Executive coaching is a practice involving different boundaries that sometimes can be blurred or even crossed. In this chapter, we will examine the issue of boundaries in relation to the coach’s role and the intermediary position between the coachee and the organization. The two cases we present will illustrate how some complex situations might force the coach to cross boundaries, leaving the neutral position. As a result, the coach has to re-assess her identity and re-examine her role. We suggest that coaches raise their awareness of the different boundaries underlying their practice and share this knowledge with the various stakeholders.