This naturalistic inquiry investigated how instructional designers engage in complex and ambiguous problem solving across organizational boundaries in two corporations. Participants represented a range of instructional design experience, from novices to experts. Research methods included a participant background survey, observations of problem-solving activities, in-depth interviews, and analysis and evaluation of project documents and other tools. The findings revealed differences between experts and novices with regards to tolerance of ambiguity, expectations about their own roles in finding solutions for their clients, adaptability, attention to appropriate details, and management of workplace stress. The contrast between instructional design processes taught in universities and actual workplace practice was noted by both expert and novice participants. Experienced participants demonstrated adaptability in processes and communications to efficiently arrive at viable solutions for their clients. Expectation setting and relationship building emerged as techniques for creating environments supportive of instructional designers' problem-solving activities.