The Office 365 Adoption Challenge: “I barely have time to do my work. When am I supposed to find time to innovate?”

Lil Sawyer

Lil Sawyer

When Lil Sawyer and Grand & Toy, a subsidiary of Office Depot, began the roll-out of Office 365, it looked like smooth sailing. After a brief flirt with Google, employees were delighted to return to the familiar Microsoft Office suite.  

However, adoption of the full suite of Office 365 apps proved much more challenging. While employees were comfortable returning to Word, PowerPoint and Excel, the majority of the other more powerful collaboration apps remained largely unused. Most employees did not have any “natural” desire or sense of urgency to leverage the new apps to achieve operational efficiencies. Everyone was doing just fine with the familiar apps, and besides when would they have time to get acquainted with tools like OneNote or Teams anyway?

During the technical implementation Lil began to see the potential and possibilities for operational efficiencies with the interoperable O365 toolset, so she made it her mission to find creative and innovative ways to drive adoption once she saw difference the tools could make for her colleagues and ultimately for Grand & Toy’s culture and innovation priorities.

So, clearly Lil is a digital enthusiast. Not just in the way that she enjoys using digital tools, which hopefully holds true for the vast majority of us. But in the sense that she seems to be constantly aware of the overwhelming value a digital workplace offers:

“The challenge for Office 365 adoption, is that the overwhelming parts, tend to overshadow the value part. I believe we need to be transparent about the obstacles and leverage various resources including change management practices to guide us successfully through the transition.”

What follows is Lil’s story, and it goes something like this:  

  • Showing people how these amazing tools could help them capture their time thieves, has become both my mission and passion.

  • While there are many adoption hurdles, the individual and team successes stories are growing in our organization. While tempting, I don’t think it is smart to throw the (O365) baby out with the bath water so to speak.

  • Since deploying the “capture our time thieves” campaign, we find that by leveraging the apps, engaged individuals and teams are saving 5% to 15% of their time and getting back 2 to 6 hours per week to invest in learning the new tech, innovate, collaborate and pursue various growth goals.  


Article by Lil Sawyer

Office 365 adoption obstacles

Coping with Rapid High-Volume Change and Competing Priorities

While we can all agree on the many benefits of the digital revolution to enhance the way we work and do business, we don’t often agree on the value of taking the time to understand fully the change implications on the people being impacted. Employees are now living through the age of change accelerations underpinned by converging technological advances and competing business priorities. On the human side, the pace of change (speed) and rate of change (exponential) are in many cases exceeds our capacity to adopt, process and cope with the sheer volume and variety. Office 365 may be one of several pieces of technology being implemented at the same time in the business cycle. I have started the adoption project with several teams and have had to put it on pause because of competing business priorities. This is the normal rhythm of business, but we have to remember the long-term benefit and put it back on the priority list.   

Paradox of Choice

Microsoft has given us a single platform with an overabundance of technology to address business challenges digitally. Presenting both an opportunity and a challenge. In his book The Paradox of Choice – Why More Is Less, Barry Schwartz suggests that in the western countries a large amount of choice is commonly associated with freedom and wellbeing. However, having too much choice results in feeling less happy, less satisfied and can even lead to paralysis. It is quite common for an O365 users to tell me that they have ignored selected app because they did not know how it can deliver value to them. There are 20 plus apps on the platform. It’s amazing, but I completely understand why users might feel overwhelmed, but we can’t let them stay there.

The overlapping features within the apps is also overwhelming for users. Should I store my documents in OneDrive or SharePoint or the files tab in Teams? When should I use Yammer vs Teams for conversations? It is common to address questions around when to use what app.

Planning to Go Beyond the Core Apps and Basic Training

When we rolled out Office 365, everyone received basic cloud version training since most people already had a foundation in Outlook, Word, Excel and PowerPoint. We realized one challenge when we began thinking about driving adoption of the additional tools. We had not planned or budgeted for additional training. In fact, we did not really understand the value of the additional tools, before and during the initial rollout. It was an afterthought, and I think this may be all too common in organizations.

Talking Technology Tools vs Business Value

Initially our training and conversations with users were focused on explaining the amazing features of the apps but when I switched the conversation to using the interoperable O365 toolset to capture their specific time thieves, lightbulbs began to switch on.

While many people expressed the desire to learn the tools, I found that most people won’t take the time to learn the new tools unless they are mandated, or we can help them find the time necessary to invest in the tools themselves. Quick wins are important to foster engagement with users to support a mind shift to view the toolset as a resource to solve current and future business problems digitally.

The rapid rate of change using a common platform or the same types of tools allows the team members to solve problems faster, more collaboratively and support each other with learning the mechanics of the apps.

Scaling Adoption and Keeping Everyone Current

While we have had some very promising success stories with the proof of concept the challenge now is scalability and sustainability. Keeping employees current on relevant feature enhancement deployed continuously by Microsoft is also a challenge.  

Overcoming the Obstacles

The Inspiration – Culture Transition Goals

I was inspired to think through this concept of capturing our time thieves as a companywide benefit by a brave colleague. During a presentation on the benefits of a culture of innovation and collaboration he verbalized that while he clearly understood the benefits of the culture transition, he was challenged because by the time he completed his daily tasks he had absolutely no time left to innovate or think about how to improve collaboration. His comments resonated with me because I had the same challenges despite my role of leading the O365 implementation. I had to invest a lot of personal time to learn the other tools in the O365 suite, but it meant that by this point I was capturing some of my time thieves.

Change Management

I researched change management and made the decision to become certified as a Prosci change practitioner. I developed a resistance management plan as well as sponsor, coaching, training and communication plans for the proof of concept (POC). Each plan is tweaked from the learnings of the POC for the expansion phase.

Training options for employees are live classroom, via webinars and through the self-serve tips ‘n tricks OneNote notebook guide. The OneNote guide curates internal and external training videos links and other learning resources. Basically, I collected all the resources that people would need in one central place in a OneNote notebook which is linked as a tab in everyone’s Teams.

The reality is that people are busy doing important work and have different learning styles and preferences. While the digitally savvy folks will self-serve, those transitioning to true digital working need more direction and guidance, as learning can seem as yet another time thief.

Proof of Concept and Champions

Two awesome champions saving 11 hours per week together

Next I started conducting interviews throughout the organization and identified a couple of teams that I started working closely with to do a proof of concept or pilot. The hope was that these early adopters would eventually become champions, and they would help multiply the adoption efforts throughout the organization.

I started with one team of 5 and ended up with 2 awesome champions saving 11 hours per week together. The 3 other people on the team stayed focus on getting the team’s tasks completed while 2 members played and experimented with the apps to find solutions that would benefit all. One of the team’s champions was just returning to work with a vision deficit. She was hugely motivated to find technology solutions that could help her save time and she cared deeply about the team’s success.  

Culture and Mind Shift

Although the results have been very good with the proof of concept, the challenge will be scaling and sustainability. As the proof of concept has expanded to include additional teams throughout Grand & Toy, we continue to achieve between 5-15% time savings. I have also seen how this adoption is now strengthening a culture that embraces change, creativity and care.

With a higher functioning digital workplace, we are gaining the ability to be more effective, since we can share information and collaborate seamlessly. Pilot participants shared that working in silos felt much safer, so they must remind themselves of the benefits they get from team collaboration to manage fears related to giving up control, ownership and needing to be more transparent.

Openly sharing our knowledge and automating job tasks can feel risky. Participants question their value or contribution. After all our compensation is based on getting a set of tasks done? After we automate my work, will I lose my position? After acknowledging the concern my response is focused on helping the person to reason or imagining how the improved version of themselves with the new skills and confidence would do in a job market prioritizing digital dexterity. We talk about how learning these new skills will better equipped them to get the next job internally or externally. Replacing fear based thoughts with facts. Because the fact is that with a proven track record of leveraging technology to achieve operational efficiency we each become much more marketable.

Leveraging the Coaches

At this point, I am prioritizing working with the people managers (coaches), to quickly get to measurable results from using the O365 toolset in my efforts to foster greater adoption. The POC/pilot has given me a good framework and a roadmap to support and measure the O365 adoption action plans. We are still very much in an iterative expanded pilot phase, where we are revising the change management plans based on feedback and learning from employees. However, I have no doubt as to where the focus for future digital workplace implementations will be. These are my closing thoughts:

  • The cloud based Office 365 is often criticized for being templated and inflexible, but templating minimizes technology support costs and training costs so we can reallocate spend on empowering human beings to solving business problems with technology.  

  • With much of our technology infrastructure in place to support operational digital transformation, going forward people in my type of role can prioritize supporting our people through the change.

  • The shortage of digital talent is something I hear about often as a member of HR. The proof of concept has given me confidence that we can leverage the toolset in O365 to also retrain analog traditionalists to become tomorrow's digital leaders and not be as dependent on external hires only to fill the gap.  

  • Our network of O365 champions are helping to train the workforce and putting ownership of our digital workplace transformation journey in the hands of frontline workers not just IT or business until leaders.


Are you looking to drive Office 365 adoption or foster collaboration in your organization? Then consider joining Lil and other professionals for the Modern Workplace conference track at the Boye 19 Conference in Brooklyn May 7-9.

She implemented several tactics that she felt could prove the time saving potential of the applications; make it easier to get started, and now focused on promoting widespread adoption.