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?

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    However, I later found out that he hadn't heard of shared folders before...who told you that? Commented Dec 3, 2019 at 11:38
  • @TorstenOjaperv Sam comes from the Windows ecosystem, otherwise I wouldn't have this issue. It's a bit silly to suggest that strangers on the internet are silly without knowing about their situation. Commented Dec 3, 2019 at 15:10
  • @SouravGhosh Long story short, Sam's coworker, Tim, who is Sam's neighbour in the office, inadvertently glanced at Sam's monitor a couple of times. He guessed what Sam was searching for. Since he wasn't quite aware of it himself, he asked Sam, who confirmed that he was indeed searching for 15 minutes. Then I found out from Tim while talking about an entirely unrelated topic. Commented Dec 3, 2019 at 16:01
  • Just keep in mind that if someone is giving you office gossip they're probably also gossiping about you.
    – HenryM
    Commented Oct 12, 2020 at 13:44
  • One of the greatest fallacies as a computer person is to come to expect that everyone knows the same as you. Next time just use a USB-drive. Commented Mar 27, 2022 at 10:41

5 Answers 5


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?

First off, I doubt Sam was that embarrassed. He must have told you something that led you to believe he didn't know about Windows shared folders. So he didn't try to hide the fact.

It's good that Sam was able to figure it out on his own. In future cases you now know sam can figure simple stuff out on his own (& In only 15 minutes!)

Side notes: I work in IT & I've never had to share a windows folder & I don't think 15 minutes is a long time. I've spent more than that this morning on this site...

You are making LOTS of assumptions. If it were my first time hearing about shared drives, I'd probably spend some time researching it too. Maybe Sam wanted to know more than just which buttons to click on?

Or maybe Sam did have other things come up & your information is bad? Or Sam likes to browse Reddit while learning new things?

In any case Sam figured it out on his own which is more valuable than you showing him how & definetly more valuable than you doing it for him (What if 3 years from now Sam is showing the new Sam how to do it?)

  • @UchihaMadara I never assumed Sam was in IT, sorry for the confusion. My point was I am an IT person whose never used windows Shared drives -- Sam has to reason to be embarrassed. We shouldn't assume Sam is embarresed
    – dustytrash
    Commented Dec 3, 2019 at 15:32

Thanks for asking the question. While this has happened with you while working on something trivial and non-recurring scenario, many people face similar problem in their day-to-day work when they are trying to assign / delegate the work to someone else.

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?

You cannot possibly know of every shortcoming magically, and offer solution to that. The only way you can help in a constructive way is that if the other person let you know about the help they need.

Thereby, if you're expecting someone to do something (be it a direct work assignment or something not directly related to primary work), please ask for confirmation about three things:

  1. Whether they understood what needs to be done.
  2. Whether they know how it needs to be done.
  3. Whether they have an understanding of why something needs to be done.

The last point, while not being a proper case here, in general, is as useful as the first two. That way, you'll be able to ascertain the fact that the communication happened both ways and all the participants are on the same page.

So, in this case, a better way to have the conversation would have been:

[....] Uchiha: So, how do we do it? Without that file dump, we cannot proceeded.

Sam: That's a problem!

Uchiha: Why don't we do one thing? We can put the file in a particular folder, which is shared between us, so I can have it copied to my machine.

Sam: OK, that sounds great.

Uchiha: Cool. So, do you have a shared folder already that we can use? or do you need to setup a new one?

Sam: I don't have one already, I may need to set one up.

Uchiha: OK, In that case, may I offer some help? I can help to set one up, if you need.

Now, based on Sam's response this can end one of the two ways:

  • Scenario 1:

    Sam: Thanks, but I'm fine, will share in a while

    Uchiha: Sure, will be waiting for the notification.


    Here, Sam clearly mentions they don't need help. After this, if they struggle, there's nothing much you can do about it. You offered help.

  • Scenario 2:

    Sam: I'm not entirely sure how to do that, never done this before.

    Uchiha: Not a problem, let me show you how to do it - you want to have a screen-share now?


    Here, Sam is open to help, go ahead and help them.

In either of the cases, you did your best to offer help and you made sure you did not overstep, you asked them whether they need the help or not. I believe that's the most you (or anyone) need to do.

  • This scenario does not cover what happens if Sam is offended by the offering of help. That is probably the most difficult part of OP's question
    – user180146
    Commented Dec 3, 2019 at 12:44
  • @user180146 No one is offended for offering to help them, people get offended for unsolicited overstepping disguised as help. If Sam does not need help, they can say the same: just as scenario 1. We can't say whether Sam actually needed help or not, they just refused it, that's all. Commented Dec 3, 2019 at 12:47
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    Although I think that no one should get offended by the offering of help. I do not think that this is the case. If I offer help for something trivial the other person might think Ithink less of them because I think they cannot do this trivial thing on their own. IMO this is what OP is worried about
    – user180146
    Commented Dec 3, 2019 at 14:10
  • Although I think this is good advice for more complex tasks, I could provide a long list of people who would be quite offended if you asked them your three questions after telling them to do a trivial task like setting up a shared folder. In fact, the scenario presented by the OP is such a fringe case, I really don't think it's an addressable question.
    – dwizum
    Commented Dec 3, 2019 at 15:45
  • Thanks, your answer is helpful to me. I forgot to mention that Sam isn't my "subordinate", he is senior to me, so I don't "delegate" to him. Nonetheless, your "sample conversation" and rest of the explanation is useful. I guess changing the last line in your conversation to "Ok, may I help?" would make it sound less condescending. Though maybe it won't. But regardless, your "step by step" approach is less direct than "Hey, let's use a shared folder. If you don't know how to do it, I will show you." :-) Commented Dec 3, 2019 at 16:06

You could have gone with something like: "Hi, Sam are you happy setting up a share on your computer, or would you like me to do it on mine and you can copy it over?" If he say's he'll do it then just say. "Ok, any problems just let me know."

You've given him two chances to ask you for help. If time is critical and he doesn't seize this then that is really on him. If time isn't critical you can spend 15 minutes doing other tasks while he teaches himself to do the task and 'saves face'. Finally you've offered him an alternative which is you setting something up for him to drag the file to.

Either way you've pretty much covered yourself from accusations that you weren't helpful.

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    I don't think there is any point of view from which OP can be accused of not being helpful. Commented Dec 3, 2019 at 11:31
  • In the scenario in the question it is unlikely anyone would accuse the OP of being unhelpful. However, people who have a reputation for assuming knowledge in others do often get described as being unhelpful. This might not be fair but I have seen enough of it.
    – Dustybin80
    Commented Dec 3, 2019 at 12:12
  • 1
    Your answer is helpful to me. It wouldn't have helped in this specific scenario because my account isn't yet setup to give write permissions. That was actually the first thing I tried before asking him to share his folder. However, in more general situations, this approach of providing an alternative and then following it up with another offer for help certainly helps makes the interaction less "in your face" (if you will) and gives the other person a better chance to save face in case they need to. Commented Dec 3, 2019 at 15:28

I think it might be helpful to first explore the point of view of your coworker.

The sad truth is that in many workplaces asking questions "in the wrong way" can be very harmful to asker. Your coworker is likely acutely aware of that and thus spending significant time figuring out how to do filesharing on Windows 10 is seen as "easier" and less risky than asking for help from a busy colleague.

People are judged by the questions they ask (stackexchange sites are entirely based on that!). I've seen someone question out loud, right here on this site, whether they should terminate 2 recently promoted employees for asking questions they deemed too basic (can't find the question right now). The risk is real.

I think the best thing you can do is to regularly demonstrate that you're approachable and willing to help out. You seem to have already done that? That's the right attitude. More practically, if you're not in an extreme rush it's OK to let people figure things out on their own in a supportive environment. If there is a rush, your history of trust with this coworker will enable them to ask questions when they need it.

Of course, there do exist "help vampires" but that's rare, and you coworker seems determined to avoid being seen as such. You won't turn them into a help vampire by offering assistance in a time-pinch.

  • Thanks for your answer. This is useful information. Unfortunately, I didn't make it clear in my question that Sam is actually senior to me. At least in this case, there isn't the issue of me judging him based on the questions he asks. Though I can see the issue of someone judging their senior for ignorance of mundane things. Of course, I don't do things this way, but I can imagine someone else would. So I won't edit the question and (sort of) invalidate this answer, which is useful as it is anyway. Commented Dec 3, 2019 at 15:32
  • @Uchihamadara, I was trying to describe the point of view of your senior colleague. Regardless of whether he is senior or junior to you he will be concerned about how it looks for him to ask a basic question. If anything, Seniors are even more sensitive about being judged upon asking something which they should have known.
    – teego1967
    Commented Dec 3, 2019 at 17:37

You’re assuming too much. Someone could’ve pinged him while he was helping you. Got on a phone call, etc.

Even if you’re correct in your assessment, you could’ve shared a folder at the 2 minute mark of your session and told him to drop the file there instead. If he’s really interested, he’s going to ask you how to do it.

  • 1
    I'm not assuming anything. I have explicitly stated in the question that I first thought he was doing other things, and then found that it wasn't the case. He was searching for 15 minutes. "you could’ve shared a folder at the 2 minute mark of your session" Sure, I did that and it didn't work because that requires me to give Sam write permissions, which I am not yet authorized to do (I'm in my first week at the job, and IT is still setting up my account). It is easier for Sam to give me read permissions. You might want to avoid assuming too much yourself. Commented Dec 3, 2019 at 15:23
  • @UchihaMadara Your co-worker could react the same way you did to my attempt to help you. At the end of the day, it’s still up to you, if you want to proceed...just know that your reaction is one of the possible outcomes.
    – Goose
    Commented Dec 3, 2019 at 15:34

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