You try to upsell room categories, experiences, or amenities at just two points: during booking (when guests are price-sensitive and focused on the base price) or at check-in (when guests are tired from traveling and rushed to get to their rooms). Your staff follows this traditional approach because these are the only two guaranteed touchpoints, but it results in upsell success rates below 15%. Meanwhile, your premium rooms and services often remain unsold, representing a significant lost revenue opportunity.