Office 365 is Productivity’s future, Google Apps isn’t

By: Matthew Bookspan

[This is part four in the four-part series on productivity]

After almost six years of using Google Apps for Work (GAfW – and all of the name changes in between), Blacktip is moving on from the venerable productivity platform. We are power users of the platform, eschewing all desktop Apps in lieu of the faster online collaboration features (see Part 2 of the series). We love not having a server and being able to access our data from anywhere. And, we love that GAfW has had very little downtime during this era.

How are we power users? Let’s dive into that…

  • We built templates and leveraged Google scripts across the suite.
  • We utilized Google Drive’s colors and powerful document sharing.
  • We co-edited documents until we turned blue.
  • We are Gmail power users with advanced filters and leveraged labels to their fullest (without going crazy).
  • We mastered the Google Apps Admin and third-party management tools (BetterCloud).
  • We mastered Hangouts and the ill-designed Google+.
  • We leveraged all things mobile (iOS of course) with Google.
  • We integrated all of GAfW into Chrome via custom extensions to drive our productivity forward.

And yet over time, Google Apps for Work became cumbersome for our workflow. We stopped using Google Hangouts for communication and moved to Slack, as it was more powerful and more effective at stripping away the layers of email (making us more productive). Further, Slack’s user interface is much nicer and there are native Apps for OS X and Windows.

We had issues with Google Drive’s speed. It was slow, forced us to reload the page (due to a lack of responsiveness) within Google Chrome and had some drag-and-drop issues. We synced via the Google Drive desktop App and thankfully had minimal issues compared to others. The fundamental issue with Google Drive is that it tries to supplant an existing file server. There is no modern thinking here – only replication of existing knowledge. This is not a productivity enhancement, it makes for a productivity replacement.

Consequentially, we ran into issues with sharing (mostly with external parties) who didn’t have GAfW. Yes, these users could open files, although many times they were required to create a Google account to access the information. This is clunky and causes people to turn away (or ask that we send an email message with a file attachment).

Google Calendar worked well for our team. We would overlay individual calendars to find team member availability easily. As Google ramped up this tentpole, we could see the greatness of Google Calendar – it really is one of the stand-out Apps in the suite. The only real negative was Google’s CalDAV implementation, which never worked right in any desktop App – like Calendar/iCal (sync issues, duplicates – what a mess). To really make use of the App, you had to use it in the browser, preferably Google Chrome.

Gmail was a mixed bag for our team. While I personally used it exclusively for the last three years, our other team members preferred using a desktop App (Mail, others) given their familiarity and the single capability of having multiple email accounts in one tool (AKA – multiple inboxes).

Gmail is all about speed and access of information. Gmail’s search is undeniably powerful and fast. However, as we added more email over the years, Gmail would slow down. And we mean slow – waiting up to 15 seconds to display a label’s contents over a very fast Broadband connection. Gmail also is very non-standard and doesn’t work as well outside of the browser. The team would run into issues over the years, utilizing Google’s “version” of IMAP. As the years progressed, Gmail ran better in the native Apps (Mail, Outlook, etc.), although there are glitches from time-to-time.

Using Gmail takes a different thought process – you’re using email in a browser. Labels replace folders. Email messages can be “tagged” with multiple labels for easier finding. It’s all quite clever. Google provided many new ways to sort/filter email messages with an enhanced inbox mechanism (set by priority, set by category, etc). Many of these options were tried over the years, although we would always come back to the standard inbox due to familiarity and speed. Keyboard shortcuts were readily available, which helped with both the creation of messages as well as the filing/searching.

In order to share email messages between the team, we leveraged Hiver, a shared label tool (AKA public folder) for Gmail. Hiver works well, although its synchronization speed could be faster. Google’s notion of a shared inbox doesn’t exist (even the Collaborative Inbox in Google Groups is insufficient), so this is what we used to ensure all of us were aware of the latest information.

Google Contacts is a marginal product. Maintaining contact data is cumbersome. Sharing contacts is poorly implemented and there are very few integration options with third-party Apps. Contacts is undoubtedly the weakest link in GAfW.

Next, Google Sites is great for those who want to build a simple Intranet. Yes, Sites is a Wiki platform and it can be used for hosting web sites (please don’t – it’s a less than ideal scenario). When we implemented Sites years ago, we found ourselves replicating much of the content in Google Drive. Then, we would link to that content (or host the data in a Wiki page). We ultimately abandoned our internal Site because we were leveraging Drive more and more. Sites as a tool became a burden. Would it be the same issue for someone else? Maybe, maybe not, as it all depends upon the structure and usage of the site.

Lastly, the core suite of Collaboration Apps (Docs, Sheets, Slides) are all quite reasonable to use, with the exception of Slides. If you’ve ever used Apple’s Keynote or Microsoft’s PowerPoint, there really is no comparison. Simply stated, Slides sucks. Both Docs and Sheets, and especially Sheets give most business users the core capabilities to create and manage their data. We’ve built some impressive Docs (you would think they were authored in Microsoft Word given the formatting) and some powerful Sheets over the past few years. Honestly, GAfW delivers on these two Apps.

So why change? Why leave a toolset that we’ve become so intimate with and have a deep set of shared knowledge? Well, read on and learn…

Moving to Office 365 – Changing Blacktip’s Productivity

A few years ago, if you would have asked anyone at Blacktip about Office 365, they would have scoffed at the notion. The platform was visually unattractive, was known for downtime and it seemed to be a runner-up to Google Apps for Work when it came to productivity (Office Online initially wasn’t as functional as Google Drive + Docs).

Today, Office 365 has the core components of email, calendar and document collaboration (the two platforms are relatively equivalent). In fact, here is a venn diagram (lifted from ZDNet) comparing the two:

Google Apps Office 365 Venn Diagram

This diagram is a little out-of-date (from 2015), although it still closely reflects the comparability between the two offerings.

The desire to change for Blacktip became two-fold:

  1. Make the business even more responsive.
  2. Improve how the team communicates internally and externally.

First, Office 365 caught up with and has surpassed Google Drive + Docs in practically every way. The Office Online Apps are more functional than their GAfW counterparts. Sharing files became less cumbersome and co-editing is more visually synonymous with Google’s offering. In typical Microsoft fashion, it took until version 3 (a very old reference here) for Office 365 to become a more viable product.

One of the major features of Office 365 is user choice. We now have the choice to co-edit online or in the desktop Apps. This is significant because it provides a more flexible workflow for our team. Some of us prefer the desktop Apps, while others prefer the cloud editors. The best part of this is that you, the end-user can select the type of monthly licensing based upon your user’s needs. There is no reason to force the desktop Apps and further, there is no reason to spend money when you do not need to do so.

Personally, after three years of using Gmail, I look forward to the simpler user experience of Outlook Online. I’ll miss the colorful labels in Gmail, although I won’t miss the slowness (Outlook Online screams in speed compared to Gmail). Outlook Online’s email composition editor is easier to user and has more formatting capabilities (can someone say tables?). Next, Outlook Online’s + Outlook 2016’s calendar both now work similarly to Google Calendar when it comes to viewing multiple users (we now see the same overlap capabilities).

A long-time staple of Outlook’s calendar is that we can now easily propose new times for meetings within Outlook itself (or Outlook Online), rather than having to manually check the calendar to see availability (which is what we must do in Google Calendar). This saves time and effort. There are always client meetings, product demos, etc that require multiple team members to attend. And honestly, everyone is tired of playing schedule chicken.

Further, Outlook’s Addins enable us to extend scheduling and other capabilities without having to modify the browser with an Extension or other piece of code. Yes, we are modifying Outlook, although via a secure, sandboxed model, rather than injecting code into the web page (again, via an Extension or otherwise).

Another motivating factor is having Exchange Public Folders. Since we have many shared mailboxes (as mentioned above), we’re now able to use a native component of the suite (Microsoft recently refactored Public Folders in Exchange 2013, so now they are faster and more consistent with standard mailboxes) and we no longer need a third-party service. This saves us money and removes risk of invoking a third-party App to solve a business problem.

Similar to GAfW, Office 365 is enhancing productivity on a very fast monthly schedule. Microsoft sees the future of productivity and knows that the Online model is more efficient than the desktop Apps. Do we foresee the ending of the Office Desktop suite? Not anytime soon, although we do see more flexibility and capabilities being added to Office Online given the pace of development.

The Big Productivity Change

Last Fall, Microsoft announced their Office 365 Groups feature. At the time, it wasn’t completely baked, although you could see their intended direction. Today, about eight months later, Office 365 Groups have become incredibly powerful. This capability set alone is what is driving Blacktip’s motivation. We mentioned this feature in part three of this series. As a refresher, here is a slide deck:

Office 365 Groups UpdateChristophe Fiessinger


Think about working in context with your data amongst projects or teams. Today, most of us still work in silos and/or small teams. We leverage multiple tools (Apps/Software or Pen/Paper) to convey our work. We sit in meetings and have status reports. It’s all tedious and non-productive. It has to change.

With Office 365 Groups, we now have this contextual model of usage. We can access client information within Outlook (Online or 2016). We can view related files (via OneDrive for Business), meetings and notes (via OneNote) all in on view. It’s simple. It’s fast. We no longer have to search through Google Drive to find the related information – because again – it’s all in context.

Further, with Office 365 Planner, we have integrated tasks within Office 365 Groups. We can create and assign shared tasks with each team member. Everyone has clear objectives and we’re all able to review them in a single, unified view. Again, we’re enhancing productivity in a contextual way, which in turn, makes the team more effective.

Lastly, utilizing Office 365 Connectors, we can enhance Office 365 Groups with third party information. Now, imagine seeing related sales opportunities (via or Dynamics). Imagine seeing the latest business trends via news sites. Or, imagine having the latest software development data available in-context with your Office 365 Group. This is now all possible and the list of third-party integrations is only growing.

More Office 365 Productivity

Microsoft recently announced a revamped SharePoint. As someone who worked at Microsoft during the incarnation of SharePoint (Tahoe anyone?), it’s incredible to see how far this solution has come. Where Blacktip sees value in utilizing SharePoint is how it integrates with Office 365 Groups (the new version of SharePoint is the back-end file system for it) and how it makes things easier to manage.

Compared to Google Sites, the new SharePoint is leagues ahead in functionality and usability. Most importantly, we’ll have a mobile App (iOS to start), making it easier to review and potentially administer the information.


As we mentioned in the beginning, after almost six years, Blacktip is leaving Google Apps for Work. It’s a great product and a perfect fit for many businesses. However, we believe that if given the choice, the new Office 365 platform is the better option between the two. Microsoft is delivering productivity in a new way, which only means more progress for business.

Will Blacktip regret this choice? Will it be a difficult transition? These are both significant questions, so let’s answer the second question first (it sheds light on the first). Transition and change are always conceived as difficult. However, it all depends upon how you rollout the change and how you validate your choice. At Blacktip, we have no agenda other than being better. We want to use the best tools and provide the best capabilities internally. We can then share these ideas with our clients and with prospects looking to improve their businesses.

So will we regret this choice? Doubtful. In fact, we see a very bright future with this new platform. Will there be glitches along the way? Of course. We’d be foolish to think otherwise. Still, we’re prepared to make this transition and have very open eyes about the process as we go along. We believe wholeheartedly that we’ll be a better organization once this transition is complete. And, we believe any organization that is looking to improve can leverage our learnings.

Of course, we’re always happy to share more about Google Apps for Work or Office 365. Feel free to click the Connect With Us button below to discuss how either of these solutions can make your business better.

Onward and upward!