Gary Winters

Coach  Workshop Facilitator Author

S is for Start the Presses!

JIT_cover_rev2Stop the presses! Stop the presses! No wait – START the presses!

My newest ebook, Managing the Soon To Retire Employee has just been released and is available on It’s filled with tips, insight, and practical solutions to issues that can arise when you manage people who are approaching retirement.

Highly effective managers vary their approach and use different techniques with various subsets of employees. A style that might work well with seasoned veterans could be highly ineffective with a group of new hires. One group that has received little attention, from a manager’s perspective, is people I call Sooners. 

These are folks who are three years or less from full retirement. As a group, they share some critical characteristics:

  • They are likely to be older than most of their peers and perhaps their boss. 
  • They are in the midst of a major transition – from employee to retiree
  • They face the unique challenge of staying focused on their job while looking ahead to the time when they will no longer be working. 
  • They may be overwhelmed with anxiety, a sense of isolation, nostalgia, positive anticipation or negative reluctance, burnout, etc.
  • They may face stereotyping (such as being seen as resistant to change or aloof or self-absorbed)

 Managing the Soon To Retire Employee is an ebook you can read in an hour or so. You’ll learn just what it’s like to be a Sooner, the three stages of transition, why some Sooners become problem employees while others become outstanding contributors – and what you can do to facilitate a positive experience in their remaining months and years. You’ll read an Open Letter from a real-life Sooner which makes a compelling case for managers to adjust their approach to better lead Sooners. 

This may be the first book of its kind – with a focus on equipping managers with the tools they need to get good performance from their Sooners while “being there” for them in terms of helping them prepare for retirement.  If you have Sooners on your staff, you should check this one out. 



“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.