Gary Winters

Coach  Workshop Facilitator Author

Managing the Soon to Retire Employee

“What the caterpillar calls the end of the world, the master calls a butterfly.”  – Richard Bach

There’s a particular management challenge that’s rarely discussed but increasingly important, and I’m making it the subject of the next book in my Just In TimeLeadership Series. It’s about Managing the Soon to Retire Employee.

As of 2012,  10,000 Americans reach age 65 every day, and of them, 6,000 retire at that time. Since we’re all going to retire sooner or later (assuming we live to retirement age), I call folks who’ve announced their plans to retire within the next three years or less “Sooners,” and everyone else “Laters.” This will be a book about managing Sooners.

Why are Sooners special, and why do managers need to think carefully about how they’re managing them?

Sooners are different from other employees

  • They’re at the end of their career. They’ve achieved most of what they’re going to achieve professionally.
  • Unlike others, Sooners are shifting their focus from their work and career to the next phase of their life.
  • During this shift, Sooners may not seem like their “usual self.”
  • They’re often accused of being resistant to change.
  • They’re likely to be older than many, if not most, of their colleagues (and, perhaps, their manager).

The Sooner’s transition process is different from that of other employees.

Most managers have experienced “regular” employees in transition – from the new employee becoming a member of the team, to the one who’s been promoted, to the employee who’s getting married or divorced, to the employee who’s transferred and adjusting to a new supervisor. All of these are times of transition, which, as William Bridges teaches in his book Managing Transitions – Making the Most of Change, have three phases – Endings and Letting Go, the Neutral Zone, and New Beginnings.

The transition from employee to retiree contrasts with these in several ways:

  • It usually takes longer.
  • It involves a complete “re-invention” of the self, including letting go of one’s professional identity
  • Most importantly, as far as the manager is concerned, the transition is completed after belonging to the organization.

Not all Sooners are “problem employees,” but when they are, it can be very challenging!

Most so-called problem employees can be turned around with an assortment of classic management tools, including the Performance Improvement Plan, which includes consequences for not improving performance. The PIP is useless with a Sooner, who would likely react “What are you going to do if my performance doesn’t improve? Fire me? Ha!”

The manager of a Sooner must put away his/her hammers, and find another, more positive approach.

Whether a Sooner is a genuine problem employee, or a person who is simply going through a difficult time, or is a steady performer who will be greatly missed after retirement, managers need to understand the dynamics of the transition, and the approaches to leading Sooners that have been proven effective.

I invite you to engage in a conversation about your experience managing – or being – a Sooner in the comments section below.


“What ELSE Your Boss Never Told You” is the sequel to the very popular “What Your Boss Never Told You.” Packed inside are more tips, techniques, and insights about the challenging, but rewarding leadership position.

“What ELSE Your Boss Never Told You” is written in a conversational tone, as though you and the author were enjoying a cup of coffee and talking about the issues that emerge for new leaders. It stands alone, and/or could be read before or after the first volume, “What Your Boss Never Told You.” You can start with any chapter and read in any order you like.

if you search for a book on management, you’ll find a staggering 600,000+ books currently available. How can you narrow that down? “What Your Boss Never Told You” is the best place to start.

No textbook here – this book is short and sweet. It’s designed to help you “unpack” your new job and be effective from the first day with your new team. It contains twenty-one chapters filled with the wisdom Winters has gathered from real managers – effective, successful leaders in organizations much like yours.

Leaders make decisions every day – big and small. Most know that if they include others in the decision-making process, the quality of those decisions – and the commitment to them – will likely improve. That said, they also know it’s impractical, if not impossible, to include others in every decision they confront.

“To Do or Not To Do” tackles the question of when to make decisions on your own, and when to involve your team. It gives you a deceptively simple but proven method to determine, when you are facing a difficult decision, how to decide how to decide.

Far too many meetings are dreadful, mind-numbing, energy-draining, productivity-sapping, colossal wastes of time. As someone once said, “To kill time, a meeting is the perfect weapon.”

Here’s the deal: if you’re willing to learn and apply the techniques in “So, How Was Your Meeting?”, you’ll call fewer meetings, while vastly improving the ones you do lead. They’ll take less time, have more balanced participation, produce better decisions, and result in concrete action items for follow-up afterwards.

While there are thousands of books written for people about to retire, this may be the only book for people who manage soon-to-retire employees. Written in a casual, conversational style, “Managing the Soon To Retire Employee” will give you everything you need to know to move forward with confidence and grace.

You can be successful with Sooners. It won’t happen by chance, and it’s not a matter of pulling some management “trick” out of your hat. But you can learn how to do it, and you can apply what you’ve learned right away.

Managing friends or former peers can be awkward. When you become the boss, everything about these relationships can suddenly be uncomfortable. There’s a new set of ground rules to establish – as manager, you are going be accountable for the work performance of friends or former co-workers on the team, and they are going to have to adjust to the fact that they now report to you. Everyone involved can feel awkward and hesitant about the future. 

Have you been approached by management with an offer to promote you to supervision? Or, are you mulling over the possibility for the future? Find yourself not sure whether to accept the promotion?

If so, you’ve come to the right place. Help! They Want to Make ME a Supervisor will help you sort out a very big question: Should you accept the offer to become a supervisor? Once you’ve read this book, you’ll be confident that you’ve made the best decision for you and for your organization.