Image of two climbers, one pulling the other up onto a boulder.


A mid-market company had experienced rapid growth since its inception in an emerging market over a decade ago. The CEO and Founder had been together since the beginning and had been successful in obtaining venture capital funding to support the growth trajectory of the company.

The company had grown to over a thousand employees and had expanded into new global markets. By all measures it was no longer a startup. The CEO found himself at the helm of a much larger and more complex organization than he had led in his career. The Founder was in a critical role for the organization and, like the CEO, did not have the leadership experience the role required.

Perceptive was brought into the company to be an Executive Coach for the CEO and for the Founder.


Executive Coaching for the CEO and Founder

As with all coaching engagements, we began by learning more about the leaders, their perceptions of the business challenges, of themselves and their leadership, and the outcomes they wanted to achieve.

Perceptive designed a customized Executive Coaching program for the two leaders. Obtaining 360-degree feedback was an important element in the coaching. Neither leader had received much candid feedback from the organization. At Perceptive, we find this is often the case. Understandably, it can be difficult for people to give feedback to their top leaders.

The CEO and Founder would need to scale their leadership to effectively scale the organization for continued growth and future success.

We conducted an extensive interview-based 360-degree feedback process with key stakeholders. This gave both leaders insight into perceptions of their leadership, including their leadership strengths and areas where they were seen as less effective. We spoke with members of the Board to get their perspective what success in the Chief Executive role would look like into the future.

Organizational Assessment

We recommended an Organizational Assessment be completed in parallel with the executive coaching. This Assessment would provide a broader perspective on, and deeper insight into, organizational issues and challenges as the company endeavored to scale for continued growth. Perceptive utilized its proprietary organizational assessment methodology for midmarket companies. Confidential interviews were conducted with key stakeholders across the organization and aggregated into Key Findings and Recommendations.

Signs of an Organization Struggling to Scale

Themes readily began to emerge in the assessment interviews. Several were common indicators of a company struggling to scale, including delayed product launches and customer attrition as alternative solution providers became more available.

The business had responded to market pressures by reigning in its expenditures. This was causing consternation as areas of the business competed for narrowing resources. Valued leaders in the organization were starting to leave which had been unprecedented in the company’s history.

There were mid to senior level leaders in critical positions who were struggling in their role. This was noticeable to many, and they looked to the CEO to make the tough decisions where those leaders were not able to perform well in the role.

At Perceptive, we find that this too is a common indicator at this stage in a company’s evolution: people have been with the company for many years, been promoted into roles with increasing levels of responsibility, and oftentimes without the requisite skills and/or support to be effective in the role.

Creating a Path Forward to Scale

Working with an executive coach gave the CEO a clearer understanding of what the organization needed in its Chief Executive, insight into perceptions of his leadership, and a clear path forward in his development as a leader for the organization.

The CEO and Founder had shared their feedback with each other. This led to powerful conversations in which they came to better appreciate their differences and yielded insights into how they would need to evolve their leadership in support of the organization.

The Organizational Assessment gave the CEO a valuable perspective that he didn’t have up to that point. He now had a deeper understanding of the organizational issues and their impact on the organization and recommendations that helped create a path forward. He shared the findings with the Executive Leadership Team and together they began to implement the recommendations in a cadence that made sense for the organization.

The Assessment combined with the 360-degree Feedback brought the CEO and Founder face to face with something they found personally challenging: dealing with long-time employees who were struggling and the possibility of letting them go.

The CEO and his coach candidly talked about the changes he would need to make in his leadership if he were to be successful as its Chief Executive in this phase of the company’s evolution.

Evolving as top leaders means developing new perspectives and leadership competencies to lead effectively in an ever-changing landscape.

Similarly, the Founder and his coach talked about the changes he would need to make in his leadership style if he were to be successful as one of its top leaders, asides from his success as its Founder. We also discussed his current role and whether that was a best fit for him and for the organization.

Both leaders cared a lot about the company and its people, had invested a lot of their career and financial future in the company, and they wanted to be successful well into the future. They were motivated and they had the resources they needed to evolve their leadership.


Perceptive worked with the CEO and Founder over the next eighteen months to help them build the critical leadership competencies they needed to be successful into the future.

The CEO evolved his leadership style while leveraging his considerable strengths and learned new capabilities that served hm and the organization well.

The Founder took a big step in moving out of his existing role into one which better leveraged his strengths. Importantly for the organization, this also allowed the business to bring in top talent to lead this critical part of the business in ways that developed the capabilities of its next level leaders.

Both leaders described that they grew immensely in their leadership with the support of an executive coach. They appreciated having someone they could talk openly with about the leadership challenges they were facing and help them develop as leaders for the organization. Both described that the 360-degree feedback was incredibly valuable, so much so that they wished they’d have done it sooner.

Creating a Coaching Culture and Leadership Coaching Program

The CEO could see clear benefits for himself, the Founder, and the broader organization owing to the investment they made in executive coaching. The company decided to extend Leadership Coaching to its Executive Leadership Team and next level leaders.

Along the way, the company had adopted a coaching culture from the top. Perceptive worked with the VP of HR to create a custom Leadership Coaching Program for leaders on the senior team and its next level leaders.

Over the next few years, their investment in leadership development served the organization well in developing and retaining their top talent. This became an important strategy in their efforts to scale the organization for continued growth.

Note: To honor confidentiality and protect the privacy of our clients we do not use names and have altered possibly identifying details in this Case Study.

Interested in learning more about how to help Founders and CEOs work more effectively in leading their organizations?

About Perceptive Leaders LLC

Perceptive is a boutique leadership development and professional transitions consulting firm based in Denver, Colorado serving clients in the US and Canada, since 2005. We have worked with over 1,000 senior organizational leaders and accomplished career professionals to help them recognize opportunities for impactful and substantive change and how to realize that transformational change. For more than 15 years, Perceptive has been helping leaders and their teams transform their leadership. For more information, visit

© Perceptive Leaders, 2022. All rights reserved.