Editorial
In Plato’s "The Allegory of the Cave," prisoners are chained inside a cave, able to see only shadows projected on a wall before them. Even when someone is freed and shares his knowledge of the real world with the others, the prisoners reject him, preferring the comfort of the shadows they’ve always known.
It’s a story that’s thousands of years old, yet feels relevant today. How often do you feel like the freed individual, trying to convince direct reports, colleagues or your bosses of a new reality — whether it’s to use a new technology or adopt a new process? Or do you relate more closely to the prisoners who are content with watching shadows on the wall? Why do people resist change, even when it’s for the better?
The Allegory of the Cave offers a framework for understanding the challenge of digital transformation. We, as leaders, must free ourselves and do the work of bringing along the rest of the organization, even those who feel comfortable watching shadows.
The Comfort of Legacy
As readers of the allegory, we understand being a prisoner is bad. Yet, as leaders, we must empathize with those who enjoy the comfort of the known. In many cases, it's not just that employees are comfortable — rather, they have achieved mastery in their areas of expertise or work processes.
I’ve seen this many times in software development. As business priorities change or tools evolve, developers grapple with learning a new coding language. Some may have even gone to school to learn a language around which they would build a career. It’s the only reality they know.
But these “shadows” — repetitive manual tasks, legacy systems or outdated languages — are only the perceived reality. What might have once been innovative (local file servers, the fax machine!) may now be the shackles that have kept us back.
Refusal to See AI’s Benefits
Whether you are an executive leading a new organizational strategy or a team lead driving a new initiative, it’s your responsibility to not just set a directive, but inspire others to break free.
We see this each time there is a major technology shift. The concept of the paperless office has been around since the 1970s, yet entire industries still rely on paperwork in their daily operations. The migration of applications to the cloud began more than 20 years ago, but organizations still prefer to self-host, even when the cloud offers scalability, reliability and maintenance advantages.
Now, a similar pattern is emerging with AI. There are those who embrace it and then, on the flip side, those who refuse to use it. Some employees even hide their AI use due to a lack of guidance or guardrails.
Just as the freed prisoner was momentarily blinded by the light outside of the cave, we may struggle to acknowledge our own setbacks, whether those are wasted budget or unhappy customers. But once we do so, we can build a vision for what’s on the other side: efficiency, real-time collaboration, more responsive service and more time to do the work that really matters.
Together Into the Light
The leader who has seen the potential of digital transformation must go back for their team. This is easier said than done. No matter how strong our business case is, or how many roadblocks we’ve knocked down to clear the way, there is bound to be resistance.
This is the stage where change management initiatives often fail. Leaders try to force change, but that isn’t the way to success. They must illuminate the path and show the value of a new reality.
In Plato's allegory, the newly freed prisoner risks ridicule and rejection by returning to the darkness. Similarly, a leader’s challenge isn't the technology, but the human element. Prisoners cling to their shadows because they are their reality, their structure and their understanding of the world. Your team clings to the familiar because that is the source of their competence and professional comfort. For transformation to succeed, you must become the empathetic guide who makes the journey feel safe, necessary and rewarding.
Leaders should aim to:
- Lead with empathy, not authority: Understand that people's resistance comes from fear of the unknown — fear of failure, obsolescence or lost mastery — not malice. Address their concerns. Listen to the fear behind “we've always done it this way” and acknowledge the expertise they hold. When you value their current contribution, they'll be more open to a new one.
- Focus on “why”: Don't just implement the new tool or process. Explain the purpose and the destination. What does this change do? Instead of saying, “We're moving to the cloud for cost savings,” describe freeing the IT team to focus on innovation, providing the features or integrations other teams have been requesting. This gives the change meaning beyond technical details.
- Illuminate the path; don't drag people kicking and screaming: Provide training, support and clear road maps. Understand that direct sunlight is painful at first. Your job is to create a controlled ascent, offering the right information and resources at the right pace. Create internal champions — trusted colleagues who have already seen the light — to help to guide their peers.
- Celebrate the small wins: Recognize and reward the small victories, whether that’s the first successful AI integration or the smooth migration of a department to the cloud. Each small win is a step out of the cave. These celebrations serve as proof points, making things clearer and better. They help to break the prisoners' belief in the shadows.
Staying Out of the Cave
Digital transformation is not a one-time event, but an ongoing process of adaptation. Once you've led your team out of the cave, foster a culture that values curiosity and adaptation. The goal is to prevent a new set of technological shackles from forming and to keep the organization facing the sun.
Digital transformation is a journey from manual processes and legacy systems to the clarity of the future, where data and speed provide business insight and agility. The role of a leader in this journey is of a guide and visionary. Meanwhile, the goal is not to simply implement new technology, but to liberate people’s potential. The light of transformation is uncomfortable at first, forcing us to squint and adjust, but it is the only place where growth and innovation happen.
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Editor's Note: Want more change management tips?
- Tips for Conquering the Whiplash of Change — The rapid rate of change over the last few years has left employees feeling wary of future initiatives. Here's how leaders can help ease transitions.
- Communicating Change: Overcoming Resistance Through Empathy — A critical element of any change management initiative is communications. What kind of messaging can transform potential adversaries into allies?
- Making Change Stick at the U.S. Air Force — Air Force enterprise change manager Heather Knuffke gives an inside look at the digital transformation underway at the U.S. Air Force.
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