The CEO’s Dilemma: Why Executive Isolation Is Your Biggest Strategic Risk
Feb 16, 2026
Today we're addressing a problem that gets whispered about in boardrooms but rarely confronted head-on: executive isolation. Are you feeling isolated?
Reviewed by Thuy Sindell, PhD. Written by Milo Sindell, MS.
Published on July 9, 2025
3 minute read
AI and Succession Planning: Why Your Leadership Pipeline Is Shrinking & How to Prepare for a Leaner Future
Your HR team’s AI just flagged a rising star based on performance metrics, but overlooked the steady innovator who led calmly through a crisis.
AI is great at spotting patterns, but building future leaders takes more than algorithms. In a leaner, tech-driven world, succession planning must evolve.
With AI handling more decision-making and fewer mid-level managers being developed, companies are facing a shrinking leadership pipeline. Are you ready?
Gartner predicts that by 2028, 15% of business decisions will be made autonomously by AI agents, and 33% of enterprise software will embed AI as a core feature. This means fewer roles where future leaders gain hands-on experience.
As companies invest heavily in AI and digital transformation, resources are shifting toward hiring specialized technical talent, such as data scientists and AI engineers, reducing focus on cultivating managerial and leadership skills.
As organizations flatten and become more cost-conscious, fewer leadership-track roles are being opened, limiting opportunities for succession development.
AI is not the enemy—it’s a tool. When used strategically, AI can:
According to McKinsey, cross-functional operations transformations outperform siloed approaches by 30–40%, highlighting the value of varied experience - something AI can help uncover.
But relying on AI alone is risky:
Over time, this can result in a homogeneous, less adaptable leadership team.
To turn insight into action, start simple:
Step 1: Use AI to identify your top 10% of performers across multiple metrics (not just output but collaboration scores, learning agility and cross-functional impact).
Step 2: Host a quarterly human-led workshop to assess leadership potential through case studies, peer feedback sessions, and behavioral interviews.
Step 3: Assign mentors and revisit in 90 days with specific milestones and real-world leadership challenges.
This combination of data and human judgment is your best defense against leadership gaps.
AI can help you see more clearly but it’s not a crystal ball; it can also result in lazy decisions.
Human insight, empathy and lived experience are still essential to identifying and preparing future leaders. The best succession plans are built at the intersection of precision and perspective.
Founder and President
Executive Coaching Division
Thuy Sindell is the President of Skyline Group's Coaching Division, an executive coach, and author. Skyline's Coaching Division manages over 170 coaches, facilitators and consultants worldwide. Thuy's executive coaching experience spans over 20 years with companies across a number of different industries and sizes from technology to insurance and from start ups to Fortune 500s.
President
Coaching Scaled Division
Milo Sindell has over fifteen years as a business and human capital expert. He worked as a senior consultant for Intel and later at Sun Microsystems in areas including strategy development and implementation, change management, knowledge management, and leadership and employee development. At Skyline he is focused on market positioning and product development for Skyline's coaching technology solutions.
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