Gary Winters

Coach  Workshop Facilitator Author

Say, boss, I think I’m gonna retire…

If you’ve read What Your Boss Never Told You, my Quick Start Guide for New Managers, you met three types of employees – those who support you, those who sabotage, and those who split (but don’t actually leave).

In March, I’m publishing a book to help managers with yet another kind of employee: those  who are about to retire. In Managing the Soon-to-Retire Employee, you’ll find practical suggestions on how to keep these folks motivated and productive even as they have one foot out the door.

“Sooners,” as I call them, are folks who intend to retire within the next two or three years. Their career is winding down and they are beginning to transition from employee to retiree. The psychology of this process is complex, and it’s sometimes difficult for Sooners to remain as engaged and productive as they have been.

10,000 Americans retire every day.

Baby Boomers are completing their careers at a phenomenal pace. Once they announce plans to retire, they can be stereotyped as resistant to change, withdrawn and not “their usual self.” Often older than their colleagues, peers and supervisor, Sooners find themselves trying to figure out how to wind things down gracefully while maintaining a productive track record.

As the manager, you are focused on the game, while Sooners are starting to focus on what happens after the game.

How do you help keep Sooners engaged and productive throughout their final months or years with the organization?

You can’t simply ignore the issue, look the other way and hope for the best. You must get involved – as a coach, a confidant, and a colleague. You must have empathy for what they are about to experience and a thorough knowledge of the psychology of personal transition.

Recently I’d asked Craig Bronzan, the Director of Parks and Recreation for the City of Brentwood, California, to describe his feelings about his pending retirement. In an “open letter” to his boss he wrote: “Can I still add value to the job? … yes, I can. Although the day I walk out of here for the last time is coming quickly, I want to be valued to the very end and add value to what I do. … I have been here a long time, mostly because I am passionate about what I do. I want to make a difference and be appreciated for my efforts.”

Sooners like Craig, who are going through a significant life transition, present a unique set of challenges which you can learn to handle. Managing the Soon-to-Retire Employee, available in April on will be your compassionate, practical guide through this time of transition.

“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.