Ask Buddy to look into a question, compare options, or pull together information you can act on. Tell him what matters to your decision so the answer is useful to you.
Compare a few places for a quiet weekend within a two-hour drive of Denver. I'd like somewhere I can walk to dinner, and I want to keep lodging under $200 a night.
That request gives him a place, a preference, and a budget. You can add dates when availability matters, or narrow the choices after the first answer.
Current information, with sources
Buddy can search the public web for changing information and include sources that support his answer. Ask him to compare the tradeoffs, explain a confusing point, or check a particular claim more closely.
An answer can only be as complete as the information he can reach. A listing is not a confirmed reservation; a displayed price may change. Check the final terms before committing to something important.
Bring your own material
You can also ask Buddy to work from a file you share or information in an account you connect. Tell him which material matters. Files and connected apps explain those paths.
Choose the form of the answer
You might want a quick recommendation, a comparison, or a document you can return to. Say what would help. If the first result is too broad, a follow-up can focus it on the part you care about.
If you want Buddy to book or buy something as well as research it, include that in your request and tell him any spending limits or other conditions that matter.