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.

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.

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.

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