Journey of Growth, Playing to Win in Leadership

leader leaders leadership Oct 25, 2023

In the book "Playing to Win" by Larry and Hersch Wilson they define the journey of growth as playing to win. To grow requires you to challenge your core maps and redefine them to align with your values and true sense of self.


This is the epitaph they share:

"I took the risk.
I discovered who I was.
I changed.
I grew.
I learned.
I was an adventurer."

Related: How Leaders Make Decisions

To choose growth is to choose risk.

What risk are you holding back from that is in alignment with your true self?
What conversation do you need to have with yourself that you have been holding back on?
What would you do if you accepted this premise "I cannot fail, I can only learn and grow"?
Why should you choose growth which will stretch you and make you uncomfortable?
Why would you choose a path that is not comfortable or convenient?

Share your thoughts when you are ready.

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Risk Taking or Dream Making in Leadership

"I am always doing that which I cannot do, in order that I may learn how to do it." Pablo Picasso

Risk is inherent in any endeavor. Leaders know the more time they spend not taking risk the slower they grow. Risk is simply growth, taking on new skills or opportunities you have yet to learn about. By limiting risk, you limit learning, and if you are not learning, you are not growing .... you are shrinking.

Warren Bennis noticed leaders who take risks make one or two big mistakes a year and leaders who don't take risks make one or two big mistakes a year. Leaders get mistakes will happen and remain open to learning from mistakes to improve. When we limit our growth, we stagnate and so to do others around us.

"Yes, risk taking is inherently failure-prone. Otherwise, it would be called sure-thing-taking." Tim McMahon

If you are always focused on getting it right you are losing the opportunity to see new possibilities. It is through trial and error that growth happens.

Related: Creating...

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Being Creative in Leadership

"A wonderful emotion to get things moving when one is stuck is anger. It was anger more than anything else that had set me off, roused me into productivity and creativity."
Mary Garden

After working with a vast diversity of leaders from around the world it is clear the most successful leaders seek out new possibilities and are extremely creative. Creative leaders understand that the conduit to creativity is through emotion. The emotion could be passion, love, anger, playful, sadness, happiness, laughter, joy, frustration, irritation, surprise, etc. but the key to creation comes through emotion.

Creativity cannot be made to happen, you have to let it come through you.

Leaders who want to inspire others and find new ways are comfortable with allowing their emotions to flow through. They take the time to notice and understand what is at the core of the emotion. In this understanding new possibilities and growth emerges ....also known as new creative options and possibilities.


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The Adventure of Trust in Leadership

"As soon as you trust yourself, you will know how to live." Goethe

There is no word that creates more energy and discussion than this word. In leadership, so many passionate discussions are based around this word:

Do I trust this new hire?
Do I trust this salesperson?
Do I trust this business deal?
Do I trust my colleague?
Do I trust my new manager?
Do I trust this decision?
Do I trust the economy?
Do I trust the politicians?
Do I trust the media?
Do I trust the mail?

I am sure you could add a few.

Related: Leadership Requires Bravery

The list goes on and on... and if you listen closely and look you can see behind the questions is ....doubt. Doubt and uncertainty, are two words that have more energy than trust.

Leaders are dealing with these doubts, fears, and uncertainty of emotions every day. In a time of great unrest and change the core skills you need to be prepared with the shifting tides of doubt which erodes the trust you have built over time are as follows:

"When I’m trusting...

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The Secret of Good Decision Making as a Leader

"It's not hard to make decisions when you know what your values are." Roy Disney

Decision-making is a core leadership skill. The secret or trick is to know yourself. Good decisions will grow yourselves, your companies, your team, your family, and your community and will require you to be a bit (sometimes more than a bit) uncomfortable.

Related: Stepping Forward in Leadership

Thoughtful decision-making requires the following:

1. An understanding of yourself and your own value system (clarity here makes all decisions flow)

2. An understanding of the situation and what it means to yourself and others

3. Input from trusted peers who have different and contrary perspectives

4. The desire for personal growth as a leader

5. The willingness to hear the truth when you are in love with an idea or skeptical of it

6. The keen awareness when you decide that you are ready to "take the ride" because you will grow and change


"Do not plant your dreams in the field of indecision, where nothing...

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Visions in Leadership

"The important thing is to strive towards a goal which is not immediately visible. That goal is not the concern of the mind, but of the spirit." ~Antoine de Saint-Exupéry, Flight to Arras, 1942, translated from French by Lewis Galantière

The most important role any leader has is to dream and to have vision. Without this focus, all things become stagnant and uninteresting. The second most important role is to move towards it no matter how tedious and unpleasant some of the work or effort may be.

Related: Vision Planning for Leaders

"Goals are dreams with deadlines." ~Diana Scharf Hunt

Here are some general practices that keep you moving and flowing toward your vision, the dream.

If you dread doing it - make it the first thing you do in the morning and get it off your list
If you keep forgetting to do it - make a to-do list/reminder and then do it
If you second-guess yourself - go back to your first answer and get it done
If you want to leave it to later - move up to...

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Great Leadership Is Not For The Faint Hearted

"All of the great leaders have had one characteristic in common: it was the willingness to confront unequivocally the major anxiety of their people in their time. This, and not much else, is the essence of leadership."
John Kenneth Galbraith, U.S. economist, "The Age of Uncertainty"



The illusion of outstanding leadership is it looks easy. Yet behind the scenes, leaders grapple with complex scenarios, unclear situations, undefined possibilities, and regular risks. It is not an easy job....and it is a very satisfying job for those who are willing to put in the hard work, effort, and personal growth necessary to define new roads forward. Leaders who shine have the ability to step into the tension to understand a situation and let go of "what is the right way" and search for the "best way". They have a honed skill to not focus on who is "right or wrong" but to focus on what is the path forward that creates a new flow for all involved.

To do this it requires the core...

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Impactful Leadership

"Some people strengthen our society just by being the kind of people they are." John W. Gardner

Perhaps the most challenging exercise of authentic leadership is the coming home to self. To remember that embracing yourself, having confidence in your way of learning, and being are enough. When a leader is in the strength of who they are and are true to their nature they thrive and are able to make significant impacts with their work just by being themselves.

The only thing that gets in the way of all of this is ego. The ability to be self aware and self manage allows leaders to constantly stretch, grow and adapt.

“The Tao Te Ching says,
When I let go of what I am,
I become what I might be.
When I let go of what I have,
I receive what I need.
Have you ever struggled to find work or love,
only to find them after you have given up?
This is the paradox of letting go.
Let go, in order to achieve. ” – M. M. Morrissey

Each day leaders have the ability to impact others in a way...

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Creating Strategy in Leadership

“What do you want to achieve or avoid? The answers to this question are objectives.
How will you go about achieving your desire results? The answer to this you can call strategy.” William E. Rothschild

The ability to have a vision and build a strategy to move into the vision is one of the core necessities of leadership. Often I am asked can this be taught or is it born. And it turns out it is neither. It is a commitment to "step out of the day to day" and look objectively and with new eyes at the world around you. This ability is what builds strong and vibrant leaders and like wise organizations.

For leaders who spend time gaining new experiences, trying new hobbies, learning new concepts and skills outside their day-to-day, and practices putting themselves in others shoes....strategy is easy and fun. These leaders provide bold and strong growth.

For leaders who tend to stay with like minded people, are surrounded by people who do not question or explore their thinking,...

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Vitality of Leadership

“There is a vitality,
a life force,
an energy,
a quickening,
that is translated through you into action,
and because there is only one of you in all time,
this expression is unique.”

Martha Graham

Leadership is made up of many components that have been studied by the greats. One of the key components is physical vitality and stamina. When you see positive leaders which energize an organization and have the keen ability to influence people see an "aliveness" that captures the minds and spirits of others.

So does this mean you have to be fit like Lance Armstrong or Serena Williams?

No. It does mean that you have to maintain a healthy lifestyle to make sure you are engaged and energized in role as a leader. An equal part of vitality is having passion and finding the pieces in your role that create excitement, energy and aliveness which translates well into your organization.

Related: Goal Review as a Leader

Key Attributes of a Leader

Here are key attributes of leaders...

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