Organizational debt (OD) is a major challenge to software organizations that seek to maintain agility, adaptability and sustainable competitiveness in the dynamic business environment. OD can be refers to suboptimal decisions, outdated procedures, misaligned structures and cultural barriers that limit an organization's ability to adapt and innovate quickly. This multifaceted process includes several factors, including ineffective workflows, knowledge silos, cultural issues, and inadequate resource utilization. When organizations are focused on short-term gains at the expense of long-term organizational health, the symptoms of organizational dysfunction may manifest themselves as reduced output, reduced quality and customer satisfaction. This study aims at assessing the extent of knowledge, factors, and consequences of organizational maladjustment in software organizations. A survey performed in three organizations identified several highly visible issues such as complex code, inconsistent UI, unclear requirements, and outdated processes. These themes often emerge due to exponential growth, prioritizing speed over quality, lack of cooperation and coordination, and outdated processes. The adverse effects of OD are comparable to technical debt, affecting the maintainability, user experience, and project management. This study also offers strategies for identifying, assessing, and mitigating OD through a combination of quantitative metrics, user feedback, and interdepartmental collaboration. By fostering a culture of continuous improvement, open communication, and cross-functional alignment, organizations can proactively address OD and create an environment conducive to innovation, quality, and customer-centricity.