A change of an enterprise-wide magnitude needs to be explained to everyone, including people whose actual tasks may not change at all. Connections, collaboration, priorities, and ways to make decisions may, and frankly some should change—and be explained, set as new expectations. People feel less confident about change because they do not have clarity on what is expected going forward. How can we manage expectations better? We need to understand what every player in the transformation needs: Employees need clarity and sincerity; they want to understand how exactly their work is changing. Managers need to preserve the capacity and sustain the morale. And the company must hit the window of opportunity for the transformation. Market dynamics do not wait for our readiness. Establishing the new expectations in a scalable way means getting to people’s needs effectively, manage the network of coordinated actions, and the right players in a new orchestration for execution. The company and managers share the responsibility to create engagement. This chapter provides key success factors and ways to accomplish that.