An on-prem gal in an O365 world

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I’ve been thinking about writing this post for awhile now. Its about the crossroads I found myself at in my decade-long SharePoint career.

What crossroads am I referring to? I’m an on-prem gal whose spent the last decade or so installing, configuring, and supporting SharePoint Server, designing solutions, even writing code when the need arose. I’m a mile-wide and an inch deep on many aspects of the SharePoint field. You could say I’m a SharePoint generalist.

A couple of years ago, I could see the writing on the wall that in order to stay relevant in my profession I would need to move into the cloud world in some capacity. I’m committed to the Microsoft ecosystem and am comfortable with that decision so the cloud transition for me meant O365 and Azure.

For my current skillset, I believe there were 2 paths that were suitable.

Path 1: become a technical expert on the pieces that need to be well understood in a cloud environment: Azure, identity management, hybrid scenarios, tenant administration, etc. With many organizations not able/willing to move all of their workloads to the cloud, these skillsets will be in demand for many years to come in my opinion.

Path 2: focus on the adoption piece, working with customers who are moving to the cloud or in transition to it to help them leverage O365 for their business objectives. Although this is generally not a technical role, it does require a certain level of comfort with technology, ability to work with a fast pace of technology change and a strong willingness to dig in and figure out how features work. This is a critical role in the successful deployment of O365 in an organization in my opinion.

Although you can do bits of both and I’m sure I will, to be most effective I believe you should focus on 1 path and become an expert at it.

I’ve chosen path 2. Although I think it was the right decision for me, I’d be lying if I said it’s been an easy transition.

What have I learned so far about the skills required?

  1. You must learn how to evangelize the O365 product at the same time as giving practical “boots on the ground” advice to customers. They need to know how to use this stuff in the real world. It’s where marketing meets reality.
  2. Be able to articulate the “when to use what” talk to your end users. This is a BIG one – and with new (seemingly similar) products being released on a regular basis this is something customers struggle with. They are looking to the adoption expert (me? you?) to help them make sense of the options.
  3. Help the organization with governance – think O365 Groups and site sprawl. This is a real issue and if left unchecked could become a big problem.
  4. Be able to stand in front of a group of people and explain why a feature in O365 works the way it does when you sometimes don’t fully understand yourself (and look confident doing it). I’m kidding a bit on this, but you kind of know what I mean right? You need to stay ahead of the curve.


My tips?

  1. It helps to have a strong support network.  This means tapping into the collective wisdom of those around you. I’ve found fantastic support from these things:
    1. Twitter (connect with me at @JoanneCKlein)
    2. Microsoft Tech Community (
    3. (
    4. Microsoft’s FastTrack (
    5. Support ticket thru your Microsoft official channel (O365 Admin)
    6. Personal connections from the SharePoint/O365 space. It’s a very strong community extremely willing to help.
  2. Help others around you struggling with something you’ve already figured out. This is “work like a network” in action.  Also, don’t be afraid to ask a question if you don’t understand something. At times you’re the one seeking an answer, at times you’re the one giving the answer – its the way a network “works”. 🙂
  3. Get a partner tenant set up to try and stay ahead of the curve. Try new features out before they’re rolled out to your tenant and the questions start coming in.
  4. If you can, enroll in the first release program for your tenant for the same reason as above.
  5. Don’t like how something works or have a good idea for an improvement? Put it in UserVoice.  Microsoft is watching this. It’s a fantastic product improvement channel in my opinion – feedback from those of us in the wild that use the product day-to-day.
  6. You don’t have to know it all. Give yourself some time to figure it out – it’s a big product with lots of moving pieces.

I’m excited for what lies ahead and the new skills I’m developing.  Even though I find myself outside of my comfort zone at times, I’m confident I’ll be a stronger resource because of it.

If you’re making the move to O365, what’s your path?



  1. Great post, Joanne!

    I had this realisation a few years back after running a SharePoint farm for a very large customer for a year. I changed employer and got a role focusing on your path #1 option. And I recently changed role to be more focused on your path #2. I think you’re right that you will always have a little bit of both, but a focus on one path is important.

    I think you’re spot on with your skills list and your tips! That’s great advice for others going down this road.

    My additional tip would be: Have an opinion.
    Your customers want the benefit of all the time you’ve spent in the industry working with this technology. Let them know what you think they should do, or at least how they should figure out what to do.

    And finally, I’m sure you’ve seen these, but I thought I’d share some of my go-to resources:
    Office 365 Roadmap
    Office Blogs – To learn more about how the service is changing.
    Office 365 Service Descriptions – Helps to understand what features you get for a given license type.

    All the best!

    1. Thanks Aaron! Great feedback. You’re right about the importance of having an opinion and leveraging your own experience in the industry. Thanks for that reminder. Sometimes it’s easy to forget how valuable that really is particularly to customers that don’t have it. I’ll update my post with some of your resource additions on an addendum. I do use them but never thought to include them. Appreciate the comment. 🙂

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