The 5 Most Common Mistakes CEOs Make When Scaling a Business

Over my years as a CEO coach, I’ve been privileged to guide many CEOs through the complex process of scaling their companies. Through this experience, I’ve identified several common mistakes CEOs make when attempting to grow their businesses. In this article, I’ll share some of these insights with you and provide practical advice on how to avoid these pitfalls and successfully scale your business.

Mistake 1: Failing to Create a Clear Vision and Strategy

One of the most fundamental mistakes I see CEOs make is failing to have a well-defined vision and comprehensive strategy for scaling their business. Without a clear roadmap, you can easily get sidetracked and make decisions that don’t align with your long-term goals. As a CEO, you must invest time in crafting a compelling vision that inspires your team and guides your decision-making.

I worked with a CEO who needed help to scale their e-commerce business. Their strategy required a defined target market and a unique value proposition. Working together, we clarified the vision and developed a targeted growth strategy that identified new opportunities outside their original total addressable market (TAM) and optimized operations by focusing on AI. As a result, the company experienced a significant revenue increase and positioned itself for long-term success.
CEOs who define their vision and strategy can now make informed, data-driven decisions that support growth objectives. They can effectively communicate goals to their team, investors, and stakeholders, ensuring alignment toward the intended outcomes (see “How CEOs Can Overcome Resistance to Change Within Their Organization“).

Mistake 2: Neglecting to Build a Strong Team

Another common mistake is CEOs trying to scale without investing in a strong, capable team. As your company grows, you must delegate responsibilities and trust your team to make important decisions. Failing to hire the right people or provide necessary training and support leads to decreased efficiency, poor morale, and high turnover.

I emphasize hiring for skills and cultural fit. Define your company values and seek individuals who align with those values. Create a cohesive, high-performing team committed to your vision and capable of supporting growth initiatives.

Develop a robust hiring process that includes multiple rounds of interviews, assessments, and reference checks. This ensures you hire team members with the necessary skills, experience, and shared values. Investing in ongoing training and professional development to help your team grow and adapt as your business scales reduces burnout and turnover risk (see “Maximizing Employee Retention: Strategies Every CEO Should Know“).

Mistake 3: Overlooking Systems and Processes

As your business scales, operations become exponentially complex. CEOs who overlook implementing robust systems and processes struggle to maintain quality, consistency, and efficiency. Invest in developing standardized operating procedures (SOPs) and leveraging technology, like AI, to streamline operations. One of my clients, the founder of a rapidly growing software company, was overwhelmed by increasing demands as her business scaled. By identifying key processes to automate and delegate, we freed up her time to focus on strategic initiatives and drive growth.CEOs who prioritize systems and processes are better equipped to handle scaling challenges. Document SOPs, leverage project management tools, and invest in automation where possible. Prioritizing processes ensures your business runs smoothly and efficiently, even as your team and customer base grow.

Mistake 4: Losing Focus on Customer Needs

CEOs can become disconnected from customer needs and preferences as they pursue rapid growth. Losing sight of what matters most to your target market leads to poor product development, decreased customer satisfaction, and scaling failure.

Prioritize regular communication with customers and actively seek feedback. This will help you stay attuned to the evolving needs of your target market to ensure your products and services remain relevant and valuable as you scale. Invest in customer research, conduct surveys, and establish a customer advisory board for ongoing insights and guidance.

Participate in customer support and sales calls. Hear directly from customers about their challenges, needs, and experiences with your products or services. Gain valuable insights to inform your growth strategy and make customer-centric decisions.

Mistake 5: Underestimating Cash Flow Management

A critical mistake when scaling is underestimating the importance of cash flow management. Scaling requires significant financial resources, and poor cash flow management quickly derails even the most promising growth plans.

I work closely with CEOs to develop detailed financial projections, monitor key metrics, and create contingency plans for potential cash flow issues. As you scale, you must clearly understand your burn rate, runway, and funding needs. You may need additional funding from investors or debt to support growth initiatives.

Establish a robust financial reporting system that provides real-time visibility into revenue, expenses, and cash flow. Regularly review these metrics and make data-driven decisions to proactively manage finances and ensure you have the resources to support your growth objectives.

Scaling a business is challenging and requires meticulous planning, execution, and adaptability. Avoid these common mistakes and seek expert guidance to position your company for sustainable growth and long-term success.

As a CEO coach, my mission is to help you navigate the complexities of scaling your business with confidence and skill. If you’re ready to take your company to the next level, schedule a chat with me today. Together, we’ll develop a customized growth strategy that addresses your unique challenges and opportunities, setting you on the path to success. Don’t let these common mistakes hold you back – take action now and start scaling your business with the support and guidance you need to thrive.

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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