Set in December 2017, this case follows Tyler Lawson, an engineering manager at Fortune 200 technology firm. Lawson thrived under the leadership of his previous manager, Jake Fierro, who shielded Lawson from office politics and gave him a high amount of autonomy. When Fierro departed for a start-up, Lawson remained to lead a complex internal initiative. Without Fierro’s political support, however, Lawson struggled to manage up to his skip-level manager, Steve Schultz. Frustrated with Schultz’s bureaucratic demands, Lawson sought to join Fierro at his new company. However, at the conclusion of the case, Schultz frames Lawson’s decision in terms of his broader career goals: Does he want to remain in his current position and develop the soft skills necessary to become a leader, or does he want to join Fierro and continue his career as an individual contributor? This case would be appropriate for undergraduate or MBA-level courses in organizational behavior, management, leadership, and career planning.