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sql_squared Podcast: Ep. 5 - Mastering Azure Migrations & DevOps w/ Elliott Leighton-Woodruff

19 July 2025 by
SQL SQUARED, David Morgan-Gumm
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In our latest episode of The sql_squared Podcast, I had the pleasure of sitting down with Elliot Leighton-Woodruff, a Principal Architect and Azure expert, to discuss the ins and outs of cloud migration. We went far beyond the typical "lift and shift" conversation, exploring how to truly modernize systems, enhance the developer experience, and maximize the return on your cloud investment.

For anyone involved in cloud strategy, development, or data architecture, this episode is packed with valuable insights. Here’s a high-level look at what we covered.

The "Why" of Migration and the Five Rs

A key takeaway from our discussion was the importance of understanding the motivation behind a migration. Is it to save money, improve scalability, or simply follow a mandate to move to the cloud? Elliot emphasized that identifying the primary driver—be it time, quality, or value—is the first step to success.

He then walked us through the "Five Rs" of cloud migration, a framework for determining the best path for your applications:

  • Rehost: The classic "lift and shift" of moving VMs directly to the cloud.
  • Refactor: Moving infrastructure to PaaS, leveraging services like SQL PaaS databases and web apps.
  • Rearchitect: Rebuilding application components in a new way, such as moving to microservices.
  • Rebuild: Starting from scratch with a new solution, like replacing a custom CRM with Dynamics.
  • Replace: Getting rid of the old system and adopting a SaaS product.

Navigating the Pitfalls: Cost, Complexity, and Developer Experience

We also delved into some of the common pitfalls of Azure migrations. Elliot highlighted how easy it is to underestimate costs, especially with "hidden" expenses like Microsoft Defender for Storage and excessive logging. A shocking example was a client who spent £14,000 in a week on logging alone!

A significant portion of our chat was dedicated to the developer experience—a crucial, yet often overlooked, aspect of any migration. Elliot made a powerful point: "A developer's job is not to deploy infrastructure. A developer's job is to provide the best application code in the shortest amount of time."

He explained how leveraging Infrastructure as Code with tools like Terraform can automate the repetitive, mundane tasks of infrastructure deployment, freeing up developers to focus on innovation and creating value. This not only improves their job satisfaction but also leads to better, more consistent outcomes.

Build vs. Buy and the Future of AI

The age-old "build vs. buy" debate was another hot topic. Elliot advocated for a "SaaS first" approach, especially when a service is not your core competency. However, when custom integrations and full control are necessary, building your own solutions can create significant internal IP and a competitive advantage.

Of course, no tech conversation is complete without touching on AI. Elliot shared his excitement for the future of AI in science and its potential to solve some of humanity's biggest challenges. We also discussed the rise of "agentic AI," which promises to automate complex tasks and workflows, further boosting productivity.

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The sql_squared podcast is your guide to navigating the ever-evolving world of data. We go beyond the code to explore the tools, techniques, and trends that shape the data landscape, from SQL Server and cloud platforms to AI and developer productivity. Join us as we chat with experts from the community to help you learn, grow, and make the right decisions on your data journey.

SQL SQUARED, David Morgan-Gumm 19 July 2025
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