Succulents, like hens and chicks, grow the most during the spring and summer. Once fall rolls around the plants like to take a break. During their fall/winter dormant period, watering should be reduced.
Succulents that you keep inside or in a warm greenhouse during the winter (like echeveria and other tender succulents) should be watered only enough to prevent the roots from dying off. This can range between once every couple weeks and once every couple months.
Cold hardy succulents like sempervivum and sedum need even less water in the winter. When the temperatures are below 50F it is best not to water at all. Wet roots at low temperatures are the perfect conditions for rot.
Many plants suffer from dessication in the winter. This is when a plant loses more water through evaporation than it can absorb through its roots. Before severely cold weather we water evergreen plants well to help prevent damage (once the ground freezes the plants cannot absorb water, but continue to lose it). Do NOT do this with succulents. Hens and Chicks like the opposite treatment. When freezing temperatures hit you want the soil with your succulents to be as dry as possible.
Of course, dry soil and winter is sort of an oxymoron (only possible if your plants are in a covered area). So, winter is also when it’s most important that your soil has excellent drainage.
Your reduced watering schedule should last until you begin to see new growth on your plants in the spring. The weather may still be a little cold, but your succulents will appreciate more water as they start to grow again.