Our study focused on the leadership strategies of Estonian and Finnish principals aimed at encouraging teachers to participate in school development. We also looked at context-bound factors that form the framework within which principals discuss their work regarding (1) creating a shared vision, (2) implementing shared leadership practices, (3) fostering a collaborative school culture, and (4) supporting teachers' development and recognizing teachers' work. We interviewed five principals from each country and used directed content analysis to examine the data. According to the findings, most of the principals had experienced challenges when involving teachers in school development. This seems to be connected to the high levels of professional autonomy prevalent in both countries that is built on a long tradition of understanding autonomy as an individual property of a teacher rather than seeing it in relation to the autonomy provided to an organization. Regarding the aims set for education, Finnish principals emphasized the implementation of the national curriculum and local coherence, whereas principals in Estonia were keener to respond to the expectations set for schools to stand out based on their educational innovations, and this implies a higher level of competitiveness among the schools in Estonia.