In Judges chapter 6 Gideon is hiding in a wine press threshing grain--the Midianites are occupying Israel and are systematically destroying everything they find of value. An angel greets him with: "The Lord is with you, O valiant warrior." You can sense the eye roll when Gideon responds: "O my lord, if the Lord is with us, why then has all this happened to us? And where are all His miracles which our fathers told us about..." Notice the little "l" in the first "lord" that Gideon uses here, which is reasonable given this a person that has just showed up in the wine press.
The next section is a little confusing because the responder to Gideon's question is God, rather than an angel. "And the Lord looked at him, and said, "Go in this your strength and deliver Israel from the hand of Midian. Have I not sent you?" Gideon responds with a "how" question: "O Lord, how shall I deliver Israel? Behold, my family is the least in Manasseh, and I am the youngest in my father's house" Notice that Gideon has switched to big "L" for Lord at this point -- probably a good idea when you have just dissed the Master of the Universe to His face. The Lord's response is: "Surely I will be with you, and you shall defeat Midian as one man". Traditional political/ familial power is unnecessary.
Gideon then switches his line of questioning--he reasonably wants to verify that the speaker truly is the Lord. Up to this point nothing overtly supernatural has happened--just talking with a visitor that has a high opinion and expectations of Gideon. Gideon assumes that it is the Lord’s messenger, prepares an appropriate offering, and has his doubts removed when the offering is vaporized and the angel vanishes. However Gideon isn’t done testing God. Later in chapter 6 Gideon makes his famous double request: Fleece wet and fleece dry on two successive nights. Gideon is very polite with his requests, and at this point has already called the people together for war, but I can’t help but contrast God forbearance with Gideon to another situation in Luke chapter 1 where an angel delivered a message: the angel Gabriel tells Zacharias that he is going to have a child (John the Baptist) even though his wife was barren and they were both old. Zacharias’ single request: “How can I know this for certain?….”, was immediately punished by striking him mute until John the Baptist was born. Gideon’s faith is honored in Hebrews 11:32-34 along with greats like David and Samuel--Zacharias didn't make the list. Asking how God plans to do His work, and asking for validation is consistent with great faith —but don’t ask for certainty.