Your Best People Retire Soon. Who Is Ready to Lead Next?

Every executive I meet in Durham Region and the Greater Toronto Area knows the moment is coming. A trusted plant manager, a head of operations, or a senior director who has carried the organization for years is going to retire, move on, or step back. And when I ask who is ready to step into that role today, the honest answer is usually a long pause.

I have spent more than 35 years in senior executive roles at organizations including Honeywell, Johnson Controls, and Armstrong Fluid Technology, and I have watched strong companies get caught flat-footed by a departure they should have seen coming years earlier. Preparing the next generation of leaders is not a human resources exercise you delegate and forget. It is one of the most important strategic decisions you will make, and the good news is that it is entirely within your control if you start now.

Why Is There Such a Shortage of Ready Executives?

The shortage is not imagined, and it is not unique to your organization. Leadership readiness has been declining for over a decade, and the numbers are stark. According to DDI's Global Leadership Forecast 2025, only 20% of HR leaders say they have leaders ready to fill their most critical roles, and on average, internal candidates can fill only 49% of critical positions immediately.

This creates a dangerous paradox. Three out of four organizations want to promote from within, yet fewer than half of their critical roles can actually be filled by someone who is ready today. When that trusted senior leader leaves, the organization is forced into a rushed external search, an underprepared internal promotion, or a painful period with the role sitting empty. None of those outcomes is good, and all of them are avoidable.

What Does It Mean for an Executive to Be Truly Ready?

The most common and most costly mistake I see is confusing strong current performance with readiness for a bigger role. They are not the same thing. A high-performing salesperson does not automatically become a great sales leader. A brilliant engineer does not automatically become an effective head of engineering. The skills that make someone excellent in their current job are often not the skills the next role demands.

Readiness means a person has the capability to step into a new and larger role and succeed there: to lead bigger teams, execute strategy, and handle the greater scope and complexity that senior roles bring. Before we define terms and use them freely, here is what I mean by a few of them. Behavioural change is a lasting shift in how a leader actually operates day to day, not just what they know. Return on investment, or ROI, is the measurable value an organization gets back relative to what it puts in. And a leadership bench is simply your pool of people who could step up when a role opens.

How Do I Judge Who Is Ready Without Guessing?

In most organizations, promotion decisions still come down to opinion, and leaders consistently overestimate who is ready. Opinion is a weak foundation for a decision this important. The antidote is objective data. Structured assessments give you both a broad and a deep view of a leader's current skills and, critically, how those strengths and gaps will translate to a more senior role.

The payoff is measurable. DDI's research found that promotions are 1.6 times more likely to succeed when objective assessment informs the selection decision. That is a meaningful reduction in the risk of a costly mis-promotion, and it also surfaces hidden potential in people who might otherwise be overlooked.

What Are the Steps to Prepare My Next Generation of Leaders?

You do not need a years-long, enterprise-wide program to begin. In fact, trying to solve everything at once is why most succession efforts stall. The most effective path is a focused sequence of decisions you can start this quarter. Here is the approach I use with organizations across the GTA.

1. Start with your most critical roles. Identify the handful of positions that would create the greatest risk if they were suddenly empty: the roles that drive revenue, lead strategy, or influence large teams. Focus here first rather than trying to map every role in the organization.
2. Pinpoint where the risk is highest. For each critical role, ask which have no ready successor, which leaders are likely to retire or leave soon, and which would be hardest to replace from outside. This tells you exactly where to concentrate your effort.
3. Evaluate your bench honestly. Look at who could step in today and who could be ready with the right support. This step can feel uncomfortable, but even a short list is progress because it turns a vague worry into a concrete plan.
4. Identify high potential early. Use structured talent reviews, input from senior leaders, and real leadership experiences such as stretch assignments and cross-functional projects to spot people who could grow into critical roles before a gap appears.
5. Accelerate readiness with targeted development. Growth does not happen on its own. Give your future leaders development aimed squarely at the demands of the role ahead, combining real stretch assignments, structured leadership programs, and cross-functional experience.
6. Make succession a shared leadership priority. Bring your executives into talent discussions, define a few clear pipeline metrics, and hold managers accountable for developing their people. Succession sticks only when it is owned across the business, not left to one department.

What Kind of Development Actually Builds Ready Leaders?

Not all development is equal, and the difference shows up clearly in the outcomes. Generic, one-size-fits-all programs build baseline skills but do little to prepare someone for a specific senior role. What moves the needle is a combination of structured learning and real experience with genuine stakes.

DDI's research quantifies which approaches make internal promotions more likely to succeed. Internal promotions were 3.7 times more successful when leaders took part in cohort development programs, 3.2 times more successful with sequential leadership learning that builds over time, and 2.6 times more successful when leaders received regular manager support and development. In practice, that means blending stretch assignments that expose people to real future responsibilities, structured programs that provide assessment and practice, and cross-functional experiences that broaden how a leader thinks about the whole enterprise.

This is exactly where a customized program earns its return. When development is built around the specific capabilities a leader will need at the next level, and reinforced with real accountability, readiness accelerates. Across prior engagements, this kind of focused leadership development has delivered a return on investment of typically 10:1 or better, though every organization is different and results depend on your situation.

What Can a Leadership Program Not Do for You?

I believe in being straight with the executives I work with, so let me be clear about the limits. A leadership development program cannot manufacture readiness overnight. Building a genuinely ready successor takes time, deliberate practice, and real experience, and any program that promises instant results is not being honest with you.

A program also cannot succeed without your commitment. If executive sponsorship is absent, if managers treat development as optional, or if there is no accountability for follow-through, even the best-designed program will fizzle out. Development cannot substitute for the hard organizational work of giving people real stretch opportunities and holding leaders responsible for growing their teams. And no program can guarantee a specific individual will succeed in a specific role, because people and circumstances vary. What good development does is dramatically improve the odds, reduce the risk of a costly mistake, and give you a clear, evidence-based view of who is truly ready. The rest depends on your organization choosing to make leadership development a genuine priority.

If you are ready to build that priority into something concrete, the practical next step is a straightforward conversation about your specific roles and your specific people. You can learn more about Malcolm Gurley and see why organizations choose Gurley Leadership Solutions.