For the autumn and winter, when Conophytum plants are growing, you need to water whenever the soil is dry and the plants are starting to look like they need water. Being able to tell when they need water is something of an art. If they always look fat and turgid, or if the leaves start to crack, you're watering too much. If the leaves are always wrinkled, or if they're don't expand at the start of the growing season, you're not watering enough. Sometimes, a plant may not respond to watering because it has lost its roots, in which case it is probably best to unpot it, cut away dead roots and stems, and root the resulting cuttings in damp potting mix. Water requirements vary widely within the genus, from C. minusculum which likes constantly moist soil, to C. burgeri which needs quite arid conditions.
Conos start to go dormant in late winter to early summer, depending on the species and your growing conditions (C. angelicae is usually the first to fold up shop, and C. bilobum the last). The color of the old leaves fades, and they shrivel to a dry sheath that protects next season's growth. While the leaves are senescing, encourage the process by watering lightly and less frequently. While the plants are inactive, occasionally moisten the soil, which will decrease the likelihood of root dieback or burning. When conos start to grow again (as indicated by the new leaves cracking out of their sheath), begin regular watering again. Growth may start anytime from midsummer (with the vigorous bilobed species) to early winter (with C. minusculum and its relatives, especially if it is hot).