Greg Leonardo is a Principal Cloud Architect, Certified Azure Solution Architect Expert, and Microsoft Azure MVP with over two decades of experience driving high-impact cloud transformations for global enterprises. Greg’s work sits at the crossroads of architecture, innovation, and mentorship, where he crafts scalable, cost-efficient, and future-ready solutions that align technology with business strategy. He’s a recognized authority in Azure-native architecture, FinOps optimization, and AI integration, known for delivering measurable results—from reducing cloud spend to accelerating DevOps agility through Terraform and infrastructure as code. His leadership extends beyond technical execution, as he actively cultivates cloud talent and fosters a culture of continuous improvement. A former Gulf War veteran, Greg brings discipline, resilience, and strategic foresight to every initiative — whether building global cloud ecosystems or leading high-performance engineering teams. He’s also a passionate advocate for the cloud community, sharing insights daily through technical writing and open mentorship.

Topics of Discussion:

[5:46] Greg discusses his approach to AI, emphasizing responsible AI and the importance of understanding its limitations.

[8:12] AI’s journey through the Hype Cycle.

[11:09] Greg introduces the concept of AI as “virtual employees.”

[16:44] Greg talks about how he uses both Microsoft 365 Copilot and ChatGPT Enterprise to compare their capabilities.

[18:36] How Greg tests and compares AI tools.

[20:21] Comparing AI to previous search and research methods.

[23:31] Improving AI results through better prompts.

[26:17] The agent framework, sharing, and limitations of AI agents.

[36:47] AI’s ability to generate architectural diagrams.

[41:49] Exploring autonomous coding agents.

[41:45] Why we aren’t quite ready for the “fire and forget” side.

[43:08] Struggling with the memory behind chat.

[44:02] Closing thoughts — what can we expect in the future, and what are more practical applications of AI?

Mentioned in this Episode:

Clear Measure Way

Architect Forum

Software Engineer Forum

Gregory Leonardo LinkedIn

Greg Leonardo Website

Ep 326 with Greg Leonardo: The Latest in Azure

Ep 282 with Greg Leonardo: Optimizing Cloud Budgets

Want to Learn More?

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John Bristowe brings over 20 years of experience in technology to his role as Community Director at Octopus Deploy. His career includes time at Progress and Microsoft, where he developed his skills in management and technology. Known for a straightforward and engaging style, John often speaks at industry conferences, sharing practical tips and insights. John is a HashiCorp Ambassador and part of the Progress Champions program.

He enjoys creating content such as articles, webinars, and podcasts, aiming to help others in the tech community. In his free time, John likes to stay informed about the latest tech developments and shares his learning with an online audience. His approach is always about sharing knowledge and learning together.

Topics of Discussion:

[2:47] John shares his career journey, starting at Microsoft in 2005, and his involvement in developer evangelism.

[4:03] The evolution of Octopus Deploy, from an open-source project to a commercial tool.

[5:47] The importance of setting up deployment pipelines and the challenges of deploying on weekends due to brittle pipelines.

[6:36] Check out the Octopus Deploy roadmap for updates on new features and innovations.

[9:04] The potential of AI in the deployment space and the importance of maintaining a balance between AI and human involvement.

[10:46] More about Codefresh.

[11:23] The integration of AI capabilities in Octopus Deploy, including the AI assistant.

[15:17] Designer Experience vs. Text-Based Workflows.

[24:43] Common use cases for runbooks, including server maintenance, database management, and cost management in Kubernetes.

[26:22] The importance of automated health checks and runbooks for ensuring reliable and cost-effective deployments.

[29:58] Platform Hub and Enterprise Scalability.

Mentioned in this Episode:

Clear Measure Way

Architect Forum

Software Engineer Forum

Octopus Deploy

Codefresh

Want to Learn More?

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Mads is a Principal Product Manager on the Visual Studio team at Microsoft, where he champions developer productivity, performance, and extensibility. With a deep passion for streamlining the development experience, Mads has created dozens of widely used Visual Studio extensions — including Web Essentials, File Nesting, and Markdown Editor v2 — and maintains the Extensibility Essentials toolkit to empower other developers to build better tools. Mads brings over a decade of experience in web development on the Microsoft platform. He is also the founder of SchemaStore.org and a home automation enthusiast. Known for his engaging presentations and hands-on insights, Mads is a frequent speaker at developer conferences worldwide. He lives in the Pacific Northwest and his mission is simple: to make Visual Studio the most delightful development environment on the planet.

Topics of Discussion:

[2:38] More about Mads’ career journey at Microsoft.

[5:14] The new and improved Visual Studio.

[7:44] Backwards compatibility is a key feature — .NET solutions will still work across different Visual Studio versions.

[8:55] How Microsoft’s strategy differentiates between Visual Studio and VS Code.

[10:42] Visual Studio is the premier development environment for .NET and C# on Windows, offering the most comprehensive and optimized experience. While VS Code can handle .NET development, it’s not as feature-rich or performant as the full Visual Studio.

[12:58] Visual Studio has moved to a monthly release cadence to be more competitive with VS Code’s frequent updates.

[13:48] Deep AI integration in Visual Studio allows for context-aware assistance, including a new profiler agent that can help optimize code performance.

[23:53] Compilation performance is improved in Visual Studio 2026.

[26:35] The new profiler agent can be invoked through Copilot chat, running benchmarks and suggesting performance improvements scientifically.

[30:30] Developers can create custom MCP servers to integrate private systems and databases with AI tools using a project template.

[35:39] The AI coding agent in Visual Studio can work autonomously or with developer supervision, creating pull requests or working alongside the developer.

[39:11] Visual Studio’s Copilot can be used as a companion to bounce ideas off, helping with architectural decisions and new feature explorations.

Mentioned in this Episode:

Clear Measure Way

Architect Forum

Software Engineer Forum

Mads Kristensen on LinkedIn

@mkristensen on X

Mads Kristensen

JSON Schema Store

Visual Studio

Want to Learn More?

Visit AzureDevOps.Show for show notes and additional episodes.