Observe Before You Advise: The Secret to Smarter Agile Coaching with Chesterton’s Fence

In agile coaching, it’s tempting to dive in headfirst—implementing new frameworks, reorganizing teams, and scrapping old processes that seem inefficient. But what if I told you that charging ahead without fully understanding the existing systems could actually do more harm than good? Enter Chesterton’s Fence—a principle that cautions against changing anything until you know why it exists in the first place. For agile coaches, this concept is a powerful reminder to slow down, observe, and respect the history behind the processes and behaviors we’re called to improve.

By taking the time to understand the historical context and rationale behind existing processes, we can avoid hasty, misguided changes and instead make smarter, more sustainable improvements. In this article, we’ll explore how Chesterton’s Fence applies to agile coaching, why observation is such a critical tool in our work, and how balancing client demands with thoughtful observation can lead to better outcomes for everyone involved.

What is Chesterton’s Fence?

Chesterton’s Fence is a principle that cautions us against removing or altering something unless we fully understand why it exists in the first place. The concept originated from an essay by G.K. Chesterton, where he famously argued that if someone comes across a fence and doesn’t know why it’s there, they should not remove it until they’ve figured out its purpose. Chesterton’s point is simple: existing systems, structures, or rules—no matter how arbitrary they seem—were likely put in place for a reason. Dismantling them without understanding that reason can lead to unforeseen negative consequences.

At its core, Chesterton’s Fence is a reminder to take a step back, ask questions, and resist the urge to immediately “fix” something that appears broken. It’s about showing respect for the history and context behind decisions, even if they initially seem outdated or inefficient. This principle encourages deeper thinking and a more considered approach to change.

Relating Chesterton’s Fence to Agile Coaching

In agile coaching, Chesterton’s Fence is a critical mindset shift. As coaches, we are often brought into organizations to drive change and improve processes. It’s tempting to see outdated systems or practices and assume they should be immediately discarded in favor of something more agile. But applying Chesterton’s Fence teaches us to pause and understand why those practices exist in the first place. Every process, no matter how “un-agile” it may appear, likely evolved to solve a specific problem or address a particular need within that organization.

For example, you might encounter a team that insists on lengthy approval processes or cumbersome reporting structures. On the surface, this could look like bureaucracy that needs to be eliminated. But before making that change, Chesterton’s Fence suggests that you investigate why these processes were put in place. Perhaps the team faced compliance issues or a lack of clarity in decision-making in the past. Once you understand the rationale, you can make a more informed decision on whether those processes should be adjusted, replaced, or perhaps maintained in some form.

By embracing this principle, agile coaches avoid the trap of “change for the sake of change.” Instead, they become more effective by respecting the history behind existing structures while thoughtfully guiding organizations toward more efficient, agile practices.

Observe Before You Advise!

Patience Over Impulse

As agile coaches, we are often eager to solve problems and show immediate value. It’s tempting to dive headfirst into recommending solutions or implementing changes when we encounter practices that seem blatantly un-agile. After all, we’ve been brought in as experts to help teams improve, right? However, jumping straight into action can often backfire.

The impulse to fix things quickly is natural, especially when faced with resistance from teams that are stuck in outdated processes. But it’s important to resist that urge. Agile coaching isn’t about imposing changes for the sake of looking productive; it’s about making meaningful, sustainable improvements. Patience allows us to approach the situation thoughtfully, avoiding knee-jerk reactions that could ultimately do more harm than good.

The Value of Observation

One of the most valuable tools in an agile coach’s toolkit is observation. Taking the time to quietly observe the team, their processes, and their interactions without immediately offering advice can be incredibly powerful. I’ve learned through experience that giving myself at least one or two weeks to observe pays off. While it’s tempting to jump in with advice or solutions when something looks obviously wrong, restraining myself has often led to much better outcomes.

Observation allows you to gather important context. For example, I’ve had situations where what seemed like an “un-agile” practice—like a heavy reliance on detailed documentation or a rigid approval process—was actually solving a specific problem that wasn’t immediately apparent. By observing the team in action, I could understand the underlying rationale for these practices. In some cases, they were indeed necessary, and simply removing them would have caused more chaos. In other cases, observing first helped me propose more nuanced, effective changes.

For example, I once worked with a team that seemed bogged down by excessive reporting. Initially, I thought it was a prime candidate for removal. But after observing their workflow, I realized that the reporting process was their only way to ensure alignment across multiple stakeholders who were spread out geographically. Simply eliminating this process would have created confusion and undermined their communication. Instead, I was able to suggest a streamlined reporting approach that maintained alignment but reduced the administrative burden.

Key Point: Observation Reveals Hidden Context

The key lesson here is that observation often reveals hidden context behind processes. At first glance, something might seem inefficient or counterproductive, but once you understand its history and rationale, you can see why it’s in place. Processes that seem to slow things down might be protecting against specific risks, or habits that seem un-agile might have evolved to address past issues that still exist in the background.

This understanding gives you the insight needed to make smarter decisions. Instead of blindly introducing changes or forcing agile practices into the team, you can make targeted improvements that address the real problems without losing the benefits that existing processes provide. Observation isn’t about doing nothing—it’s about gathering the information needed to make truly effective, informed recommendations.

In sum, taking the time to observe first allows us to approach each situation with a deeper understanding, helping us avoid unnecessary disruptions while positioning us to drive meaningful, long-lasting improvements.

The Pressure to Act: Balancing Observation and Client Expectations

Client Expectations

One of the biggest challenges agile coaches face is managing client expectations. Many clients want immediate action. They’ve brought you in to help their teams become more efficient, more agile, and more productive—and they want to see results quickly. When clients see you spending the first few days or weeks observing rather than actively implementing change, they might perceive your approach as passive or even ineffective.

From the client’s perspective, passive observation can sometimes look like “doing nothing,” which creates a tension: how do you justify the time needed to truly understand the deeper issues within a team or organization before proposing changes? Clients are often under pressure themselves, needing to demonstrate progress to their own stakeholders, which only amplifies their demand for immediate results.

As coaches, we know that diving in too fast without observing can lead to misguided decisions. But explaining the value of observation can sometimes feel like an uphill battle when the client is focused on speed and outcomes. This tension can make it difficult to earn trust, and at times, it can even jeopardize your relationship with the client.

Personal Experience

I’ve experienced this firsthand. On one occasion, I was pulled off a project because my approach seemed too passive to the client. I had taken the time to observe the team and the processes in place, but from the client’s perspective, it wasn’t enough action, fast enough. They wanted to see changes right away, and my methodical approach didn’t meet their expectations for quick wins. It was a tough situation, but it also reaffirmed my belief in the importance of observation.

On the flip side, I’ve also had great successes where I prioritized observation before making any recommendations. In one instance, my initial observations revealed that what the client saw as inefficiency was actually a carefully calibrated system that, with just a few tweaks, could perform much better. By taking the time to observe and understand, I was able to pinpoint the areas where I could make the biggest impact. Not only did this lead to more effective solutions, but it also helped me build better rapport with the teams, who appreciated that I wasn’t rushing in to change everything without understanding their context.

These experiences have taught me that finding the right balance between observation and action is critical to maintaining client trust. It’s not always easy, but when done well, it leads to stronger relationships and better long-term results.

Striking the Balance

The key to balancing observation and client expectations is to blend periods of quiet observation with visible, immediate contributions. One approach is to offer quick wins alongside your observation period. These might be small but impactful changes that you can identify early on—actions that demonstrate your value while still allowing you time to gather the insights necessary for deeper, more meaningful improvements.

For example, while observing, you might notice a small process tweak or a communication gap that can be easily addressed. Offering advice on such small, tangible issues can satisfy the client’s desire for immediate action and buy you the time to dig deeper into the more systemic problems.

Another strategy is to communicate your observation period as a key part of your process upfront. Explain that this time is crucial for understanding the team’s dynamics, challenges, and existing processes so that any changes you recommend will be more effective and sustainable in the long run. Framing observation as a deliberate and valuable phase of your work can help reset client expectations.

Ultimately, the goal is to strike a balance: demonstrate value early and often, while also giving yourself the space to make thoughtful, strategic recommendations. By blending action with observation, you can satisfy your client’s immediate needs without sacrificing the deeper insights that lead to lasting success.

Real-Life Example: When Un-Agile Solutions Are Actually Smart

Anecdote: Understanding Resistance Leads to True Agility

At a global manufacturing client, I encountered a small but vocal group of employees who were resistant to the agile methods we were trying to implement. Management, my direct client, was frustrated by this resistance and pressured me to “crush” the opposition or simply ignore it. The expectation was to push through with the transformation regardless of the concerns raised.

But my experience had taught me something crucial: people who resist change usually do so for a reason. And more often than not, their concerns stem from good intentions rather than a desire to be difficult. So instead of bulldozing through their resistance, I took the time to talk with these employees. I wanted to understand their history, expertise, and what was fueling their reluctance.

It turned out that their resistance wasn’t because they disliked the agile approach itself. In fact, they were hands-on practitioners who valued getting things done. Their issue was that they feared the agile transformation would become yet another layer of planning and delay—a way for management to avoid making tough decisions and starting the real work. Their deep experience with building these systems gave them a different perspective: they wanted to avoid endless iterations of planning and get to the real implementation as soon as possible.

By taking the time to understand their perspective, I was able to change the conversation. Instead of forcing agile methods on them, I showed how agility could actually help them achieve what they valued—getting hands-on quickly. This shift led to them not only accepting the agile methods but also becoming strong supporters of the transformation. They helped me advocate for a more practical approach where we would start implementation sooner rather than later, using agile principles to adjust as we went along.

This insight also helped management realize that agility didn’t mean spending months planning in small iterations—it meant acting and adapting. Without that initial observation and empathy, this critical support from the team would have been lost, and the transformation could have failed before it even began.

Anecdote: Automated Testing Resistance Rooted in Real Challenges

In another situation, I worked with a testing team that was resisting the move to automated testing. On the surface, their opposition seemed like nostalgia—a desire to hold on to the manual labor-intensive processes that had been a hallmark of testing for years. They often spoke of the “feeling” and intuition that came with hands-on testing, making it easy to assume that they simply weren’t ready for change.

But instead of dismissing their concerns, I took the time to dig deeper. I observed their testing processes and talked to them about their experiences. What I discovered was that their resistance wasn’t rooted in fear of automation—it was based on very real, practical challenges. Their architecture, made up of many different hardware and software components, wasn’t yet ready for automated testing. They had experienced serious issues where machines that had passed their tests were failing once they were installed at the client’s factory. Automation, in its current state, wasn’t capturing the nuances of the complex systems they were working with, which led to costly errors and delays for their customers.

With this deeper understanding, we were able to chart a better path forward. Instead of rushing into full automation, we worked together to build a plan that respected the team’s concerns while moving toward a more automated process. We focused on creating a solid CI/CD pipeline that would support both automated and manual testing, giving the team confidence that their expertise wasn’t being sidelined. This hybrid approach allowed us to gradually improve the automation capabilities without sacrificing the critical insights that manual testing was providing.

Learning from History

Both of these examples illustrate a crucial point: what initially appears to be an outdated or un-agile solution often turns out to have deeper roots and valid reasons for existing. The manufacturing team’s resistance wasn’t about rejecting agility—it was about preserving the hands-on approach that they knew worked. The testing team’s hesitation wasn’t about clinging to the past—it was about ensuring quality control in a complex environment that wasn’t ready for a full shift to automation.

By respecting the existing systems and taking the time to understand their history and purpose, I was able to uncover valuable insights that guided more thoughtful and effective changes. Had I pushed forward without observing and understanding, I would have missed these nuances—and likely caused more problems than I solved. Chesterton’s Fence, once again, proves its worth in guiding us to make better decisions by respecting the reasons why things are the way they are before we change them.

The lesson here is simple: respect the history behind the processes and listen to the people who are deeply embedded in them. Often, they aren’t resisting for the sake of resisting—they are protecting something valuable that you can only see if you take the time to look.

The Smarter Path to Agile Success

Balanced Approach

The core of successful agile coaching lies in striking a balance between action and observation. Rushing in to change processes without understanding their context is a recipe for failure. But staying passive for too long can leave clients feeling neglected and impatient for results. By taking a patient, observant approach, coaches are able to make better decisions, foster stronger collaboration with teams, and implement more sustainable changes.

This approach helps uncover the hidden reasons behind processes that may initially seem outdated or inefficient. Through observation, we’re able to discern the rationale that keeps those processes in place and determine whether they still serve the organization’s goals or if they need adjustment. When we understand why something exists, we can either preserve its value or replace it with something better, ensuring that our solutions are not just theoretically agile, but practically effective.

Moreover, the patience to observe builds trust with the teams we work with. Employees are more likely to open up and share insights when they feel respected and understood. This collaborative relationship leads to smoother transitions and better adoption of new practices because the changes are rooted in a shared understanding, rather than imposed from the outside.

Empower Your Clients

One of the most valuable gifts an agile coach can give their clients is empowerment. By helping clients understand the history and purpose behind their existing processes, we enable them to make informed decisions about what to keep, what to change, and why. This doesn’t just result in better processes—it leads to a deeper understanding of agility itself.

When clients are educated on the reasoning behind their current systems, they can approach transformation with a mindset that is both critical and constructive. They become partners in the change process rather than passive recipients of external recommendations. This empowerment builds their capability to sustain agile practices long after the coach has left, which is the ultimate goal of any agile transformation.

Helping clients see the value in observation and understanding also shifts their perspective on what it means to be agile. It’s not just about quick, flashy changes. It’s about thoughtful, informed evolution that respects the past while moving toward a better future.

Call to Action

So here’s my call to action: Slow down. Resist the urge to jump straight into fixing things the moment you walk through the door. Take the time to observe, to ask questions, to understand the rationale behind the systems and behaviors you’re working with. Channel the wisdom of Chesterton’s Fence and recognize that what might seem like an obstacle could actually be a vital piece of the puzzle.

By doing this, you’ll make smarter, more strategic decisions that lead to lasting change. You’ll build trust with your teams, strengthen collaboration, and empower your clients to own their agile transformation. In the end, it’s not about how quickly you can implement change—it’s about how deeply you understand what needs to be changed and why.

True agility isn’t a race. It’s a thoughtful, iterative process of continuous improvement. Start with observation, let understanding guide your recommendations, and watch as your coaching delivers real, sustainable results.

Conclusion

The key takeaway here is simple yet profound: observation is one of the most powerful tools in an agile coach’s toolkit. By applying the principles of Chesterton’s Fence, we ensure that we don’t make ill-considered changes that could undermine the very systems we are trying to improve. Taking the time to observe, understand, and respect the existing processes allows us to make informed, thoughtful decisions that lead to more sustainable, long-lasting change.

In agile coaching, patience and observation aren’t signs of inaction—they are the foundation of success. So, embrace the power of observation, take the time to understand before you act, and remember that sometimes the smartest move is simply to listen, watch, and learn. True transformation comes not from rushing to make changes but from understanding when and why those changes are needed.