With more and more companies moving to DevOps culture and test automation, there is more focus and resources devoted to this area. Like all projects, the challenges faced with implementing test automation starts at the initiation phase. In order to avoid unexpected outcomes, these challenges should be taken into consideration and addressed as early as possible. No matter how good your tools are, your strategy and your ideas are akin to “if I don’t get the team to buy-in, then I will end up spending extra time in managing the unexpected scenarios;” this area of thought may cause project delay or even lead to failure.