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Common Mistakes Made in Managing Microsoft 365

Managing Microsoft 365 is a multifaceted endeavor that may take some by surprise with how involved it can be. That said, it’s never too late to start adjusting your approach and optimizing your governance strategies.

In this week’s episode of #O365 Hours, I sat down with Office Apps & Services MVP Richard Harbridge to discuss some of the pitfalls organizations often fall into as well as some of the overarching issues with Microsoft 365 governance in general. Watch our discussion below or read the full transcript at your convenience!

Guests: Richard Harbridge, CTO at 2toLead (visit their website here)

Topics Covered:

  • When you think about common mistakes for managing Microsoft 365, is there one that stands out the most to you?
  • We often talk about the management issues around technology versus process versus people. As technologists, we often focus on the technology first. When looking at management mistakes, where do you think we should be prioritizing our efforts?
  • We often talk about governance, and people’s eyes glaze over. Are organizations being as thoughtful on governance as they should be?
  • Is there a different way we should be talking about governance?

When you think about common mistakes for managing Microsoft 365, is there one that stands out the most to you?

RH: It’s a hard one to narrow down. But if I had to pick one, it’s taking on too much cost of ownership and not involving the business in the right ways. At the end of the day Microsoft 365 is a digital experience platform. It provides a lot of different capabilities that empower the business to do more. There has to be continued sustainment and support of the business. The other challenge is if IT doesn’t involve the business in some of the leadership and other gaps then IT takes on too much cost to ownership and they have to manage everything right regardless of how the business is using these technology platforms. So I know it’s kind of cheesy to say that the biggest gap in management is the IT-to-business relationship and how the business should help and be scalable, but that is actually the biggest problem area for most customers today.

CB: I know that it can be difficult too, with the size of an organization. I mean, you have a smaller organization, where more people might be very vocal and active members of the leadership team, but those discussions become more difficult as a company gets larger. And so in some ways, is it just about making sure that you’re working closely together and having those discussions early on and maintaining them as the company grows?

RH: Yeah, I’d say be it in a small org or a large org, the reality is management is distributed. And so while it’s true that today some of the management experiences are very technical and driven to IT-centric discussions, the reality is that if you use the technology the way it’s meant to be used, you can actually distribute a lot of ownership for things to the business.

So it might do some due diligence baseline enablement, but there is an intentional decision to hand off and have at least some management-level capabilities executed by the business with IT support proactively. I think don’t some organizational leaders fully appreciate that they are just as responsible for digital excellence as IT. I think that’s where a lot of the problems stem from.

CB: Right, that’s definitely part of it.

RH: And then there’s the issue of business leaders suddenly deciding to use technology outside of IT’s recommendations. So they’ll go use Dropbox or Box, which are less secure and have a host of problems compared to Microsoft 365. But IT has no choice but to support it. They’re unsanctioned file sharing tools and support for them will come at a cost.

In scenarios like this, IT has to be able to say to the business, “Here’s the choices you’re making, here’s the cost impact, and here’s how we could be more cost effective for licensing, management for administration, and so on.” Executives need that visibility or they’ll never pivot to what is more sustainable for the business long-term.

When looking at management mistakes, where do you think we should be prioritizing our efforts?

RH: Well, let’s summarize a few of the challenges we have. One of the challenges today is that users really struggle to identify the content and the work that they do so that we can proactively support them with processes, policies, etc. So a solution that we’ve had for many years that’s still viable today is to have users put their content into the departmental HR project site where we can apply the proper labels and properties to these items. Then, based on that, there’ll be better searchability, protection, compliance retention, etc. There’s a lot we can do there, but most customers don’t automate enough of that.

Then there’s the question of “What if they put content in the wrong place?”And there’s almost always a clear process-based reason for it. For instance, it could be a training or education issue where a user didn’t know that they could put content in a certain place to be shared properly, and thus they try to share it through other means. It all comes down to understanding where the pain point is stemming from, and we should do a better job of tracking that.

The goal is to introduce new technology to users in an intuitive way so they’ll see how much more seamless the proper external sharing solution is (for instance), and how much more painful the old way of sharing was. There are certainly times when technology holds things back, but I think most of the issue is in the process.

Are organizations being as thoughtful on governance as they should be? 

CB: Governance is clearly not a one-time thing. It’s an ongoing, dynamic conversation with your various stakeholders about how technology’s changing and how business needs are changing. You need to talk about shadow IT. And if you’re not having those conversations, users won’t hesitate use unsanctioned third-party solutions. As you mentioned earlier, it’s all about educating your users and working to ensure they’re aware of what the official solution are capable of.

At the same time, it’s possible that the policies that were in place were too restrictive and users weren’t able to do something that they needed to do. Honestly, I see that most often when it comes to the inability to go and collaborate externally with people.

RH: Yeah. And let’s be honest, the reason that happens a lot of times is because the users don’t know the tools in the ecosystem that make external sharing manageable. While I love what’s available out of the box, there are plenty of improvements (like shared channels) that can be used to supplement Microsoft’s native offering.  So, you know, understanding that these issues are surmountable, should lead to users feeling enabled.

Is there a different way we should be talking about governance? 

RH: The Microsoft 365 space is a variety of different workloads, needs, and spaces around the digital employee experience. And when you think of it holistically like that, it makes sense that the policies around it and people who work with it are going to evolve year over year. So, I think fundamentally people should see governance in the same light that they see everything that essentially makes organizations more effective and supportive.

There are some basic rules that everyone needs to be aware of for them to be successful, but there are also some things that are just domain expertise. They don’t know what they don’t know. And so the more customers can invest in understanding what those foundational core elements are, the better they are to build from there.


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Christian Buckley
Christian Buckleyhttp://buckleyplanet.com
An Office Apps & Services MVP, Microsoft Regional Director, and the Brand Alliance Director at AvePoint, Christian Buckley is an internationally recognized author and speaker and runs the community-focused CollabTalk blog, podcast, and tweetjam series.

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