Gary Winters

Coach  Workshop Facilitator Author

Thinking “Outside the Box” about Thinking Outside the Box


Don’t build a box around yourself and you won’t have to think outside it.

I saw this on the internet in someone’s signature quote, and it struck me as one of those simple but profound ideas.

Got me to wondering, what kinds of boxes might leaders build around themselves? Here’s a few that come to mind:

I’m in charge so I have to be smarter than anyone else.

The classic box that leaders build around themselves is the notion that because they’ve been elevated, promoted, or chosen for a leadership role, it’s their responsibility to be smarter than their team, precisely because they’ve been put in charge.

IF you’ve built this box around yourself, you’re in big trouble. Successful leaders surround themselves with smart people and learn from them.

We have a “chain of command” and people had better respect that.

The language of organizations has always fascinated me. The phrase that always chafes me is “chain of command.” It’s been borrowed from the military, and let’s face it – today’s organizations have moved far from being clones of military models. offers this definition of “chain of command” –  Order in which authority and power in an organization is wielded and delegated from top management to every employee at every level of the organization. Instructions flow downward along the chain of command and accountability flows upward. According to its proponent Henri Fayol, the more clear cut this chain the more effective the decision making process and the greater the efficiency.

Well, yes and no. Yes, it’s the job of leaders (from top management to front-line supervisors to temporary team leaders) to establish “what” we’re going to set out to do, and it’s the job of individual contributors to determine “how” we’re going to do it (for the most part).

My objection is the mental model that comes from envisioning a “chain of command,” and from the notion that leaders are effective when they wield power from their positional authority. You remember the phrases like – “My way or the highway.” Yes, it works. Short term. Under protest. And people who are led by fear (which is what this is, after all) rarely deliver superior performance.

In this organization, things are always In this organization, things are never

Let’s switch gears. Some boxes we build around ourselves are constructed with affirmations we repeat to ourselves (often non-consciously) over and over. Two of the most powerful use the words always or never.  Almost nothing is “always” or “never.” When you subscribe to the notion of always or never, you box yourself in.

Admit it – your organization isn’t always anything, and isn’t never anything. Same for your staff. Pete doesn’t always complain (even if he complains frequently). When you build a box of “Pete always complains,” you have to spend a lot of energy thinking outside that box to see Pete in another light.

Fire! Ready, Aim! or Ready? Ready? Ready? Aim, Fire! or Ready? Aim! Aim! Aim! Fire!

I love playing with these twists on the old adage, Ready, Aim, Fire! I’ve known many leaders  trapping themselves inside one of these three boxes:

  • One is the leader who demands action over preparation (Fire! Ready, Aim!)
  • Another is the leader who is paralyzed with analysis and planning (Ready? Aim! Aim! Aim! Fire!)
  • A third is the leader who is boxed in by his/her concern for consensus and unity (Ready? Ready? Ready? Aim, Fire!)

A good exercise is to find some quiet time and ask yourself – what kinds of boxes have you built around yourself? What thought habits, mental models, or non-consciously adopted belief systems do you carry around, boxing you in so strongly that you have to “think outside the box” to free your creative mind?

Instead of thinking outside the box, why not tear it down and throw it away? Boxes limit you. What do you need to do to dismantle your boxes, so you don’t have to think outside of them anymore?

I’d love to hear more examples of boxes that leaders climb inside. Got some?

“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.