There are currently five generations in the workforce. Only a few short years ago employers who were expecting to be faced with mass retirements are now looking at accommodating workers who cannot afford to retire or are simply healthy and happy enough they’d like to stay at work. However, the labour force continues to put in hard work and lots of strategy to find the right people to fill vacancies and to be able to serve their customers. This content examines the history and reality of the generation gap, especially for recruiters and succession planning. In it, we will explore whether defining the actual limits of each generation is most important, or whether the merits of people within the context of employment is the bigger issue. After all, understanding others helps us to understand ourselves and to manage the people that we work with. We will also explore problems, solutions, and strategies to help overcome issues of the generation gap.