The Psychology of Letting Go: Why ‘We’ve Always Done It This Way’ Is Killing Organizations
Why Your Greatest Asset, Your Organizational Experience and Memory, Might Actually be Your Greatest Liability
Hosts: Kevin Novak
Duration: 35 minutes
Available: November 6, 2025
🎙️Season 1, Episode 5
Episodes are available in both video and audio formats across all major podcast platforms, including Spotify, YouTube, Pandora, Apple Podcasts, and via RSS, among others.
Transcript Available Below
Episode Overview
Your best employees are blocking your transformation, and they don’t even realize it. In this episode, Kevin Novak reveals why the phrase “we’ve always done it this way” isn’t stubbornness but grief, and why your most experienced people often struggle most with change.
Discover why 70% of transformations fail despite perfect technical implementation, the neurological reason changing feels physically wrong (try the arm-folding exercise), and the specific stages your team is experiencing right now whether you acknowledge them or not.
Kevin Novak shares the exact moment a 30-year quality control inspector went from resisting AI to championing it, and introduces the R3 formula that helped Netflix, IBM, and Marvel successfully reinvent themselves.
If your transformation initiative is meeting resistance, this episode explains what’s really happening in your employees’ brains and what to do about it tomorrow.
Key Takeaways
Resistance to Change Is Actually Grief: Your Team Isn’t Being Difficult, They’re Mourning Their Professional Identity
Cognitive Bridging Is the Key to Getting Buy-in from Veteran Employees
Organizations that Skip “ending rituals” Create “psychological ghosts”
Season 1, Episode 5 Transcript
Available November 6, 2025
Episode 005: Data Noise and Decision Paralysis: When Too Much Information Kills Critical Thinking
Hosts: Kevin Novak
Show: The Human Factor Podcast
There’s a phrase that’s spoken in conference rooms around the world, a phrase that kills more innovation, stifles more progress, and destroys more potential than any competitor ever could. We’ve always done it this way. Seven words. That’s all it takes to stop transformation in its tracks. But here’s what’s fascinating. The people saying these words aren’t stupid. They’re not lazy.
They’re often the smartest, most experienced people in the room, the ones who have built the very systems that they’re now defending. Today, we’re exploring one of the most challenging aspects of human psychology and transformation. Why letting go of what worked in the past might be the hardest thing your organization ever does. And why your greatest asset, your organizational experience and memory might actually be your greatest liability.
I’m Kevin Novak, CEO of 2040 Digital, professor at the University of Maryland, and author of The Truth About Transformation and the Ideas and Innovations Weekly Newsletter. Welcome to the Human Factor Podcast, the show that explores the intersection of humanity, technology, and transformation, and the psychology behind transformation success. I’ve seen brilliant strategies fail, not because they were wrong.
But because organizations couldn’t let go of what got them here. Today’s episode is inspired by two recent articles from my Ideas and Innovations newsletter. First, unlearning the hidden key to organizational transformation, and second, the power of letting go. Both pieces have generated significant discussion among leaders in our subscriber community. Why? Because they hit on something universal.
something every leader knows, but few want to admit. The very things that made us successful are now the ones holding us back. Today, we’re going to explore the deep psychological mechanisms that make unlearning exponentially harder than learning. Why organizational memory becomes organizational paralysis, the grief cycle that organizations go through during transformation, and practical frameworks for helping people let go.
While preserving institutional wisdom. In my book, The Truth About Transformation, soon to be released in a revised and expanded format to include updates on AI and cultural trends, I argue that transformation isn’t as simple as it sounds. Organizations pour billions annually into change initiatives, yet the research consistently shows that 70 % still fail. And the reason isn’t technology or strategy, it’s human psychology that we systematically ignore. My aspiration for anyone who is watching or listening today is that you aren’t just taking away knowledge to help your organization, but you are taking away knowledge and understanding that can help you personally navigate the curves that are associated with change and transformation throughout your life
Let me share a story that illustrates exactly what we’re up against. I’ve worked with an organization that had dominated their industry for decades. Their quality control process was legendary. Multiple checkpoints, numerous sign-offs, and a timeline that stretched for weeks from production to shipment. They were proud of this process. It was documented everywhere, in their training materials, the organization’s literature, and it was even celebrated in their corporate messaging about their commitment to quality.
Then a startup competitor emerged. They were using AI-powered quality control. They could ship in days with comparable or even better quality scores. The leadership recognized the threat. We need to transform our quality processes, they said. But every time we try to change, our organization resists. When I observed their operations, what I saw wasn’t simple resistance to change.
It was something quite deeper. It was grief. The quality control team wasn’t just defending a process. They were defending their identity. For years, they had been the guardians of quality. Their careful, methodological approach had prevented countless defects, saved money in recalls, and built the company’s reputation. Now, they were being asked to trust an algorithm. One veteran inspector captured it perfectly.
This process, these checks, they’re not just procedures. They’re who we are. Without them, what are we? And there it was, the heart of the problem. We weren’t asking them to change the process. We were asking them to let go of who they believe themselves to be. This is what I call a success trap. The better you’ve been at something, the harder it is to let it go.
Success creates emotional attachment. it creates identity. It creates what I call competence addiction. Think about it from a neurological perspective. Every time the quality process caught a defect, it triggered a reward response. Over years, those neural pathways became superhighways. The process wasn’t just something they did. It became encoded as the right way. and formed the definition in their minds as to how they provide value and how they self-identify with who they are at work. Now we’re asking them to abandon those superhighways and build new roads. The brain experiences this as a loss, but here’s where it gets even more complicated. Organizations have collective neural pathways, we call it culture, but it’s really shared neural patterns reinforced through repetition, reward, and social proof. When everyone around you follows the same process, believes the same things, values the same approaches, it creates what I call organizational muscle memory. You don’t just think about it, you just do it. It’s how we do things here. This muscle memory is incredibly valuable when the environment is stable. It allows organizations to execute complex operations efficiently.
But when the environment changes, when disruption hits, that muscle memory becomes a straitjacket. The organization keeps doing what it’s always done, even as the world changes around it. It’s like a dancer performing a waltz while the music has changed the rap. Your most experienced employees, the ones with decades of institutional knowledge, are often the ones who struggle most with transformation and change. This isn’t because they’re stubborn or closed minded.
Someone who has spent 20 years perfecting a process, building their expertise, and becoming the go-to person for certain knowledge has their professional identity wrapped up in that expertise. When change and transformation comes, they’re not just losing a process. They’re experiencing a form of grief about losing part of who they are professionally, how they see and define themselves, and how they contribute value.
Here’s the billion dollar question though. How do you change work processes ingrained over time that are comfortable, stuck in the past, or so static that they no longer produce results? When systems and strategies aren’t working as well as they used to, most organizations react with familiar and knee jerk solutions. They change organizational models in a revolving door strategy. They replace centralization with decentralization or vice versa.
They fired people, they move people around. They return to what seemed to work in the past. They assigned blame. Then they rewrite their strategic and operational plans again and again. However, what nearly all organizations don’t do is change their fundamental beliefs, attitudes, and behaviors. They don’t unlearn bad habits. They simply double down on them. They address the veneer of change.
But not the systemic breakdowns. Let me be explicit about what unlearning actually means. Organizational unlearning is a deliberate process of letting go of outdated knowledge, practices, and beliefs. Even visions and structures that no longer serve the organization’s purpose and goals. Those practices that keep organizations experience the same problems over and over again. resulting in an ingrained foundation with so many cracks and structural hinge points that nothing is going to happen but simple failure. Now let’s talk about why unlearning is exponentially harder than learning and why it’s actually the most critical skill for modern organizations and individuals. Learning is additive. You build on what you know. Your existing knowledge provides scaffolding for new knowledge. It’s psychologically comfortable because you’re gaining not losing. Unlearning is subtractive. You have to dismantle existing knowledge structures. You have to admit that what you knew might be wrong. It’s psychologically threatening because it challenges your competence and your credibility. Here’s a simple example. Try this right now. Fold your arms across your chest. Notice which arm is on top. Now, unfold them and fold them back again with the opposite arm on top.
Feels wrong, doesn’t it? Uncomfortable? Does it feel unnatural? That’s unlearning. And you’ve only been folding your arms that way for one lifetime. Imagine unlearning something an organization has been doing for decades. The neuroscience is fascinating here. When you learn something new, you’re creating new neural pathways. But when you unlearn, you’re not erasing old pathways, because you can’t.
Those pathways are permanent. Instead, you’re creating new pathways that override the old ones. This requires constant diligence. The moment you stop paying attention, your brain defaults to the established patterns. This is why organizational change is so exhausting. People aren’t just learning new systems. They’re constantly suppressing old ones. It’s like driving a car while someone in the passenger seat keeps grabbing the wheel.
Here are several key attributes and behaviors that make unlearning really, really difficult. I call these non-change agents. Cognitive biases lead people to favor information that supports existing beliefs and practices. It’s that confirmation bias working overtime. Emotional attachment means people become emotionally invested in their approaches that they have helped create. Identity ties transformation.
This is how we do things into this is who we are. Success traps create commitment to strategies that produce past triumphs, even when they’re no longer relevant. Organizational memory codifies practices and processes, training and systems, and roadblocks and barriers prevent progress, deflating change agents until they eventually acquiesce.
Let me share a couple of stories that illustrate this. I worked with a marketing director, who realized that existing strategies for content and event marketing just weren’t working well anymore. A new digital manager had implemented an SEO protocol that increased visibility and response. The director took personal ownership of all marketing messaging and considered himself a domain expert on effective wordsmithing. The imposition of SEO had him clearly baffled and frustrated. Instead of clever headlines and content,
He was being asked to write and inform by SEO recommendations, deliver through search data and keyword analysis. He scoffed at this practice, considering that it had nothing to do with human intelligence and impulses. This is the unlearning of ignorance. When someone is so committed to their expertise that they simply can’t see another approach, despite the effectiveness. We know that organizations struggle to let go of things that they have learned and perfected especially false or outdated information. Memory is such a powerful deterrent to change. So are pride, hubris, stubbornness, and ignorance. But some organizations get it right. Think about Netflix. It was a DVD by rental mail service. It pivoted the streaming and later invested heavily in original content to become a global entertainment powerhouse. Or IBM. It’s been around forever. It shifted from hardware to software.
Then the AI and enterprise consulting. It has survived while other hardware makers have struggled or gone away. Marvel, it was struggling comic book company that almost went bankrupt. Instead of licensing characters, it created its own movie studio and via Disney, today is a billion dollar entertainment empire. What these companies understood that others don’t is that unlearning isn’t about forgetting the past. It’s about reframing it.
Netflix didn’t forget how to mail DVDs. They refrained their capability from DVD logistics to content delivery. The expertise in getting the right content to the right customer at the right time translated perfectly to streaming algorithms. This is what I call cognitive bridging. Finding the conceptual connection between old expertise and new requirements. These organizations mastered unlearning through what I call the R3 formula. recognition, reflection, and reframing. Again, recognition, reflection, and reframing. Recognition means honestly auditing organizational practices to identify outdated approaches. Reflection means understanding why these practices exist and what function they’ve served. Reframing means developing new perspectives and setting clear expectations aligned with the organization’s vision, mission, and values.
Let me introduce a framework that’s transformed how I approach organizational change. It’s based on William Bridges’ transition model. Bridges made a critical distinction that most leaders miss. There’s a difference between change, which is an external event, and transition, which is the internal psychological process that individuals go through in response to that change or elements of transformation. Consider this in terms of losing a family member, a friend or even a job. Every individual goes through a transition curve that represents a series of mental states from outright shock and anger to confusion through recognition and ultimately acceptance. Change can happen instantly in nearly every organization. You can announce a new system on Monday with the most optimistic intent, but not recognize the shock that results in terms of communicating out. You believe the deed is done.
But is that really the reality? Even though the system was announced, the transition still needs to occur. Transition is the inner psychological process that people go through as they internalize and come to terms with the new situation. This process can’t be rushed and it’s often different for each group and each individual. Bridges outline three key stages of transition. The first stage is ending, losing and letting go.
The second stage is the neutral zone and the third stage is the new beginning. What most organizations get wrong is they try to skip straight to the new beginning without honoring the ending or acknowledging the messy middle. Let me break down each stage. Stage one, ending, losing and letting go. This first stage involves the emotional and psychological responses as individuals confront the loss of familiar routines.
People commonly feel resistant or even grief-stricken when confronted with change on an organizational scale. During this stage, people may experience emotions such as denial, resistance, anger, frustration, grief, and anxiety. Does this sound familiar? These are the same stages Elizabeth Kubler-Ross identified in her well-respected grief cycle. When we ask organizations to let go of established practices,
They go through these three distinct emotional responses. The first denial. This new approach is just a fad. Our way has worked for decades. Anger. Why are we destroying what works? This change is for change sake. Bargaining. What if we keep our process, but add some new technology on top? Depression. Nothing we built matters anymore. Our experience is worthless.
Lastly, acceptance. Our experience taught us principles. We can apply those principles in new ways. Most transformation efforts fail because leaders don’t recognize these stages. They interpret anger as resistance. They see bargaining as compromise. They mistake depression for disengagement. But these aren’t problems to be solved. They’re stages to be navigated. Let me go back to that quality control organization story.
Once I recognized they were grieving, everything changed. Instead of pushing the new AI system, we held what I call the legacy celebration. We documented major defects, the old processes had caught. We interviewed long time inspectors about their proudest moments We created a digital archive of their quality achievements. We weren’t just acknowledging their past. We were honoring it. Most organizations focus entirely on the new beginnings.
They paint a vivid picture of the future state. They celebrate early wins. They incentivize adoption, but they completely skip the endings. They don’t help people let go. They don’t acknowledge the loss. They don’t honor what’s being left behind. This creates what I call psychological ghost. They haunt the organization. The old way isn’t properly buried, so it keeps rising up from the dead.
People publicly comply with new processes while privately maintaining the old ones. You’ve surely seen this. The Excel spreadsheet that parallels the new CRM, the informal meeting that duplicates the new formal process, the real decision-making that happens outside the new governance structure. These aren’t acts of rebellion. They’re symptoms of incomplete grief. Stage two, the neutral zone.
Here’s where most organizations struggle. The neutral zone is characterized by uncertainty and confusion. Individuals are adapting to new circumstances. It’s when the critical psychological realignments and repatterning actually take place. This is the messy middle that organizations desperately want to skip. In my book, I call this the productivity valley of death. Old systems are gone, new ones aren’t fully operational. And everyone feels completely lost. People are simply in limbo. They no longer know who they were, but they’re not yet who they’re becoming. It’s uncomfortable. It’s anxiety producing. Performance typically dips. People feel confused about their roles, uncertain about the expectations, and very unclear about how to proceed. But here’s what Bridges understood that most don’t. The essence of life takes place in the neutral zone phase of transition. This is where innovation happens. This is where breakthrough thinking emerges. This is where people develop new ways of working that you never could have designed from the outside. In my work with the Library of Congress, the neutral zone was when librarians started experimenting with how digital tools could create new forms of discovery. They weren’t defending the old stack system anymore.
But they also hadn’t fully embraced the digital future. In that in-between space, they invented approaches we really never anticipated. Hybrid search strategies, new taxonomies, ways of connecting physical and digital resources that only people living in both worlds could actually conceive. Organizations that acknowledge and plan for the neutral zone, rather than trying to power through it, create the space for genuine transformation.
This means providing additional support, training, and psychological safety. It means being patient with decreased productivity. It means creating forums for experimentation and learning. It also means constant communication. In the neutral zone, people need frequent updates, even if the news is we’re still figuring this out. Silence in the neutral zone breeds anxiety and rumors as people simply just don’t know what is going
Stage 3, the new beginning. Finally, the new beginning stage represents a positive acceptance of the change, where individuals begin to embrace new roles and ideas, leading to renewed enthusiasm and connection to the organization. But here’s what’s crucial. You can’t rush people to this stage. You cannot skip the first two stages and jump here. Transition is a process.
And it doesn’t happen with the same timing for every individual. The new beginning isn’t just about learning new systems or processes. It’s about developing a new identity. It’s about people seeing themselves differently, understanding their value in new ways and feeling reconnected to the organization’s purpose. Back to that quality control story. The new beginning came with one inspector said, you know, the core of what we did was pattern recognition.
We learned to see what didn’t belong. AI does pattern recognition too, just a lot faster. That was the breakthrough. They weren’t losing their identity as quality guardians. They were evolving it. We refrained the change, not as AI replacing inspectors, but as inspectors teaching AI. The same people who had been checking products were now training algorithms, validating AI decisions, and handling exceptions that the AI flagged. Their deep expertise wasn’t obsolete, it was being amplified. The new beginning stage is marked by people starting to experiment with new behaviors, developing confidence in new approaches, and experiencing wins that reinforce the change. Energy and engagement return. People start seeing possibilities rather than just the problems. But here’s the key.
The new beginning only happens after you’ve properly navigated the ending and supported people through the neutral zone. Try to force a new beginning prematurely. People will resist or go through the motions without genuine commitment. Let me share another powerful example. In my work with major institutions like the Library of Congress during their digital transformation, we weren’t just changing systems.
We were asking professionals who’d spent careers as guardians of physical knowledge to become digital innovators. The grief was palatable. One staff person shared, I know digitization is necessary, but I’m mourning the loss of people discovering knowledge by wandering the stacks or seeking my counsel. That serendipity is gone. They weren’t wrong. Something was being lost. Until we acknowledged that loss, honored it, supported them through the confusion of the neutral zone, we can help them reach a genuine new beginning where they saw themselves as expanding access to knowledge rather than diminishing the experience of discovery.
So how do we solve for this? How do we help organizations let go without losing their soul? This is where my human factor method provides a framework. It’s built on four key principles. Principle one, honor before you heal. You can’t move forward until you’ve properly acknowledged what you’re leaving behind Principle two, bridge before you build. Connect old expertise to new requirements before introducing new systems. Principle three,
Preserve principles, not practices. Identify the timeless principles behind outdated practices. Principle four, make the implicit explicit. Service and examine unconscious assumptions and beliefs. Let me show you how this works in practice. A financial services firm needed to move from relationship-based selling to data-driven engagement. Their salespeople, many with decades of experience, were in revolt.
Relationships matter more than algorithms, they said. And you know what? They were right. But they were also wrong. They were creating a false choice between relationships and data when the answer was relationships through data. Here’s what we did using the R3 formula and the human factor method. First, recognition. We honored their expertise. We had top salespeople share stories of deals they’d won through relationship insight.
We documented the subtle cues they’d learned to read, the patterns that they recognized. Then we moved on to reflection. We showed them how data could amplify these insights, how AI could identify relationship patterns across thousands of interactions that no human could process alone. How digital tools could maintain relationship touch points at scale. Finally, we moved on to reframing. We weren’t replacing relationship building we were actually scaling it. The key insight was that their years of experience, Had taught them what mattered in relationships. The new tools would handle how to maintain those relationships at scale. One veteran salesperson had a breakthrough moment. I spent years learning the clients want to feel heard. said, this system helps me hear more clients than I ever could before. That’s cognitive bridging. finding the connection between old wisdom and new methods. But here’s what’s critical. This only works if people feel psychologically safe, if they believe their experience is valued, and if they trust that letting go doesn’t mean losing their personal value. Leading this process requires specific actions. First, create ending rituals. Acknowledge and celebrate the contributions and successes of the past.
Create a sense of closure by honoring what is being left behind. This could be as simple as a legacy wall where employees can write what they were proud of from the old system, the process or the structure before moving on to the new one. Next, acknowledge the neutral zone. Stop pretending it doesn’t exist.
Make the implicit explicit.
Start discussing the changes early and let the team know what to expect. This helps people understand how they can redefine themselves as they shift from what was to what will be because most resistance comes from uncertainty, not the actual change itself. Next, connect identity to purpose, not process, help people see that their value isn’t in what they do, but why they do it.
The quality inspector’s purpose is ensuring customer safety, whether through visual inspection or AI oversight. Next, lead by example, model desired behaviors consistently. When leaders exhibit accountability, adaptability, and open-mindedness, employees are more likely to follow. Encourage psychological safety. Create an environment where employees feel safe to take risks. Challenge the old ways of thinking. and experiment without fear of punishment. Next, promote a growth mindset. Encourage employees to see challenges as opportunities to learn rather than threats. Share success stories of individuals or teams who have successfully unlearned harmful habits.
So what can you do tomorrow to help your organization let go? First, start with yourself. What are you holding onto that no longer serve you? What processes do you defend simply because you created them? What beliefs about how things work haven’t been examined in years? Second, create forums for organizational grief. Hold sunset ceremonies for retiring systems, create legacy walls celebrating past achievements,
Simply give people permission to mourn what they’re losing as they make that transition to who they will be next. Third, practice cognitive bridging when introducing change, always connected to existing expertise. Show how old skills apply in the new context. Help people see themselves in the future state so that they can redefine their value and their contributions. Fourth, measure psychological safety, not just engagement.
Ask, do people feel safe questioning established practices? Do they believe their experience is valued? Do they trust leadership’s vision for change? Fifth, recognize the stages of organizational grief. When you encounter denial, anger, or bargaining, don’t push harder. Acknowledge the stage and provide appropriate support.
Remember the goal isn’t to forget the past, it’s to honor it while releasing its hold on who people will be in their work life in the future. Here’s the truth about letting go. It’s not a failure of intelligence or willingness. It’s a fundamental human response to loss. And until we start treating it that way, we’ll keep seeing that 70 % failure rate. Unlearning is a deep way to change and transform an organization sustainably. Our very human nature, wants us to hold on to certainty and predictability and avoid confrontation. Our personal default, of course, is to be comfortable and organizations are the same. In a highly dynamic, ever-changing environment, our defaults feed the very potential for the failure. Organizations that will thrive in the next decade won’t be those with the best technology or the most resources. They’ll be those that have mastered the art of letting go.
This isn’t about abandoning wisdom. It’s about distinguishing between timeless principles and temporary practices. It’s about preserving what matters while releasing what constraints. Legitimate lasting change starts at the top. It takes vision matched with operational expertise and personal empathy to transform an organization. Effective leaders are models of vulnerability by acknowledging when they need to unlearn something.
They remove structural barriers to unlearning. They create psychological safety for questioning established practices. And they reward employees who constructively challenge the status quo. Remember, you’re not just asking people to use new tools or follow new processes. You’re asking them to let go of part of their professional identity and the conception they have for how they contribute value. You have to honor that. You have to acknowledge that.
And you have to support them through that. As I wrote in both unlearning the hidden key to organizational transformation and the power of letting go. The future belongs to organizations to learn how to master the art of letting go. Not because letting go is giving up, but because it’s making room for what’s next. Your organizational memory is both your greatest asset and your greatest liability. The key is knowing which is which. Next week,
Elizabeth Stewart comes back to join me to discuss the communication paradox when more words create less understanding. We’ll explore why over communication often backfires and how to achieve clarity and transformation change and really any messaging. If you found value in today’s episode, leave a rating and a comment and please share it with your team. It’s important for everyone to understand the psychological forces at play
And if you’re wondering how ready your organization is to let go and transform, take our free assessment at transformationassessment.com. transformationassessment.com, all one word. Subscribe to my ideas and innovations newsletter on Substack and explore the 10 part transformation psychology series I wrote on 2040digital.com. Until next time, remember transformation isn’t about technology. It’s about people.
And people need time to grieve what they’re losing before they can embrace what they’re gaining. I’m Kevin Novak and this has been the Human Factor Podcast. Thank you for watching or listening.
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Upcoming: Available November 13, 2025
Episode 006: The Communication Paradox: When More Words Create Less Understanding
Communication is the most frequently cited problem in employee surveys. Every organization says they need to “communicate better.” So they communicate more. More meetings. More emails. More town halls. More updates. More cascading messages. More intranet posts. And somehow, understanding actually decreases.
