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Succession Planning During the Retirement Boom



Actions taken today will help ease transitions for a later date.


By Jake Meister, Contributing Writer  


There always seems to be some type of trend in business. In the late 1990s it was the Dot Com Bubble. The 2000s were marred by a housing bubble that burst so badly it spurred a global financial crisis. Then there was the COVID-19 pandemic, which has left an indelible mark on all of society. With the Baby Boomer Generation at or on the brink of retirement age, a great retirement period of sorts will certainly be one of the next significant trends. Fortunately, unlike the recent national and global trends, businesses can prepare for continuous retirements with a quality succession planning process. 

“I do see a trend in the next three to five years of 50 percent of all sitting directors retiring, so it’s going to create quite an impact,” said Keith Watkins, Director of Facilities III for the City School District of New Rochelle, New York, and former president of the New York State School Facilities Association and National School Plant Management Association. 

If anyone can make such a prediction with confidence, it is Watkins. Not only has he held significant roles in the industry, but he will also soon be an addition to the trend. Watkins will retire from his leadership position in August 2026. While he belongs to Gen X — he will be 55 when he retires — he started in the industry at 18 and already has more than 35 years in facility management. 

The ability to retire has not always prompted an exit. Some people have decided to keep working. Things are a bit different right now. Watkins said changes that began during the pandemic have workers feeling “worn out” and “beat up.” Some, he said, were treated badly. 

“I think people are retiring as early as they can and not hanging around just to stay busy because of the environment,” Watkins says. 

Hard times 

Watkins does believe facility management is starting to catch a sort of post pandemic second wind and that some are even feeling reinvigorated. However, that might bring about more long-term change. Retirements will continue to be pervasive in the coming years. 

“I think what happened is, during COVID, those who could retire retired, and those who were asked to stay on, stayed on and now they're making a big push to retire,” said Stormy Friday, founder and president of The Friday Group, a Maryland-based firm that provides facility management consulting services. “I think they did a study and found that the average age [of workers] was somewhere between 49 and 50 something, and I think for the next 10 years at least, we're going to be having retirements.” 

In Friday’s experience, retirement in facility management is occurring at an inopportune time. There is a tremendous shortage of workers in the skilled trades, and many companies are vying for a small number of young workers. As a result, it can take more time to fill positions. She also sees a large gap between the number of open middle management positions at all sorts of companies and the number of candidates available to fill those jobs. 

The ongoing trends of increasing retirements, stagnant growth in qualified middle management candidates, and fewer young skilled laborers compounds the impact of each other. If a facility management operation is caught off guard by a few unexpected resignations, it could be one staffing problem too many. And statistically speaking, a retirement or surprise resignation is likely to occur at any level of an organization in facility management. Just look at the numbers. 

Watkins oversees a department of 117 people. A few hold the title of assistant director or nighttime custodial supervisor, but the majority of his staff could be classified as a “laborer.” On average, five or six of his employees in those positions will retire in a year. On top of that, more will often step away due to health issues or to care for family. 

Plan ahead 

With so many staffing uncertainties, facility management operations need to control what they can. A great place to start is constructing a succession plan - or at least a long-term staffing plan - well in advance. A lot of facility executives view planning a team of workers for the future as a luxury that can be put off. Friday actually believes long-term roster planning is something that should be addressed right after a senior executive completes their first 100 days on the job. 

“It has nothing really to do with retirement at first because it is how you start planning your bench of up and coming FM staff,” she said. “A senior executive needs to look at staff and determine how they will move up and around the organization. It doesn’t necessarily mean that it is a succession plan for the most senior official, but for everyone in the organization that has the potential to retire. It is part of planning for the future.” 

Sometimes people will retire on a bit of a whim, but many workers begin planning their final day of employment well before it takes place. Once that final decision is made, the retiring employee can do their employer a solid by letting them know. Watkins recommends facility management professionals in senior leadership positions notify their supervisor or employer of the decision a year before retirement. That way, staff can work together to build around the planned date. 

“I'm a big believer that you should be closing a capital project, working on a capital project, and planning a capital project at all times,” Wakins explained. “So, to be able to understand what happens when you become unplugged from the normal duties of your job, and how that's going to impact the district, you don't want it to have a negative impact.” 

In an ideal situation, the person hired or promoted to succeed the departing senior leader will have a few months to shadow them before they retire. Watkins thinks this overlap could be four to six months - long enough for the employee taking over to understand the capital projects taking plan, the day-to-day work in the position, the vision the company has for the position, and human resources concerns. 

“If the person that's leaving has been successful, you want that person who's replacing them to understand how they operate, how they function, so [the employer] is not taking a step backwards when that transition actually happens,” he explained. 

Friday’s ideal timeline is even more employer friendly. She believes people retiring from the most senior-level positions should be giving at least two years’ notice. She believes those holding positions just below high senior-level should give at least a years’ notice. 

The success planning process should not solely rest on the work of the departing employee. Facility management organizations should do a regular analysis of staff. That includes identifying everything from potential shortages in one department to employees who might soon retire. 

Good managers hold periodic reviews and conversations with employees to find out, at the very least, how things are going for them. If such a check in is taking place with an employee who is at or nearing retirement age, it does not hurt to ask the employee if they have given it any thought. 

“Usually you can have a pretty decent conversation. Most people are open about it,” said Friday, adding that employees are of course less likely to disclose that they are looking to work elsewhere. 

There can certainly be situations where an employee is compelled to suddenly retire because of a situation in their personal life. If this occurs - or if the employee chooses not to announce his or her retirement until months or weeks before it takes place, there are a few things a facility management organization can do. One way is to assess the current staff and identify someone who can step in - even if on a temporary basis. If nobody fits that criteria, then the organization could look at external service partners or into its network of people in the industry. Maybe someone who used to be with the organization before their own retirement would be willing to step in temporarily under the correct terms. Perhaps it makes sense to bring someone in as a consultant to help keep things going until the right fit is identified. None of these options are ideal. That’s why the best move to make in succession planning is to simply get started. 

“Don’t wait until someone has announced that they’re leaving,” Watkins said. “Just keep your finger on the pulse and make sure you’re doing your due diligence so you can prevent the opportunity of absence in a position that is very important.” 

Jake Meister is a freelance writer based in Port Washington, Wisconsin. 




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  posted on 1/6/2025   Article Use Policy




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