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This study aimed to analyze the challenges, learning experiences, and effects of the COVID-19 pandemic in a social, healthcare, and special education development project financed by the European Social Fund. The theoretical framework of the project relied on the theories of dialogic development and leadership. The method was participatory action research using data collected from various assessments and a questionnaire. Reports of neutral, negative, and positive experiences among two participant groups of the project—the implementers and pilot organizations—in remote work, devices and applications, and remote and technology-based development processes, were recorded. Both participant groups reported increased pressure at work, social isolation, professional loneliness, and improved work control and efficiency. The pilots have learned the development method, and development has been able to continue by utilizing technology despite the pandemic. Development through technology was more difficult, and new dialogic interaction tools have been created. The project was most effective with regard to leadership, teams, renewal, and information flow. There is a need for wide-ranging dialogues with various working life actors when outlining the ways in which future work will be carried out and to reflect on how remote work, technology, and digitalization affect well-being at work, social relations, and leadership.