How can I associate a "document" with a SharePoint list, and have the workflow wait for the document to be checked in?

Question

I have a SharePoint list workflow running on the latest/greatest SharePoint OnLine. I'm using SharePoint Designer 2013. Unfortunately, PowerApps Flow is not an option.

I'd like to add some new steps to the workflow:

1. The workflow should launch a Process Task to the Sales Rep ("Current Item:Created By") asking him to fill out a "CustomerForm".
2. An MS Word doc, "CustomerForm Template", exists in the Document Library. The email that the Process Task sends to the Sales Rep has a link to the template.
3. The Sales Rep needs to complete the template, "Save As" to a new .doc, and forward it to the company's DocuSign team for customer signature.

Q: Is there any way I can facilitate the Sales Rep saving the completed form to the Document Library (instead of "Save As" to a .docx file on his hard drive)?

Q: If so, how can I associate the completed .doc file with that specific workflow's list item?

Q: Are there any SharePoint workflow actions or events I can use to automate some or all of these steps?

Q: Can I somehow leverage SharePoint versioning (e.g. trigger on document check-in to automatically send an e-mail to the DocuSign team)?

Answer 1

Q1: Yes, it is quite easy to do so if the Sales Rep is using Office 365, detailed process here. If you are using earlier version of Office, you may need to check with the some articles.

Office 2010 Office 2013 and 2016

Q2: The easiest way to do so is using the attachment. You can attach the file to the task in your task list like the screenshot below:

Q3: You can send a notification email to the sales rep after a Process task is created. Also you can check in/out files with workflow.

Q4: Technically you can do so, just need to create a event receiver for this. Examples you can check:Start workflow when file is checked in