The funniest thing about Outlook being an anachronism from their perspective is this paragraph: "Please note, on the mobile side, corp mail is not yet supported in our Mail app for Android or iOS, but that will change (PB&J!)."

Desktop only in this day and age is pretty anachronistic too.

Office 365 is killing it because Microsoft is entrenched in enterprise. They aren't leaving any time soon, no matter what Apple, Google, Yahoo!, or any Random Startup X does.

It has less to do with the quality of the service, its ease of use, or whether or not people actually like using it than the above note about entrenchment.

That's not what the small businesses I speak to are saying...

Well, this is an internal memo beating the drum to get their own people to use their product. It's not all that surprising that it isn't a fair and balanced discussion of Outlook's pros and cons.

EDIT: Come to think of it, this is an interesting attempt at manipulating people. He claims that Outlook is an outdated piece of technology straight from the 90's and literally paints the picture of a dinosaur. Tech people - who are probably the main target audience for this memo - oftentimes take pride in being in the know about the latest technologies and invest quite a bit of time and effort in being on the bleeding edge. Those paragraphs are actually an insult in disguise designed to get people by their pride about being behind the times.

I guess my comment is more directed at the following:

1. If you're going to promote design-thinking in a company (which I believe Yahoo needs to do in order to grow) than making comments like this is a disservice. This creates a culture of "well if it's old and looks like shit then it must be shit" that should instead be "listen to your audience".

2. This is also talking about the sentiment from outside of Yahoo (and possibly in the echo chamber of HN). I get why Yahoo internally would say it, which I would then revert back to my point #1.

Dogfooding your own products is a sufficient reason.