I was assigned to replace the designated project manager to attend the short course in Workplace Coaching and Mentoring due to his several project assignments. The instruction to replace him in the workshop was a great challenge. In applying the coaching plan, I’ve learned that this job was not only a coachee’s challenge but also the coach’s as well. One has to strategize to apply the skills to facilitate learning, experience, and willingness of the coachee. Moreover, one must exert tremendous patience, rapport, and key elements in working relationships. Listening to the coachee’s opinions is also helpful, as it allows the exchange of views and feedback. Every conversation was planned and facilitated to contribute to the improvement of the coachee’s performance. The level of expectations from coach to coachee was raised during the end of the coaching journey. Nonetheless, both parties took pride in the accomplishment of our own goals. The high-performing coachee had already reached the first level of his plan; therefore, we considered this experience as an achievement towards work. Ultimately, being a good coach to the newly hired employees is also a learning experience for me as a senior professional. New hires are primarily millennials these days, so proper coaching and guidance are necessary for instilling good work ethics to become competent and compassionate professionals. The coaching journey does not end after this first coaching task. Instead, it is a continuous test and biggest challenge on how the new hires can consistently apply their learnings to their actual tasks. Hence, it is necessary to continuously determine the best practices on coaching policies that can greatly benefit the organization. This program in itself is a two-fold process: (1) for the coach to effectively mentor and (2) for the coachee to effectively apply.