O Leonard

O Leonard

Instructor | Operations & Workflow Specialist, Rainwater Growth

Silver Spring, Maryland, United States

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Lifelong learner with a passion for simplifying complex business processes and driving digital transformation to help others!

With 20+ experience providing excellent service to both internal and external customers, designing and developing IT training, managing people, projects, and programs, and providing tech support, I work to find ways to make technology accessible and effective for everyone.

Area of Expertise

  • Business & Management
  • Government, Social Sector & Education
  • Information & Communications Technology

Topics

  • Time Management & Productivity Hacks
  • Project and Product management
  • Workflow Automation
  • Digital Wellbeing

Lessons from SharePoint: User Adoption, Governance, and Sustainable Success

"History doesn't repeat, but it often rhymes" - Mark Twain (attributed)/Unknown

Abandoned Sites. Ungoverned chaos. Accidently deleted data. Users who swear they'll never touch the stuff. The latest headlines about Generative AI? Nope. Horror stories from the world of SharePoint.

In this session, we will discuss the lessons learned from years of governing SharePoint from both a business and technical perspective and how we can apply these lessons in our current environment. Real patterns, relatable mistakes, and what works well when introducing a powerful but deceptively easy to use technology into the enterprise.

Debra brings 25+ years of enterprise data governance experience, including SharePoint. O speaks to the other side with 15+ in public sector Operations technology support and administration.

Instead of a technical deep dive, we've have an honest conversation about why SharePoint still has a reputation problem, what it looks like when it's done right, and what we can do to help users stop fighting new tools and start leveraging them!

Digital Wellbeing in the Age of AI

“Technology is a good servant but a bad master.” – Gretchen Rubin

New apps and gadgets are released every day, and it can feel overwhelming to keep up. With the democratization of AI, the pace of development is speeding up. Digital wellbeing is about finding balance between your digital life and overall health.

It's important to take time for self-reflection on our relationship with technology and explore some practical tips to help maintain a more intentional use of digital technology even when it is at the core of our daily lives.

Memphis Microsoft Community Days 2026 Sessionize Event

June 2026 Memphis, Tennessee, United States

M365 Community Day St. Louis Sessionize Event

May 2026 St. Louis, Missouri, United States

Black Woman Owned Amplified Learning Series

February 2026

PMI LA Professional Development Day

October 2025 Los Angeles, California, United States

Introverts Business Collective

September 2025

O Leonard

Instructor | Operations & Workflow Specialist, Rainwater Growth

Silver Spring, Maryland, United States

Actions

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