As regular visitors would already know I mostly write technical articles here on Exchange Server Pro and tend to stay away from writing content that might be considered to be “sales and marketing” material.

By that I mean I do not dedicate pages of this website to promoting one particular product over some other competing product*. In fact, as I’ve discussed with Microsoft staff in person, I see my contribution to the Exchange Server community to be one of assistance for people who have already decided to migrate to, or are already operating, an Exchange Server environment.

So I read with great interest two blog posts (part 1 and part 2) by Cloud Sherpas, a cloud services company that is partnered with companies such as Salesforce and Google.

The articles exist to debunk the myth that “Google is too big of a change for my users, Office 365 is easier and more familiar.”

I disagree with some of the statements in the article and have left a comment on one of the articles pointing out in particular the infographic used in the article. When my comment emerges from moderation it will be interesting to see their response and whether others agree.

Aside from that a healthy rebuttal has already appeared from fellow MVPs Tony Redmond and Sean McNeill. I could add to the debate but I think another single voice isn’t what this discussion needs.

I would rather hear from you actually.

I’m sure many of you have points of view based on personal experience, or the experiences of your customers, on how good/bad the transition from one service to another was, or how confusing/simple your end users find one service compared to another.

Please feel free to leave a comment below, or if you’re especially keen by all means join the debate on Cloud Sherpas’ blog as well.


* To the best of my recollection, and a search of this site, the only previous “comparison” posts I’ve written were this one in 2010, and my recent move from Google Apps to Office 365.

About the Author

Paul Cunningham

Paul is a former Microsoft MVP for Office Apps and Services. He works as a consultant, writer, and trainer specializing in Office 365 and Exchange Server. Paul no longer writes for


  1. David Nicholls

    Ignacio, I think your point on training is spot on, I remember my old Systems Analysis module at College when user resistance to change was drilled into us by the Tutor, and I also agree that very often I.T people get so carried away with the technicalities involved that they forget the end user.

  2. Raoul Teeuwen

    Thanks for pointing out the comparison. I’m a Google guy myself, use Gmail, Google Drive etc. I started looking for something other than Microsoft long ago, since i believe in the benefits of competition.

    Anyway: i’m not a fanboy. I use all platforms. And besides having an eye open for enough competition, i use what’s best for me.

    Last year i helped a company move from an outsources WinTel hosted desktop to Office365. What i found:

    – sometimes you’ll having a hard time to get to speak to a person that will actually solve your problem. A colleague of mine spent many days and hours on the phone with MS-people around the globe
    – but: we were able to call someone. And when posting questions in forums, i received replies fast, and most of the time it solved my question
    – i got to dive into security and found out about Bring Your Own Key offers and the RMS protection of files, both Microsoft developments

    In the same period i signed up for a Google webinar. Did not receive any reply. Contacted the organiser: received a link to prerecorded slides. Replied, as i’d cleared my schedule since it would be a live webinar. Did not get an answer. Tried to contact Google about Apps for Business through their web form twice: did not receive any reply. Sent a tweet to a Google twitter account. No reply. Good luck getting in contact with Google! Non responsive!

    For now, i would recommend O365 over Google Apps in most cases, apart maybe from small organisations or specific cases. I hope Google is able to improve, but in my view Google is loosing the Office-for-business battle as Microsoft is developing the office online apps (Word etc), improving SharePoint online, releasing apps for mobile etc

      1. Raoul Teeuwen

        Thanks Andrew, great to hear there are ‘pockets of support’ ;-). But Google has scored “minus points” by not responding to 4 attempts i did though official channels … They should either reply on those channels, or stop having them…

  3. Ignacio Parlade

    Even if you can invoke GAM inside a powershell script, it’s usefulness is limited, in my experience. Let me explain this in the context of the project I talked about.

    We had some non-technical constraints that we had to take into account. One of those was the need to migrate about 100 users each day, divided into five different time zones. We had much of the process automated, but at one point we had to set up forwarding for each user to the O365 account. Now, technically GAM allows you to set up forwarding, but if you read the fine print of the documentation, it does NOT work unless the user has previously acknowledged the address that you are forwarding to. That was a showstopper, because you cannot rely on users to do that. Forwarding the whole email domain was not an option for us in this project.

    The funny thing is that the web administrative interface for Google Apps allowed us to set up forwarding in a way that didn’t require user permission, but GAM didn’t have that option.
    We had to resort to automate everything but the forwarding, that had to be made manually. It didn’t take up much time, but was prone to more errors and affected our migration schedules.

    Another example, Google has the option for the user to put a limit on the number of items that will be downloaded via IMAP. The problem is that if that limit is set by the user, the mailbox migration tool will only move content up to that limit and will tell you that the move was successful and that all content was moved. Now, imagine the problem if we migrate a mailbox, we think all was migrated and the user doesn’t notice until after the Google account has been decommissioned. We had a handful of cases that we discovered before deleting the Google mailboxes, but GAM didn’t offer any way of knowing if that option was set for an user or not, nor were there any reports that gave that information.

    What we did was to check the statistics of the number of items moved in each folder. If we found a suspicious number (say, 10,000 items), we would reset the user’s password, entered into his configuration options in Google and see if the option was enabled or not. That’s how we discovered a couple of cases.

    Again I don’t believe this way to be optimal, at least if you have 2000 users as we had. In Powershell I would most probably be able to query that property of the mailbox object and automatically disable that.

    Also, we found GAM to be very unreliable. Sometimes, a well tested command would not work, without giving any reason why, and if you retried the same command just after failing it would work, to fail three times after that. We had a scheduled task that exported some GAM generated reports nightly, that we later treated in Excel in some creative ways to use them as input in our powershell migration workflow. About 25% of the nights the commands would run but wouldn’t produce any result.

    Bear in mind that we did that project last June, and things might have changed from then but, again, that was our experience. My opinion is that it’s just not in the same league, administration-wise.


    1. Andrew Price


      I dont know your mailflow – however I probably would of routed the mail – with a regex rule + default Route config for users / domains needing to be routed.

      With the forwarding you are correct in away – The restriction is for Domains that arent owned by Google or an alias for the user. Again unsure of your setup. But you could of applied Aliases to the Google Users, then set the forwards via GAM, as these users own the addresses they don’t need to provide a code for authentication.

      For Migration – I would of used – Cloud Migrator by Cloud Solutions –

      Unsure of the tool you were using for the migration. It is true that Google can cap out on IMAP limits, and this is a floating number without the privilege if being able to change the quota. There are a few ways to get around this..Use a tool built with Google IMAP limitations in mind / migrate in date ranges in phases . I haven’t seen this before specifically when doing IMAP to IMAP for example Google to Google, where estimation is wrong, I have seen it slow down however.

      With the reports , I think I would lean to report API limits on Googles end , rather then the GAM application , obviously unsure of what the reports were and how often they were run. I have used these extensively, and haven’t really had an issue with them

      Its not good when a migration doesnt go well – @andrewpriceau if you ever do it again.

      1. Ignacio Parlade

        Hi, Andrew.
        There were external limiting factors that didn’t allow us to do as you suggest, we explored that way also.

        As for the tools, we used MigrationWiz that indeed knows how to work around the limits that Google and Microsoft imposes on the migration speed.
        But I was not referring to that limit, but rather the IMAP item number count limit all users can set up if they so wish. There’s no way to know if the user has enabled it or not, and it’s a large potential risk for mail loss.

        Finally, I might add that the migration project was a large success, in fact it has been showcased in Microsoft’s page. Everything went smoothly and according to the plan, and the customer was really satisfied. I don’t know what prompted you to think otherwise, perhaps I didn’t explain myself correctly. What I tried to say is that, compared to O365, Google Apps tools are way behind in capability and funcionality.

        For the record, I work as Project Manager / Architect in a Microsoft Gold Certified Partner, Cloud Accelerate and Preferred Deployment Partner for O365. That being said, I’m no fanatic and try to keep an unbiased opinion about most things.

        As I said, each platform has its advantages and will suit better some customers than others. And in the end, most probably the user won’t care 🙂


  4. Ignacio Parlade

    Hi, Paul. In the last months I undertook a project to migrate from Google Apps to O365 a multinational company in Spain, Mexico, Peru, Chile and Brazil, so I can share a few of my experiences during it. The project was a success from the technical point of view, but we do projects in order for people be able to do their jobs better, so all aspects must be considered.

    Regarding the differences between both services, most users fell into the “don’t really care” category. There were some enthusiasts for one or the other platform, and most of the pro-Google people often complained they were unable to do things in exactly the same way. Mind you, those were persons who had fully exploited all the different functionalities and features of Google services, and needed to do things differently to get to the same or similar outcome in O365. For instance, one user protested he couldn’t live without Labels the way Gmail used them, and complained that the Gmail app in Android was better than using the native mail client (Androind 2.3, btw). And the CEO was briefly annoyed that searching for mail in his iPad didn’t look into the folders he had in his mailbox (we did find a workaround). But there were also power users on the other side of the fence, that found very useful features for their job in O365.

    However, most of the time complaints were because of the natural resistance to change everybody has, regular users really don’t care about most features. Many people in the company still hadn’t embraced the change from the old system to Google Apps, so the second change to O365 made them a bit more resistive and hostile, so to speak.

    Only in one thing I think the complaints were right, and it was that Google Mail felt more snappier and responsive. They were using old computers, mostly with XP (yes, I know…), and the OWA interface was heavier and slower in those PCs.

    And the need to train the users is real, it doesn’t matter if they are familiar with Outlook, they’ll need help to be able use sharepoint and lync. Apart from OWA and Outlook, the rest of features in both O365 and G-Apps require training for the users, in my experience.

    The migration itself presented some challenges. The Microsoft provided method for migration OOB (IMAP) wasn’t feasible because of the need to know user passwords, so we had to rely on third party tools to handle that via OAUTH authentication. We evaluated quite a few, and found BitTitan’s MigrationWiz clearly the best of them (although not perfect and expensive).

    One other thing you must take into account while designing the migration project is that you aren’t migrating just an email system, but need to handle all the associated services from Google as well. For instance, we had to find a way to export Google Drive contents into Skydrive and, if Google Sites are used, you are in for a nasty surprise since tools for migrating content to Sharepoint are not exactly cheap (nor reliable in my limited experience).

    Other things to plan for is that mailbox size will increase at least 30% on average, since labeled mail items must be duplicated, and that your schedule must accomodate bandwith limits from Google and Microsoft. Migrationwiz handled it quite well, but with other tools you could end up going way slower.

    My personal opinion is that O365 is better from the point of view of integration and features. It shows that enterprise computing is Microsoft’s main business opposed to advertising, and it’s very aligned with Microsoft strategy and portfolio of products. If it were for me, I would choose it anytime over Google Apps.

    On the other hand, Google Apps is cheaper, and I would recommend it for customers who don’t demand lots of features from their mail or productivity suite. I feel that feature-wise is somewhat like time travelling to the days of WordStar (Ok, I’m exaggerating, but you get the point) and many people in that company felt Google Apps were more toy-like that Microsoft’s.

    And yes, one more thing: O365 can be managed from Powershell (most of the migration was made form there), try to do something like that for Google Apps, it’s night and day.

    I hope others might find this information helpful for preparing or evaluating a Google–>O365 migration. Other than that, it’s just my opinion.


    1. Derik VanVleet

      Ignacio, Great write-up and I agree nearly 100%. Your experience on the cited project is very spot on with user behavior. We have migrated on premise Exchange and Office 365 companies to Google and experience nearly identical responses. That was the point of my articles to begin with. I can see you “got it”.

      1. Ignacio Parlade

        We techies tend to forget that users really don’t care much about features. You might set up a perfect system to, say, share the information of a project with others, but they will keep sending 25 Mb files over email. It’s inertia. How you define success?

        For many users and their companies, we are little more than plumbers, a necessity. We tend to forget that. When they get home they won’t share the greatness of the new OWA or how nice are Labels in Gmail with their families. They would if it were something that allowed them to get home earlier or radically change their lifes.

        I have over 12 year of migration projects in my backpack, and it’s always the same, if you want any technology to be adopted, it has to:

        * Make life easier for the users (that is, give them some advantage once their adjustment period passes)

        * Provide some CLEAR benefit for the company (because if not, it won’t be purchased)

        And you have to:

        * Find some “champions” (or early adopters, preferably high profile persons in their companies that lead the charge and iron out the glitches)

        * Train the users (because even if they don’t really need the training it becomes the perfect excuse for not using the new system)

        * Give it time before evaluating whether it was a success or not

        At the end of the day, they don’t care whether it’s Gmail or Office 365.

        I always put the same example:
        Imagine self driven cars start to appear at the car dealers. Would people buy one? Most of the people would say “Nah, I’ll stick with the old way, this is too new for me. Who knows what that car will do in a dangerous situation…” and such.
        But once streets start filling with self-driven cars that work, the next time that person wants to buy a car, he will feel stupid about not taking advantage of all the benefits of a self driven car, and will probably return home with one. He will try to save face “you know, those were real cars, but this is just so much more convenient…”.

        Remember smartphones? Who needs to be connected all the time? 🙂

        Bear in mind this is my experience. In some countries , companies and “cultures” it’s easier to force users to adapt to things or start using something new, and perhaps your experience in that matter is different.


  5. Derik VanVleet

    So, if I go Office 365, let’s say E3 since that is what Microsoft pushes the hardest, you say “Workshops or training comes for the *additional* services, like Lync, OneDrive or Yammer.” Now, you can argue that people can use an E1, or some other SKU and transition to E3 as they mature in their deployment; still adds complexity. Leverage a hybrid deployment? Microsoft’s own IT department stated in their TechEd session last year that a Hybrid deployment is complex and costly.
    In order for customers to gain full leverage of Office 365, and leverage all the “additional services”, they need training; you also state as much. That is all I’m saying, nothing more than that so, please, stop making it more than that.
    We both can go back-and-forth about customers that hated one platform over another; Forrester and Gartner agree on that as well, so that has no value to me, or to customers to be honest.

    1. Steve Goodman


      Point was simple – just to do their normal day to day job that they were doing before doesn’t require training like your said it does.

      You also said that 40-60% of people use Google Apps at home, if my comment and response to that has no value to you, why make the point in the first place?

      You do not address my comment on the inaccuracies in part two of your article. Are you going to update your article listing every single desktop and mobile app that accompanies Google Apps, or instead put the “desktop, web and mobile” or “web and mobile” in columns as appropriate?


      1. Derik VanVleet

        Again, read the context; take emotion out of your response. The 40-60% comment was in the context of, many users in an organization are already familiar with Google, Gmail specifically. It had nothing to do with “a move to Google (or Office 365) disrupted my organization”. Are all users in a given organization familiar with Outlook? Sure, because they are forced to use it, and have been for 20+ years. It is, unquestionably, the industry standard; nobody disputes that. However, 40-60% of users, in any given organization, are using Gmail at home, which means they also have a strong familiarity with that mail platform as well. As simple as that; don’t make it more than that, because it is not.
        How about I update my info graphic when you post a rebuttal to Microsoft assertion that Google Apps for Business scan users email to sell them advertisements, when everyone knows that they are no advertisements in Google Apps for Business. I failed to see it if you did rebut that FUD in the past…

        1. Steve Goodman


          No emotion is in my response. You accused Sean of attacking you personally in your comments yesterday, is it my turn because I am entering a conversation? My apologies up-front, I’m just talking about things I know about.

          Yes, some people are familiar with Google and GMail, but that doesn’t make a massive difference. For some people, a move to Gmail will be great – they may hate Outlook and have felt forced to use it. For many who are familiar with Gmail at home, there are tasks that require more than a web interface offers. Similar applies to K-plans in Office 365.

          Why would I post a rebuttal about Microsoft stating that Google scan emails for advertising or whatever purpose? I am more interested in calling them out on some of the things we probably agree on (more than you’d think). I don’t always need to do that in a blog post though, some things are better addressed through other channels.


  6. Derik VanVleet

    Thank you for the post; I put this same reply in our blog in response to your comment as well. In the context of the article I do specify that Google has two interfaces; Web and a mobile client. Can I reflect that in the info graphic? Sure; and I will have that change made to reflect “Web and Mobile App” for each. Including Outlook and other clients doesn’t make sense because to list every possible client applications for each of the platforms would not be reflective of what we see in the real world, again, for either platform.
    Again, the point of the blog posts is simply this; Microsoft, and their partners, tell customers that moving to Office 365 is simple and does not require end user training. I think that is a very false statement due to the changes in Office 2007/2010 to 2013 and the different file storage options and the introduction of Yammer (if you choose to use it). I also agree that there is training required when going to Google. Many people have a Gmail account, but may not be as used to Hangouts or Drive in the context of a business environment. I am simply saying, Google is not as big of a change as many people think, and to say training is not required for Office 365 is a very dangerous proposition. I think people are making it more than what it is meant to be and I think it is because the comments are all coming from diehard Microsoft supporters; which I used to be as well, so I get it. Thank you.

    1. Steve Goodman


      Why do you assume we are die-hard Microsoft supporters? You will find many MVPs, myself included, vocally critical of Microsoft on occasion too.

      So, there are multiple apps for different Google services, so it’s not just “web and mobile”, unless of course you agree Microsoft is “desktop, web and mobile”. Google does have desktop apps, so Google is just as much “desktop, web and mobile”.

      Training is *required*? Recommended, maybe, but certainly NOT required.

      Office 2007/2010 to 2013 is not a big learning curve. The learning curve was 2003 > 2007/2010/2013 due to the introduction of the ribbon. The client does not always need to be upgraded immediately, especially if organizations have a priority to move email first. Many end-users see no difference initially, therefore need no initial training. Workshops or training comes for the *additional* services, like Lync, OneDrive or Yammer.

      The big upheaval for users with Google is sadly that although the “techies” like yourself might not need to do anything special with email, the users do and have invested time and effort in learning the best way to do things. They may have desktop applications outside of the Office suite that integrate with Office and allow, for example, mail merge or document creation and form population. This extra workload it thrusts on users means that even when the end user might be familiar with Youtube or Google Search at home, they detest the new service forced upon them in the name of “Going Google”.

      Equally some users do not like services like Yammer, they might feel “watched” by Lync or don’t like the new look and feel to the Office 2013 suite, however I doubt they go home and tell their families about how it’s making their life a misery, unless it’s due to technical issues. I’ve first-hand experience of relatives, who don’t know what I do for a day job, telling me that the Google Apps implementation has caused chaos in their organization.

      The point is Derik, your article is incorrect and misleading. People who know their stuff will see through your FUD – for example as an Exchange Expert, you called OWA “Outlook Web Access”, which it hasn’t been known by for over 4 years. But some might not, and as people who usually try and make sure we keep *Microsoft* honest, we’re not going to give you a free pass either.


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