Before Your Next Leader Leaves: A Case for Succession Planning

What happens when the person who has spent 20 years running your business decides it’s time to leave? You probably know their title and responsibilities. But do you know how much of the business still runs through them?

They may be the first call for your biggest customer; the person employees turn to when something goes wrong and the only one who remembers why a critical business decision was made. Replacing their position is one challenge. Preparing the organization to operate without them is another.

For Saskatchewan businesses, those relationships can take years to build. Giving the next leader time to get to know customers, employees and the community make the handover easier for everyone.

Saskatchewan’s experience gap deserves attention

The Government of Saskatchewan’s 2025–2029 Industry Labour Demand Outlook projects approximately 119,100 job openings across the province. Sixty-four per cent are expected to result from people leaving the workforce, primarily through retirement.

Those figures cover the whole workforce, rather than leadership alone. For employers, they raise a practical question: how much experience could leave your business within the same few years?

Your next executive may need support from an experienced department head who is also approaching retirement. The employee who understands your most complex accounts may be considering their own next chapter. Looking at these departures individually can hide the bigger exposure. Succession planning should consider the people around a leader, not just the leader.

“We have someone in mind” is not enough

Many businesses can name a person who might take over. Fewer can explain what they are doing today to prepare that person. A capable manager may know the operation inside out without having managed a business-wide budget. A strong technical leader may have little experience working with a board. Your most reliable employee may have no interest in taking on the top job.

These are useful things to discover while you still have time to act. Give potential successors opportunities to stretch beyond their current responsibilities. Bring them into strategic discussions. Let them lead a project across departments, manage a larger budget or take a more active role in important customer relationships.

Then assess how they respond. What comes naturally? Where do they need support? Do they want to keep moving in that direction? A name on a succession chart offers limited reassurance. A person gaining relevant experience gives the business something to build on.

The handover starts in everyday work

Think about what your longest-serving leader knows that nobody else does. It could be the history behind a supplier agreement; the warning signs that a customer relationship needs attention or the reasoning behind a decision the business is considering again. That knowledge rarely transfers neatly in someone’s final two weeks.

Start making it part of everyday work. Include another leader in key meetings. Record the context behind major decisions. Introduce customers to more than one senior contact. Allow others to solve problems before the usual decision-maker steps in.

This also helps to reveal where the organization has become too dependent on one person. Addressing that dependence can strengthen the business immediately, even if a leadership change is years away.

Hire for where the business is going

From an executive search perspective, one of the most important questions is what the next leader must accomplish. After 20 years, a role can become shaped around the person holding it. Their responsibilities may have expanded with the business, their strengths and the people around them. Simply updating an old job description can carry those assumptions into the next hire.

Take the opportunity to look ahead. Does the business need to enter new markets? Improve systems? Build management capacity? Lead through an acquisition or ownership change? Those priorities should shape the leadership profile. Internal development and external recruitment can both support that plan. You may have a future leader who needs more time, alongside an immediate need for experience the organization does not yet have.

Exploring the external market early helps clarify your options, including available talent, compensation expectations and relocation considerations. It gives you a stronger basis for decisions when the time comes.

Don’t wait for a retirement date

It can feel awkward to ask a long-serving leader about succession, particularly if they have no plans to leave. But their involvement is valuable. They know which parts of the job will be hardest to hand over and where someone else needs more experience.

Start by looking at the responsibilities that would be hardest to hand over. If only one person manages your largest customer or approves major spending, who else understands enough to take over? You may have someone capable who needs more experience, or a gap that will require hiring.

Involve those employees while the current leader is still available to help. Working through a budget together or gradually taking over a customer account gives them time to learn, ask questions and earn trust before they carry the responsibility on their own.

At Aplin, we believe strong hiring decisions begin with understanding the business behind the role. Succession planning brings that same discipline to leadership: knowing what needs to be protected, understanding what needs to change and giving people time to prepare. If your longest-serving leader announced their departure tomorrow, what would you wish you had started a year ago? That is a good place to begin.