Helping IT Technicians Emotionally Unattach from Outlook Classic

My second submission is for Level 300+

As organizations transition from Outlook Classic to the New Outlook, helpdesk teams will face a surge of user questions, confusion, and workflow disruptions. But not every ticket is a “technical issue", many are training opportunities disguised as break/fix requests.

This session teaches helpdesk technicians how to distinguish the difference, reduce repetitive ticket volume, and guide users through change with patience, clarity, and structure. We’ll cover what features have changed, what hasn’t been added yet, what workarounds exist, and how to communicate these shifts in a calm, consistent way.

Attendees will leave with new ideas on how to work with end users and help with the New Outlook transition.

Audience: Helpdesk technicians, Tier 1/Tier 2 support teams, junior Exchange admins, onboarding specialists, training coordinators.

Helping IT Leadership Unattach from Outlook Classic

Leadership often assumes this transition is “simple” because the app icons look similar. In reality, this requires coordinated communication, training planning, and realistic expectation management.

This session gives IT leaders ready-to-use messaging, rollout timelines, and a communication strategy that aligns with the unpredictable pace of New Outlook feature releases. You’ll learn how to prepare for user pushback, questions, missing functionality, and ongoing updates, all while keeping the organization calm and informed.

Key Takeaways
Executive-level messaging for the transition.
How to build a phased rollout plan that reduces disruption.
What unknowns and missing features to prepare for.
How to talk about limitations without undermining user trust.
Policies, documentation, and training cadence recommendations.
How to track adoption and measure success.

MSPs, IT Directors, CIOs, tech leads, project managers, and anyone overseeing the transition across departments.

Mastering the New Outlook: A Full-Day Technical Workshop for IT Professionals

The New Outlook represents a structural shift from Outlook Classic client to a web-aligned, service-connected architecture. For IT professionals supporting Microsoft 365 environments, understanding these changes is no longer optional.

This Level 300, full-day technical workshop is designed for intermediate IT administrators, support engineers, and Microsoft-focused professionals who are actively managing user transitions and troubleshooting New Outlook in production environments.

We will examine:

Architectural differences between Classic Outlook and New Outlook

Profile, account, and data handling changes

Exchange Online dependency and service-side behavior

Migration impact: what does not carry forward (PSTs, COM add-ins, VBA/macros, profiles)

Real-world ticket patterns and troubleshooting frameworks

This session assumes working knowledge of Microsoft 365, Exchange Online, and Outlook Classic. We will focus on operational impact, support readiness, and deployment considerations, not feature overviews.

Attendees will leave with a clear technical understanding of how the New Outlook operates, where architectural limitations exist, and how to proactively reduce support friction during adoption.

New Outlook: A Technical Deep Dive for IT Professionals

New Outlook is not a UI refresh. It’s like moving to another city, state or country and having to learn a whole new environment. Nothing about New Outlook is remotely close to Outlook Classic. Technicians, Engineers and IT leaders will learn from an actively working Microsoft Outlook Expert everything that goes on in the back end of this switch.

This 4-hour technical workshop is designed for Microsoft professionals who want to learn more about New Outlook from the technical side (back of house). I will not be covering training (front of house) or "features", all on the technical side of the switch. We’ll dig into Outlook account types, where data is stored, what migrates cleanly, what doesn’t migrate at all, and
why I believe PSTs are slowly going away. We will also cover onboarding, manual migration, setup, and the technical issues.

We’ll focus on different email types (Exchange, Gmail, iCloud, IMAP, POP/PST), data handling and migrations, and troubleshooting patterns that no longer follow Classic Outlook.

You’ll see live demos, real failure scenarios, and practical strategies you can take back to your environment immediately. The switch from Outlook Classic to New Outlook will make anyone that uses Outlook slightly confused. It's a completely different program and for IT professionals, it's a huge change in how we support our clients, manage their services, accounts and data.

Who This Is For
• IT pros, admins, consultants, Microsoft Professionals
• Anyone already supporting New Outlook
• Teams preparing for the long goodbye to Outlook Classic

What You’ll Leave With
• A clear understanding of New Outlook on the technical side.
• Fewer “why is Outlook doing this?” moments
• Less frustrated end users

I look forward to this workshop, and this would be my first 4-hour workshop.

Helping People Emotionally Unattach from Outlook Classic

I am submitting three presentations centered around the transition from Outlook Classic to the New Outlook, each tailored to a different audience. With Outlook Classic reaching end of life in 2029 and no other submissions currently addressing New Outlook, this topic is timely, relevant, and in high demand across all levels of IT. This application is for the first presentation in the series.

The first session is a Level 100 talk designed for anyone who uses or enjoys Outlook Classic. Titled “Helping People Emotionally Unattach from Outlook Classic,” it introduces end users to what’s changing, why it’s changing, and how to approach the transition with confidence. If I am selected to speak and given the opportunity to present only once, this is the session I would choose to deliver. As someone new to the speaking circuit, this presentation also provides a strong, accessible entry point for me to share my experience with a broad audience.

The second presentation in the series is aimed at MSP Owners, IT technicians, helpdesk teams, and junior Exchange administrators. It covers the same core themes but focuses on troubleshooting, training vs. fixing, and preparing for the influx of support requests during the transition.

The third presentation is designed for IT Directors, MSPs, and IT leadership teams. This version emphasizes planning, communication strategy, feature readiness, and organizational change management to ensure a smooth adoption process.

Helping IT Technicians Emotionally Unattach from Outlook Classic

My second submission is for Level 300+

As organizations transition from Outlook Classic to the New Outlook, helpdesk teams will face a surge of user questions, confusion, and workflow disruptions. But not every ticket is a “technical issue", many are training opportunities disguised as break/fix requests.

This session teaches helpdesk technicians how to distinguish the difference, reduce repetitive ticket volume, and guide users through change with patience, clarity, and structure. We’ll cover what features have changed, what hasn’t been added yet, what workarounds exist, and how to communicate these shifts in a calm, consistent way.

Attendees will leave with new ideas on how to work with end users and help with the New Outlook transition.

Audience: Helpdesk technicians, Tier 1/Tier 2 support teams, junior Exchange admins, onboarding specialists, training coordinators.

Helping IT Leadership Unattach from Outlook Classic

Leadership often assumes this transition is “simple” because the app icons look similar. In reality, this requires coordinated communication, training planning, and realistic expectation management.

This session gives IT leaders ready-to-use messaging, rollout timelines, and a communication strategy that aligns with the unpredictable pace of New Outlook feature releases. You’ll learn how to prepare for user pushback, questions, missing functionality, and ongoing updates, all while keeping the organization calm and informed.

Key Takeaways
Executive-level messaging for the transition (templates included).
How to build a phased rollout plan that reduces disruption.
What unknowns and missing features to prepare for.
How to talk about limitations without undermining user trust.
Policies, documentation, and training cadence recommendations.
How to track adoption and measure success.

MSPs, IT Directors, CIOs, tech leads, project managers, and anyone overseeing the transition across departments.

3 part 20-min sessions: Admin Settings Every Solo Business Owner Must Know

These sessions are offered at no cost to any business that has a reach to invite many people to the session. Organizations, non-profits, legal associations are all welcome to host a session.

Presented as 20 min "Lunch and Learn" type events, these are a great way to get folks to sign up and attend and learn from you hosting the event.

Session 1 — Running Microsoft 365: Ownership, Users & Access (This is important if you set up your own Microsoft 365 account)

Topics

Global Administration (what it actually means)
Break Glass Account (why every business must have one)
How to Add Users properly (Mailbox vs Shared Mailbox vs Alias)
License Verification / Overpaying
Microsoft Support vs Vendor (who really controls your tenant)
Importance of MFA and how to test if you have it set up

Session 2 — Security & Email Protection
Identity Security

Check Entra for logins
Azure/Entra security review
Recognizing suspicious sign-ins
Email & Domain Protection

Basic DNS issues for email delivery
DKIM records
Quarantine (what it is vs spam folder)
Restricted accounts

Session 3 — When Things Go Wrong (Breach, Recovery & Business Risk)
Active Breach Response

What hackers do inside your account
How to kick them out
Using Entra login logs to investigate
Locking down accounts
Business Continuity

No Backup (what Microsoft actually does vs what owners assume)
Why deleted email is often unrecoverable after a point
Vendor vs Microsoft during an incident
Ongoing Protection Plan

Scheduled Entra security reviews
License reviews

7 Things I Learned on My Journey to Becoming a Microsoft MVP

This is a 70-minute session blending storytelling, real-world experience, and light demos, sharing the lessons I learned on the long, non-traditional path to becoming a Microsoft MVP.

I was first nominated for Microsoft MVP in 2022. I applied immediately and just as quickly learned that I had gone about almost everything the wrong way. I wasn’t selected, but the experience was eye-opening and became the foundation for what came next.

In 2024, I made a deliberate decision to pursue the MVP award again. This time with focus, consistency, and a much clearer understanding of what meaningful community impact actually looks like. In 2025, I was nominated once more and awarded Microsoft MVP for Outlook.

I’m excited to share my journey; including the missteps, course corrections, and practical steps I took to help others understand what it really takes to earn an MVP award and how to approach the process with intention and confidence.

How I Started My Microsoft 365 Consulting Business in 7 Steps

How I Started My Microsoft 365 Consulting Business in 7 Steps

Everyone says “just start consulting,” but no one explains what actually works. I built my Microsoft 365 consulting business by turning decades of real Outlook, Exchange, and 365 support work into a focused, sustainable practice without becoming an MSP or burning out.

In this session, I’ll walk through the 7 practical steps I took to go from “the Outlook person” to a paid consultant: choosing a niche, setting boundaries, onboarding clients, tracking time, billing clearly, and learning when to say no.

This isn’t theory or hustle culture. It’s what worked and what didn’t. If you’ve thought about consulting but want a realistic path, this session is for you.

Key Takeaways

How to define a profitable Microsoft 365 niche
Consulting vs support (and why it matters)
Simple onboarding, time tracking, and billing
Pricing expertise without apologizing
Mistakes that cost consultants time and money

Audience
IT pros, admins, MVPs, and Microsoft community members considering independent consulting.

10 Outlook Classic Problems You Won't Miss with New Outlook

Join me for a 70-minute session covering 10 Outlook Classic problems that helpdesk staff, IT technicians, engineers, and leadership definitely won’t miss.

This is a lighter, humor-driven session designed to give technical audiences a break between deep technical talks. We’ll laugh, commiserate, and call out long-standing Outlook Classic frustrations that have consumed time, tickets, and patience over the years.

No deep dives, no migration pressure just relatable scenarios, shared pain points, and a chance to enjoy some Outlook therapy with people who’ve lived it.