Organizational and societal transitions require workers to upskill and reskill their expertise within and across the boundaries of their current domain(s). This may also require them to materialize their renewed expertise in novel settings in interaction with stakeholders who hold different expectations regarding their know‐how and contributions. To stay employable, workers need to deal with shifting expertise needs by creating beneficial outcomes for themselves and their stakeholders, as captured by the so‐called flexpertise concept. Thus far, expertise research left largely unaddressed how workers adapt through intra‐individual changes over time and social interactions in naturalistic settings in which they encounter various new expertise needs. To increase our understanding of the dynamic nature of workers' adaptation processes, we conducted a Group Model Building study with HR/D practitioners. Through this structured group facilitation method, these practitioners cocreated a dynamic process model, based upon their varied experiences in practice regarding the flexpertise phenomenon. The newly developed model portrays how workers make balanced decisions to adapt, go through loops of learning‐by‐mistakes and ‐successes, and ultimately turn their new know‐how into outcomes, with or without impact, leading to new adaptation cycles. Furthermore, the practitioners defined leverage points where HR/D practices can stimulate individual adaptivity. This GMB study may set the agenda for future expertise and employability research and provides the foundation for designing bundles of HR/D practices to foster flexpertise.