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Conceptual diagrams are used extensively to understand abstract relationships, explain complex ideas, and solve difficult problems. To illustrate concepts effectively, experts find appropriate visual representations and translate concepts into concrete shapes. This translation step is not supported explicitly by current diagramming tools. This paper investigates how domain experts create conceptual diagrams via semi-structured interviews with 18 participants from diverse backgrounds. Our participants create, adapt, and reuse visual representations using both sketches and digital tools. However, they had trouble using current diagramming tools to transition from sketches and reuse components from earlier diagrams. Our participants also expressed frustration with the slow feedback cycles and barriers to automation of their tools. Based on these results, we suggest four opportunities of diagramming tools — exploration support, representation salience, live engagement, and vocabulary correspondence — that together enable a natural diagramming experience. Finally, we discuss possibilities to leverage recent research advances to develop natural diagramming tools.