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the leader's journey

Your Guide to WinShape Teams Leadership Retreats

Navigating The Leader's Journey

August 29, 2023
Leader's Journey
Joseph Cook

The Journey

Every single one of us is on a journey called life. Most of us know what a journey is – it is defined as traveling from one place to another. And we are all moving from one place to another, whether that is physically, mentally, emotionally, or spiritually. Therefore, we are all on a journey.

The journey of life is the biggest scale, but that grand quest from birth to death is also filled with many different types of journeys along the way. Every time we go on a trip, go after a personal goal, or join a team to accomplish a powerful purpose, we embark on a journey.

the leader's journey

One of the types of journeys my family and I take every year is called a vacation; this term might be foreign to some who are reading this, but our family vacations typically involve taking time off from work and traveling to another location to enjoy something we might not always get to enjoy where we live daily.

Another common quest is a leader’s journey. A leader is not merely defined by a specific title, position, or talent; leadership involves the stewardship of our influence, and we all have influence in one way or another.

That means we all have the opportunity to lead regardless of our position, but that does not mean we are all successful. What separates effective leaders from ineffective leaders is found in how we steward the influence we have.

The leader’s journey involves discovering how to lead yourself, how to influence others, how to cultivate a high-performing team, and how to lead a sustainable and successful organization. All these focal points in a leader’s journey are significant, but they involve distinct yet complementary skills.

The purpose of this article is to clearly identify what makes each aspect of the leader’s journey significantly distinct.

We will accomplish this by comparing the two types of journeys mentioned above: going on a trip with a group of people and progressing through the leader’s journey.

the leader's journey - lead self

Lead Self

As we step into the metaphor of going on a trip, there is a crucial part that often gets overlooked. Yes, it is important to think about the desired destination, the budget, available dates, and many other planning details. But none of those details actually matter if there is no way for us to get to where we want to go. Leading yourself can be compared to your mode of transportation (the plane, train, automobile, boat, etc.).

When going on a trip, I sometimes take for granted that my vehicle will serve us the way we need it to, but what if I did not take the steps necessary to maintain it? If I did not regularly change the oil, check the tires, or ensure there is fuel in the tank, we would never reach our destination regardless of how badly we want to get there.

Trying to lead other people before learning how to lead yourself is similar to getting all the details planned for a trip but failing to take care of the vehicle meant to get you there.

Leading yourself is not a one-time event; constant, effective maintenance is the trick.

Only filling my fuel tank at the beginning of our trip might get me to destinations not too far from where I am starting, but to go further, I must pay consistent attention to my fuel gauge and re-fuel when necessary. Similarly, every leader on the journey must consistently return to the mirror to maintain leading yourself well.

The focus of our Lead Self retreats at WinShape Teams is helping leaders develop their leadership character, self-awareness, and shaping a servant-leadership mindset. Simply put, Lead Self focuses on the heart of a leader. The decisions you make and what you do are extremely important, but who you are is more important because who you are sustainably determines what you do.

the leader's journey - lead others

Lead Others

As we continue to effectively maintain our modes of transportation on our trip, all the fundamental skills of planning the trip also greatly impact our collective experience.

For a trip to be successful, we must determine our desired destination, gain buy-in from those that are with us, plan strategic routes, know how to progressively change course when circumstances change, and make wise decisions along the way that serve our purpose for the trip and the people involved. In short, we must create a good plan and know how to execute the plan well.

One of the most important distinctions between Lead Self and Lead Others is the “others.”

In leadership, your decisions do not just affect you; they affect everyone within your sphere of influence.

I might want to go to the mountains for our family trip, but my wife may want to go to the beach instead. There are others in the equation that need to be considered.

Every decision I make regarding bathroom breaks, specific routes, our spending budget, and even what we listen to on the way to our destination all influence the fulfillment of the people I am traveling with.

Our Lead Others retreat at WinShape Teams is dedicated to enhancing the fundamental leadership skills that drive vision, engagement, and innovation. While Lead Self focuses on a leader’s character, Lead Others develops the skills necessary to help a group of people reach their preferred destination.

the leader's journey - lead teams

Lead Teams

The desired destination for our trip has been determined, the route and budget have been planned, and our vehicle is ready to get us there. Another aspect of the journey involves the group of people you are traveling with.

My family is one of the many teams I am a part of, and it is my most important team. When going on a trip together, another set of skills I need is the ability to cultivate an environment that fulfills each team member along the way.

As a team, we need to acknowledge what a successful trip looks like for all of us. This includes details like what responsibilities each team member will have (navigator, driver, lunch spotter, game creator, etc.), when and how to communicate when a pit stop is needed, or how efficient we want our trip to be.

If any of you have been on a family trip before, you know that how your family travels together greatly influences the success of the overall trip regardless of where the destination is.

The clear difference between Lead Others and Lead Teams is that leading a team requires additional skills to ensure team cohesion that leads to higher performance.

Seeing a vision for the future, developing people, and strategic reinvention are all critical leadership skills, but leaders of teams must also possess the ability to affect team culture.

It is not just about reaching our destination. Is the team fulfilled along the way? Would we want to go on another trip with this team? Do our team dynamics help us or prevent us from accomplishing our objective? High-performance teams consistently accomplish their purpose while also fulfilling their people.

the leader's journey - lead organizations

Lead Organizations

Our small family, or team, really enjoys going on trips with just the four of us, but many of our trips also involve multiple extended families. Think of a family reunion with several families traveling from different locations to reach a shared destination. These trips provide incredible opportunities to remember how we are all linked and remind us of the importance of staying connected, but they also require additional skills to ensure success.

With multiple families involved, we must organize to determine an aligned destination and assign clear expectations for each family. On our trips, each family takes ownership of providing dinner for everyone else one of the evenings. Without organizing each family’s plan, we could end up creating similar menus or have misaligned expectations for eating out versus cooking our own meal.

An organization is nothing more than multiple teams organizing to accomplish a greater purpose. Without organization, there is no organization.

The skills needed to lead an organization include clarifying the overall purpose, creating alignment across multiple teams, winning and keeping engagement, and maintaining accountability towards the aligned purpose.  

Each individual team may have a unique culture, strengths, and function, but organizational leaders know how to leverage the specific abilities of each team to help accomplish the organization’s great purpose.

the leader's journey - leadership retreat

To review, Lead Self develops a leader’s character and is represented by the vehicle needed to reach our destination. To get to where we want to go, we must maintain consistent care for our vehicle.

Lead Others focuses on fundamental leadership skills and is symbolized by planning the details of the entire trip. For the trip to become a reality, we must determine where we are going, who will be going, and what route we are taking to get there.

Lead Teams involves the leadership skills needed to strengthen a team’s culture and is dedicated to the team of people traveling together. A trip’s success is not merely determined by arriving at a new location; it is largely driven by how we journeyed together along the way.

Finally, Lead Organizations aims at organizing and aligning multiple teams and departments to strategically accomplish the greater purpose. It is represented by the family reunion where multiple families come together in one trip with a shared purpose and destination.

Each of the above aspects of a leader’s journey is necessary, distinct, and complements the others. To develop the leadership character and skills needed to help you and those within your sphere of influence reach your desired destination, sign up for one of our upcoming Leadership Retreats.


Learn more about how to effectively encourage your teammates by attending a Team Retreat!

Each of the above aspects of a leader’s journey is necessary, distinct, and complements the others. To develop the leadership character and skills needed to help you and those within your sphere of influence reach your desired destination, sign up for one of our upcoming Leadership Retreats.