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The CIO Corner | Succession Planning & Building a Future-Ready Leadership Bench

By Retained | April 14, 2026

Building a Future-Ready Leadership Bench 

Succession planning used to be something leaders revisited once a year or when it became urgent. It was structured, often static, and centered around identifying a replacement. That approach doesn’t reflect how organizations operate today. 

The pace of change, especially across technology, has redefined leadership. Roles evolve quickly, expectations shift, and the idea of a single “ready-now” successor is becoming less realistic. Succession planning is continuous and not a one-time exercise. 

From Replacement to Readiness 

Forward-thinking CIOs are moving away from simply filling roles and toward building leadership readiness over time. Instead of asking who could step in tomorrow, they’re focused on who they are actively developing for what’s next. It becomes less about titles and tenure and more about adaptability, decision-making, and the ability to lead through change. 

Succession planning, in this sense, is less about prediction and more about preparation. 

A Mindset Shift 

Succession planning today isn’t just a process; it’s a mindset that shapes how leaders evaluate, hire, and develop talent. Rob Milstead, CIO of Intertape Polymer Group described it as something that’s always in motion: 

“To me, succession planning is an ongoing mindset. There may be HR-supported milestones along the way, but ultimately, it’s a philosophy and a mindset focused on actively trying to identify my successor. Often, it’s not so much about the technology itself, but how the function partners with the business, communicates, prioritizes, and delivers results.” 

That mindset starts much earlier than in development. Walt Carter, President of THG Advisors, shared: 

“From the first interview with a candidate, succession planning is also in the interview: ‘Is this person a possible CIO/key leader for our team?’ I look for three attributes: IQ, EQ, and LQ, plus several narrative qualities: Grit, teaming/collaboration preferences, bias for action, and ‘pragmatic optimism.'”

Together, these perspectives show that succession planning starts earlier and plays a bigger role in leadership decisions than many organizations realize.

Where It Actually Happens 

This kind of approach shows up in everyday decisions. Who gets exposure to high-impact work,  who’s included in strategic conversations, or has opportunity to stretch beyond their current role. Over time, those decisions build a much clearer and more dynamic leadership pipeline. Organizations that do this well aren’t relying on a single successor, they’re building depth across the team. 

Looking Ahead 

For today’s CIOs, succession planning is no longer just about ensuring continuity. It’s about preparing for what’s next, before the need becomes urgent. The organizations that will be best positioned for the future are the ones consistently developing their leadership bench over time. Because in a constantly evolving landscape, succession planning is about staying ahead.