This research project focuses on understanding and improving the leave-taking experience in KLM Royal Dutch Airlines. The main focus was to explore how KLM HR can provide a better leave-taking experience for employees and managers. The study started with literature review, followed by context-mapping methodology as the main methogs. The findings and the results are summarised as a design toolkit. This toolkit depicts the overview of context analysis and provides hints and tips when designing for different target groups in KLM. This design toolkit serves two purposes: 1. An organised and interactive information carrier for the stakeholders to have the full picture of the findings and 2. A design facilitator that guides the developers and designers when generating new ideas to solve these problems. With the use of the toolkit, three concepts were proposed in corresponding to the three problems. Through the impact/effort matrix, one of the concepts ‘Manager dashboard’ was selected and further developed into three products. The products are mainly designed for the managers who have big team of staff work in shifts, as they have the most pain in supervising leave-taking, sickness and absenteeism. With the roadmap provided, it is expected that two of the products can be launched in 2020 Q1, and the other can be launched in 2021 Q4. The budget of the product can not be calculated due to the limited information, but a rough estimation leads to a safe of € 26.557.500 if the absenteeism rate in KLM can drop by merely 1%.