I started a new job recently. A coworker (let's call him Sam) is tasked with helping me do the initial project setup. At one point, he wanted to share a huge file (about 1 GB in size) with me. Now unfortunately, there's no common storage or "cloud" or anything that we could use for this purpose, and sending it over email or skype is prohibited by IT policy due to the file size. Hence, I suggested him to put it in a shared folder on his computer, and give me permissions to access it over the network.
He eventually provided me the shared folder after about 15 minutes. At first, I thought nothing of it, since there was no reason to assume he had nothing else to do. However, I later found out that he hadn't heard of shared folders before, so he had spent the past 15 minutes searching about it and how to provide permissions, etc. Do note that on the Windows 10 operating system, sharing a folder involves little more than a few mouse clicks. I feel bad that Sam spent 15 minutes searching for this trivia when I could have told him in 30 seconds.
Sam likely didn't ask me because he felt it would be "embarrassing" to admit that he didn't know what sounded like something he should have known. Now, I don't believe that not knowing this (or anything else, for that matter) is such a big deal, and I also don't judge people for asking what they don't know. Of course, Sam cannot read my mind, and he doesn't know me that well anyway. However, I also couldn't offer to tell him right off the bat, because that would be condescending. If Sam already knew how to setup the shared folders, he might be offended because I assumed he doesn't know, etc.
As a result, we were stuck in this deadlock. Sam couldn't ask me because he thought it would be "embarrassing", and I couldn't tell Sam because he didn't ask! Unfortunately, this happened over chat, and for certain reasons which I cannot go into here, we couldn't switch to a voice or video call. Hence, neither of us had access to each other's facial expressions or other non-verbal cues, which would have made this a non-issue in face-to-face communication.
I would like to do better the next time I am faced with this situation. How should I handle such situations, so that the other person doesn't feel embarrassed or offended, while at the same time, I can offer to help them with what I know?