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Women in technology, particularly in Microsoft 365, cloud solutions, and IT leadership, continue to face barriers such as self-doubt, imposter syndrome, and underrepresentation in leadership roles. While technical expertise is crucial, confidence is the key to unlocking career growth, driving innovation, and becoming a leader in the M365 ecosystem.

In this empowering session, Sheena Yap Chan, keynote speaker, best-selling author, and advocate for women in tech, will explore how self-confidence enables professionals to step up, influence workplace technology adoption, and advocate for their expertise in Microsoft 365 solutions. Drawing from her book, The Tao of Self-Confidence, Sheena will share strategies for overcoming self-doubt, taking leadership roles in digital transformation projects, and building visibility in the M365 community.

Through real-world examples, research-backed insights, and interactive discussions, attendees will learn how to:

✅ Develop confidence as an IT professional and M365 expert to lead digital transformation initiatives
✅ Overcome imposter syndrome and self-limiting beliefs to advance in tech careers
✅Leverage M365 tools to enhance collaboration, productivity, and leadership presence
✅ Engage in networking, mentorship, and knowledge-sharing to amplify their voice in the tech community

Below are the questions and answers from the June 2025 Meetup Session.

Q. Tell us a bit about yourself? – City, family, hobbies, job title
A.  My name is Sheena Yap Chan and I am a Wall Street Journal Bestselling Author, Keynote Speaker, Consultant and podcaster on Confidence and Leadership.  I was born in the Philippines but moved to Canada when I was 7 years old.  I like to workout, travel and spend time with my loved ones.

Q. Tell us something about yourself that not many people know about you?
A.  When I was about 5 years old, I was a flower girl for my aunt's wedding and I was obsessed with Cinderella.  When my aunt was about to say I do to my uncle, I went up to the altar and started singing Cinderella in front of everyone.

Q. What does a typical workday look like for you?
A.  A typical day would to do outreach, give talks in person or online and setup meetings with clients.

Q. 1st job out of college
A.  My first job was a sales associate position at Walmart

Q. Your 1st version of SharePoint that you experienced and what year
A. My first experience with SharePoint was around 2010.  It was chunky, a bit overwhelming but it got the job done.  It taught me how to adapt fast in tech environments, even when the tools weren't perfect.

Q. Last challenging project and why? (this should relate to your demo)
A. My last challenging project was building out a SharePoint site for cross-functional collaboration. The tough part was making it intuitive for non-tech users while still meeting complex compliance needs. But that’s why I chose it for this demo — it pushed me to blend technical skills with user-first design, and I’m proud of how it turned out.

Q. What is the biggest mistake that your feel holds back your clients from the results they want (this should relate to your demo)
A.The biggest mistake I see is overcomplicating the process. Clients want results but get stuck adding too many features or approvals. With my SharePoint demo, I show how simplicity and clarity in design drive adoption—and that’s what leads to real results.

Q. Describe a SharePoint train wreck project, and what did you learn?
A. One SharePoint project was a total train wreck—no clear ownership, too many custom web parts, and zero user input. It crashed before launch. What I learned? Simplicity wins, and you need users involved from day one. Now, I always build with the end-user in mind, not just the tech

Q. Your favorite M365 feature/tool and why
A.  My favorite M365 tool is the Power Platform — it’s like having a full toolkit to solve real problems fast. Whether it’s Power Automate, Power Apps, or Power BI, it lets you build smart, user-friendly solutions without needing heavy code. It empowers everyday users to create impact.

Q. Where do you think Microsoft is going with M365.. Be totally honest
A. Honestly, Microsoft is going all-in on AI, automation, and integration. M365 isn’t just about apps anymore — it’s becoming an intelligent ecosystem. With tools like Copilot and the Power Platform, they’re pushing for a future where everyday users can build, automate, and analyze without needing IT. But the flip side? It’s getting complex fast. The challenge now is helping users keep up and actually unlock the value without getting overwhelmed.

Q. What are the 3 cool features of the demo?
1. Automated workflows using Power Automate — no more manual approvals.
2. Custom user-friendly interface built in SharePoint — simple, clean, and easy to navigate.
3. Integrated Power BI dashboard — real-time insights right where users work.
It’s all about making work smarter, not harder.”

Q. What is the sizzle?
A. The sizzle is how everything works together. SharePoint, Power Platform, and M365 — all seamlessly connected to give users a smooth, powerful experience. It’s not just a site, it’s a smart workspace that saves time, boosts productivity, and actually gets used.

Q. What was your first job out of hire school
A. Walmart

Q. What's your biggest nightmare project you have worked on … And what did you learn from this experience
A. I had to speak at an event that was totally unorganized and it was badly planned.  I learned that it's important that what you advertise and what you actually put together must match.

Q. What’s the best and worst tech advice you’ve been given
A. Best advice? “Keep it simple.” Tech should solve problems, not create them. That mindset has saved me—and my clients—countless headaches.
Worst advice? “Just copy what another team did.” What works for one org can totally flop in another. You have to build for the people actually using it, not just follow a template.

Q. What are you working on to become a developer/consultant / CTO
A.  I’m investing in soft skills — consulting isn’t just about tech, it’s about listening, leading, and translating problems into smart solutions. That’s how I’m building toward being a trusted consultant — and eventually, CTO

Q. Where do you want to be in 5 years?
A.  Still be able to do what I love to do

Q. What's your blind spot in your Microsoft knowledge? Pitfalls
A. My blind spot has been the deeper admin and security layers — like compliance center configurations and advanced governance. I’ve gotten tripped up when assumptions didn’t match reality. The pitfall? Thinking you don’t need to know that side until it’s too late. I’m actively learning more about the back-end controls so I can build smarter and safer from the start.

Q. Where do you source your knowledge? - Twitter- who do you follow, site urls
A. Various people.  Mostly on LinkedIn

Q. In your mind, if there was 1 song that could describe SharePoint, what would it be? - David Bowie - Heroes
A. Honestly? ‘Work It’ by Missy Elliott. Because SharePoint can do a lot — but only if you know how to work it, flip it, and make it user-friendly. Otherwise, it’s just noise.

Q. Where can people find you?
A.  They can find me here - https://sheenayapchan.com/links