Context Engineering: AI That Works in Production | Lena Hall, Akamai

Why do so many AI projects stall after the demo? Lena Hall, Senior Director of Developer Strategy at Akamai and founder of Droid AI, joins host Henry Clavo to explain context engineering: the infrastructure, data and guardrails around a model that decide whether AI actually works in production.

Lena draws on her years leading developer experience at AWS and big data developer relations at Microsoft to explain why picking a model matters less than the harness you build around it, how subagents and phased development keep coding agents accurate, and why AI agents should be designed like microservices in a distributed system.

Chapters

0:00 Cold open

0:21 Orlando Insights Podcast intro

0:58 Meet Lena Hall: AWS, Microsoft, Droid AI and Akamai

3:41 When it became clear models alone don't solve business problems

6:34 Which decisions to keep instead of delegating to an LLM

8:51 From prompt engineering to context engineering

11:23 Subagents, phased development and agent orchestration

14:49 AI copilots in data engineering tools

16:25 Scaling AI like distributed systems: the two generals problem

20:48 Should you trust AI agents with your data?

23:37 Where AI agent frameworks fall short in production

27:27 Leading teams through AI adoption and productivity

31:07 What's next for Lena in 2026 and where to find her

33:02 Outro

About the guest

Lena Hall is an expert in practical AI adoption, data engineering, cloud architecture and pragmatic system design, with more than 15 years of technical experience. She is Senior Director of Developer Strategy at Akamai and founder and CEO of Droid AI. She previously served as Head of Developer Experience, North America at AWS and led Big Data Developer Relations at Microsoft. She is an international keynote speaker and shares practical AI knowledge on her YouTube channel.

Watch on YouTube: https://youtu.be/49YrwURYI2Y

More episodes: https://orlandoinsightspodcast.com

Lena Hall on LinkedIn: https://www.linkedin.com/in/lena-hall

Find Lena: LinkedIn (lena-hall) and YouTube (AI with Lena Hall).

Host Henry Clavo on LinkedIn: https://www.linkedin.com/in/henryorlandoclavo/

The Orlando Insights Podcast is brought to you by Orlando Insight Group, data and AI advisory for CIOs and Chief Data Officers: AI Readiness Assessment, Data Governance & AI Foundations Sprint, and Fractional Chief Data & AI Officer. Book a free 30-minute AI readiness consult: https://calendar.app.google/xkJqUsFzrHAVkY4W7

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