Here’s How to Know If You’re Getting the Most Out of AI – with Bryan McCann, CTO of You.com

About this episode

In this episode, Bryan McCann joins Henrik and Jeremy to explore how search is evolving from simple queries into more conversational and agent-driven systems, and why prompting is likely a temporary skill. Bryan shares how his definition of productivity changed as an AI researcher, moving away from doing the work himself and toward designing plans and experiments that machines could run continuously.

The conversation expands to leadership and organizational design. Bryan explains why helping others learn how to work with AI became his highest-leverage activity, and offers a simple rule of thumb: try to get AI to do the task first, and treat anything it can’t do as an interesting research problem. Henrik and Jeremy connect this to Bryan’s view that organizations may increasingly resemble neural networks, with information flowing more freely and decisions less tied to rigid hierarchies.

Key Takeaways:

• Productivity can be measured by machine output, not human effort
  Bryan explains how “keeping the GPUs full” became his primary measure of productivity.
• Prompting is useful, but likely temporary
  The episode discusses why future systems may rely less on explicit prompts and more on inferred context.
• Try AI first, then learn from what it can’t do
  Tasks AI struggles with can reveal meaningful research opportunities.
• Leadership is about scaling others
  Bryan shares how his focus shifted from scaling himself to helping his team increase impact.
• Organizations may benefit from neural-network-like design
  Better information flow and fewer bottlenecks can improve decision-making.

YOU: You.com
Bryan's website: bryanmccann.org

00:00 Intro: Keeping the GPUs Full
00:22 Meet Bryan McCann: CTO & co-founder of You.com
00:43 Why Search Is Breaking - and Why It Becomes a Skill
01:41 From Search to Agents
03:18 The Case for Proactive, Context-Aware AI
04:30 We Don’t Need New Hardware - We Need Trust
05:43 The Trust Problem of Always-On Listening
07:57 Trust as the Real Bottleneck (Not AI Capability)
09:52 Delivering Immediate Value to Earn Trust
12:13 Business Models and Escaping the Attention Economy
17:27 What “Agents” Really Mean - and Why the Term Will Fade
20:37 Productivity, Parkinson’s Law, and Keeping the Machines Running
23:52 Scaling Yourself vs. Scaling Your Team
29:57 Building Culture: Automate, Throw Away, Rebuild
35:46 Designing Organizations Like Neural Networks
45:02 Recruiting for Initiative in an AI-Native Organization
49:18 The debrief 

📜 Read the transcript for this episode:

For more prompts, tips, and AI tools. Check out our website: https://www.beyondtheprompt.ai/ or follow Jeremy or Henrik on Linkedin:

Henrik: https://www.linkedin.com/in/werdelin
Jeremy: https://www.linkedin.com/in/jeremyutley

Show edited by Emma Cecilie Jensen.