Originally Posted by RollCNY

Have a plan in mind when you start the hill. IMO, what makes hills fun is having a plan and executing it.

If you plan to stay in the big ring for the hill, then leave yourself room to shed gear as you go up the hill, and use the full cassette as needed. Cross chaining big big is not a cardinal sin in this case, but I save it for last resort. I find climbing easier knowing I have always saved one bailout gear.

If you plan to use the little ring, shift into it early. When you drop big to little, especially on a compact, do it when chain is middle of cassette. Drop to smaller cogs right after the chain drops in front, usually three bangs smaller. Then shed gear as needed to climb the hill. Double shifting is your friend, escpecially with a compact.