising funding. To build sales, improve customer engagement, use intelligent strategies, leverage automation tools, and deliver exceptional service. Building authentic relationships and being helpful are essential for networking and business development. When raising funds, craft a compelling story, showcase your vision and potential return, and leverage your board.

Consider implementing a customer success program to ensure customer satisfaction and loyalty. You can increase retention and generate positive word-of-mouth referrals by proactively engaging with customers and addressing their needs. Additionally, explore partnerships and strategic alliances to expand your reach and tap into new customers and markets.

When it comes to fundraising, it’s essential to clearly understand your business’s financial health and growth potential. Develop a comprehensive business plan that outlines your market opportunity, competitive landscape, and financial projections. Be prepared to answer tough questions from investors and demonstrate a solid understanding of your industry and target market.

Financial Management and Metrics

Financial management is a common area of concern for CEOs. They often inquire about presenting earnings before interest, taxes, depreciation, and amortization (EBITDA), handling investor relations, and crafting annual budgets. Effective communication and benchmarking against industry peers are crucial. For SaaS businesses, monitoring Monthly Recurring Revenue (MRR), Customer Acquisition Cost (CAC), Customer Lifetime Value (CLV), and Churn Rate is essential. Maintaining written annual budgets for clarity, accountability, tracking, control, and communication is advisable.

In addition to these metrics, it’s important to clearly understand your cash flow and working capital requirements. Regularly review your financial statements and make data-driven decisions to optimize your business’s financial health. Consider working with a financial advisor or CFO to develop and implement a sound financial strategy.

Team Management and Performance

Effective team management is critical for the success of any organization. To get team members on board, make goals inspiring, co-create goals with your team, communicate plans clearly, encourage team recommendations, and create strong goal alignment. Conduct regular check-ins, measure progress, and take personal responsibility for ensuring team performance.

To further enhance team performance, invest in your employees’ professional development. Provide training and coaching opportunities to help them acquire new skills and knowledge. Encourage a culture of continuous learning and growth where employees feel supported in their career aspirations.

Conflict resolution is another important aspect of team management. As a leader, you must be able to navigate interpersonal conflicts and find solutions that benefit the team and the organization. Encourage open communication, active listening, and a focus on finding common ground. When necessary, be willing to make tough decisions to address performance issues or toxic behavior (see: “How to Deal with Difficult Employees as the CEO.”).

Navigating the Path to Success

Leadership and management challenges are common among CEOs, but you can address them through strategic planning, effective communication, and a commitment to growth. As your CEO coach, I will help you navigate these challenges and achieve your full potential. Whether creating a leadership development program, building a strong company culture, growing sales, managing finances, or leading a high-performing team, the key is approaching these challenges with a growth mindset and a willingness to learn and adapt.

Remember, leadership is a journey, not a destination. Embrace the challenges and opportunities that come your way, and never stop learning and growing. Surround yourself with a supportive network of mentors, coaches, and peers who can provide guidance and accountability.

Take your leadership skills to the next level. Schedule a complimentary consultation with me to discuss your unique challenges and goals. I will help you achieve the success you desire. Don’t wait – take the first step towards becoming the leader you want to be.

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 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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