During the process of software development, senior managers often find indications that projects are risky and take appropriate actions to recover them from this dangerous status. If senior managers fail to detect such risks, it is possible that such projects may collapse completely. In this paper, we propose a new scheme for the characterization of risky projects based on an evaluation by the project manager. In order to acquire the relevant data to make such an assessment, we first designed a questionnaire from five viewpoints within the projects: requirements, estimations, team organization, planning capability and project management activities. Each of these viewpoints consisted of a number of concrete questions. We then analyzed the responses to the questionnaires as provided by project managers by applying a logistic regression analysis. That is, we determined the coefficients of the logistic model from a set of the questionnaire responses. The experimental results using actual project data in Company A showed that 27 projects out of 32 were predicted correctly. Thus we would expect that the proposed characterizing scheme is the first step toward predicting which projects are risky at an early phase of the development.