Why email and attachments don’t mix

While there are many tools available to help you collaborate on documents, spreadsheets, and presentations (still the work horses of business) many people still rely on sending email with attachments.

What’s wrong with using email like this?

Have you ever seen attachment with a name like Important_Overview_4_30_16_ps_td_foo_final.pptx? What this means is that someone built a PowerPoint presentation named “Important Overview” and marked it as April 30th to denote it was different than the one the day before. And then someone with initials of ps, and then td, and then foo edited it. And then someone finally said “it’s done” and marked it final. And that’s a simple case that might have actually worked.

Here’s what happened:

  1. The Original Person emailed Colleague A, B, and C the presentation.
  2. Colleague A edited the presentation and appended 4_30_15. She sent the presentation back to everyone.
  3. Colleague B edited the presentation and appended _ps. Colleague B was busy and didn’t send his edits back.
  4. Colleague C forwarded the presentation to Colleague D who appended colleague_d to the presentation and made edits.
  5. Original Person reviews Colleague A’s edits, changes them a bit, and emails them out to everyone.
  6. Now Original Person receives Colleague B’s edits, updates to Important_Overview_4_30_2016_ps_td.pptx.
  7. Colleague C, working on a very old, original version, makes edits and sends back to everyone. Everyone is very confused because wait, C’s version has none of the other changes but it has new changes. In sheer frustration Original Person schedules a meeting and they go through the presentations and manually edit things. This results in Important_Overview_4_30_16_ps_td_foo_final.pptx.
  8. Original Person emails this to everyone.

Everyone is happy, right?

Well no. First, a huge amount of time was wasted as people edited content that had already been edited, modified or otherwise improved. Second, all those manual merges means inevitably some change was lost. Don’t worry though, you will surely find that embarrassing typo during the middle of your big presentation.

And this is what happens when everyone is working hard, trying, and honestly wants to get the best outcome possible. Imagine what happens if/when that isn’t true?

Hey wait! you say. Colleague D did a bunch of edits, were those included? Nope. You see because D was forwarded the presentation Original Person never even knew Colleague D was working on edits. So that work is 100% wasted and Colleague D is now frustrated because he had important points to make.

So what is better?

The important thing to remember is “single source of truth”. Tools can be better or worse. Workflows can be better or worse. But as long as there is a single oracle, a single source that represents “the truth” then it will turn out better. Some easy patches:

  1. Store the file in a shared place. Dropbox, OneDrive, Google Drive, etc. It doesn’t matter too much as long as a) everyone can have access and b) there is change history. Change history is important because sooner or later someone will delete the whole damned thing. And if you can revert to a known good state you can be a hero.
  2. Send links, not attachments. Every time you send an attachment an Office Angel weeps. Need to send someone a copy for reading but want to ensure single source of truth? Send a read-only format like PDF.
  3. Use a tool like Slack, Microsoft Teams, Facebook Groups, etc. for communication. This means there is a single channel. It’s not perfect but this way you never leave poor Colleague D out of the loop, there is an ongoing dialog about where and what the source of truth is, and in the worst case there is a history of changes so you can unfuck it.

Combine all three and you’ll be better off. Or of course you could hire someone to “own the documents” – that person will go crazy and quit within a year.



  1. I like email, why can’t I just do what I’ve always done? Because you are implicitly creating work for other people. Email is a good tool for external communication – it was designed to cross organizational boundaries. It was never designed for group collaboration.
  2. Sending links doesn’t work when someone is offline. Not always true, increasingly the shared file systems work just fine offline and on mobile. But true, sometimes links don’t work. Spend the time to get your teams set up with Dropbox/OneDrive/Google/etc and then your life becomes easier. Otherwise you are sacrificing 95% of the benefits for 5% of the time when you are *really* offline.