Gary Winters

Coach  Workshop Facilitator Author

How do you keep them
engaged until the end?

Let’s face it. Once someone’s let it be known that they’re going to retire soon, things can get a little difficult for the boss.

Every day, over 10,000 Americans retire. The Baby Boomers are reaching the end of the line. 

I call employees who’ve decided to retire within three years or less Sooners, because they’ll be retiring sooner than everyone else.

Furthermore, once someone becomes a Sooner, he’s on “S-time” – Sooner time. That’s the period of time between going public about one’s intention to retire and spending the last day on the job. The Sooner now finds his attention divided between meeting his goals and objectives at work, and determining how he wants to arrange his life after he leaves the organization.

While everyone goes through transitions from time to time throughout their career – getting married or divorced, moving to a new home or adjusting to an empty nest, or perhaps acclimating to a new supervisor – what the Sooner is doing is unique. He will complete his transition outside the organization and after his employment has come to a close. 

The difference is significant, and begins to explain why managing Sooners presents a unique set of challenges. Dealing Sooners who are overwhelmed by their transition – is tough. Just as aging isn’t for the faint of heart, neither is managing a troubled Sooner! 

Sadly, “how to manage the soon-to-retire employee” is rarely, if ever, addressed in leadership academies or workshops. 

In fact, this may be the first book on the topic.

A reviewer on Amazon said…

“This book was spot on for me and timely. I study generational differences and present on the generations topic quite a bit and am now encountering Generation Xers who want advice on how to manage boomers and “soon to retire” boomers. This book could not be more helpful to me professionally and for me to refer to others. While it stings to read some of the observations about those boomers who are resistant to change or not pulling their share, Gary Winters’ advice is practical and doable and humane. He gets to the point.”


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.

“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.

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.