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I've been working on a particular website project with a friend from an old job I had. We started with our idea, and are at the point of going through network security for the login information, but I'm not quite understanding how it all ties into the website and how encryption of usernames and passwords really work.

Now we're both busy on our respective portions, but this part was given to me as a matter of practicality I guess as I'm the one who has access to the root or something (If I understood it, I wouldn't be asking...). He's in charge of the programming for the website, and I for the administration and accounting for it from two separate locations where we use separate logins to a management portal for our pieces.

Now because I don't understand what he's looking to do or how to do it necessarily and he does, I've asked him to show me. After going through the process, it seemed like he was frustrated that it didn't immediately click for me. We ended that conversation with "we'll get back to this later...." in a bit of an upset tone. We had another session to go over it last week, but had the same result; I just don't get it. Whether it's the way he's teaching it or the way it's going into my head, it feels like I understand the concept but not the application.

He gets increasingly frustrated that he's for all intents and purposes explaining himself over and over without me getting it. We've been good friends for a long time, and I'd like to continue this friendship. I've asked if he wants to login and do it himself, but he says that he doesn't understand that part of the website management software and can't do it; he's vehement on not doing it and insists that I do. I've tried googling the information, but it's just as confusing there.

How can I ask him to just keep explaining it until I get it without him getting upset that I'm for all intents and purposes wasting his time?

  • There is probably a better way to phrase the question, so please if anyone finds it please edit. – Anoplexian - Reinstate Monica Mar 6 '18 at 21:48
  • If you add in a few more details of what he is trying to explain to you some of us may be able to explain it better. Even if they are added at the bottom as an aside. – RyanfaeScotland Mar 7 '18 at 2:31
  • Often, when one finds oneself unable to fully and clearly explain something, this points to a lack of ones own knowledge. In these cases, being annoyed by detailed inquiries is a natural defensive reaction. In your case, your friends refusal to do it himself also points in this direction... he says that he doesn't understand that part ... Could that be the real cause of your troubles? – user6109 Mar 7 '18 at 8:59
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Communicating technical information to non technical people is a complicated subject. As a non technical person asking to be shown the thing isn't the best strategy for understanding complex concepts. For instance unless you are a chemist, looking at a chemist's lab notes is going to be useless in improving your understanding of what problems they are facing.

There's a reason you are handling the administration and accounting and they are handling the programming. You are both playing to your strengths. If you need to understand every technical decision that they make you are going to greatly slow down the development process as your friend will constantly be stopping work to teach you.

Ask yourself what is the relevant information to you before asking them. Trust their judgment. They're the expert, not you. If they're experiencing a problem, ask them for a quick summary of the problem, can they resolve it, how long do they think it will take to resolve, do they need additional resources to resolve it, and what are the consequences of not resolving it. If you want to know more ask them what you can do on your own time to better understand a concept.

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As a technical person, this is a common challenge I struggle with - explaining complex technical issues to a person who doesn't do this 40 hours per week. Oddly enough, I've found that it's easier to explain things when the knowledge debt is greater than when it's not. Why? Because people who have a lot of knowledge tend to assume that others know the same things that they do.
| I'd suggest reframing this in your own mind: don't think of the technical challenge. That's his job. Think of the service you want. What is the result you want to achieve? Then let him show you how to do that.

I'd suggest admitting that you don't get it. A good technical person can accept that and work with it. It's a lot easier for me to deal with someone who doesn't get it and tells me than to have someone keep asking the same question over and over. If they say they don't get it, at least I can figure out where I'm failing in my explanation.

Let's face it: technology is complicated and requires a certain thought process and skill set; otherwise everyone would do it. In the end, you may be better asking him to take on this responsibility since he grasps it and you don't. There's no shame in that - there's a reason I work with Project Managers and Business Analysts. (Hint: they work at a level of detail that would put me in a swamp).

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There are some things that just don't click for certain people.

It might be worth considering bringing in a third person. Maybe it should be a conference call to the vendor's support, maybe a contractor for this specific issue.

It sounds like you are both busy with your respective parts of the project. Acknowledging that you both have a shared weak point shouldn't be a deal breaker in any friendship... as long as you keep looking for a way through it.

  • This is what I was going to suggest. Bringing in a third person. Also I would add: Each can write an outline in preparation for the next meeting (you: things you heard but didn't understand; he: what he needs you to do; both: list of terms and what they mean to each). Finally: make sure you're not tired or hungry when you talk about this. – aparente001 Mar 7 '18 at 1:53
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Interesting question. One part of me wants to try and address the question for you, the other part wants to resolve the network security problem you are having!

I could be way off the mark here but from you 'having access to the root or something' I'm guessing you have some sort of online hosting solution which you have the details of to log into the admin panel which allows you to manage the e-Mail address, monitor the visitor numbers and so on. And from you being in charge of the 'administration and accounting' I'm assuming this means you are in charge of adding / removing users and paying for it.

From these two things I get the impression that you are using the word administration in different ways: he expects you to be a system administrator whilst you were thinking it was more of a secretarial position, adding and removing users and the like. You are now being tasked with something akin to turning off anonymous authentication and you have no idea what he is on about.

You may be more technically minded than I'm giving you credit for here but regardless I think my advice would be the same:

  • Start by explaining to him that you think the project is coming along well but you are still having trouble with this part of it.
  • Ask if he would mind going over it again, but this time with you taking notes and breaking it down to bullet points so that you have them to aid you later and so anything you are still unsure about you can get cleared up.
  • Do this, take notes and break each step up into bullet points. Note that these are YOUR bullet points, make sure every one of them makes sense to you, if one doesn't then ask him to break it down smaller, if he gets frustrated at you not understanding remind him that that is why yous are doing this, because you BOTH need to get this working and in order to do so you need a clear breakdown of what you need to do.
  • If there are still gaps in the steps, or points he simply cannot break down smaller then these are the steps you take to your website management software provider and say "How do I do this?" (or read their documentation to find out, or Google these now hopefully more specific points).

The key thing for me here is that although you may want to ask him to just keep explaining it until you get it, unless he explains it a different way each time you are just going to keep going round in circles and he is going to get frustrated and upset (as will you).

By breaking it down to bullet points you can focus in on the bits that aren't being explained well enough, or that he doesn't realise you aren't understanding, and hopefully that will be enough to get him to go into more detail, or adjust his explanation. Anything that is still lacking that he can't explain is hopefully concise enough for a targeted Googling.

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I know your question is how do I get him to keep explaining it till I get it, but I'm not sure that's fair. Unless you're paying him for training. I do think it would be fair to ask him for recommendations of concepts he thinks you need to understand to get his plan (like public key encryption). There is so much information out there, and I think you should take some responsibility to get the necessary background if this is something you really want to do. If it's not a computer science question, and it relates more to your specific design, ask him to diagram it out in a picture format so you two can look at it together. It is a possibility that his idea doesn't actually work, and that may be the issue. If it is, drawing a diagram will help him to process this and think about the changes you may need to make on your implementation. His frustration with explaining it may not be due to you at all, it may be because over time he's realizing he's not connecting some of the dots or there's stuff he hasn't figured out yet. I would ask him if that's the case, and offer to research those areas.

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