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So at work I am one of the more experienced fellows, and I am constantly explaining to newer employees why we do some things a certain way - usually it's because we have looked into what they suggested and found that it wasn't feasible - my problem is how do I explain that in a way that's not condescending, but I don't want to encourage them in particular either, only for them to waste their time & end up with the same conclusion - it's not worth it / it won't work / etc. - but without being cynical about it or making myself seem like more of a pessimist than I already am.

Most of the time it's not a very clear-cut black-and-white as to why it won't be worth it, I can give a couple reasons, but for a full analysis that would take a lot of time and effort to dig up ALL the reasons (yes, some better documentation could help, but no-one really likes documenting dead-ends, but rather abandons them as soon as they realize it's a dead-end).

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    Welcome! We thrive on questions with specific examples. Can you perhaps flesh out your question with a specific recounting of a particular event you had a concern with? This should include the situation, what you did, and how the other person/people reacted to you. It'd also be helpful to know where you are in the world (generally). Also, I think it's great that you take the time to try to explain why things are done the way they are. So many people just say "that's how it is, so get used to it". – Catija Sep 20 '17 at 15:37
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Don't discourage unless the approach is/was completely unworkable. It is very rare that the team would have tried every approach/angle when working through something. More often than not, it is not that the solution isn't feasible, it's that it was constrained by time/money/people. That may have changed.

Especially if you are in a technology field, there may have also been advances made in technology, methodology, capability that may not have been there the last time something was visited.

Instead, I would approach it along the lines of "Yeah, _____ has always been a problem. We tried doing X and Y a few years ago, but couldn't really get it to work. I think ____ has some documentation on what we did do/try, maybe you could take a look and find a different angle".

That shows that what they are considering has been tried, gives them a source to see what was done, and lets them research it a bit. They may see that what they are thinking has been tried and that's the end of it. But, it may be that they really do have a better way or different approach that would work.

In either case, you can let them know that it's been at least looked at, but in an encouraging fashion rather than a shut down fashion.

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