Lisa Hendrickson is the owner of Call That Girl. She is an Outlook Expert and Microsoft 365 Consultant.
If you’ve ever heard an employee quietly mutter, “why is Outlook doing this?”, you already understand the challenge. I’ve been supporting Outlook long enough to know it’s never just Outlook.
I’m an active, working technician and consultant with 28 years in IT and Microsoft, supporting Outlook since its earliest days and guiding organizations through every major change along the way. In 2025, I was awarded Microsoft Outlook MVP status and a 2025 Experts Exchange award. My background spans corporate IT, consulting, and 19 years as a business owner, which means I understand both the technical side of change and the business impact behind it.
Outlook isn’t just an application. It’s habit, routine, and comfort. When Outlook Classic changes or goes away, the disruption is often underestimated. Confidence drops, frustration rises, and leadership feels it quickly. This session focuses on why employees become attached to Outlook Classic, what that resistance really means, and how organizations can lead a thoughtful, low-stress transition to New Outlook.
I use real workplace stories to explain what’s changing, what isn’t, and what leaders actually need to worry about (and what they don’t). With deep experience across Microsoft 365, including account types, email delivery, Outlook configuration, OneDrive, Teams, and SharePoint, I translate technical change into clear, human terms executives can act on.
This is not technical training and not a vendor presentation. It’s a practical, executive-friendly conversation that helps organizations move forward with confidence, and a little humor, instead of resistance and confusion.
Clear explanations of Outlook change without technical overload
Practical guidance leaders can share with teams immediately
Reassurance, context, and a few moments of humor that make the change feel manageable
No sales pitch. No vendor slides. Just clarity, experience, and perspective
Bonus points if you’ve ever blamed Outlook for something that turned out to be OneDrive
Microsoft Outlook MVP and 2025 Experts Exchange award recipient
Active working consultant supporting organizations daily (www.callthatgirl.biz)
Speaker and workshop leader for in-person and online sessions since 2007
Author of multiple professional-level technical books, with a New Outlook book coming soon
Ongoing contributor through articles, podcasts, and YouTube training
Cross-platform experience supporting Windows, Mac, iPhone, and Android in Microsoft 365 environments
Available for executive briefings, company-wide sessions, and leadership events
Online or in-person engagements
Topics:
To get in contact, use the form below or call 612-865-4475
If you’ve ever whispered, “why is Outlook doing this?” under your breath, you’ll feel very seen in this session. I’ve been supporting Outlook long enough to know it’s never just Outlook.
I’m an active, working technician and consultant. This is real work, not theory. I’ve spent 28 years in IT and Microsoft, supporting Outlook since the beginning and living through every major change. In 2025, I earned Microsoft Outlook MVP status and a 2025 Experts Exchange award. My background includes corporate IT, contract roles, and 19 years as a business owner. 2026 is the year I break into conference speaking, focused on my favorite topics: Outlook Classic and New Outlook.
I tell real-world stories from the trenches. The kind that make audiences laugh because they’ve absolutely been there. I bring deep, practical experience across Microsoft 365, Outlook and New Outlook. Including the realities of home user accounts vs. business tenants, email delivery issues, Outlook setup, OneDrive (and yes, why Microsoft puts PST files there by default), Teams, and SharePoint.
First-year conference speaker, ideal for side rooms, breakouts, and opening sessions that warm the crowd up before keynotes
Practical takeaways, real-world fixes, and at least one moment where you laugh because you’ve lived that ticket
No sales pitch. No vendor slides. Just real MSP life, real fixes, and stories you’ll swear came from your own queue
Bonus points if you’ve ever supported Outlook on a Mac, synced it to an iPhone, and then blamed OneDrive
After 16 years of being active in technical online communities, I’ve read thousands of MSP-related posts. While I don’t run my own MSP, I deeply understand how MSPs actually operate. How they think, how they manage Microsoft 365 tenants, and how Outlook is usually their least favorite product to support.
Active working technician/business owner handling 30–50 support calls during a typical week
Longtime online contributor answering real technical questions to the IT crowd
Leading in-person and online webinars and workshops since 2007
Author of multiple technical books written specifically for IT professionals, with a New Outlook book coming soon
Ongoing content creator through technical articles, podcasts, and YouTube training
Cross-platform experience supporting Mac, Windows, iPhone, and Android, and the chaos that happens when they all meet inside one Microsoft tenant
Need a speaker for an online event soon? Reach out. I may be able to adjust my calendar to help you out
For in-person events, I typically need a few days’ notice
My online contribution pages:
https://techcommunity.microsoft.com/users/lisahendrickson/2048307
https://www.experts-exchange.com/members/CallThatGirl.html
https://www.linkedin.com/in/callthatgirl
Use the form below to get in contact, call 612-865-4475, or email lisa@callthatgirl.biz
This is a known issue and has been a trending issue for many months now. Many online articles will point you to turning off contacts in the sync settings but for my clients, that wasn’t a good option as they need their contacts to be viewed everywhere.
Not a favorite solution for hard core Outlook Classic desktop lovers, but moving to New Outlook works and my client was good with that switch. It’s not easy to tell a client (or you if you are reading this) that the sync software is not fixable. I have tried to get them working again with many clients and from what I know as of Jan 17, 2026, it’s not fixable quite yet.
If you need my help, please use the form below. Moving to New Outlook should be simple but some folks need some data set up or migrated.
