Matthew Saunders discusses various challenges that can arise when managing client projects and development teams. He describes examples like clients who call early in the morning complaining about issues that are actually problems with their internet connection. He also discusses the difficulties of projects with multiple decision makers who cannot agree or clients who spend too much time brainstorming without defining requirements. Saunders advocates for adopting aspects of agile methodologies like having defined timeboxes, iterative development, and collaborative requirements gathering to help address these types of issues and bring more structure and flexibility to projects.