A month after 9/11, my wife Annie and I sat in a restaurant on Annapolis’s Main Street, enjoying a rare dinner with a young plebe.

He wouldn’t admit it, but we could see he just wanted to sleep. He politely made small talk while darting glances at the door, ever vigilant for the appearance of an officer. Then, pausing between bites, he quietly announced he had discovered a new way to learn.

We put down our forks and turned to him with interest. “First,” he said, “I read profusely, whether I completely understand the subject or not. Then, after a while, I put away the books and think intensely about what I have read, heard, and observed. In time, things come to me, the subject becomes clear; I conceive of new concepts and ideas.”

This young plebe had discovered how to do the deep work. Fifteen years later, Cal Newport would write “Deep Work – Rules for Focused Success in a Distracted World.” Making sense of this practice for a general manager is what this article is all about.


As an executive coach, one of my main objectives is to help the client understand what is most important, to foster a curious mindset, and to ask the right questions. When embraced, the enjoyment experienced by the client with the “aha!” moment has its rewards and leads to thinking strategically. The reality is that a GM is paid to operate in the moment and to think in the future.

In my experience, creativity starts with acknowledging guiding principles because a foundational principle demands integrity of thought and action and the impetus to stay the course. Take, for example, a GM who embraces the principle of never relieving oneself of the responsibility for the well-being of the
club. What responsibility for action does that principle require?

The effective GM decisively exploits opportunities and embraces innovation by seeking to provide members with something new and better. With a desire for growth, the GM overcomes problems and pushes aside the nagging tug to hunker down under stress and problems.

A good leader knows when to “put away the books,” the knowledge-gathering phase, and when to focus on delivering a winning action plan. Curiosity is a valuable mindset. After a period of information gathering about important issues, the curious GM’s next step is to craft possible answers to the most compelling questions. This basic premise is outlined in Roger Martin’s book, “Playing To Win.” He states that effective strategy is always a choice of how to win, not just compete.

Asking good open-ended questions is an important skill. How does this process look in practice? A GM should cultivate the skill of asking open-ended questions to help define the problem. Below are examples of this exercise:

  • In what market are we playing?
  • What do we have to do to win?
  • In what ways do members have an emotional connection to our club?
  • Does our current operating model foster excellence throughout the member experience?
  • In 5-10 years, what will prospective members want in a club experience?

Answering strategic questions is a process. The next step at the heart of organizational change and development is to think through the details. Dr. Max Bazerman of Harvard Business School proposes the rational model, a six-step process for optimum decision-making:

  • Define the problem
  • Identify all relevant criteria
  • Weight the criteria
  • Generate alternatives
  • Rate each alternative of each criterion
  • Compute the optimal decision.

I experienced this firsthand in Bazerman’s HBR Executive Education class, Changing the Game: Negotiation and Competitive Decision-Making, and put the concepts into practice at the Detroit Athletic Club. From experience, I suggest keeping your mind fresh during this process and working with others to be thorough.


Using our minds and thinking deeply is the most energy-consuming activity in which humans can engage. It is also the most important. Why does it seem that much of a GM’s life gets in the way of doing the one thing that allows the GM to conceive of how to do something new and better? Yet, it is the ability to think, focused on the right things, that makes a leader valuable.

We strive to be efficient and subconsciously do things to conserve our energy and save time. The problem with this habit is that it is at odds with thinking deeply and comprehensively. Where speed is considered a virtue, deep thought is often postponed.

Another caution for a GM to be sensitive to is the practice of regularly going to personal strengths and experiences for answers. Rather, put effort into growing strengths and understanding to create more options from which to draw. It is not speed and volume that should be valued but the thoughtful consideration of the information we gather. If you find you are locked into overusing your strengths and taking too many shortcuts, you might want to read “Fear Your Strengths: What You Are Best at Could Be Your Biggest Problem,” by Robert E. Kaplan and Robert B. Kaiser. Curiosity is a series of strategic questions. Of course, finding the answers will assuredly tax the minds of all involved, but stay the course. Remember why you started down this path and adhere to foundational principles to guide and inspire.

The good thing is that sound strategy and deep thinking are not lonely work because the process naturally calls for collaboration. Working with bright minds will give you the best chance of conceiving a win-win set of strategic choices that will make all the difference for your club and the people you serve and work alongside.

In summary, the deep work of concentration is the most significant practice a leader can engage in. General managers should consider measuring the success of a career by what they have learned and successfully implemented to impact the people and the clubs they serve.

Contributed by J.G. Ted Gillary, CCM, CCE, ECM, CMAA Fellow. Ted is a search and consulting executive with KOPPLIN KUEBLER & WALLACE.

BoardRoom Magazine – November/December 2022