Thanks to KC Lemson for spurring me to finish and post this!
I’ve been outside of Microsoft for 3 months, and am now leading a medium sized social venture. The outside world is different. I suspect the assumptions born and lived inside of Redmond lead to all kinds of bad decisions. If the below is obvious to you, please ignore. If, like me, you’ve lived the last 10 years inside the all-encompassing embrace of the Redmond domain and Exchange servers, read on…
- eMail is important, but not for personal or work communications. Inside of the Redmond domain, your friends and colleagues are all on one email system with a convenient address book and contacts. This means email is very important, probably your primary communications channel. Outside, your inbox (see mine below) is used for mostly commercial emails – receipts, junk mail subscriptions, and such. As a result, email is much less central to me. I often check email one or two times a day, not multiple times per hour as I did while at Microsoft, because there’s just not that much that’s interesting to me.
- Nobody has solved for calendaring outside of the enterprise. I miss Exchange scheduling. Calendars aren’t well solved by gMail or Google apps, where I can’t see free/busy well. I did migrate my entire Microsoft address book to my Google account before I left, so there’s that. But generally, my email communications are pretty hodge-podgy now.
- Outlook + Gmail doesn’t really work on the PC. My new company uses Google apps for email, but setting it up to work with Outlook is painful. And then, it doesn’t do calendaring?! But webmail with multiple accounts drives me crazy. Outlook needs to embrace Gmail and vice versa. At Microsoft, everyone has a well managed Exchange system. Outside, I’m gradually being dragged to the Mac, where the calendar and email clients aren’t relentlessly trying to drive me to the linked email service as Gmail and Outlook do. This is a huge missed opportunity for both Google and Microsoft.
- Gmail doesn’t work well in the native iOS app. No real push? Silly.
- My most important address books are LinkedIn and Facebook, and messaging on these is my most important channel. Friends and family are all on SMS or iMessage so you use that. But LinkedIn and Facebook are where my contacts are, constantly updated, and everyone else now appears to check for messages routinely. It works very well.
- With coworkers, messaging is crucial. I’ve now become President of a small/medium sized social venture, and my team members are heterogeneous as hell about communications. Few use email for work communications. Many use text messaging. Others use a wide variety of messaging services, from WhatsApp to Google hangouts to facebook messenger. This creates a real mess of different services and apps I must install.
- iOS and Chrome tie everything together. Thank goodness there’s one set of channels for notifications for all these damned services. The most important for me are iOS notifications (so there’s one service that reminds me when one of a dozen channels has a new message) and Chrome browser notifications on my PC.
- I still haven’t made Slack work. At Microsoft I tried to get my teams to use Slack – everyone said it was awesome. It didn’t work for us since everyone uses and loves email. Now I’ve tried getting Interconnection to try it out, but it’s just not sticking. Perhaps it’s me, but it feels like just another damned messaging app. Which leads us to….
- There are too many damned messaging apps. Seriously, it’s a pain. Thank goodness for Chrome and iOS – they make the situation tolerable – but seriously, I wish everyone but one would just die already. Of course that won’t happen so I think we’re stuck.
William Gibson said that the future is already here, it’s just not evenly distributed. I think this is a great example of that phenomena. I wonder if it’s just Microsoft or all Microsoft-centric enterprises that live and die on Exchange? I also wonder if the new employees joining Microsoft experience things differently, or if once they’re pulled into the Redmond Domain they experience the same warm embrace of email? Let me know.
caultonorg 
Personally, my biggest post-Microsoft challenge has been contacts management. I toyed with several of the cloud contacts services, and I ultimately chose iCloud. The iCloud integration with Outlook is clunky, their web interface is very cumbersome, and modifying contacts from iOS is really annoying. I long for the days when I could add or look up a contact on Exchange-backed Outlook, which worked SO much better than any consumer system I’ve tried.
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Agreed, I asked my system administrator to enable some similar looking functions in Google apps, but they haven’t worked yet. So for work, it’s back there’s a poorly maintained Excel spreadsheet of employees. Over time, my contact list will include an mru which will improve things.
What does amzn use? Not exchange?
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Good post. I used Gmail at Seagate for 4 years – 3 of them on straight GMail after finally giving up on Outlook-Gmail integration. We’re on Office 365 at my current company and that works better but I’m on a Mac which has issues. My general take:
1. Gmail/GCal is not taken seriously by Google. In the 4 years we were on it – they did not fix a SINGLE new bug or add a requested Feature. You can track community feature requests – but it’s a waste of time b/c Google invests nothing. Periodically, Google will show up and say they’re now committed to Enterprise and then they go away and do nothing. With that said – GMail’s searching and multiple labels work really well. It’s their email editing that’s buggy and their calendaring has very little thinking behind it.
2. MSFT on the other hand seems content to give the market to Google. I switched to Mac Office several years ago and Mac Outlook 2016 is essentially Outlook 2010 with less features. MSFT hasn’t come up with a significant improvement in email in what a decade? Then the worst part about MSFT – x-platform support is terrible. Mac Outlook won’t connect to iCloud Contacts or Calendars (support is supposedly coming) – the Contact Management doesn’t even work with Outlook.com (an artifact of the warring tribes culture probably…). And MSFT hasn’t learned from anything Google actually does well.
3. MSFT’s constant, continual updating is maddening. I never realized how terrible Windows was until I went to Mac OS and realized a weekly update is silly. I now get no updates other than Office 365 which happens all the time – usually with trivial, who cares features or security updates.
4. MSFT x-platform still has a way to go. We were on Lync when I joined [24]7 and it just does not work on Mac. We took Lync out and went back to Webex – much more reliable and works well x-platform. MSFT team took a page from the Google playbook on Lync and kept telling us it would be fixed real soon, we got tired of not getting a commitment and went to Webex.
David on your last point about switching to things like Slack – I’ve never seen it work. We tried Salesforce Chatter at Seagate and we’ve experimented with Slack in my current team – but the issue with all of these is that email is almost impossible to replace — it can only happen if you get an entire company to do it and ALL their customers, partners and suppliers. For anything other than a small startup it doesn’t work. So when you add Chatter, Slack or anything else – now you have multiple things you need to check – life gets worse not better.
What I tell people about Redmond is that it truly is a bubble – Google is the same really. All your software is provided my MSFT (other than the occasional Adobe PDF), it’s heavily skewed towards a mono-platform environment and MSFT always rolls out the latest beta release of enterprise applications like Exchange. I suspect most folks there still carry Windows Phones.
Whether it’s the Valley or our enterprise clients (we have the largest companies in Banking, Retail, Telecom in the US on our platform) – no one else looks like MSFT. Companies have PC platform diversity (Valley in particular skews 80%+ to Mac in my experience), more heterogenous enterprise infrastructure with a lot of legacy and they don’t flip the switch and suddenly roll out the latest beta to everyone.
When I first got there I was surprised – it was all iPhones and Android devices. Then what I realized when I went Mac OS is that the Mac is actually a BETTER enterprise PC client than Windows in a lot of scenarios. It works with web apps, almost every enterprise company supports it (b/c they have to support iOS for mobile), it’s more secure and it gets less frequent updates. Apple isn’t perfect – their software quality has degraded significantly in last 24 months – but it’s still better than the alternative.
Whew… I’ve been meaning to write that for a while. I really would love my former compadres in Redmond to do better and succeed. I think the marketplace needs them and there seem to be certain teams that realize that end users (like me) don’t care about platform plumbing – they want something that works. But Outlook team doesn’t seem to be one of those teams. And all the attention seems to be focused on Mobile. If Google every does get their act together – they will clobber MSFT in Office and Outlook – my kids (20 and 18) use Google Apps 95% of the time because that’s all their schools needed. With no innovation by MSFT – Google is narrowing the gap — and addressing a generation that hasn’t been trained to need all the features in Office. Scary…
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Lots of great points in your screed 🙂 I’ve been close to all those teams and have a pretty good sense of what’s going on. It feels like office on the PC has been more or less abandoned, or is so burdened by Legacy Code that it’s almost impossible to make significant changes. Then there’s lots of work going on in mobile apps of various sorts, but other than the core office ones it’s not super clear why they exist. I know that there’s a lot of internal payback for years of windows dominance going on, so the windows doesn’t matter thing may be impacting it. Generally, it doesn’t feel like there’s a strategy other than to try to get consumers to pay a subscription, which is a good idea from a Microsoft financial perspective but not much of a a product vision.
Google is kind of mystifying, I agree. There’s a hole in msft they could drive a truck through, but I suspect they just can’t wrap their heads around caring about the enterprise. It doesn’t get them significant data, it can’t be ad-based, and it’s not cool science fictiony technology.
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Great read David. And hello David! Why has no one really solved the contacts problem yet? I’ve got duplicates and my contacts, even though I try to stay on top of them, are a bit of a mess.
Miss you both.
Larry
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