Critical Factors for Success and Failure in CEO Leadership

Last updated: August 21, 2026

Ron Johnson had a plan. Brought in to run J.C. Penney in 2012, he eliminated the coupons and constant sales that shoppers had built their habits around, betting on a cleaner, more modern retail model instead. In 17 months, the strategy had cost the company close to a billion dollars and cost Johnson his job.

The plan wasn't obviously foolish. The execution was the failure, and execution is where most CEOs actually get tested.

A CEO's role is akin to the captain of a ship. They are tasked with setting the course and ensuring that the entire crew is working cohesively to reach the destination. This involves transforming a vision or strategy into tangible results, a task that is easier said than done. A vision without execution is just hot air, and it is in the execution phase that many CEOs encounter significant obstacles.

The barriers CEOs face during this transformative process are multifaceted. They range from clear communication and coordination, to navigating conflicting personalities and priorities within their own Executive Leadership Team (ELT), to creating a cohesive culture.

In this article, I aim to delve deeper into these barriers and highlight a few examples from industry leaders, as well as my own experience as an Executive Leadership Coach and my research on self-leadership.

1. Communication and Coordination

One of the most crucial elements in executing a vision is clear and effective communication. The CEO's message needs to resonate with every level of the organization. Consider the case of Satya Nadella, CEO of Microsoft. When he took over the company in 2014, Microsoft was struggling with a stagnant business model and declining market share. Nadella's vision was to transform Microsoft into a cloud-first, mobile-first company. This was a significant shift and required buy-in from everyone in the company. Nadella's clear and persistent communication about this new direction helped get all employees on board and contributed to a remarkable turnaround for Microsoft.

There have also been instances where CEOs have struggled with these challenges, leading to less successful outcomes. The story of Mike Lazaridis and Jim Balsillie at BlackBerry illustrates a failure in timely communication and adaptation when faced with the challenge of the iPhone.

Ron Johnson's changes at J.C. Penney left customers confused rather than convinced, and confusion at that scale is a communication failure as much as a strategic one. The lesson here is that a vision, no matter how brilliant, cannot be executed without clear and effective communication with all stakeholders.

During the pandemic, I worked closely with a number of CEOs to frame their communication and adjust their styles to the situation. Leaders usually understand the importance of executive presence, projecting gravitas and poise under pressure, but sometimes they forget it also means reading the room.

2. Managing Conflicting Personalities and Priorities

Reading the room means CEOs must deal with the conflict of personalities and priorities within their ELT. Steve Jobs, the legendary CEO of Apple, was known for his ability to manage conflicting personalities and align them with his vision. Jobs was able to bring together a team of highly talented yet diverse individuals and inspire them to create products that transformed multiple industries.

CEOs often fail to execute because they didn't get buy-in from key stakeholders, or because different agendas were competing within their own ELT.

Marissa Mayer, the former CEO of Yahoo, did not have a cohesive, well-articulated strategy, which resulted in a lack of buy-in within the organization. She tried to implement various disparate initiatives that seemed like one-off mandates, leading to a conflict of priorities and flawed execution.

3. Perseverance in the Face of Challenge

Another critical quality for a CEO in transforming a vision into reality is perseverance, the quality of doing something despite difficulty or delay in achieving success.

Howard Schultz, CEO of Starbucks, provides a classic example. When Schultz first proposed the concept of selling brewed coffee in his stores, he faced considerable resistance from the board. Undeterred, Schultz persevered with his vision, ultimately transforming Starbucks into a global brand synonymous with coffee culture.

Shakespeare understood this quality of leadership. In Henry IV, he wrote:

"Heavy is the head that wears the crown."

It's a four-hundred-year-old line that still describes the job accurately. For more lines like it, and what they actually mean for leaders today, see Leadership Quotes That Actually Mean Something.

4. The Missing Skill: Self-Leadership

There's no denying that CEOs have one of the toughest jobs on the planet. They are tasked with navigating complex landscapes, driving innovation, and delivering results that impact not just the bottom line, but the lives of countless individuals. However, despite the myriad of resources and capabilities at their disposal, the harsh reality is that CEOs often fail.

The reason is usually a critical oversight in cultivating a crucial skill: self-leadership (Bryant & Kazan, 2012).

Self-leadership is the practice of intentionally influencing your thoughts, feelings, and actions toward achieving your objectives. It's the first step to becoming an effective leader, because how can we lead others if we cannot first lead ourselves?

Applying self-leadership, being clear about ownership, responsibility, and accountability, is not only about the growth of the CEO. It sets the tone for the whole organization.

When the ELT also practices self-leadership and role-models the values of the organization, the culture becomes tangible and contributes to success. This is distinct from a one-off culture initiative; it's the daily discipline that makes any culture initiative actually hold. See how CEOs and ELTs build a culture of self-leadership for more on that side of the work.

While the journey to effective self-leadership is deeply personal, effective self-leaders engage with coaches and mentors and actively process feedback and feedforward.

In the foreword of The New Leadership Playbook (Bryant, 2022), the CEO of Planful shares his experience of being coached on self-leadership:

"Self-leadership has produced results I had no idea were possible. I have grown enormously as an executive: my relations with my managers and staff are far more harmonious; I have been able to coach my team through significant personal development."

That CEO, Grant Halloran, and I have worked together for twenty-five years now, since well before either of us had the track record we have today. What that kind of long-arc coaching relationship actually builds, for both the person being coached and the person doing the coaching, is the subject of What Is Your Leadership Legacy?

Frequently Asked Questions

What are the biggest barriers to being an effective CEO?
Four show up repeatedly: unclear or inconsistent communication of the vision, unmanaged conflict between strong personalities on the executive team, giving up on a strategy under board or market pressure before it has time to work, and the absence of self-leadership, the discipline to regulate your own thinking and behavior before trying to direct anyone else's.

Why do CEOs fail?
Rarely because the strategy was wrong. More often it's execution: a vision that never got translated into language the whole organization understood, an executive team pulling in different directions, or a CEO who abandoned course too early. Underneath most of these is the same root cause, a CEO who never developed the self-leadership to lead themselves before leading the company.

What is a CEO success profile?
Less a fixed personality type than a set of practiced disciplines: clear and repeated communication of direction, the ability to align a diverse executive team around shared priorities, the perseverance to stay the course through resistance, and the self-awareness to know when the resistance is right and the strategy needs to change.

What makes a CEO effective at executing a vision, not just setting one?
Execution fails between the boardroom and the front line, not in the strategy itself. Effective CEOs over-communicate the vision until it feels repetitive to them and only then clear to everyone else, and they build an executive leadership team that has genuinely bought in rather than one that is simply complying.

Feel free to contact me if you would like to learn more about developing self-leadership, a self-leadership culture, or booking a leadership speaker for your next event.