This longitudinal, qualitative and Delphi technique-designed research study sought a reasonable consensus for identifying and prioritizing the best and most appropriate Web 2.0/3.0 nonlinear visual tools that can revolutionize the educational processes of thinking, teaching, learning, and leading in the digital knowledge age. The study also sought reasonable agreement on the criteria to measure the educational success of these new breeds of information and communication technology (ICT) tools. The results were very promising. The Delphi ICT experts, 80 personnel in total, reached significant agreement on the issues that were carefully deliberated in this study. The Delphi participants prioritized a list of the most relevant, reliable, and appropriate Web 2.0/3.0 nonlinear visual tools that can enhance the educational processes of thinking, teaching, learning, and leading in the digital knowledge age. Additionally, the participants recognized and prioritized certain criteria (i.e., measurements, standards, factors, benchmarks, and principles) that can assess and measure the success of Web 2.0/3.0 nonlinear visual tools and any ICT platform from educational perspectives. No significant differences were found among the Delphi subgroups when inferential statistics were performed. The qualitative nature of the Delphi technique research design, the deployment period, and the capability of examining a large sample size of ICT experts all notably helped in strengthening the statistical significance, reliability, and confidence in the collected data. The findings of this study comply with the postulated assumptions. These results can assist academics, educators, instructional technology leaders, practitioners, administrators, and policy and decision makers in ascertaining and defining appropriate solutions to educational challenges.