The State of Feature Flagging in 2026 - Outperform

What this episode covers

What’s going to happen with the adoption and development of feature flagging tools in 2026?Just ask Aaron Silverman. As an engineering manager at Datadog, Aaron has spent the past year speaking at conferences, meeting engineers, and talking with teams around the world about how they actually use feature flags and why adoption still looks so uneven heading into 2026.In this episode, we explore the current state of feature flagging and A/B testing, and how teams are evolving their approach as systems scale and risk increases. Aaron shares lessons from working directly with customers, explains why the biggest blockers to adoption are cultural rather than technical, and unpacks the hidden costs of building custom feature flagging solutions. We also discuss what’s next, including deeper integrations with observability tools and designing flags with their full lifecycle in mind to reduce friction and technical debt.In this episode:Where feature flagging adoption stands heading into 2026Why cultural and habit-based barriers slow adoption more than technologyHow feature flags reduce deployment risk and improve customer experienceThe hidden complexity of building DIY feature flagging systemsWhat’s next for feature flagging, from observability integrations to smarter flag design

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How long is this episode of Outperform?

This episode is 27 minutes long.

When was this Outperform episode published?

This episode was published on January 29, 2026.

What is this episode about?

What’s going to happen with the adoption and development of feature flagging tools in 2026?Just ask Aaron Silverman. As an engineering manager at Datadog, Aaron has spent the past year speaking at conferences, meeting engineers, and talking with...

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