Research has established powerful relationships between career guidance, work, and wellbeing. However, some practitioners have only low or moderate confidence in using guidance to support wellbeing. Catalysed by COVID-19, this practitioner-researcher collaboration explored the question: how can we embed wellbeing more explicitly into guidance practice? Concerns and potential solutions were examined with 36 career development practitioners, service managers, and researchers from Canada, England, Scotland, and Wales. This article presents the results of a subsequent pilot in Scotland and Wales to test the resulting initial guidance interview framework. Quantitative evaluations, supported by four case examples, show customer wellbeing progress during initial guidance interviews and gains in practitioner confidence following training.