Episode 47 – Microsoft’s (Truly) UNBELIEVABLE Mistake

We’re rolling with the punches today!

The Marketing Gateway is a weekly podcast hosted by Sean in St. Louis (Sean J. Jordan, President of https://www.researchplan.com/) and featuring guests from the St. Louis area and beyond.

Every week, Sean shares insights about the world of marketing and speaks to people who are working in various marketing roles – creative agencies, brand managers, MarCom professionals, PR pros, business owners, academics, entrepreneurs, researchers and more!

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TRANSCRIPT:

Quick heads up to regular listeners of The Marketing Gateway – we’d planned and even promoted an interview episode today, and technology got in our way and ate half the interview

 Unfortunately, it was the half where I wasn’t talking, so we’re working on getting that restored!

Until then… here’s a fresh new episode for today

 Sorry about that!

So as you might recall, I’m often bewildered by Microsoft, a company that is so large that they can afford to make a lot of mistakes when it comes to branding, mainly because they’re essentially a legal monopoly and there aren’t any serious alternatives for a computer operating system for businesses and desktop consumer users to switch to if they’re unhappy with Microsoft

I mean, yeah, there’s Apple’s macOS and iOs, and Google’s Android and ChromeOS, and then there’s Linux… but anyhow

 71% market share on desktop computers is what I’m talking about

 Nobody’s threatening that right now

Along with basically owning the desktop computer market, Microsoft has over 400 million paid subscriptions to its productivity software suite popularly known as Microsoft Office

 I used Microsoft Word, which is part of the suite, to write this episode, and if you’re in the corporate world, I’m sure you’ve used Word or Powerpoint or Excel or one of their other traditional Microsoft Office products too

 Believe it or not, Microsoft is in second place in the global office software market with 30% market share

 Google has them beat at 44%

But Microsoft’s been pushing really hard on its generative AI suite of software, formerly known as Bing Chat, but now known as Copilot

 They’ve invested over $80 billion into their AI platform, and an October 2025 report they commissioned through Forrester suggests that small or mid-sized businesses who use Copilot for projects can see an ROI ranging from 132% to a staggering 353% over a three year period

I’m skeptical

 But that’s why they’re pushing this Copilot stuff so hard – they’re hoping businesses will bite, because 3

7 million businesses currently use Microsoft 365

Or do they? Because there’s some news going around that Microsoft Office is no more

 If you to www.office.com today, you will be greeted by a screen that says “Welcome to the Microsoft 365 Copilot App

” And there’s a line on the page that says, “The Microsoft 365 Copilot app (formerly Office) lets you create, share and collaborate all in one place with your favorite apps now including Copilot

And so the word on the street is that it looks like Microsoft is rolling out a rebranding of its entire Office product portfolio to be not just integrated with Copilot – it’s being called Copilot

But why would Microsoft do something so obviously stupid as rebrand their historic Microsoft Office suite of products to something far more confusing?

The answer is, it actually happened back in 2020 when they renamed the subscription version of their Office Suite “Microsoft 365,” and again in April 2025 when they renamed the Microsoft 365 app “Microsoft 365 Copilot

” Nobody but tech enthusiasts and Wikipedia editors even seem to have noticed

But the more complex answer is, Microsoft really does want people to think about Copilot, and no matter what they call their productivity suite, the brand they care about going forward is the one powered by AI

I’m Sean in St  Louis, and this is the Marketing Gateway

OK, so let’s back up to 2022 when Microsoft decided to rebrand their Office suite in the first place

 Microsoft Office has been around for a long time, first debuting on Windows 3

0 in 1990 and going through several iterations before going through new version updates that more or less kept pace with the rollout of new operating system versions

 Office 95 was for Windows 95, Office XP was for Windows XP, and the versions of Office that shipped roughly every three years from then on were for the update packs for XP, Windows 7 and Windows 10

Sorry, Windows Vista

 You didn’t get your own exclusive version of Office

 But hey, the Macintosh, iOS and Android all have their own versions!

While Office is not a terribly exciting product to talk about from a glitz and glamor point of view, the most evolutionary change in the suite in the 21st century was in Office 2007, where Microsoft ditched the traditional drop-down menus and icon bars you still see in other competing software like Google Workspace or LibreOffice and replaced it with this graphical ribbon that’s needlessly complex and which people really hated when it first launched, but we’ve had about 20 years to get used to

Up until the last 10 years or so, Office was generally sold as a standalone product

 You’d go to the store, buy a boxed copy of the software, put the floppy disc or CD-ROM or DVD-ROM into your drive and install it with a license key that was yours to keep forever

 But Microsoft really wanted to turn Office into an annual subscription service as opposed to a piece of software that cheapskates could keep using until the heat death of the universe, and so they made a diverging product originally called Office Web Apps that launched in 2008 and went through many different name changes as Microsoft tried to figure out how to make it work online

 The most recent name from 2014-2019 was “Office Online,” and it was part of a broader umbrella of services called “Windows Live

But there was this other parallel product within Microsoft’s portfolio called Office 365

 It was launched in 2010 and was mainly focused on the corporate market

 And Microsoft confusingly had a different service geared at enterprise customers called Microsoft 365 that was introduced in 2017 and which bundled together the operating system, Office 365 and security features

In Spring of 2020, right at the beginning of the global pandemic, Microsoft decided to rebrand Office 365 as Microsoft 365, reserving the Office 365 brand for institutional and enterprise users

But then in 2022, they announced they were phasing out the Microsoft Office brand for everything except for legacy products and that going forward, the entire suite would be called Microsoft 365

Except there’s still a non-subscription version of the software called Microsoft Office 2024 that includes software like Word, Excel, PowerPoint, OneNote and Outlook for a one-time purchase

Is your head spinning yet? I’ve said it before and I’ll say it again – Microsoft absolutely stinks at branding

 They make things so needlessly confusing

OK, so that brings us to their current controversy

 The internet started buzzing on January 5th that on Microsoft’s Office

com website – which remember, they haven’t been using to market Microsoft Office 365 as a product since 2022 – the site now appears to be suggesting that Microsoft 365 is being renamed The Microsoft 365 Copilot App

Now, unlike the hyperbole you might be seeing on the internet, Microsoft is not changing the brand name of “Microsoft Office” to “Microsoft Copilot App 365” this year

 That is factually incorrect

The truth is it happened gradually over the last 5 years and no one even noticed

As I mentioned earlier, that change actually did take place last year in April when Microsoft decided to rename its Microsoft 365 App

 And Copilot was still a relatively new brand even then – it was adopted to replace the earlier name of Bing Chat in late 2023 – and by the way, do you remember when Microsoft was trying to get us to “Bing” everything a few years ago? Good grief, Microsoft

 Nobody wanted that

So anyway, then Microsoft started selling premium access to Copilot in January 2024 and gradually integrated it into the Microsoft 365 software so that it became “Microsoft 365 With Copilot

And Microsoft also launched a new version of Windows for certain hardware that runs Copilot in the background to optimize processes and they’ve also since pivoted to making every Windows 11 PC include built-in integration with Copilot

Like I said, Microsoft stinks at branding

 It’s confusing to know what software you’re buying and what you’re running

 But if you read their Windows Experience Blog post from October of 2025, they really want you to interact with your PC by talking to Copilot the same way you might talk to Siri or Google Assistant on your phone

Or Cortana on Windows, but Windows got rid of that AI assistant in 2023 and replaced it with Copilot

 Geez, Microsoft, you really love to confuse the heck out of people

So, what we’re ultimately heading towards is that Microsoft wants you to think about Windows 11 when you think operating system, Microsoft 365 when you think about buying subscription services and Copilot when you think about sitting down to your computer and doing any work

Which means, effectively, they really have killed the Office brand in favor of Copilot

And the real question is… why?

Let’s look at another tech company that competes with Microsoft – Google

 So about 10 years ago, there were all these panicked headlines that Google was changing its name to Alphabet, Inc

And yep, that happened

 But what it really involved was a restructuring of the corporation so that Google and all its other businesses would operate under a holding company

 This made a lot of sense because Google was invested in a lot of other ventures and needed to reorganize so that multiple CEOs could run those businesses without Google being directly tied to them

So, that rebranding happened, and Google is still operating as Google

 And while Google has done a number of confusing and outright stupid things over the year when it comes to branding, they aren’t messing with their core products

 Gmail is still Gmail, even when it’s  a part of Google Workspace

 Google the search engine is still just called Google

 Youtube is still very much its own thing

 And Gemini, their recent AI program, is being touted as its own platform, not a replacement for Google

On the other hand, we saw Facebook go through a pretty silly rebrand when Mark Zuckerberg decided to re-organize under the name Meta

 His big dream at the time was to build the Metaverse, an online virtual reality platform that resembles the futuristic, highly personal, anything goes internet you commonly see in science fiction and cyberpunk stories

 Meta has sunk around $50 billion into trying to make the Metaverse a thing, launching several iterations in their VR headset line, putting out AI-powered Ray-Ban sunglasses and pushing hard for people to use this silly VR platform called Horizon that even regular VR users like myself think is pretty stupid and pointless

Meta was an example of a terrible rebrand for a tech company, but it didn’t impact Facebook, Instagram or WhatsApp too much

 They all still operate under their successful brand names

Microsoft has never been a name that people have liked very much

 It’s always seemed too cold and corporate

 In the 1990s, when Star Trek: The Next Generation was still a big deal, Microsoft was often humorously compared to the cybernetic hive-mind known as the Borg who traveled around the galaxy in ugly giant mechanical cubes instead of sleekly designed starships – “We are Microsoft

 We will assimilate you

Copilot is also a really nebulous brand name because it’s essentially a frontend for a variant of ChatGPT

 People know what ChatGPT is, but Copilot seems like the generic brand

 That it’s being integrated with boring old Office software doesn’t make it sexy or interesting; it makes it seem like the ribbon forced on users in Office 2007 – you’re going to have to learn to like it because it’s really hard to operate the software without it

So, yeah, Copilot is Microsoft’s way of saying, “you don’t need Office anymore

 Our AI assistant will take care of all that boring document creation and data analysis and deck building for you

 You just need to tell it what to do

As far as I can tell, the only people who want to do that are the people working at Microsoft

 Most of us don’t want to talk to our computers when we’re working, and we sure as heck don’t want Copilot messing up our work by trying to do things for us, but badly

 I know I would rather spend a few hours writing a script for The Marketing Gateway than asking Copilot to do it and then spending all day fixing its mistakes

No matter how loud the AI hype gets, the proof is in the results – AI tools are really lousy at producing useful, reliable output that goes beyond a very basic level of helpfulness but are incredibly adept at churning out useless, soulless garbage

And Microsoft? You guys have more money than almost any entity in the world

 Would it be such a terrible thing to hire a marketing team that can just settle on a few product names and keep them that way? The rest of the world would love if it you could do that

I’m Sean in St Louis, and this has been The Marketing Gateway

 See ya next time!

PLUG

Today’s plug is for being adaptable

 We had to do it today when our plans for an episode fell through, and it’s pretty much how I have to live my life every day with teenagers in the house and cats waking me up at 2 in the morning to let me know that my toes suddenly look like exciting little toys they’d love to play with!

I was listening to Margaret Atwood’s book The Penelopiad recently

 Penelope is, of course, the clever wife of the ancient Greek hero Odysseus, and she has to outthink several situations she finds herself in while her husband’s away

 In Atwood’s novel, Penelope is the daughter of a Naiad, which is a water nymph

 And her mother tells her this

“Water does not resist

 Water flows

 When you plunge your hand into it, all you feel is a caress

 Water is not a solid wall, it will not stop you

 But water always goes where it wants to go, and nothing in the end can stand against it

 Water is patient

 Dripping water wears away a stone

 Remember that, my child

 Remember you are half water

 If you can’t go through an obstacle, go around it

 Water does

That’s great advice

 That’s what being adaptable is

 When the world puts you in a position where you have to change, it’s much easier if you adapt and flow around the obstacle than to try to work against it

But I also like the idea that in being adaptable, we also have to be patient

 That’s exactly where we are today, waiting for a technology platform to fix a problem so we can release the episode we intended to put out

 And I’m hopeful we’ll have that for you tomorrow

But in the meantime, we’ll continue to be adaptable here at The Marketing Gateway! It’s far better than being frustrated


SOURCES:

https://electroiq.com/stats/microsoft-365-statistics

https://expertinsights.com/email-security/microsoft-365-usage-and-security-statistics-for-2024

https://blogs.windows.com/windowsexperience/2025/10/16/making-every-windows-11-pc-an-ai-pc

 

https://www.microsoft.com/en-us/microsoft-365/blog/2024/10/17/microsoft-365-copilot-drove-up-to-353-roi-for-small-and-medium-businesses-new-study/

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