It definitely takes some time to get used to the position. My parents taught me this from the time I had a drop handlebar bike so it always been pretty natural for me, but it's one of the things we usually have to tell new racers all of the time - get in your drops, get in your drops, get in your drops! You should always descend in your drops as it is more stable, ideally you want to take corners in them too. Most people are afraid that they cannot reach the brakes when they first try the position. While some people really cannot and need to adjust the position of the levers on the bars or get shimmed out, a lot of people just need to get more comfortable doing it. Even with my tiny hands I don't have to have shims or short reach levers. I do usually keep my brakes a little loose so I can have my fingers around the levers without actually braking (this also keeps me from acccidentallly braking in the pack if I'm startled). I did find with my Fuji that the shop set it up with the handlebars tipped way down so that I was sliding down the drops and yes! I had a hard time staying in the drops, much less braking in them. I had to turn the bars so that the drops were much more level and move the levers up the bars a bit to be comfortable both in the drops and on the hoods.
For racers - races like crits - always in the drops! If you are in a tight pack in a road race, its a whole lot safer too - with your hands in your drops you are much less likely to lose control if bumped or to lock handlebars with another rider. Always in the drops for descents and sprints.



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