Some can tell by weight. Gauge the weight immediately after watering for a benchmark and then lift the pot every few days or so. If the pot still feels a little "heavy" do not water. If it feels lighter, water. Personally, I find this to be a very tricky method, but there are some that have great success with it.
I pot all my plants in clear plastic pots. This allows me to see the roots and the moisture conditions inside the pot. If I can see bright green, damp roots and moisture droplets on the inside of the pot, I do not water. If there is no moisture or the visible roots have a silvery/grey hue, then I water. I grow my orchids in conditions with average temps that range from 65 F to 83F and humidity ranging from 50% to 70%, and I have found that this method works well for me. One thing to remember with this method is that you will not be able to tell if the inner core of the medium is dry/damp, but with fresh, well-draining bark I have not found this to be an issue.
Hope this helps!
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