Students deserve teachers who are going to help them grow in their education and who are going to challenge them. No longer should it be allowed to continue this disservice to students; the literature states that students lose ground and fall further behind when they are in classrooms taught by ineffective teachers. Since teacher quality is at the forefront of educational research, it is essential that researchers discover the factors that contribute to quality teaching, especially since “teacher quality is the single most important feature of the schools that drives student achievement” (Haskins & Loeb, 2007, p. 53). The purpose of this study is to share the stories of principals who worked with ineffective teachers and how tangling with these teachers affected these principals personally, professionally, and politically. I explored the actions and emotions of ten different principals who crafted action plans, collaborated with supervisors and site-based administrative teams, and either saw success from their strategic coaching or saw teachers walk away because the pressure was too much. One major finding of this study is that not a single principal wanted to ultimately dismiss their teacher; they wanted the teacher to grow and become better for students. Additionally, there was no set time period other than the minimum 90-day timeline; one principal worked with one teacher off and on for over 6 years! Every principal agonized over their teacher, the students s/he was serving and achievement. There are several implications for the conclusions of this study for future practice. These included providing professional development for administrators on having tough conversations with struggling teachers, offering them practice at giving effective feedback to teachers, and helping them understand the laws and local school board policies that affect teachers and teacher practice. Our principals also need to know that teacher quality matters and that the biggest predictor of student achievement is effective teaching