Flexible work arrangements (FWA) are not new but have taken on a new dimension since COVID-19. The novel dynamics of FWA from the workers’ perspective in the financial services sector in South Africa are examined specifically how employees and companies balance varying desires, needs, tools and other factors to make flexible work beneficial to all parties. This juggling act significantly influences organisational management practices globally. A hybrid research approach including a pilot study, and survey with closed and open-ended questions for qualitative coding and quantitative analysis of the codes to correlate the variables, was employed to understand these dynamics. The findings reveal significant variability in preferences, requirements and demographic influences among employees and companies. Younger workers with fewer family commitments and lower incomes generally prefer working from home. Those older, family heads and higher incomes prefer office-based work. There may also be a cultural component with younger workers growing up in a culture of greater social flexibility aided by technology. Employees recognise that their success is intertwined with business success and understand that companies can now offer more flexibility due to changing management paradigms. Employees and companies need to have more discussions on how work is performed. A more tailored approach to flexible work, rather than previous blanket policies, is necessary, as stakeholders must engage in ongoing discussions to balance internal needs with customer expectations. Moreover, a realistic roadmap for how employees can contribute by conversing with employers on FWA is suggested by combining literature with the study’s findings.