How a 17th century urban planning lesson can save your AI strategy

‍

The Story That Changed Everything

Imagine the Boston of 1630. A young Puritan colony sprawling on a rocky peninsula, where roads do not yet exist and cattle roam freely through meadows and hills. The cows, with that pragmatic animal wisdom of theirs, trace natural paths following the path of least resistance: bypassing boulders, avoiding swamps, connecting pastures and watering holes.

‍

Decades later, when the city's founding fathers were faced with the need to create a road system, they made a decision that seemed reasonable: instead of designing a logical and orderly grid from scratch, they simply paved the paths already laid out by livestock.

‍

The result? The chaotic maze of winding streets that still characterizes downtown Boston, where Washington Street meanders like a river gone mad and where even the most sophisticated GPSs sometimes give up in frustration.

‍

Historical source: The story is documented in the poem "The Calf-Path" by Sam Walter Foss (1858-1911), which tells precisely how the paths traced by a calf later became the streets of a city.¹

‍

When Efficiency Becomes Inefficiency

The Boston story is fascinating because it perfectly illustrates a paradox: what works locally and immediately can prove disastrous on a larger scale and in the long term. The cows were right to follow the path of least resistance for their immediate purposes, but their paths were not designed for carts, cars, trucks, or city buses.

‍

The lesson is profound: not everything that develops organically is optimal for the future.

‍

The Business Analogy: When Processes Become Paths.

On modern farms, "cow paths" are everywhere. They are those processes that have developed organically over time. As Jim Highsmith explains:* "In the IT world, 'paving cow paths' means automating a business process as it is, without thinking too much about its effectiveness or efficiency"².

‍

• The form that needs to be printed, signed, scanned and emailed back to you
• The weekly meeting that no one remembers why it started, but that "we've always done it this way"
• The Excel file shared among 15 people that serves as a corporate "database"
• The approval process that goes through 7 different people, 3 of whom don't even know why they have to sign it

These processes were formed like cow paths: following the path of least resistance at the specific time they were born. But now, in the digital age, continuing to follow them can be devastating.

‍

The Great Temptation: Paving the Cow Path

When companies decide to "digitize," they often fall into the same trap as Boston's founding fathers. They take existing processes and "pave" them with technology:

Digitization: Paving the Path.

‍

"Have we always filled out this form by hand? Perfect, let's create a fillable PDF!"

This is digitization: converting analog to digital without changing anything substantial. As Gartner defines, "Digitization is the process of converting analog information into digital format."³ It is like paving the cow path - it becomes smoother, but remains tortuous and inefficient.

The Hidden Cost of Inertia

A manufacturing company I know had a quality control process that required 14 different steps, developed gradually in the 1980s and 1990s. When they "digitized," they simply transferred all 14 steps to tablets. The process became faster, but it remained fundamentally irrational: 8 of those steps were duplicate or obsolete.

‍

The Real Transformation: Digitization vs. Digitization

Digitization: Designing the City of the Future

True digitization means doing what Boston should have done: looking at the end goal and designing from the ground up the best way to get there.

‍

According to the Gartner glossary, "Digitization is the use of digital technologies to change a business model and provide new opportunities for value and revenue; it is the process of moving to a digital business."⁴

‍

Examples of actual digitization:

• Netflix did not digitize video rental; it completely rethought home entertainment
• Amazon did not digitize paper catalogs; it reinvented commerce

The Crucial Difference

• Digitization: "How can we do what we do, but digitally?"
• Digitalization: "What are we really trying to achieve, and what is the best way to get there in the digital age?"

AI and the Temptation of Super-Lastricity.

Today we are seeing a new wave of "paving the cow path" with artificial intelligence. Companies are taking inefficient processes and enhancing them with AI, creating what we might call "super-lasticity."

‍

As highlighted in the Harvard Business Review, "The idea of business process reengineering is coming back, this time driven by artificial intelligence. In the 1990s, the implementation of ERP systems and the Internet enabled changes in business processes, but expectations of radical change were often not met. However, AI enables better, faster, automated decisions."⁵.

Examples of AI Cow Path Paving:

‍

• Using ChatGPT to write faster emails in a communication process that requires 12 emails to make a simple decision
• Implement AI to analyze reports that no one really reads
• Automating with machine learning approval processes that should not exist

The Result

‍

Inefficient processes that are now inefficient faster and more accurately.

‍

The Anti-Cow Path Methodology

‍

1. Obliterate → Integrated → Automated

Before implementing any technology, follow this order according to Michael Hammer⁶ methodology:

Obliterate: Eliminate anything that does not add real value

‍Integrate: Connect remaining processes into logical flows.

‍Automate: Only at the end, apply the technology

‍

As Hammer writes, "It is time to stop paving cow paths. Instead of incorporating obsolete processes into silicon and software, we should obliterate them and start anew."⁷

2. The Greenfield vs Brownfield Approach

These terms, borrowed from urban planning and software engineering, define two radically different approaches⁸:

‍

Brownfield (Paving the path):

• Maintain existing and add technology
• Faster in the short term
• Preserves inefficiencies

Greenfield (Design from scratch):

• Starting with a whiteboard
• Riskier but potentially revolutionary
• Allows you to take full advantage of the new possibilities

As highlighted by McKinsey, "While 90 percent of companies have begun some form of digital transformation, only one-third of the expected revenue benefits have been realized"⁹.

3. The Right Questions.

Before any technological implementation, ask:

• "Why are we doing this process?"
• "What would happen if we stopped doing this?"
• "If we were to design it today from scratch, what would it look like?"
• "What constraints of the past no longer exist?"

Case Studies: When Avoiding the Trail Pays Off

Case 1: The Bank that Rethought Lending.

One European bank had a loan approval process that took 45 days and 12 different steps. Instead of "digitizing" the existing process, they completely redesigned it:

• Before: 45 days, 12 steps, 73% of files approved
• After: 24 hours, 3 passes, 81% of files approved

The secret? They realized that 90% of the controls were redundant and that AI could assess risk more accurately than 6 different offices.

Case 2: The Hospital that Eliminated Queues.

One Italian hospital had waiting times of 4 hours in the emergency room. Instead of "digitizing" the queuing system, they completely rethought patient flow:

• AI-based predictive triage
• Pathways differentiated by type
• Real-time monitoring of workloads

Result: Waiting time reduced by 80%, patient satisfaction +60%.

‍

The Three Modern Traps of the Cow Path

1. The Familiarity Trap

"Our employees are used to this" is the most insidious killer of innovation. It is like saying that cows were used to their own paths.

2. The Trap of Subdued Investment.

"We have already invested so much in this system" ignores the fact that continuing on a wrong path amplifies the error.

3. The Trap of False Complexity.

"It's too complicated to change everything" often hides a fear of admitting that the current process does not make sense.

‍

The ANTI-COW Framework for Digital Transformation.

Analyze- Analyze the Desired Outcome

Don't start with the technology, start with the business objective.

Navigate- Navigating Beyond Current Constraints

Ask yourself, "If I were a company born today, how would I solve this problem?"

Transform- Transform, Not Translate

Redesign processes for the digital age, not translate them into digital.

Implement- Implement in Phases

Using an incremental approach but with a radical vision.

Check- Check Effectiveness

Measure not only efficiency, but overall effectiveness.

Optimize- Optimize Continuously

The process of transformation never ends.

Watch- Watching for New Paths

Be careful that new spontaneous "cow paths" do not form.

‍

AI as an Architect, not as a Worker

Artificial intelligence can be either the best tool for paving cow paths (making them super-efficient but fundamentally wrong) or the best architect for designing the cities of the future.

As the World Economic Forum subtends, "To reach its full potential, AI needs to speak the language of business, it needs to understand how work flows, and it needs process intelligence"¹⁰.

The difference lies in the approach:

AI as Worker (Paving the Cow Path):

• "How can we use AI to do this process faster?"
• Automation of existing activities
• Incremental improvements

AI as an Architect (City Planning):

• "How can we completely rethink this business outcome?"
• Redefinition of the problem itself
• Radical transformation

The Courage to Demolish

The deeper lesson of the Boston story is not technical, but psychological: it takes courage to admit that the paths we follow are not necessarily the best possible ones.

In business, this means:

• Questioning "sacred" processes
• Accepting that "we have always done it this way" is no justification
• Investing in changes that may not pay off immediately
• Resisting the temptation of the quick fix

Conclusion: Designing Roads for the Future

Today, faced with the endless possibilities of AI and digitization, we have a choice: we can do as Boston's founding fathers did and pave existing paths, or we can have the courage to design the cities of the future.

‍

The next time you hear the phrase "let's digitize this process," stop and ask, "Are we designing a modern road or are we paving a cow path?"

‍

The future belongs to those who have the courage to leave the beaten path and design new roads. Even if this means admitting that cows, wise as they were, were not urban planners.

‍

"It is time to stop paving cow paths. Instead of incorporating obsolete processes into silicon and software, we should obliterate them and start over. We should 'reengineer' our companies: use the power of modern information technology to radically redesign our business processes to achieve dramatic improvements in their performance." - Michael Hammer, Harvard Business Review, 1990¹¹

‍

Sources and References

1. Stack Exchange English Language & Usage: https://english.stackexchange.com/questions/44800/what-does-don-t-pave-the-cow-path-mean-in-this-context
2. AgileConnection - Paving Cow Paths: https://www.agileconnection.com/article/paving-cow-paths
3. SAP - Digitization vs. Digitalization: https://www.sap.com/products/erp/digitization-vs-digitalization.html
4. SAP - Digitization vs. Digitalization (Gartner definition): https://www.sap.com/products/erp/digitization-vs-digitalization.html
5. Harvard Business Review - How AI Is Helping Companies Redesign Processes: https://hbr.org/2023/03/how-ai-is-helping-companies-redesign-processes
6. The Digital Leader - Is Your AI Plan Just Paving the Cow Paths?: https://thedigitalleader.substack.com/p/is-your-ai-plan-just-paving-the-cow
7. Harvard Business Review - Reengineering Work: Don't Automate, Obliterate: https://hbr.org/1990/07/reengineering-work-dont-automate-obliterate
8. Synoptek - Greenfield vs. Brownfield Software Development: https://synoptek.com/insights/it-blogs/greenfield-vs-brownfield-software-development/
9. McKinsey - Rewired to Outcompete: https://www.mckinsey.com/capabilities/mckinsey-digital/our-insights/rewired-to-outcompete
10. World Economic Forum - How to use process intelligence and AI to rewire businesses: https://www.weforum.org/stories/2024/01/process-intelligent-ai-rewire-business-sustainable-transformation/
11. Harvard Business Review - Reengineering Work: Don't Automate, Obliterate (1990): https://hbr.org/1990/07/reengineering-work-dont-automate-obliterate