Kesiapan kerja lulusan Sekolah Menengah Kejuruan (SMK) masih menjadi tantangan utama di Indonesia, dengan Tingkat Pengangguran Terbuka (TPT) tamatan SMK yang tercatat sebagai yang tertinggi dibandingkan jenjang pendidikan lain. SMK Ketintang Surabaya sebagai mitra pengabdian memiliki 1.786 peserta didik dengan lima kompetensi keahlian, namun siswa masih menghadapi kendala dalam hal pemahaman budaya kerja profesional, etika profesional, komunikasi kerja, dan kemampuan pengambilan keputusan. Kegiatan pengabdian ini bertujuan untuk meningkatkan kesiapan karier siswa melalui pelatihan strategic thinking dan adaptasi dunia kerja. Metode pelaksanaan terdiri dari tiga tahap: persiapan, pelaksanaan (sosialisasi dan pelatihan), serta evaluasi. Pelatihan mencakup strategic thinking untuk pengembangan diri dan karier, penguatan adaptasi terhadap budaya kerja profesional, pembelajaran berbasis studi kasus dan simulasi, serta refleksi kesiapan kerja. Hasil kegiatan menunjukkan peningkatan pemahaman siswa mengenai strategic thinking dan budaya kerja profesional, dengan 80% peserta mampu menjelaskan kembali konsep dasar strategic thinking dan 75% peserta menyusun rencana pengembangan diri. Kegiatan ini memberikan kontribusi nyata dalam penguatan soft skills siswa SMK sebagai bekal memasuki dunia kerja. Abstract. Work readiness among vocational high school graduates remains a major challenge in Indonesia, as graduates of Vocational High Schools (Sekolah Menengah Kejuruan [SMK]) continue to record the highest Open Unemployment Rate compared with graduates from other levels of education. SMK Ketintang Surabaya, as the partner institution in this community engagement program, has 1,786 students across five vocational competency programs. However, students continue to face challenges related to understanding professional workplace culture, professional ethics, workplace communication, and decision-making skills. This community engagement program aimed to strengthen students’ career readiness through strategic thinking and workplace adaptation training. The program was implemented in three stages: preparation, implementation (orientation and training), and evaluation. The training covered strategic thinking for personal and career development, adaptation to professional workplace culture, case-based learning and simulations, and reflection on work readiness. The results indicated improvements in students’ understanding of strategic thinking and professional workplace culture. Specifically, 80% of participants were able to explain the fundamental concepts of strategic thinking, while 75% successfully developed personal development plans. These findings indicate that the program contributed meaningfully to strengthening vocational students’ soft skills and better preparing them for the transition into the workforce.