AI and the Absurdity of Enterprise Apps

June 21, 2025

by

alexjcooper

The Big Beautiful Logic of Enterprise Applications and the AI House of Cards

The logic of Enterprise Applications is impeccable. They just make so much sense. One place for all of the data. One single source of truth. Timely, accurate information to guide all important and unimportant (there is no such thing as an unimportant decision in the enterprise) corporate decisions. Business nirvana accomplished! Except for one small problem, the real world doesn’t quite work as neatly as Enterprise Applications would have you believe.

Customers and prospects don’t always fit nicely into your beautifully conceived five stages in your CRM system. Is there a stage between lead and prospect? Maybe we should schedule a meeting with the team to discuss adding a new stage in between. These stages are arbitrary. They are convenient for classifying things to generate reports, but they don’t capture the subtle reality that is happening behind the scenes. The real information is rarely captured by CRM. The nuance is lost. CRM doesn’t capture tone of voice, facial expressions or even hidden sarcasm. It is literal to a fault.

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These problems aren’t limited to CRM systems. It applies to all enterprise systems, even tools like ERP and Finance which are as literal as it gets. While AI is known to hallucinate occasionally, it is still a data driven tool. Even though unarticulated information and subtext is everywhere, AI is being hailed as the answer to the shortcomings of enterprise systems.

AI promises to fill in the gaps of enterprise systems that previously relied on humans filling in the all of the fields in the corporate database. Now thanks to AI, these issues are now a thing of the past. AI will construct a great meeting summary with a high level of detail, it will craft a perfect follow up email with perfect grammar and it will surface lots of possibly related information.

If this sounds like more of the same to you, you may be smarter than your average AI bot or the marketing team at the average Enterprise Software company.

This is just more information, not meaningfully better information. It will just become the new table stakes of enterprise software. Perhaps there will be a short-term advantage to the organizations that adopt these new best practices ahead of those industry laggards, but this kind of application is self perpetuating in its lack of sustainable advantage.

Ultimately, it is the human to human relationships that matter. It is the communication and trust that develop between humans that makes things happen. It is the conversation that gets to the real why something is important and not just the surface level why. Why is a much more important question than what, but AI and Enterprise Systems in general are still stuck on what. Maybe someday AI will get to the real why, but until then we will still have to work with the underlying human psychology.

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