Deliveroo's 'missed call from mom' notification on Mother's Day was intended to be delightful but caused pain for users who had lost their mothers. This highlights a critical risk: what is joyful for one user segment can be deeply upsetting for another. Delight initiatives must be vetted for inclusivity.

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Don't treat evals as a mere checklist. Instead, use them as a creative tool to discover opportunities. A well-designed eval can reveal that a product is underperforming for a specific user segment, pointing directly to areas for high-impact improvement that a simple "vibe check" would miss.

A seemingly small user interface issue—the proximity of the iMessage dictation button to the send button—escalated into a significant PR problem for Apple. Justin Bieber's viral social media complaints translated a minor design choice into a tangible stock drop and public relations headache for the tech giant.

The hit "Discover Weekly" playlist was meant to serve only new music. Its success was accidental, stemming from a bug that inserted familiar songs. This revealed a key principle of delight: pure novelty can be jarring, and blending it with familiarity is crucial for user adoption and comfort.

True differentiation comes from "deep delight," where emotional needs are addressed within the core functional solution. This is distinct from "surface delight" like animations or confetti, which are nice but fail to build the strong emotional connections that drive loyalty.

Users crave novelty but are grounded by familiarity. Discover Weekly's initial success was accidental; a bug mixed in known songs with new ones. 'Fixing' the bug to be 100% new caused metrics to drop, proving that a balance of surprise and comfort is key to delight.

The most effective user segmentation is based on underlying motivations. Identifying both functional ("inspire me with new music") and emotional ("help me feel less lonely") drivers is the crucial first step to engineering meaningful product delight that resonates deeply with users.

Features designed for delight, like AI summaries, can become deeply upsetting in sensitive situations such as breakups or grief. Product teams must rigorously test for these emotional corner cases to avoid causing significant user harm and brand damage, as seen with Apple and WhatsApp.

Delight goes beyond surface-level features. It's about creating products that solve practical problems while also addressing users' emotional states, like reducing stress or creating joy. This is achieved by removing friction, anticipating needs, and exceeding expectations.

A failure to show basic courtesy, like tilting an umbrella for someone on a sidewalk, is analogous to inconsiderate product design. Most products are oblivious to their user's experience. Building with genuine empathy and consideration is a powerful, rare competitive advantage that fosters emotional connection and advocacy.

Avoid the 'settings screen' trap where endless customization options cater to a vocal minority but create complexity for everyone. Instead, focus on personalization: using behavioral data to intelligently surface the right features to the right users, improving their experience without adding cognitive load for the majority.