Gary Winters

Coach  Workshop Facilitator Author

Workshops, seminars, retreats - Oh my!

I’ve designed and delivered hundreds of workshops and seminars for supervisors, managers, and prospective leaders on a wide variety of topics. Here are five of the most popular, and many other topics are available as well. All can be tailored for your organization. All can be delivered via Zoom.

I have also designed and facilitated dozens of team building sessions for departments, cross-functional teams, executive teams, even city councils and other government organizations. 

My Top Five Most Requested Workshops (plus Teambuilding)


This popular program has over 1,500 graduates since 2011. It is a comprehensive two-day workshop. Here are more details: S.T.A.R.T. 

Is Management for Me?

This is a half-day “mini-S.T.A.R.T.” which helps participants understand what the job would be like, what they’ve might gain or give up should they choose it.

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To Do or Not To Do?

Based on my book of the same name, we explore five decision-making styles and determine whether and how and when to involve staff. 

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Leading Change

How to plan and lead a change initiative. The nature of resistance, the difference between change and transition, getting buy-in and more. 

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Difficult Conversations

What makes a conversation difficult?  Why do we avoid them? What are the dynamics of difficult conversations? How to prepare for and manage a difficult conversation.

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Team Building

I have facilitated lots of team-building retreats for city councils, senior leadership teams (public and private) and a wide variety of others. Each is customized for the specific client.

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“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.