Originally Posted by Drew Eckhardt

Don't speed up because you'll waste too much energy on aerodynamic drag and speeding up can radically reduce your endurance - endurance drops from 60 to 20 minutes with a 5% increase, and another 5% drops that to 10 minutes.

Conversely, if you're riding at a sustainable pace there's no reason to slow down.

Pedal at the same sustainable power output after reaching the hill, changing gears and/or cadence as necessary. Get lower gears if that requires dropping below ~50 RPM for any distance.



Changing to an equivalent gear in a smaller ring won't hurt you and avoid the need to change rings climbing. 50x23, 39x18, and 30x14 are all the same ratio.

Moving to a larger cog before the hill is unnecessary.



Shifting cogs should be almost instant when you keep the pedals turning without pressure, especially going larger which can't be impeded by friction from housing wear or dirt.

If going to larger cogs is sluggish, you need to look at tension and make sure the hanger isn't bent. Cable housings settle after installation and need a little more tension to compensate. If your rear cable tension was adjusted correctly to begin with and that's not the situation you may have a bent hanger that changed alignment. B-tension with too little or too much clearance between top jockey wheel and cog could cause issues too.