You don't need a guide for most Colorado hiking. You might want one anyway. The difference between those two sentences is where most people get stuck, so let's take them in order.
When it's worth it
Hire a guide when the terrain outpaces your experience: early-season snow, class 3 and 4 scrambling, anything with a rope. Hire one, too, when you want to compress years of trial and error into a single long day of watching someone competent move through the mountains. Both are good reasons. The second is underrated.
What to ask
Ask about their turnaround habits before you ask about their summit record. A guide who brags about never turning around is telling you something important, and it isn't good. Ask what the weather needs to look like for the day to happen, and what the backup plan is when it doesn't.
What it costs
Expect a guided day in Colorado to run roughly $300 to $600 per person. Private days sit at the top of that range, small groups near the bottom, and technical objectives cost more than trail days: ropes, permits, and a lower client-to-guide ratio all push the number up.
It sounds like a lot until you price it against the years it replaces. One well-run day teaches more than a shelf of books, and the habits come home with you.
The tell
The best guides talk about weather, snowpack, and their clients' feet. The summit comes up last, almost as an afterthought, because to them it is one. The mountain will be there next season. The goal is that you are, too.
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