The instructional coaches in Kildeer Countryside School District 96 (KCSD 96), outside Chicago, are like tugboats, a key part of a maritime navigation system. Just as tugboats nudge and guide barges and ships that need steering assistance to navigate tricky waters, the coaches in KCSD 96 nudge and guide educators to navigate toward school and student learning goals. KCSD 96 uses data to adapt its coaching program to respond to shifting currents and evolving needs. Now in the district's 12th year with coaching, KCSD 96 leaders have identified key factors, which are presented in this article, to ensure that its coaching program and coaches nudge and guide all staff toward districtwide success.