New to Microsoft 365: A Journey of Discovery

After 25 years of avoiding anything with a Microsoft logo, I found myself in a new role with a shocking new reality: I was now deep in the Microsoft 365 ecosystem. The company laptop had arrived with the colorful Windows logo staring back at me (don't worry, that laptop was short-lived and I'm back on a Macbook Pro). Teams notifications pinged from my phone. My calendar was suddenly populated with Outlook invites. For someone who had carefully crafted a tech ecosystem built entirely on Apple, Google, and a bunch of other apps I loved, this felt like being dropped into a foreign country where I barely spoke the language.

Let me take a step back and introduce myself.

I'm Jason Lee, the Marketing Director here at Sentry Technology Solutions. Throughout my career, I've been the quintessential creative professional – Mac in hand, AirPods in ears, fully embraced Apple Ecosystem and a determination to stay as far away from Microsoft products as humanly possible.

My last meaningful interaction with Microsoft was in the Clippy era. Yes, that Clippy – the animated paperclip that would pop up uninvited to ask if you were writing a letter. After that traumatic relationship ended, I built my professional life around Apple, Google and a carefully constructed technology ecosystem:

• Google's G Suite for documents, spreadsheets, presentations, and email
• Apple's Keynote for when presentations really mattered
• Slack for team communications
• Asana for project management
• Trello for visual workflow management
• Zoom for video conferencing
• Evernote for notes and documentation
• Calendly for scheduling meetings

This carefully selected suite of tools served me well for years. They were familiar, reliable, and – I thought – superior to anything Microsoft could offer. I was wrong.

The Integration Advantage I Never Knew Existed

My first week at Sentry, I found myself in back-to-back Teams meetings, fumbling through SharePoint to find documents, and attempting to decipher Outlook's calendar system. It wasn't pretty.  As a digital native and technology first human, I left lost.  

By month two, something unexpected happened. It wasn't really that the apps looks better, or the tools on their own functioned all that better (while sometimes they did) it was the INTEGRATION.  The integration between all the tools is a game changer.  A document shared in a Teams chat automatically appeared in my SharePoint. Meeting notes were instantly accessible to everyone on the call. The boundaries between applications that I was accustomed to simply... disappeared.  At first it was a little crazy, everything was showing up everywhere!

I had spent years manually moving information between tools – downloading files from Google Drive to attach to emails, copying Zoom links into calendar invites, taking screenshots of project timelines to share in Slack. Suddenly, in the Microsoft ecosystem, these tedious tasks were completely unnecessary.

And then there was Copilot – Microsoft's AI assistant that understands your entire work ecosystem. I watched in disbelief as it summarized a 45-minute meeting I had missed, complete with action items assigned to me. It could find documents I vaguely remembered from weeks ago based on a half-remembered conversation. It knew when I was free for meetings without me checking my calendar.

The Business Value Hidden in Plain Sight

As a marketing professional and now as Marketing Director at Sentry, I'm always thinking about the ROI of any tool or platform. What I've discovered about Microsoft 365 has significant implications for any business leader, particularly at the C-Suite level.

Many organizations are simultaneously paying for:

• A Microsoft 365 subscription that includes most of these tools
• Separate subscriptions for Slack, Asana, Zoom, Evernote, and more

This redundancy isn't just financially inefficient – it creates disconnected information silos that reduce productivity and create security vulnerabilities.

What I've learned is that Microsoft has quietly built an ecosystem where the whole is significantly greater than the sum of its parts. The individual applications might not always have the specific feature you love from a standalone competitor, but the seamless integration creates a workflow that wasn't possible before.

The Journey Ahead

This blog post marks the beginning of a series where I'll share my journey transitioning from a carefully curated collection of specialized tools to the integrated Microsoft 365 ecosystem. Each post will focus on a specific application or feature, comparing it to its competitors and highlighting both the limitations and the unexpected advantages I've discovered.

I'm writing this series for fellow skeptics – the Apple devotees, the Google workspace enthusiasts, and anyone who, like me, has deliberately avoided Microsoft products. I'm also writing for business leaders who might be paying for redundant tools without realizing the capabilities already available in their Microsoft subscription.

Over the next few months, I'll be covering:

• Teams as a replacement for Slack
• SharePoint vs. Google Drive
• Planner vs. Asana and Trello
• Teams video vs. Zoom
• Outlook's surprising capabilities
• OneNote as an Evernote alternative
• Microsoft Stream for internal video
• Bookings vs. Calendly
• Forms vs. Google Forms
• The evolving Word and Excel
• How Copilot transforms everything

I'm not saying the transition has been perfect. There are aesthetic elements of some of the apps I miss terribly. There are specific features in some of my favorite apps that Microsoft hasn't quite matched. I'll be honest about those limitations alongside the benefits.

What I can say with certainty is that the Microsoft 365 ecosystem in 2025 is not what I expected. It's not what most people who haven't used it recently imagine it to be. And as I've talked to business leader after business leader, it's also an untapped resource of productivity and cost savings. 

Whether you're considering a shift to Microsoft 365 or you're already using it but supplementing with other paid tools, I hope this series will help you make more informed decisions about your business technology investments.

Next up: "Teams as My New Work Hub: An Ex-Slack Devotee's Perspective" – where I'll break down how Microsoft Teams compares to Slack and why the integration with other Microsoft tools makes it more than just another messaging app.

Jason Lee is the Marketing Director at Sentry Technology Solutions, a trusted guide helping businesses navigate today's complex technological landscape. With over 25 years of experience in marketing and creative direction, Jason brings a unique perspective on technology adoption and digital transformation. Connect with Jason and the Sentry team at sentrytechsolutions.com.