Integrating a Chief of Staff aged 50–70 may involve certain practical challenges, but also great opportunities if the process is handled correctly. A common challenge is technology adaptation, where senior employees may sometimes need extra support to quickly adopt new digital tools and work practices. There may also be generational differences in communication style and expectations regarding the work environment, which requires open dialogue and clear role distribution. To counteract any prejudices or age-related biases, it is important that the employer clearly communicates that the selection is based on competence and business benefit, and offers continuous professional development regardless of age. The best approaches include offering digital upskilling, creating forums for intergenerational learning and mentoring, and clarifying the CoS role’s mandate as a facilitator rather than a hierarchical one. It is also important to involve the senior CoS in strategic networks and decision-making forums to benefit from their experience and network of contacts. By actively working on inclusion, skills development and clear communication, the organization can maximize the value of a senior Chief of Staff.