This multiple case study explored the relationship between school district and school site environments and the character of instructional coaching. Across the US billions of dollars are spent every year on professional development for teachers, and over the last few decades, coaching, as a form of professional development, has grown in prominence. However, studies have identified that many coaches are spending only a fraction of their overall time engaging in high-leverage coaching practices with teachers. This study sought to explain the district and site environmental factors and the personal attributes of coaches that impact the work of coaches through close inspection of the coaching programs for three mid to large sized California school districts. Propositions were drawn from the study's framework and used for pattern building. Interviews were conducted with instructional coaches, coaching supervisors, and district administrators, and documents regarding the coaching program were collected. The results indicate that the districts all had systems of information, support and practices that impacted the motivation and skills of the coaches and the character of coaching for the district. The aspects of the environment with the greatest impact on character of coaching were role clarity, prioritized time for coaching, systems of support, and aligned opportunities for training and practice. The study's findings indicate that districts wanting to strengthen their coaching program would benefit from providing intentional levels of support for coaches and should strive for alignment in role, training, and expectations. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]