If you have trouble swallowing tablets and pills, even when you drink something to have it go down easier, it might be worth checking out different consistencies of food to go along with it. Many elderly people take their pills in yoghurts and puddings and stuff like that. Soft foods in general also work. A drink should usually help though.

If it’s tablets and pills that explicitly need to be taken dry, you could try a swallowing technique called a “chin tuck” where you push your chin towards your chest before swallowing and then swallow while your chin is still tucked. That way, you leave less room/area for the tablet/pill to get “stuck on”. It could help but doesn’t necessarily have to help