The Change Leader’s Journey

I help executives drive transformation initiatives. One of the most challenging of these initiatives is the journey from strategy to action. This journey from head to heart to hands (or from strategy to meaning to doing) is one that requires courage, intrapreneurship and persistence.

In this article, we’ll take an empathetic approach to understanding personal and organizational inertia and strategies to overcome it. By following the story of a leader through a transformation journey, I hope readers will have compassion for those who dare to embark on this journey.

To lead others through a transformation journey, one must be willing to be transformed. When leaders face the trials that arise during the journey, they shed beliefs that no longer serve them and uncover a more authentic and compelling leadership approach. In transforming, they are themselves transformed.

The journey starts from within, as our hero or heroine accepts the transformation project. By nature, these projects feature an uncertain solution, and quite possibly and uncertain problem as well. To succeed, the leader needs to let go of the habit of solving problems alone and instead enlist the help of others. Next the hero models the discipline of experimentation, making small bets and asking the team to bring back evidence every week or two. Making learning visible in such a transparent way builds psychological safety as leaders and team members reflect on what worked and didn’t. This evidence-based approach enables the team to gradually mitigate risk, and increase investment confidence. After accomplishing the learning mission, the hero returns and pays support forward by serving as mentor or sponsor for the next change leader. This enables change leadership behaviors to scale. This path is similar to the Hero’s Journey as described by Joseph Campbell.

The Hero’s Journey Myth exists in all human cultures and keeps getting updated because we humans reflect on our world through symbolic stories of our own lives. You leave your comfort zone, have an experience that transforms you, and then you recover and do it again. You don’t literally slay dragons or fight Valdermort, but you face problems just as scary. Joseph Campbell said, ‘in the cave you fear to enter lies the treasure you seek.” — Matthew Winkler,

What makes a hero? — Matthew Winkler

Borrowing Joseph Campbell’s narrative form from “The Hero with a Thousand Faces,” and with a hat tip to brand storyteller @marvinador, let’s walk through the parts of the change leader’s journey:

The Change Leader’s Journey

…the journey of striking out from home and overcoming challenges and searching for your true calling [is] …a journey of listening to yourself, figuring out what you really want in life and then going out and finding it.
— Guy Raz, the TED Radio Hour: What is the Blueprint for Stories about Heroes? (December 18, 2015 | length: 6:46)



Our story begins with a successful large enterprise organization. This organization has well-honed processes it developed over the years, and a culture that effectively and reliably delivers the desired outcomes to investors. Every employee knows the drill, and it’s “the way things are done around here.” The culture, processes, and technologies to deliver consistent results at scale. The specialized design of the organization that enables the machine to run so reliably is also what makes it so resistant to change.

One day, something new appears on the horizon, that affects our leader’s destiny. It could be a new strategy, an extensive re-org, or a merger or acquisition. It could be a competitor with a a disruptive solution that threatens to make the organization’s primary offering obsolete. Let’s call this inciting incident “The Call.”

Refusing the Call

Leaders of organizations, particularly well-established ones with traditional hierarchical structures know that answering The Call is hard. It’s messy and complicated. Answering usually requires influencing others and navigating the cultural, process and technical barriers necessary for change over short, medium and longer time horizons. These leaders also have plates that are already full. There’s no time to take on something else. As a result, most leaders let The Call roll over to voicemail to stagnate. Better to let someone else answer.

What’s the primary reason leaders refuse the call? TRUST.
Leaders need to trust their own ability to impact change. To focus a team on a direction and engage followers. To trust that adopting, embodying and evangelizing new behaviors will have a positive impact on the organization, their team and their career.

One of the hardest things about being a change leader is the feeling of exposure. Charting a new course through the unknown, in search of uncertain treasure takes tremendous courage. The organization’s history, legacy systems, tools, processes and culture creates a lot of organizational resistance. It would be much easier for the hero to stop, turn around, and accept the status quo.

Our life evokes our character. You find out more about yourself as you go on. That’s why it’s good to put yourself in situations that will evoke your higher nature rather than your lower. — Joseph Campbell

I once asked Sylvester Francis, award-winning photographer, videographer and curator of The Backstreet Cultural Museum, how someone becomes a Mardis Gras Chief. He looked at me, blinked, and and said, matter-of-factly, “they have followers.” It is in the act of stepping forward that we create space for followers.

Given a choice, most leaders would opt for the easy rather than the difficult path. What prompts leaders to step up and answer The Call is experiencing the power of TRUTH.

How does a leader do this? Consider the overall mission and get clear on your own “why.”

Get Clear on Your Why

In Simon Sinek’s “Start With Why” talk, it is clear understanding of the organization’s “why” and resonance with the leader’s own “why” that makes the adventure worth pursuing.

In Star Wars, once Luke makes a commitment to answer the call, Obi-Wan gives him his father’s Lightsaber and a basic understanding of “The Force.” In an organizational context, the change leader equivalent of a Lightsaber is an intrapreneurial mindset.

Creating Psychological Safety for Yourself and Others
In risky situations, we hold back to keep ourselves safe. If you’ve ever caught yourself thinking, “I wish my team was more creative,” more often than not it’s not a lack of creativity but a lack of psychological safety. When we focus on keeping ourselves safe, we stifle learning, growth and forward momentum. Creating psychological safety is the secret to unleashing creativity and creating engaged project teams.

Amy Edmonson TED Talk on Building Psychological Safety

The change leader, now geared up with the power of TRUTH, and an intrapreneurial mindset, steps out into the unknown to begin the journey. While cold comfort for the hero, the fear of starting is usually worse than the actual challenges we face.

The journey of a thousand miles begins with a single step. — Lao Tzu

Set Clear Direction

The first challenge for the change leader is making the vision tangible. Toss the deck of strategy slides filled with bullet points no one will remember and transform it into a story of change. Stories enable us to envision a future and our own contribution to that future. Stories, particularly when told from the perspective of the customer experiencing the pain, are particularly effective in making the case for change. Pain stories are sticky, and the tension between the what-is and what could be stories is useful for inciting action. This approach puts customer before silo, and reveals redundancies and gaps in customer experience, as well as the processes, technologies and organizational structures that need to change to support the new story.

Three steps to a change story:

  1. Using a Business Model Canvas or a Pixar-style storyboard, tell the story about how the organization works today
  2. Using the same framework, tell the new story
  3. Identify friction points and what needs to change enable the new story

Approach Learning as a Discipline

At this point in the story, the change leader transitions to the role of coach. Finding the answer to the riskiest assumption often requires a deep-dive to understand or validate a customer pain. Perseverance and influence skills are strengthened when leaders engage with other stakeholders to work across organizational boundaries.

Example: A well-known software company scheduled every new hire’s first day to coincide with new hire orientation. Every new employee wants to be productive on day one, yet it took one-to-two weeks to ensure every new hire had a laptop. IT needed employee numbers and records to issue equipment, and HR wanted to hand out computers on the employee’s first day. It was clear the processes were at odds with each other. What caused the breakthrough? Serendipity and compassion. The head of IT had just transitioned from contractor to full time employment status. When he terminated his contracting role, he needed to turn in his laptop. As a new employee, he needed to wait for IT processing. Once he felt the pain of every new employee, he was motivated to help not only himself, but others in this situation. By focusing on the new employee experience, their compassion provided the motivation to integrate the siloed processes and collaborate to deliver the laptop on day one.

2: Engage your support team

FEAR of the unknown, looking incompetent, failing, or asking for help deters the change leader from accepting the challenge. Asking for help is not the norm, particularly in the U.S., where most leaders count on their own ability to solve problems. They believe asking for help will be seen as a sign of weakness or that they are in over their head and don’t know how to do their job.

One client turned this belief on its head by enlisting help as a strategy for building support. With this approach, she engaged a trio comprised of a mentor, a sponsor and a tormentor. The mentor provided advice, observations and feedback on her talents and her work. The sponsor brought resources and air-cover. The tormentor(s), invited or uninvited, created the necessary friction that helped her build resilience and perseverance for the long journey ahead.

3: Share the Journey
The change leader holds the big picture vision while overseeing the transformation of unknowns to knowns, and the gradual unfolding of the new story. The vision comes into clearer focus with each iteration as each team identifies what they need to learn, builds a simple prototype or other way to test an assumption, collects insights and documents feedback. This evidence-based approach to chronicling the learning journey mitigates risks while making forward progress. After each learning cycle, the leader and stakeholder reflect on results and decide whether to stop, continue or increase funding and resources.

Get Curious about Organizational Friction
After the change leader identifies the new story and what needs to change, the next challenge appears. Solving meaningful problems for people (customers, end-users, employees) often require solutions that span organizational boundaries and bump up against foundational structures including silos, processes and technologies.

Organizational antibodies appear to maintain the status quo. Instead of resorting to a fight or flight response, the change leader, armed with the intrapreneurial mindset instead gets CURIOUS. With a beginner’s mind, launch a problem-finding mission to identify the root cause. Working with the stakeholders most affected by the problem, identify beliefs and make distinctions between facts (e.g., there is evidence), commonly held opinions and guesses.

Make Small Bets

The riskiest opinion or guess becomes the first focus of a learning sprint. As the team completes multiple learning sprints, they develop the discipline of persistence. This strength helps the team to imagine new solutions to overcome obstacles.

Bring Evidence

Rather than asking for an extensive execution plan, the change leader instead asks for evidence. Evidence should be sequential. For example, validate each element of the business model before executing the model.

Share the Journey

Each learning sprint presents an opportunity to engage support outside the core project team. By being transparent about what the team is setting out to learn, how they intend to learn it, metrics of success and challenges they face, they invite ad hoc collaboration. With a learning sprint every week or two, the team can develop the discipline of storytelling, bringing others along and creating momentum for the larger story as it unfolds.

4: Pay It Forward

After the change leader creates momentum and the disciplines needed to develop the new story, our hero then serves as mentor or sponsor to the next hero in waiting, scaling through stewardship over the long haul. As leaders transition from a belief that they need to have all the answers to a belief in mutual support, this gradually becomes the fabric of the culture, or “the way things are done around here.”