Mistake #7: Clinging to Old Habits – The Anchor Holding Your Transformation Back
Picture this: A cutting-edge racing sailboat, equipped with the latest carbon-fiber sails, state-of-the-art navigation systems, and a world-class crew eager to conquer the open seas. Everything is primed for victory. But there’s just one problem: the anchor is still down. The boat is tethered to a massive chain, and no amount of innovation, speed, or skill can overcome this immovable drag. It’s stuck.
This is exactly, perhaps mildly exaggerated, what happens when organizations embark on Agile transformations while clinging to old habits. They invest in Agile coaches, frameworks, and tools but refuse to let go of outdated processes, waterfall-era budgeting, or rigid decision-making structures. The result? They’re anchored in place, unable to harness the true power of Agile.
It gets worse. This clinging is often justified under the guise of “staying safe until we see if Agile works,” or the mistaken belief that old ways can coexist with the new. In reality, these outdated practices don’t just slow you down—they actively sabotage your progress. They’re the Trojan Horse of Agile Transformation.
If you’ve ever wondered why your Agile transformation feels stuck or why your teams aren’t delivering as promised, this is the article you need to read. Together, we’ll uncover what’s really holding you back. Spoiler alert: it’s not your team—it’s the anchor you forgot to pull up. So, let's do it!
The Problem: Adding Agile Without Letting Go
Some organizations embarking on Agile transformations make a critical mistake: they treat Agile as a layer added onto existing ways of working, rather than a holistic shift. This mindset leads to a clash of methodologies, where Agile practices coexist with entrenched habits, resulting in inefficiencies, frustration, and eventual failure.
Symptoms
I cannot count the number of times I have got the question: "Why are there so many meetings in Agile?" At first, I didn’t understand the reason for this question because, as you know, there are not a lot of meetings in Agile. Focus is a key value, meaning we need to be able to concentrate on the job at hand without unnecessary interruptions. For example, a typical day for a developer might involve just one meeting: the daily standup.
But when I dug deeper and asked about all these meetings, I realized that many old meetings were being kept: sync meetings, line meetings, area meetings, delivery meetings, check-in meetings, check-out meetings—you name it. This made me think: Why do organizations fail to let go of old ways of working when they adopt Agile?
Symptom 1: Keeping Old Habits, Meetings and Ways of working
Instead of embracing Agile principles of focus and collaboration, many organizations cling to legacy meeting structures, layering them on top of Agile practices. Just because "we have alwauys had that meeting". Or "we need to do it that way". This results in bloated schedules and frustrated teams, leaving them asking, “Why does Agile feel so meeting-heavy?”
Symptom 2: Waterfall Budgeting in an Agile Environment
Another common symptom is the mindset of: “Yes, we are Agile, but we will, for now, keep the way we budget projects.” At first glance, this doesn’t seem alarming. However, the reality is far more problematic.
In these organizations, management continues appointing a single project manager who is responsible for creating detailed plans, including budgets, delivery dates, content, resources, effects, risks, and so on—before any start-decision is made. It feels safe to make decisions based on these plans, doesn’t it? But this approach is exactly what we want to leave behind to become Agile.
Agility is not something you can adopt only in the development phase. It must encompass the entire lifecycle—from inception to deployment and release. By retaining traditional ways of starting projects with fixed budgets, detailed plans, and pre-defined content, these organizations anchor themselves to outdated practices. It’s just like the metaphor in the introduction: no matter how advanced the sails, the anchor will hold them back.
I explored this topic further in another article about hybrid solutions: Do Waterfall Projects Still Have a Place in Agile Organizations? To quote from that article:
This approach combines the weaknesses of both methodologies without fully leveraging the strengths of either. The result? A rigid project setup that is doomed to fail in complex environments where adaptability is essential. Teams are left attempting to navigate a fixed-scope, fixed-time, fixed-budget scenario while being asked to “be Agile” in the middle. It’s the worst of both worlds.
Symptom 3: Reverting to Old Habits in Crisis
The third, and perhaps most damaging, symptom is reverting to old habits during a crisis.
Imagine a delivery gone wrong. The customer is unhappy, the system isn’t working, and immediate action is required. Top management demands results. Middle management responds by forming a task force, giving them full empowerment and resources to solve the problem, even if it means halting the work of other teams, bypassing the normal agile decision sturctures, because, well it is a crisis, isn't it?
Daily status meetings—sometimes even more frequent—become the norm. The task force may eventually solve the issue, but what have they really achieved? Chaos. The organizational structure breaks down. Teams and individuals lose the chance to learn from their own mistakes. The “hero organization” is reinforced, where success depends on temporary fixes by a select few. Not from sustainable, team-driven solutions.
Worst of all, this approach often sets back the Agile transformation by months or even years. In some cases, organizations abandon Agile altogether after such an event, citing its “failure” when the real issue was their inability to let go of old habits.
In a later part of this article, we will explore the root causes of these three symptoms of clinging to old habits. Understanding these causes is the key to identifying and addressing them effectively.
Finding The Root Cause
Why do organizations cling to these habits? The reasons often lie in fear, lack of understanding, lack of trust in the method, and lack of courage. But let’s be honest—telling a CEO, “You need to have courage and just trust the method,” isn’t going to inspire them to take the leap. I can say it as a coach, but it’s unlikely to ignite the courage they need. So, we need to dig deeper.
Let’s keep asking “why” until we uncover the real root cause.
Why Don’t Top Management Trust the Method?
Because they haven’t seen evidence that it works. Theory is one thing, but practice is gold. Telling a CEO, “It should work,” isn’t enough. They need tangible, undeniable evidence that Agile works before they dare to pull the plug on old processes and let agility flow through the organization.
Another reason is a lack of understanding of Agile itself. Agile is easy to understand in theory, but to fully grasp its implications—that it’s a mindset, a cultural transformation, and that it starts with leadership—is not something you can learn from reading a book, a few articles, or even attending a two-day course. Understanding Agile at this depth requires immersion, experience, and commitment.
Why Haven’t They Seen Evidence?
Here’s where it gets clearer: the evidence doesn’t emerge because old habits are still in place. Organizations cling to legacy practices, preventing Agile from delivering its full potential. It’s a vicious cycle. Without letting go of the anchor, the ship can’t move fast enough to prove that the new sails and strategies work.
The Circular Trap
We now find ourselves circling back to the core issues: fear, lack of understanding, and lack of trust in the method. We haven’t seen the evidence, and we don’t dare to take up the anchor.
Could it be that we’re trying to do too much at once? That we’re ignoring the empirical nature of Agile and attempting a big bang transformation? (As discussed in Mistake #4: Adopting a Big Bang – Quick Fix Approach). Perhaps we’re sabotaging ourselves by not giving the organization a fair chance to succeed.
Instead of gradually letting go of the anchor, we hold on to it tightly, thinking it will make us safer. And when the boat doesn’t move as expected, we blame the strategy, the method, the crew, or the sails. In reality, it’s none of those. It’s the anchor.
Another Possibility
Another possibility is that we need to foster a deeper understanding of Agile at all levels of the organization. Agile isn’t something we do; it’s something we become—and becoming Agile requires hard work, persistence, and patience.
How do we solve this problem? That’s the topic for the next part of this article, but befor that, let's look briefly into the consequences.
The Consequences of Holding On
Failing to let go of old habits undermines the very principles of Agile, leading to several significant consequences:
Wasted Resources
Time and effort spent on detailed pre-studies, planning, and budgeting add little value but consume significant resources—and time. These activities create the illusion of control while diverting attention and energy away from delivering actual value.Slower Delivery
Teams become bogged down by bureaucratic processes, making it impossible to respond to change or deliver value quickly. The agility that organizations seek is stifled by the weight of outdated practices, leaving teams unable to adapt to fast-changing demands.Disillusionment
The organization becomes stuck in a hybrid model where neither Agile nor waterfall works effectively. This often leads to frustration and, in many cases, results in the organization abandoning Agile altogether. Phrases like “Agile is not for us” or “SAFe/LeSS/Scrum doesn’t work for us” become commonplace, often originating from leadership. This cemented resistance to change becomes the largest hurdle to meaningful transformation. The transformation is bound to fail if leadership and teams do not beleive in it.
Breaking Free: Steps Toward True Agility
I want to break free, I want to break free
I want to break free from your lies
You're so self-satisfied I don't need you
I've got to break free
God knows, God knows I want to break free– Queen
While Queen wasn’t singing about Agile transformations, I think the first verse fits perfectly. To succeed in Agile, we need to break free of old habits, outdated ways of working, and the anchor that’s holding us back. Is it easier said than done? Yes, absolutely. A true Agile transformation is a lot of hard work—it’s not a quick fix, nor is it something that can be accomplished through a simple project. It requires a profound shift in mindset and culture across the entire organization.
And how do we achieve it? Like eating an elephant. It’s a worn metaphor but still true: we eat an elephant one small piece at a time. Start in one corner of the organization, persevere, and don’t look back. Before you know it, you’ve eaten half the elephant.
Steps to Break Free
If your organization is struggling with the symptoms described earlier in this article, here’s how you can move forward:
1. Start Small, but Do It Fully
Don’t launch another “project.” Instead, begin a new value stream, an epic, or an initiative, and do it fully with Agile principles. Focus on one corner of the organization—one project or one value stream. Let the team(s) work with Agile practices from end to end—from idea to deployment and release.
- Key Steps:
- Abandon fixed project budgets. Instead, provide a running budget for a specific period (e.g., one year).
- Let the team create a vision, which then drives a backlog. Allow them to start delivering value iteratively.
- Focus on transparency: Your control as a leader lies in requiring transparency from the organization. Track progress through demos, visible backlogs, and frequent delivery of working systems.
Your role is to help them succeed. If they face challenges, remove obstacles, offer support, and celebrate wins. Build on these successes and gradually expand Agile practices into other parts of the organization. Pay special attention to removing—at least temporarily—obstacles stemming from old ways of working, like rigid budget processes or tollgate decisions. Release all anchors!
This first step might take six months to a year, but it’s absolutely worth it. If you’re seeing the symptoms mentioned earlier, this is your way forward.
2. Hang On
Perseverance is key. There will be setbacks. There will be problems. Transformation is hard, but the only way to succeed is to keep going.
3. Stay Tough When the Going Gets Tough
The American financier and diplomat Joseph P. Kennedy several times said, "When the going gets tough, the tough get going." Many years later, Billy Ocean sang it. And for us now, it’s a critical reminder: If you hit a crisis—say, a customer calls, yelling about poor quality or delivery delays—this is the moment when leadership matters most. Resist the temptation to revert to old habits like creating task forces or demanding endless status reports.
Instead:
- Trust the organization. Let your teams own and fix their problems.
- Help them prioritize. Guide them on where to focus, but let them figure out the “how.”
- Ask for results, not status. Avoid wasting time on reports and updates; instead, ask for working systems, software, hardware, or whatever demonstrates progress.
This is the time to demonstrate your belief in the team’s competence. Tell them you trust them—and mean it.
But What About the Rest of the Organization?
Here’s the trick: let them continue where they are, for now. Remember, the problem is the fear of letting go of the anchor. Focus on one small part of the organization until you, and all other leaders, can see and understand that this is working. Give the organization time to adapt to new ways of working by learning from mistakes, missteps, and successes.
Celebrate the successes and make them visible to the entire organization. Encourage experiments, and build confidence through transparency and results.
Breaking free from old habits isn’t easy, but it’s the only way to achieve true agility. Start small, persevere, and trust your teams. You’ve got this!
Closing Thoughts
Agile transformation is not just about adding new practices—it’s about shedding old habits that no longer serve your organization’s goals. True agility requires courage, commitment, and a willingness to embrace uncertainty. By identifying and addressing these remnants of the past, organizations can unlock the full potential of Agile and achieve lasting success.
So, what’s holding you back? It’s time to cut the anchor and let your Agile ship sail.
Reflection Question
What outdated practices or "anchors" are holding your organization back from achieving true agility—and what’s one step you can take today to begin letting go? Which corner of the organization can you start with?
Final Note
I’m sorry, I just have two songs on repeat in my head right now—and maybe you do too. But if you keep thinking about “I’ve got to be free” and “When the going gets tough,” you’ve captured the essence of this article.
Do you have experience with anchors in your organization? Share your stories and thoughts in the comments below!
This article is the eighth in a series of articles about common mistakes in Agile transformations. Subscribe to my newsletter to stay updated and continue your journey toward Agile mastery!
Find all of the articles in the series here:
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Last updated Jan 29, 2025