Why Corporate Executives Leave (and Where They Go)

Have you noticed the recent announcements of executive departures from Fortune 500 companies? Anecdotally, and only speaking about people I know personally, well-known employers such as Cisco, Electronic Arts, Google, Nike, Amazon, Apple, Walgreens, Microsoft, Meta, Darden, PwC and BNY Mellon have lost senior talent from the C-Suite, key business roles, technical leadership and HR leadership.

These firms are scions of success in the world of business, some are in the top 50 of market valuation, others are the undisputed leaders in their industry, and together they represent millions of customers and billions of transactions each year. These companies are in many ways model citizens of the best the world economy has to offer, generating billions of profits, employing millions of workers, investing wisely in leadership development and employee engagement—all blue-chip employers with so much going for them. They are the envy of their for-profit competitors for executive talent.

So why are these companies losing institutional knowledge, why are best-in-class executives taking their skillsets elsewhere, where are they going and what are these leaders doing next in search of fulfillment and meaning?

Now, before you raise your hand too quickly with a ready answer to these questions, let me provide some additional context. First, I am actively tracking the career movement of talented business leaders (real individual people) who have decided in recent years to exit the rarified air at these premier employers. Second, as of this writing, very few of these leaders have chosen to “ride off into the sunset” and retire from their business career. Third, several of these leaders have agreed to share insight into why they left, where they went and how they are finding job satisfaction after years of building a great resume.

Why do executives leave? Leadership roles in these companies innately hold a high degree of difficulty, ranging from the expectation that work is seven-days-a-week, that great performance needs to get better, that the team must be “shaken and stirred,” and that much of the accountability is intertwined with things out of their control.

Former Walgreens executive Richard Ashworth earned his pharmacy degree in 1999 and was consistently asked to take on increasing responsibility at the district and regional levels. In 2014, he was appointed to the role of President of Pharmacy and Retail Operations for the US business as Walgreens merged with UK-based Alliance Boots. Although the new entity was overwhelmed with leadership transitions in almost every area of the business, Ashworth was loyal to Walgreens, had proven himself at every level, and was liked by customers, employees, peer leaders and independent directors alike. And with this portfolio he was considered by many to be a likely CEO-succession candidate.

However, Richard Ashworth announced in 2020 his departure to first become CEO of Tivity Health, and subsequently the CEO of Amedisys in 2023. Why would a talented, admired and experienced business leader leave a company with $110 billion in revenue, 9,500 locations and 275,000 staff to join a lesser-known brand with niche fitness and nutrition products and less than 500 employees? After twenty years of incredible opportunity at Walgreens, for which he was very grateful, Tivity Health provided him with a promotion to the CEO suite, operational autonomy, and the strategic imperative to find a private-equity partner who would acquire the business.

Where do executives go when they leave? While some in the data group I am following are leaving their employer for promotions with new opportunity, many are saying goodbye to big corporate jobs and hello to self-employment arrangements of various kinds. Over half of the data group have become independent consultants, advisers, and founders of new businesses.

• Former Intel and Cisco HR leader Gabrielle Thompson resigned after a twenty-five-year career to serve on corporate and not-for-profit boards of directors.
• Former WL Gore & Associates CEO Jason Field, a 15-year veteran in various sales and executive leadership roles, returned to his hometown in northern Arizona to launch an executive coaching practice.
• Former ConAgra and Darden Restaurants HR leader Julie Griffin launched a new business, The Healthier Executive, “a mission of nurturing thriving executive women, to ensure well-being becomes an integral part of the executive lifestyle.”
• Ireland native and computer science major Tom Killalea invested almost seventeen years in his career at Amazon, before parlaying his technology leadership experiences into board of director roles at MongoDB, Akamai Technologies and Capital One.

The common denominator in these and other stories of talented executives choosing alternative careers is the promise of independence, accountability to self, simplicity of doing business, and days filled with realizing aspirations (the “pull”), whereas this new alternative is void of endless meetings, impossible expectations, competing agendas, questionable investments and the ubiquitous narcissism found in many top companies (the “push”).

How do former executives find meaning? It is not surprising that many executives who leave blue-chip employers were experiencing declines in job satisfaction and career fulfillment. Some have mentioned it felt like a “grind,” others described the “never-slowing hectic pace,” and others describe feeling broken by the “dearth of resources and inattention to critical issues” impacting employees, customers and their communities.

Former Microsoft leader, Slalom Consulting and Avanade CHRO Dave Gartenberg is too young to retire and with energy to burn. He is now committed to mentoring the next generation of human resources leaders through coaching, consulting and facilitation of readiness experiences for members of the Institute for Corporate Productivity (i4cp). Dave says he is deeply committed to this personal mission, with all his heart and soul.

Former Yale Law School alum Tim Leslie dedicated twenty years to corporate attorney and business unit leadership roles at Amazon before deciding in 2019 to look over the fence and see what’s on the other side. After a stint as CEO of Leafly, Leslie has found a new purpose by returning to his undergraduate alma mater and serving as Vice President of Career and Professional Development at Beloit College.

Former math major and Microsoft technology executive Tracey Trewin was a twenty-five-year veteran who left to join Magic Leap as Chief Product Officer in 2021. She has since joined Tadaweb as Chief Technology Officer, and it got me to wondering what it is about small companies struggling for brand identity and competitive survival that is attractive to an accomplished leader like Trewin. Who among us could turn down the opportunity for direct access to business influencers, working with people you trust and having an impact on products and customer experiences. (Somehow, all of that can get significantly diluted or materially lost in a multi-billion-dollar mega-company.)

Former technology and bio-tech executive Bob Hargadon received a degree in economics from Harvard University and invested in leadership roles at noteworthy employers such as Digital Equipment, Boston Scientific, Microsoft and Alere Diagnostics. With plenty of energy and no intent to retire, Hargadon found a second calling that combines his love for the beauty of the pacific northwest and his appreciation for award-winning wines. He is now the General Manager at Tsillian Cellars in the Lake Chelan AVA of Washington State.

Noted five-time New York Times best-selling author Dan Pink has written that mastery, autonomy and purpose are the principal drivers of peak performance on the job.

• Why do executives leave? Because the subject matter expertise (mastery) they have amassed is no longer valued in the same way it may have been valued in the past, and so they find more compatible employment.
• Where do executives go? They look for business opportunities where autonomy is valued, where a leader is free to operate within a reasonable set of accountabilities, and where the corporate bureaucracy is minimal and efficient.
• How do executives rediscover meaning? The purpose for work, the meaning of career and the satisfaction and fulfillment derived from what you do and how you contribute are re-directed and optimized in a new environment.

In my decades of experience in the business world and seeing hundreds of executive departures and the corner-office handwringing when top talent resigns, I have rarely seen an executive team pro-actively engage in a discussion around how well the leadership experience is focused on mastery, autonomy and purpose as the keys to executive retention. If you and your employer are currently under-investing in the retention of leader expertise, please take heed—and if you are the exception, well done!

Mark Englizian is a former Fortune 50 people leader, and independent adviser to CEOs and Boards of Directors. He has been a reviewer for Harvard Business Press and has appeared on CNBC Nightly Business Report. Mark is the author of “Significant: Practices and Principles for a Meaningful Life” (Kindle Publishing, 2023) and is scheduled to release “Stakeholders: The Intersection of Human Beings in the Eco-System of Business” (John Hunt Publishing) in the Spring of 2025. He is a former senior strategy adviser for the Institute for Corporate Productivity.