Crafting a Technical Strategy

It Depends: Lessons in Technology Leadership

In this episode of It Depends: Lessons in Technology Leadership, Kevin Goldsmith breaks down what it really means to craft a technical strategy that aligns your engineering organization with business goals. Drawing on decades of experience as a technology leader and CTO, he explains why simply having a plan in your head isn’t enough: a strategy must be documented, shared, and revisited regularly if it’s going to guide meaningful decisions.

Kevin outlines practical steps for building an effective strategy, including identifying business-aligned guiding principles, defining realistic technical bets, validating them with peers, and ensuring that every level of the organization maintains alignment. He also explores common pitfalls, including confusing strategy with a roadmap, making it too vague or too prescriptive, or failing to communicate it. He describes how a well-articulated strategy makes decisions easier, reduces friction, and gives teams greater autonomy and purpose.

It’s a clear, grounded guide for any engineering leader preparing for the new year, whether you’re a CTO shaping company direction or an EM ensuring your team’s work supports broader goals.

• ConFoo 2026 (https://confoo.ca/en/2026)
• Listener Survey: https://forms.gle/JVeKHsHJKhEM3dvK6
• The book: It Depends: Writing on Technology 2012-2022 (https://itdependsbook.net)
• Your host: Kevin Goldsmith (https://kevingoldsmith.com)