Many prompts led to a descent into madness, so I gave up. Can you name the album?

Near the end of 2023, I was laid off from Microsoft and I decided to do something crazy – take a year off. I really meant “off”, too, meaning I wouldn’t look for a new role or think about my next move or go anywhere near LinkedIn. I mostly succeeded. While I had no roadmaps to build or backlogs to groom, I couldn’t stay entirely away from computers, as I had personal creative pursuits lined up. And then before you know it, I was tinkering with AI, and as my sabbatical year came to a close, tinkering had evolved into a purposeful exploration, and I postponed looking for a job. That purposeful exploration has since turned into nine months of deep immersion: learning technology, building software, and working with clients on data and AI strategies. I’m not entirely sure what’s next, but for now, I feel like a big transformation is afoot, and I will continue the journey.

I’m normally a skeptic about the next big tech transformation. That may be a result of living through changes “in the trenches”, where hype for the newest thing feels like noise and gradual change. My recent career path has pushed me towards a collision with AI, as I have led products employing machine learning-based personalization and a lot of analytics and data infrastructure. So, I was a bit surprised to find that as I went deeper into the details, I was more convinced that fundamental changes are occurring for my role, industry, and probably a lot more. 

Enterprise is Dead… Dead i tell you!

Of course, I’m not the only one. Of the many public statements about AI transformation, perhaps the most viral (and apocryphal) came from my former CEO, Satya Nadella as an off-the-cuff podcast comment. Here’s a bit the verbatim:

“…the notion that business applications exist, that’s probably where they’ll all collapse, right in the agent era, because if you think about it, right, they are essentially CRUD databases with a bunch of business logic. The business logic is all going to these agents, and these agents are going to be multi repo CRUD, right? So they’re not going to discriminate between what the back end is. They’re going to update multiple databases, and all the logic will be in the AI tier, so to speak. And once the AI tier becomes the place where all the logic is, then people will start replacing the back ends, right?”

The headlines all declared that he pronounced “Enterprise is Dead!”, which he didn’t. What he did say was interesting, and it resonated with my own intuition about the implications of AI. He says that AI agents “…(are) not going to discriminate between what the back end is. They’re going to update multiple databases, and all the logic will be in the AI tier …”.  I think he’s right, and I don’t think it’s going to be limited to just SaaS/PaaS (aka business applications). I’ve always felt that too much focus has been placed on front ends and not enough on the underlying data and its behavior in applications.  A deeper take on his comments from David Chan:

“if you remove the human out of the equation, and the human employee is no longer the user of the SaaS solution, then wouldn’t it make the UI (e.g. menu items, buttons, where things are above / below the fold) extraneous? …databases and their schemas limit our ability to orchestrate seamlessly between systems.”

That resonated with me as well, and my intuition is that the two ideas conveyed in those quotes are really important for anyone thinking about how things change with AI. I think that the way we we think strategically about data will be more important to practical AI success than any one agent framework or shiny new model checkpoint. 

I’ve been prompt engineering since none of your business

I also noticed a theme emerging from a common chorus of opinions suggesting that Product Management (my job) is writ large in the wheelhouse of what businesses employing AI will need. Here’s a quote from by Marco Iansiti and Karim R. Lakhani in the Harvard Business Review’s – “Competing in the Age of AI”:

“Though building a base of software, data science, and advanced analytics capabilities will take time, much can be done with a small number of motivated, knowledgeable people. However, many organizations fail to realize that they need to systematically hire a very different kind of talent and set up career paths and incentive systems for those employees. An Agile Product Focus Building an AI-centric operating model is about taking traditional processes and transforming them into software. Developing a product-focused mentality is essential to getting this done. Like the product managers at any world-class software development project, the IT teams deploying AI-centered applications should have a deep understanding of the use cases they’re enabling, a product-management orientation that goes well beyond the approach of traditional IT organizations.

Ok, interesting. Recently, the pundit-o-sphere has also been declaring that “Prompt Engineering” and “Vibe Coding” are dead because “Context Engineering” is really how to get value out of AI. “Context Engineering” is like… well, it’s a virtual Product Manager for your AI agents and applications. There is even a component refered to as the PRP, or “Product Requirements Prompt”. I mean, how on the nose can you get!? Here’s a related quote from Sean Grove, an OpenAI engineer in this YouTube video from the AIE Worlds Fair 2025 The New Code — Sean Grove, OpenAI:

“We all work very hard to solve problems. We talk to people. We gather requirements. We think through implementation details. We integrate with lots of different sources.. What is the goal that you want to achieve? You plan ways to achieve these goals. You share those plans with your colleagues. You translate those plans into code”

I mean, other than the “translate into code part”, that’s like, also my job. And, I’m starting to do that part too. So, maybe there are some tailwinds for tech PMs in the age of AI, or maybe we are the canaries in the coal mine. Well, I’m taking the time to try and find out, and i’ll share my journey. Things are moving fast, I’m learning a lot, and I have some ideas I’m fleshing out. So stay tuned for what comes next!

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