Insights from Jeff Szczepanski’s Business of Software AMA
At the recent Business of Software AMA, Jeff Szczepanski – CEO of Reframe Technologies, delivered a thought-provoking session that dissected the paradox of modern productivity: why we have more powerful tools than ever, yet seem to be treading water.
This wasn’t just another AI hype session. Instead, Jeff challenged us to think more deeply about how we use technology, what collaboration really means, and why context (not more code) might be the key to unlocking meaningful progress.
The Problem: More Tools, Less Progress?
Jeff opened with a sobering question: If our tools are getting so much better, why aren’t we?
AI, automation, and digital productivity tools have made huge strides, especially at the individual task level. But when it comes to group alignment, decision-making, and strategy, what Jeff calls knowledge work, we’re still flailing.
We aren’t drowning in tasks; we’re drowning in context loss.
“The leaps aren’t there anymore. We’re overloaded with information but lack the insight tools to make sense of it.”
AI: Useful, But Not Magic
Jeff is no AI skeptic: He uses ChatGPT every day. But he draws a clear line between what current AI can and can’t do.
AI is good at:
- Text manipulation and summarization.
- Transforming language into other formats (e.g., bullets to slides).
- Acting as a brainstorming partner or “rubber duck” for ideas.
But AI struggles with:
- Maintaining reliable context.
- Understanding the “why” behind actions.
- Making collaborative, strategic decisions.
Jeff’s advice? Stop pretending AI is a brain. Start thinking of it as a better interface for humans.
“Language models aren’t intelligent. They’re just a new kind of user interface—very powerful, but also very crude.”
The Real Bottleneck: Human Coordination
At the heart of Jeff’s message is this: productivity isn’t about speed, it’s about shared understanding.
Most modern software tools don’t know what we’re trying to do. They digitize documents, emails, and tasks, but they don’t connect them into a meaningful why.
Jeff introduced a term for this gap: articulation—the cognitive effort needed to organize your tools, tabs, and thoughts just to get started on real work. Multiply that by every person on your team, and it’s no wonder we struggle to align.
“The computer doesn’t know what you’re trying to do. There’s no shared context. And that’s a huge problem.”
Reframe: Context is the Missing Layer
Jeff’s company, Reframe, is working on a bold solution: a “cortex layer” that organizes your digital work into streams, essentially, structured containers of context. Think of them as dynamic workspaces that remember not just what you’re working on, but why.
With Reframe:
- You can switch between projects and have the right tools/files auto-load.
- Collaborators share context without digging through Slack, Zoom, or Notion threads.
- AI can plug into your context stream and actually become helpful—not just generative.
It’s early-stage, but the demo showed a glimpse of a future where our computers finally understand our workflows.
Key Takeaways
- Efficiency ≠ Progress
Task tools are improving. Strategy and coordination? Not so much. - AI is Overhyped—and Under-Structured
LLMs are helpful, but not reliable without human scaffolding. - We Need Better Vocabulary
To fix collaboration, we first need better language for describing what we’re doing and why. - Reframe Offers a New Approach
Organizing work by context, not just tools, can change how we think, plan, and execute. - Start with the Human, Not the Model
Before throwing AI at a problem, figure out what humans are actually trying to do. - Strategic Clarity is Crucial
Many AI failures in business stem from unclear goals, not bad tech.
Final Thoughts
Jeff’s AMA wasn’t a product pitch. It was a call to rethink how we work, how we align, and how we define intelligence itself. In an age of AI everything, Jeff reminds us: the future isn’t just artificial, it’s collaborative. And without shared context, even the smartest tools will fail to move the needle.