🧠 Author’s Note: Legacy, Change & the AI Elephant in the Room
Yes, I know—I’ve been pushing AI a bit hard lately for #NEPA. And no, I have no intention of stopping. 😄
Change is hard. Adaptation is harder. It disrupts and enhances all at once. But as I tell my own children – here we are—right now—in the middle of it – so what do we do right now.
A few recent reports say AI isn’t helping workplace productivity. Honestly? I agree. But not because AI is broken—it’s because users aren’t trained. They don’t understand the features, the security, or the potential. And let’s be real: AI is scary. It’s the unknown. It’s the “what if it replaces me?” fear.
But when I researched what SMBs actually use in Microsoft 365, I had an ah-ha moment:
- Outlook
- OneDrive
- Word
- PowerPoint
- SharePoint
- Excel
- And the most advanced tool used? Teams
So let’s start there. Let’s show people what they’re already paying for. Let’s explain the inner workings. Let’s train, teach, partner—and make it all just a little less scary.
We’ll start with some strategic knowledge and understanding.
Generational Breakdown of M365 and App Usage
In today’s small business world, Microsoft 365 is the digital toolbox everyone should be using—but not everyone uses it the same way. From Boomers who treat Outlook like a sacred scroll to Gen Z who think Excel is a myth, each generation has its own quirks, favorites, and “nope” zones when it comes to M365.
Understanding these generational preferences isn’t just fun—it’s strategic. It helps you tailor onboarding, training, and support so your team actually uses the tools you’re paying for.
So let’s break it down: who’s using what, who’s avoiding what, and how you can bridge the digital divide with a little humor and a lot of empathy.
👵 Baby Boomers (Born 1946–1964)
🟢 Most Used:
- Outlook – Email is their comfort zone. Calendar and tasks are also popular.
- Word & Excel – Familiar, reliable, and printable.
- OneDrive – Used mostly for backup, not collaboration.
🔴 Least Used / Avoided:
- Teams Chat – Too noisy. “Why not just call?”
- Loop Components – “What’s a loop? Is it like a hula hoop?”
💡 Tips:
- Emphasize email integrations and document versioning.
- Use SharePoint as a digital filing cabinet with clear folder names.
😂 Humor:
“Boomers love Outlook. It’s like their Rolodex, calendar, and inbox had a baby.”
🧑💼 Gen X (Born 1965–1980)
🟢 Most Used:
- Outlook & Excel – Power users of rules, formulas, and conditional formatting.
- Teams (Meetings) – They’ll use it, but prefer structured agendas.
- SharePoint – Appreciated for organization and control.
🔴 Least Used / Avoided:
- Yammer / Viva Engage – “We already have email. Why do we need another inbox?”
- Loop Components – Still figuring out what it does.
💡 Tips:
- Highlight Teams integrations with Planner and SharePoint.
- Promote Power Automate for repetitive tasks (they love efficiency).
😂 Humor:
“Gen X: The only generation that still uses Excel like it’s a programming language.”
👩💻 Millennials (Born 1981–1996)
🟢 Most Used:
- Teams (Chat & Meetings) – Their virtual watercooler.
- Planner & OneNote – For organizing chaos.
- PowerPoint – For client decks and internal pitches.
🔴 Least Used / Avoided:
- Outlook Rules – They know they exist but never set them up.
- SharePoint (Classic) – “Too clunky. Can we just use Teams?”
💡 Tips:
- Promote mobile apps and Copilot features.
- Use Loop and To Do for collaborative planning.
😂 Humor:
“Millennials use Teams like Boomers use Outlook—constantly, emotionally, and with too many emojis.”
📱 Gen Z (Born 1997–2012)
🟢 Most Used:
- Teams (Chat, Emojis, GIFs) – Basically Slack with a Microsoft badge.
- Loop Components – Real-time collaboration is their jam.
- OneDrive (Mobile) – They live in the cloud.
🔴 Least Used / Avoided:
- Outlook Desktop – “Why does this look like Windows XP?”
- Excel (Advanced) – Unless Copilot is doing the formulas.
💡 Tips:
- Focus on mobile-first workflows and visual collaboration.
- Use short videos or memes to teach features.
😂 Humor:
“Gen Z doesn’t use Outlook—they use Teams, emojis, and vibes.”
🧠 Summary Table
| Generation | Most Used Apps | Least Used Apps | Training Focus |
|---|---|---|---|
| Boomers | Outlook, Word, Excel | Teams Chat, Loop | Email, file sharing, SharePoint basics |
| Gen X | Outlook, Excel, SharePoint | Yammer, Loop | Automation, structured collaboration |
| Millennials | Teams, Planner, OneNote | Outlook Rules, Classic SharePoint | Mobile apps, Copilot, Loop |
| Gen Z | Teams, Loop, OneDrive | Outlook Desktop, Excel (manual) | Visual workflows, mobile-first tools |
Next up . . .
🧠 Meet Copilot (Unlicensed) – Your Built-In Assistant
Throughout the guide, I do mention what Copilot (Unlicensed) helps with, such as:
- Summarizing documents, chats, and emails.
- Drafting follow-ups, posts, and reports.
- Explaining formulas, flows, and features.
- Suggesting organization and automation ideas.
It’s not magic—it’s just underused.
Now, Copilot (Licensed) – well, now that might be magic! Curious about Copilot (Licensed) abilities – Let’s chat – – – (once you’ve mastered what Copilot (Unlicensed) can do!)
So Let’s jump into your first Week!
🎯 Day 1: The Great File Hunt Ends – Meet OneDrive
Pain Point:
“Where’s that file? Is it on my desktop? USB? Email? Carrier pigeon?”
App Fix:
OneDrive – Your personal cloud storage.
Features & Benefits:
- Auto-sync files across devices.
- Share files without email attachments.
- Version history (undo your accidental chaos).
- Access anywhere – even from your phone at the DMV.
Copilot Can Help With:
- Summarizing file contents without opening them.
- Suggesting folder organization based on file types.
- Answering “Where did I save that?” with smart search.
Productivity Tip:
Set up Known Folder Move to auto-backup Desktop, Documents, and Pictures.
Generational Humor:
- Boomers: “It’s like your filing cabinet, but it doesn’t eat paperclips.”
- Gen X: “Remember Zip drives? This is like that, but it works.”
- Millennials: “It’s like Google Drive, but your boss actually approves it.”
- Gen Z: “Cloud = vibes. OneDrive = organized vibes.”
📁 Day 2: Teamwork Makes the Dream Work – Enter SharePoint
Pain Point:
“Everyone’s working on different versions of the same doc. Chaos reigns.”
App Fix:
SharePoint – Your team’s shared workspace.
Features & Benefits:
- Centralized document libraries.
- Real-time co-authoring.
- Permissions control (no more “oops” emails).
- Integration with Teams and Outlook.
Copilot Can Help With:
- Summarizing shared documents.
- Drafting updates or announcements for your SharePoint site.
- Finding documents by context (“Show me the Q3 budget draft”).
Productivity Tip:
Use metadata and views to organize files like a pro (no more 47 folders named “Final_Final_2”).
Generational Humor:
- Boomers: “It’s like the office bulletin board, but nobody steals your thumbtacks.”
- Gen X: “It’s like Lotus Notes, but it doesn’t crash.”
- Millennials: “It’s like Slack, but with actual structure.”
- Gen Z: “SharePoint is the group chat, but for grown-ups.”
📅 Day 3: Meetings That Don’t Suck – Outlook + Teams
Pain Point:
“Too many meetings. Not enough clarity. Where’s the link again?”
App Fix:
Outlook + Microsoft Teams – Schedule, meet, chat, repeat.
Features & Benefits:
- Integrated calendar invites with Teams links.
- Chat before, during, and after meetings.
- Record meetings and auto-transcribe.
- Share files directly in chat.
Copilot Can Help With:
- Summarizing meeting chats and transcripts.
- Drafting follow-up emails or action items.
- Finding past meeting notes or decisions.
Productivity Tip:
Use @mentions in Teams to get attention without sending 12 emails.
Generational Humor:
- Boomers: “It’s like a conference call, but you can see pants.”
- Gen X: “It’s like AOL Instant Messenger, but with meetings.”
- Millennials: “It’s Zoom, but with fewer ‘You’re muted’ moments.”
- Gen Z: “Teams is FaceTime with receipts.”
📊 Day 4: Data Without Drama – Excel + Lists
Pain Point:
“Spreadsheets are everywhere. Nobody knows which one is right.”
App Fix:
Excel + Microsoft Lists – Organize, analyze, and track.
Features & Benefits:
- Smart templates for budgets, projects, and inventory.
- Conditional formatting and pivot tables.
- Lists for tracking tasks, assets, or anything else.
Copilot Can Help With:
- Explaining formulas and suggesting improvements.
- Creating charts or summaries from raw data.
- Generating Lists from bullet points or emails.
Productivity Tip:
Use Power Automate to auto-update Lists from emails or forms.
Generational Humor:
- Boomers: “It’s like your ledger book, but it does math.”
- Gen X: “It’s like Excel 97, but it doesn’t freeze.”
- Millennials: “It’s like Trello, but with formulas.”
- Gen Z: “Lists are like TikTok drafts – organized chaos.”
📌 Day 5: Automate the Boring Stuff – Power Automate
Pain Point:
“Too many repetitive tasks. Not enough coffee.”
App Fix:
Power Automate – Your digital intern.
Features & Benefits:
- Automate approvals, notifications, and file moves.
- Connect apps like Outlook, SharePoint, and Teams.
- Templates to get started fast.
Copilot Can Help With:
- Suggesting automation flows based on your activity.
- Explaining what a flow does in plain English.
- Troubleshooting flow errors.
Productivity Tip:
Set up a flow to auto-save email attachments to OneDrive.
Generational Humor:
- Boomers: “It’s like your assistant, but it doesn’t take lunch breaks.”
- Gen X: “It’s like Clippy, but it actually helps.”
- Millennials: “It’s like Zapier, but you don’t need a subscription.”
- Gen Z: “It’s like a bot, but it doesn’t DM you weird stuff.”
🎉 Day 6: Celebrate Wins – Yammer or Viva Engage
Pain Point:
“No one knows what other teams are doing. Morale is meh.”
App Fix:
Yammer / Viva Engage – Internal social networking.
Features & Benefits:
- Company-wide announcements.
- Praise and recognition posts.
- Polls, Q&A, and community building.
Copilot Can Help With:
- Drafting engaging posts or polls.
- Summarizing trending topics or feedback.
- Suggesting ways to boost engagement.
Productivity Tip:
Use Viva Insights to track focus time and well-being.
Generational Humor:
- Boomers: “It’s like the breakroom, but with less gossip.”
- Gen X: “It’s like MySpace, but for work.”
- Millennials: “It’s like Facebook, but HR-approved.”
- Gen Z: “It’s like Instagram stories, but with spreadsheets.”
🧠 Day 7: Recap & Ready to Roll
Wrap-Up Checklist:
- ✅ OneDrive set up and syncing
- ✅ SharePoint site created
- ✅ Teams channels active
- ✅ Outlook calendar integrated
- ✅ Power Automate flow running
- ✅ Viva Engage post shared
Copilot Can Help With:
- Creating a summary of your week’s progress.
- Drafting a “What’s Next” email or post.
- Recommending next steps based on usage patterns.
Bonus Tip:
Create a “M365 Wins” channel in Teams to share tips, memes, and success stories.
👋 See You Next Week!
Week 2: Exploring Emerging & Underused Features for SMBs
- Planner
- MyAnalytics
- OneNote
- . . .
- Loop
Need help delving deeper for productivity?
Contact Herstek & Associates
