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Team Leaders and Managers are at the heart of driving success in today’s rapidly evolving workplace. With the rise of AI and tools like Microsoft 365 Copilot, their role in enabling collaboration, communication, knowledge sharing, and process improvement has never been more critical. This discussion will equip Team Leaders or those who empower them with the insights, strategies, and skills they need to harness the transformative power of AI.

More than just technology, we’ll also look to address the human side of AI integration, including overcoming concerns about AI in the workplace and fostering a culture of trust, confidence, and growth. Whether you’re helping your team embrace new ways of working or looking to align your leadership strategies with the possibilities of AI, this session will provide practical guidance and thought-provoking insights.

Join Microsoft MVP and industry leader Richard Harbridge for a dynamic discussion where strategy meets action, and leave with the tools and confidence to lead your teams into the future of work.

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

Q. Tell us a bit about yourself? – City, family, hobbies, job title

A. I am a Canadian who lives just outside of Toronto. I love being a dad and spending time with my 3 boys gaming, walking/adventures, and just living a happy life.
Hobby wise I really enjoy learning (I read way too many research papers and reports but I enjoy it). Mixed with audiobooks, tv, movies, and gaming.
Title wise I am a CTO/Microsoft MVP/Advisor and just really friendly.

Q. Tell us something about yourself that not many people know about you?

A. Short? I used to do extreme martial arts for a bit in college, parkour, flips, b-twists, stuff like that. 

Longer example? I have some crazy work stories/mistakes I have made over the years especially when I was starting out in my first jobs. I literally had some of the worst first day experiences at work you can imagine (breaking equipment by accident and not little ones, causing huge messes, etc. So I am always reminded that while I actually got employee of the month for the first month at the same two places I had my worst first day that we all make mistakes, and that is part of the learning process.

Q.  What does a typical workday look like for you?

A. I spend quite a bit of my time in meetings either as escalation to answer questions and provide direction, in meetings with IT leaders or executives helping establish roadmaps/priorities, or working with partners, vendors, and people much smarter than me on getting more out of Microsoft technology. Outside of meetings it's a burst of email (outlook is still my primary work tool), MSFT teams correspondence/coordination, focus time on documents/presentations, or following up on things via LinkedIn (my main social platform).

Q.  1st job out of college

A. A SharePoint Consultancy. Insane hours of sometimes 30+ hours straight working without rest, sometimes 80 hour work weeks, etc.

• Started as a dev, then architect, then business analyst, etc - always gravitating to lead roles as I tried to fill any gaps needed for project or customer success.  
• I learned great technical skills and worked in a gauntlet which made everything else easier later, but also taught me a lot more about my own value and what customers value.
• Secret to success IMO is to always be uncomfortable. If your work get's comfortable challenge yourself and move on or take on new things -> I keep telling myself I will relax in a comfortable role someday but haven't been able to yet. The learning is too rewarding.

Q. Your 1st version of SharePoint that you experienced and what year

A. 2001 or 2003. It was a different world back then!

Q. Last challenging project and why? (this should relate to your demo)

 A. We have quite a few 'frontier' customers we work with. Those who already have scaled Copilot deployments and are using Agents etc.

I was working with our team on how to do more than just prompt-a-thons and good adoption patterns which led us to quite a bit of AI for Team Leaders as a category to drive soft and hard skill growth around AI. This was because in automation-a-thons or other tactics we employed with customers we found a path for agents/solutions and scaling that well - but felt there was a gap in what Microsoft or even the marketplace was providing we could service better and customers needed. The challenge was there just isn't that great of material in the marketplace.

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. I spend quite a bit of my time on strategy/top down things like Intranets, AI rollouts, big projects etc. I think of this work as capital P process work. Working on ERP? Working on Customer Experience? Working on Employee Experience? All for the most part capital P process improvement one way or another. Yet in my professional experience it's the stuff that happens at a Team level that I think is surprisingly often more impactful, especially at scalee than what happens today at a divisional, group or department level (top down).

• What I mean by that is that businesses are really improving across two types of processes. One set is capital P processes meant for capital P process systems, think ERP, customer experience, etc. The other is the processes that are often undocumented, that are driven by people, often called people processes. These tackle exceptions and these use M365 in the form of emails, teams, and more to connect between these capital p systems and processes. If two insurance orgs have similar technology on the ERP side and capital P process side (very common) the competitive advantage is actually from their lower case p processes. This is why improving productivity, adoption, Copilot/digital assistants/agents at scale are so impactful today.
• Another way to think about it? Leaders I talk to say - we get a purchase order, we put it on the truck and that is where our business ends - everything between is a mix of exceptions and processes (capital P ones). But in the AI era it's about multiples of growth - the challenge for that executive is to think but what if your business was in the living room, what if that is where your journey ended instead. We can't do that they say - but the reason is capacity, the reason is capability - both advancing in significant ways with AI. Instead of cutting staff - keep them and drive growth, drive multiples of growth versus just small percentages of growth. The best part if you do it but your competitors don't you catapult even further ahead. The people in the business, their processes, the way teams work - that is the real sweet spot in todays AI era if you want real growth and it's also the most under served area in my opinion. 
• So how do you do this from the top down? You engage teams. Teams are the smallest unit of measure (because working with each person while admirable is just not cost effective at scale). Teams (cross functional, departmental, etc) have shared interests, often shared understanding and shared problems that digital excellence and AI, Microsoft 365, Power Platform etc can solve and be implemented by that team often with very little need for approval. They can drive their own adoption. In fact in Copilot deployments using a team based nomination and assignment model (saturating teams with Copilot licenses) gives you on average a greater than 3X return on investment. The industry data is showing this more and more as well. We have so much consensus on individual productivity with AI, but agents especially work at both an individual and team level - and it's the team level ones that are driving bigger impact and differentiation today. Here is a great recent example from Harvard that I love...
  
  SharePoint Agents are an example of a simple retrieval focused team agent. (light demo aligning with the value of teams + AI). 

This is why I think AI for Team Leaders in all it's forms is such a critical focus point. Not just on technical skilling/learning for digital excellence but soft skills too! (demo/prompt pattern examples x2 if we have time).

Q. Describe a SharePoint train wreck project, and what did you learn?

• Anything that takes too long. Most projects that are a few weeks long or even a month or two tend to do well, but ones that go for months BEFORE we get a prototype, pilot or solution in front of real users for feedback/expectation alignment? Those always have the biggest risk. 
• So many times we come into projects and say - hey what about this more practical, closer to out of the box, and quick iteration pathway - sometimes literally spinning it up in a few hours in initial calls and the customer teams are surprised by how impactful it can be, and start to rethink their requirements, what they own already or most importantly approach.

Q. Your favorite M365 feature/tool and why

A. While Copilot is a natural fit because it's the most helpful today in my work for both me, my teams and my customers I personally am a huge fan of Viva Insights and use it a lot. The behavior signals help me - example I am always trying to improve so being able to see my RSVP rates for internal meetings vs external meetings has been helpful - especially as I have worked harder to follow meetings and decline meetings versus over accept many tentatively. Things like this or seeing who I might be losing touch with for those I mentor, partner stakeholders important to me, or even leaders on the customer side - that is soooo helpful from Viva Insights.

Q. Where do you think Microsoft is going with M365.. Be totally honest

A. Copilot and AI is the future, not just for them but for any SaaS solution today. There is a way to go about it that is important where you meet customers in their journey but they need to continue advancing rapidly especially against the competitive threat of Google the marketplace and a potential slew of new up and coming competitors across their portfolio of capability in M365 today. Great example? I now have some executives telling me they have a Gemini to Copilot or Gemini to Microsoft migration - some aren't even calling it Google - while anecdotal and early it's important IMO.

Q. What are the 3 cool features of the demo?

A. I really want to show at least one example of soft skills for Team Leaders using Copilot/AI. Even if it's just a simple walk through.

I think people are sleeping still on the value of Copilot pages so want to show a few slides there to communicate a key concept on multiplayer by design/learning together this combined with Copilot Gallery makes sense IMO.

stretch (time permitting) - I think talking about Copilot Actions makes sense - if not a demo then just a few quick notes on why it matters and aligns.

 if not done more naturally earlier SharePoint agents (and other Copilot agents) I think is a good short discussion to level set, but thinking about how they are being used in real world matters more there.

Q. What is the sizzle?

A. People don't know what they have or what key changes coming shortly make a big difference/impact on teams. 

Q. What was your first job out of hire school
A. Three all at once in high school - Winners/TJMaxx maintenance, worker at a diary facility (old returned milk products and very physical), and ran our own business building websites.
most continued until the SharePoint consulting gig after college.

Q. What's your biggest nightmare project you have worked on … And what did you learn from this experience

A. 56+ SharePoint Server Farm Migration/Upgrade in a very decentralized large enterprise. The biggest learning is how to scale from tasks, to projects, to programs and steer all of that together effectively. That ore a 100k+ org that had a brand new intranet unifying 3 all in less than a month (from design to build/implementation) but that was just an insane project due to timeline. 

Q. What’s the best and worst tech advice you’ve been given

• Best advice is the value of debating with others - at community events/wherever you can - helps your grow, helps you change perspectives, and helps you often improve in really significant ways. Don't just listen and learn - ask, set time aside and disagree so you can learn why you might be wrong or right in assumptions or perspective.
• Worst advice? It works for me or on my machine. 😋

Q. What are you working on to become a developer/consultant / CTO

A. I really need to get back into more exposure with vendors/partners - been so heads down leading customers with AI and Microsoft 365 I need to understand the market better IMO. Secondarily I need to do a much better job on my personal brand/work there. Haven't really improved that in almost a decade IMO.

Q. Where do you want to be in 5 years?

A. Just scaling how I help people in bigger ways. More templates, more guidance, more presentations, interviews, podcasts, etc. I think of my life in decades and have some big goals for this decade that just started so if I achieve even a third of what I intend I will be super happy

Q. What's your blind spot in your Microsoft knowledge? Pitfalls

A. There is just too much to know in Azure today. I feel like I somehow have been able to keep up with everything in Copilot, Copilot Studio, Viva, M365 and even Power Platform for the most part - but beyond AI Foundry and other things I just need to rely on many others as things move so quickly and there is so much to know. I think over time I will have to let go of keeping up with everything Power Platform or something else too.

Q. Where do you source your knowledge? - Twitter- who do you follow, site urls

A. Biggest source is just discussions! I love 1:1 chats/1:few chats - I work remotely, it breaks up my day, varies what I learn/what we discuss, IT leaders teach me a ton, ambitious individual contributors, MVPs/passionate speakers, honestly it's a really wide mixture and I like it that way. To this day I rarely have to say to someone let's meet more than a month out - so I always have more capacity if anyone listening to this wants to connect.

Otherwise typical stuff - I love the Microsoft community blogs for most announcements, the message center/roadmap for M365 etc. I love LinkedIn and have a lot of MVPs, leaders and Microsoft people I try and watch in my feed.

Q. In your mind, if there was 1 song that could describe SharePoint, what would it be? - David Bowie - Heroes

A. Today due to the end of support for SP2016 and 2019 it would be the final countdown. 

Q. Where can people find you?

A. LinkedIn is best! I try really hard to stay on top of my messages there - though try and connect first so it shows up in the focus message feed or just post a comment/ask a question somewhere in my feed. <3