Succession Planning Starts Before Someone Leaves

 Photo by Kelly Sikkema on Unsplash  

Before you buy another recruiting tool, ask what yours was designed to do

A recent client conversation stopped me for a moment: close to 50% of its workforce may retire in the next decade. That is a planning number, not a prediction that 50% will leave. Still, it raises a practical question: what would the organization lose if even a portion of those people departed without a deliberate handoff? 

After roughly 35 years in IT, HRIS, and healthcare, I have seen organizations move quickly to fill an open position. Preparing someone to carry forward the knowledge, relationships, and judgment behind that position takes a different kind of work. It has to begin while the incumbent is still there. 

Start looking on day one

I have spent many years serving community organizations and nonprofits. As a board president, I was taught to start looking for my replacement on the first day. It sounds a little startling until you see it for what it is: stewardship. If the organization depends on one person to understand its agreements, relationships, or history, that person has an obligation to bring others along. 

That might mean inviting a future leader into a board conversation, explaining why a decision was made, or letting someone else take the lead while you can still offer support. The successor gains experience; the organization gains resilience. Yet in corporate workforce planning, the equivalent work often gets reduced to a name and a readiness rating on a slide. Available tools are left unused. 

The handoff has value

Healthcare gives us an especially human example. Imagine a community physician who has cared for patients for 25 years. When that physician leaves, the immediate task is to cover the schedule. An overlap with the next provider looks costly on paper. But have we measured the value of a warm introduction, a conversation about the history behind the chart, and time for colleagues and patients to build trust? 

I am not suggesting every role needs a long overlap. I am suggesting that the cost of a transition is larger than the cost of an empty position. Some knowledge can be documented. Some needs to be shared through working together. Succession planning should make room for both. 

Look beyond the obvious candidates

A succession discussion should also make us curious about the people already here. Who could be ready with the right assignment or mentor? Who has skills we have never asked about? Potential is not always visible in a job title. 

My coworkers know my Workday and healthcare background. Some were surprised to learn about my conservation work with a land trust, including the governance and long-range decisions involved in conservation easements. Clients may not know that I sing, play piano, and recently conducted a chorus. Those experiences are not qualifications for every role, of course. They do remind me how narrow a view of a person we get when we rely only on their current position. 

Workday supports identifying critical positions, assessing candidate readiness, and connecting talent information with development and workforce planning. Those tools can make the discussion easier to maintain and act on. They cannot discover every hidden skill or arrange the difficult conversations by themselves. 

Keep the plan alive

People and organizations change. A candidate develops, changes direction, or leaves. A new role becomes critical. If the succession plan is revisited only every year or two, its apparent precision can be misleading. I would rather see a manageable set of critical roles reviewed regularly, with clear owners and specific next steps: a stretch assignment, mentoring, a documented process, or an introduction to a key relationship. 

This is personal for me, too. I am 60 and not ready to retire, but I am ready to share what 35 years of decisions and lessons have taught me. Why was an integration built that way? What was tried before? Which old assumption no longer holds? I want newer colleagues to have that context while we can still discuss it together. 

So my question for a leadership team would be: if a critical person told us today they were leaving in six months, what would we wish we had started two years ago? 

Whatever comes to mind—development, mentoring, knowledge transfer, a chance to lead—is the work of succession planning. The name on the slide is only the starting point. 

We have tools to help us do this work. Succession Planning is part of Workday’s Talent and Performance capabilities, yet it can sit unused while organizations keep their plans in slide decks. Put it to work: identify critical roles, assess readiness, and give people the experience they need. Who will fill the next role? What are you doing now to help them be ready? 

If you want a structured way to ask this question across your critical roles, we built a 12-question self-assessment — succession, planning, and the workforce data both depend on, scored so you can see where the exposure sits: click here to download the self-assessment.