5 common mistakes in a Office 365 roll-out

In my days as a cloud consultant, I’ve seen and heard of a lot of implementations of Office 365. The conclusion is that many implementations weren’t really successful looking back at them. There is often no single factor responsible for this but rather several which I will list and talk about in this blogpost. These are the most obvious factors according to my own experiences.

The suggestions below are from my personal experience of success and not representative of any must do’s.


Everyone (not) onboard!

I’ve seen it more than once, companies and organizations feeling the need to digitize their business due to the pressures of modern technology and new ways to accomplish work, aka “the modern workplace”. Boards and stakeholders all know that to be competitive or to stay in the lead they need innovative services and tools, the help of AI and new ways to do work to keep up.

Many times, the decision results in Office 365 when it comes to the end user business flow. Licenses will be bought and the job of setting up a tenant, migrations and implementations end up on the IT staff’s table. Here is where it usually goes wrong!

This is not meant to offend the IT departments – Most of them do their job very well, however there’s often a communication gap between the people working in IT and the end users.

For example:

“A user walks in to work Monday morning – start the computer – to find updated software and newly installed applications not familiar to the user”

Technology is often thrown at people, forcing them to change their work behavior, and as we all know – to make people change isn’t a walk in the park! Especially when it’s forced upon them!

To mitigate this, careful planning is needed before the technology itself is implemented. Holding workshops with stakeholders and with representatives of the business is an important step for a successful rollout. Make sure to find the most obvious problems throughout the company and figure out how and IF Office 365 will help solve those!

What kind of services to utilize, the expected outcome of the project and how to measure success are equally important questions to raise, discuss and ultimately agree upon.

What and when?

Another mistake I’ve come across is to implement all the services at once!

The Office 365 suite include lots of services and applications. However, this does not mean you must utilize them all – and implement them simultaneously.

The first step here is to find out what services in Office 365 to use and which not to use. The next step is to decide which service(s) to begin implementing and then make a plan for future rollouts of the remaining ones.

There can be dependencies between the different services regarding features to be aware of! Plan so you won’t find yourself doing things in the wrong order, ending up losing time, functionality and in the end “money”.

Also keep the end user’s perspective in mind. They need time to adjust their way of working (change) and throwing every piece of technology on hand at them is not a good practice!

Carefully plan this out so it makes sense, both for IT and for the end users!



Not doing a test flight?

Doing pilots before every large Office 365 implementation is very important. I‘ve found it less common not doing pilots, but the importance of them is often underrated.

After determining the pains and expectations and what services to roll-out, a pilot group made up of representatives for the entire company should be put together. How you do this pilot depends on how the structure of the business looks and how it works altogether. It could be a whole department, people from different parts of the business, or even a few smaller pilot groups!

The thing to remember is that the pilot users should normally be working together on a daily basis and are conducting business as usual even during the pilot! Give them basic training of the services that are being piloted.

The main point when doing a pilot is to find out what works or doesn’t work and which services are most effective for the needs of the company!

Every company out there doesn’t look the same and there is no how-to manual that works out for everyone! Make sure to test and adjust during the pilot testing, everything from the services themselves, to settings, workflows etc.

No one to have your back

Relying solely on IT for driving adaptation among users as well as being the single point of contact regarding issues and feedback, is a lot to ask.

Having ambassador programs is becoming more common these days, but far from every company that would benefit from them is implementing such programs.

I find having an ambassador program something very useful especially in larger roll-outs. These are the basic steps to start building one:

Find people at all levels of your company to help out! For example, this could be someone who…

  • is passionate about the initiative
  • people listen to and have trust in
  • has knowledge about the services

Gather those people and ask them to be ambassadors of the Office 365 project. Make sure to highlight the benefits of the initiative and give them basic training and understanding of the services which will be used, but also let the chosen individuals know what it means to be an ambassador.

The people in this group can of course be previous pilot users or stakeholders, but it’s important that they are spread through all levels of the company in order to reach all end users.

The ambassadors should keep in contact with each other and also report back to IT and stakeholders during short scheduled meetings.

Some common ambassador tasks are:

  • To help answer questions and give advice
  • To collect feedback (good or bad)
  • To help users adapt and become familiar with the new services
  • To report progress, user feedback and common issues etc…

Ambassadors will drive user adaptation forward and make sure your end users won’t feel left out and assure them that their opinions and feedback matter!

Confused users

I previously mentioned a user coming to work Monday morning to find new “stuff” deployed on their computer during the weekend. Their mail client may look different and they now have a cloud icon on their taskbar? This is a worst-case scenario but not very far from reality!

Keeping users aware of what’s happening from the start is important. Don’t surprise users with a forced change of working behavior! Keep them updated about the initiative and briefly describe why you are doing it and how it will affect them. Also make sure to let them know of personal benefits that will come from the initiative.

Far too many times I’ve seen uncertain users continuing saving their files on their desktop or use “other” services (shadow IT), just because they didn’t understand and felt comfortable using Office 365.

…Then you’re back to square one!

While ambassadors can be of great use here, some kind of end user training is needed and in my opinion is crucial to ensure success. Depending on organizational structure and the number of users in the company, this can be achieved in different ways.

Some training methods are:

  • Instructor-led trainings
  • Online on-demand trainings
  •  Using an LMS software (learning management system)
  • Periodically send out training material and links to good learning pages (Microsoft offers great resources)

The ambassadors and pilot users may have had Instructor-led training sessions while the rest use a Learning management system for training and /or informational letters sent out to them periodically. As an option, some ambassadors can do end user trainings as well.

The conclusion is to let everyone know what is happening and why! Then give end users appropriate training through some method of choice. Make sure to plan this ahead to give users time to learn and adjust how they work. If you also implement an ambassador program it will help out during this process!

Final words

The 5 steps mentioned above is mostly focused on the end user’s perspective. Every Office 365 roll-out doesn’t look the same, and can be done in many ways, but it’s far too common to forget about the people who will end up using the services. It doesn’t matter how cost efficient, powerful and effective these services are if the users don’t use them right or find other ways around them.

Make a step by step plan of the entire implementation beforehand, but also plan out what happens after the roll-out is completed. Office 365 is on the move constantly and releases of updates and new services needs further considerations continuously.


3 thoughts on “5 common mistakes in a Office 365 roll-out

  1. Great blog and content!. In fact, I’m in the middle of an Office 365 adoption project and I have to plan a workshop with CEO board and steering committee to look for use cases and i’m a little bit lost. I asked the IT director to tell me particularities of their business to shape the ideas but he has told me that this is the reason why the have hired us 😛 Do you have any documentation o reference material that help me to address the Workshop or use cases? For example, I’m thinking using one note for meeting notes and deliver to stakeholders after meeting and save meeting minutes in shrepoint….
    Many thanks for your help.


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