How to make Obsidian a viable solution for enterprise org which is a MSFT-shop (Outlook, Word, etc.)

I’ve been debating tasking IT with prepping our note taking tools accross my org/enterprise to better prepare us for AI, so that whatever the killer use case looks like for our business, we’re better positioned to adopt it.
We’re rolling out Enterprise ChatGPT, and i’m disappointed to only see one note taking tool (Notion) available under the “available connections” settings options, but I’m sure eventually they will support many more.
While we don’t know exactly what the killer use case for users-notes+AI at an organization like mine will look like, which model will enable it, what the user workflow will look like (plugin vs api vs standalone), it seems like we can at least be ready so that when it reveals itself we are best positioned to adopt/utilize. Obsidian seems well positioned given its: (1) ability to sync/host user notes anywhere (pvt cloud) and thereby avoid 3P hosting lock-in like with Notion; (2) interoperability with whatever Ai tools you might want given the open syntax, notes stored in raw text.

However, my org wants to consider Notion – and i get it from a user experience point of view – more similar to word. I think there are some Obsidian plugins which could get it almost there from user experience standpoint, but there is one thing that seems like a deal breaker if we are talking about adoption for the masses (of my org): we are Microsoft shop. Most of the users are not particularly sophisticated with technology. The way that copy-pasting to and from MSFT related apps works (office, outlook, word, etc.) seems like a deal breaker. You simply cannot copy/paste markdown syntax text from obsidian to word, or from an office-document to obsidian, and have it maintain formatting/spacing, list hierarchies, etc.

Yes there are some workarounds if trying to paste content from html format into obsidian/markdown – i’m aware of plugins like Paste as HTML. This isn’t completely full proof as then the user has to swtich to reader mode to read the content they just pasted, and GOOD LUCK if they have to edit any of it in edit mode.

But i’m simply not aware of any even semi-adequate solution for the other side of this workflow (pasting content copied in Obsidian into a MSFT-App, like Word or Outlook). If a user writes an email in Obsidian and then intends to copy-paste it into an outlook new email window, all spacing is lost, list hierarchies gone, etc.

So all this to ask: (1) is this a limitation of the open syntax/raw text document format of Obsidian (which is also what makes it so great)?; (2) does anybody have any viable solutions to this small user experience flow that would enable me to push Obsidian to a >1k+ enterprise organization?

Any thoughts appreciated

1. The best way to copy formatted text from Obsidian to other editors like word or an outlook email is using the “Copy Document as HTML” plugin. This works much better than copying from the reader mode (and you can copy the formatted text without needing to switch to reader mode).

2. I don’t think copying formatted text from other apps (e.g. Word or Outlook) to Obsidian will ever work 100% perfectly, due to the inherent limitation where markdown doesn’t provide all of the same formatting options as an application like word.

When you paste HTML/rich text formatted text into obsidian, obsidian automatically converts the formatting to markdown by default. But as you may have seen, this conversion isn’t perfect depending on the complexity of the content being pasted.

Yeah i’m familiar. That’s what i was referring to in the original post. This is not truly an adequate solution as if you then need to edit your pasted-as-html text, you’ve got code all over the place in between text, it’s just not a good user experience. If it’s a finalize dproduct that’s fine, but if you ever need to edit it you’re in trouble. (and remember, we are talking large entp here, not developers).

Is a native or seamless solution even possible here? This would be something that converts Word doc formatting, list hierarchies, into markdown syntax instantly when copy-pasting text into an obsidian?

There is HTML to markdown conversion natively in obsidian, but it really falls short on lists

Not great because… converting the following From a word document (and yes, paragraph spacing before/after, line spacing, are all 0):

Looks like this when pasted into obsidian (notice empty line in between every line of text, and no conversion of the list hierarchy)

1). Regarding copying from Obsidian > Word (or Outlook) - Using Copy Document as HTML normally won’t end up with any visible HTML code after pasting, unless the application you’re pasting into doesn’t properly support HTML formatted text.

In my experience it works well when pasting into word or outlook (pasting into outlook emails is what I primarily used it for). The reason that the plugin typically works better than copying from obsidian’s reading mode is that it generates much “cleaner” HTML. And if you enable the “Fragment only” option, it will generate completely clean semantic HTML with no CSS styling.

Another alternative is using the “Enhancing Export” plugin which allows you to export an entire note directly to .docx using pandoc, but this can require some configuration to get working well.

2). Regarding copying from Word (or Outlook) > Obsidian, the results you get here have inherent limitations.

Obsidian uses a library called “Turndown” to convert HTML formatted text to markdown. This has inherent limitations due to HTML being much more complex than markdown, so the conversion can never be perfect.

I’m currently using Joplin for my notes and have been developing a Joplin plugin that converts text to markdown on paste using turndown like Obsidian does, so I have some experience dealing with this. Copying from Outlook in particular has issues because the HTML generated by copying from outlook has all kinds of weird formatting for paragraphs (lots of spans, divs, etc…)

There is an obsidian plugin that you can try that might help (I haven’t tried this one myself): GitHub - keathmilligan/obsidian-paste-reformatter: A plugin for Obsidian that reformats pasted HTML and plain text content, giving you precise control over how content is transformed when pasted into your notes.. It gives you various options to transform/clean up the pasted text.

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