Maximizing Learning and Development at Microsoft with Monesh Bulchandani

What if learning at work felt less like a checklist and more like a catalyst for growth? That’s the challenge—and opportunity—at the heart of this conversation with Microsoft’s Learning Lead, Monesh Bulchandani, on the topic "Maximizing Learning and Development at Microsoft" on Play for Performance with host Jolynn Ledgerwood.

As the architect behind employee and customer skilling initiatives at Microsoft for nearly a decade, Monesh brings a practitioner’s view of Learning and Development (L&D) in a fast-moving, AI-shaped world. Paired with Jolynn’s strengths-based, LEGO-inspired approach to creative problem-solving, this episode explores how authentic leadership, playfulness, and mentorship can turn training into momentum.

Modern Learning and Development: From Courses to Consultation
The L&D playbook has evolved. Instead of pushing content, Monesh emphasizes guiding teams through consultative skilling strategies that meet people where they are. That shift—from instruction to partnership—builds capability and trust. It’s not about stacking modules; it’s about aligning learning with real work and real outcomes.

“Be authentic at work. Let your humanity shine—authenticity and empathy always distinguish you.” That’s more than a quote; it’s a design principle for how learning lands. When teams feel seen and supported, they apply what they learn faster and with more ownership.

AI at Work: Empowerment Over Overwhelm
AI is changing how people learn and deliver value. The opportunity isn’t just smarter tools—it’s smarter workflows. Monesh frames AI as an empowerment layer for both employees and customers: upskilling to use AI ethically, creatively, and efficiently; reskilling to focus on judgment, communication, and problem framing. The human element becomes the differentiator.

Authentic Leadership and the Power of Mentorship
Monesh’s long-standing mentorship at USC’s Annenberg School and role on the Alumni Advisory Board underscore a theme: leadership isn’t reserved for titles. It’s built through service, reflection, and a willingness to learn from missteps. His greatest professional achievement—embracing failure as a teacher—models a growth mindset that strengthens culture and accelerates learning.

Play Fuels Performance: Joy, Collaboration, and LEGO Bricks
When work is engaging, learning sticks. Jolynn’s facilitation toolkit, including LEGO SERIOUS PLAY, taps hands-on creativity to unlock ideas, alignment, and collaboration. As Jolynn puts it, “Changing workplace culture takes time, but each playful connection makes a difference. Work can be both fun and meaningful.” Whether it’s prototyping strategy with bricks or carving out space for team rituals, joy isn’t a distraction—it’s a performance multiplier.

Key Takeaways

  • Shift from instruction to consultation to align learning with real outcomes
  • Use AI to empower people, not replace judgment and empathy
  • Embrace failure as fuel for growth and culture
  • Lead without a title through service, mentoring, and modeling behavior
  • Integrate play to deepen engagement and accelerate learning

This episode is a reminder that when learning is human-centered and creatively designed, it doesn’t just improve skills—it changes how teams think, build, and lead. Listen to the full episode for deeper insights, and follow Jolynn Ledgerwood for more conversations at the intersection of leadership, creativity, and performance.

Connect with Monesh Bulchandani: www.microsoft.com | linkedin.com/in/moneshb
Learn more about Jolynn’s approach and LEGO SERIOUS PLAY workshops on her site.

Connect with the host, Jolynn Ledgerwood, Meet The Coach - Elevate Your Talent, About LEGO® Serious Play® - Elevate Your Talent

Transcript

Jolynn Ledgerwood:
Hello, Play for Performance people. I’m so glad you’re joining us today. I’m Jolynn Ledgerwood bringing you Play for Performance. We’re honored to welcome Monesh Bulchandani to our program. He serves as the learning lead at Microsoft, where he’s been instrumental in driving employee and customer skilling initiatives. As he celebrated his 10th anniversary in July. He brings a wealth of experience from his previous roles in Amazon and Yahoo. Beyond his professional achievements, he is actively involved with the Annenberg School for Communication and Journalism at the University of Southern California, serving on the alumni board and mentoring students for the past 15 years.

Jolynn Ledgerwood:
He’s based in Seattle, Washington. He enjoys traveling, spending time with friends, and attending concerts in his spare time. His dedication to embracing and and learning from failures stands at his greatest professional achievement, while his impactful mentorship of students highlights his personal accomplishments. Today we will explore Monesh’s work at Microsoft, his passions, his volunteer efforts at USC, and his aspirations. So please join me in welcoming Monesh. I’m so glad to have you. Thank you for joining us.

Monesh Bulchandani:
No, thank you for having me. Such an honor to be here. Thank you so much.

Jolynn Ledgerwood:
Absolutely. So tell what inspired you to specialize in learning and development?

Monesh Bulchandani:
You know, I was in sales for a very long time at Yahoo and Amazon and my first role@Microsoft 10 years ago, Geez, was also in sales and I thought I was ready for some deep product knowledge and I felt like moving to the learning and development role, it would give me the opportunity to get that deep product knowledge because if I’m going to train others on it, I better know my stuff, right? So I think that was one of the big reasons. And also I think I was up for a new challenge to be able to be honest because I didn’t want to be in sales for the entire career of mine. So I thought it was an opportunity to really acquire new skills and a lot of skills were transferable just like most roles.

Jolynn Ledgerwood:
So how has your role evolved as you’ve been with Microsoft now for 10 years?

Monesh Bulchandani:
Yeah, I’ve had many different roles, but specifically in the learning and development role, I was a facilitator for the most part. I did some program management in HR, part of the leadership development program, and really piloted and scaled the leadership development program across the company globally. But in terms of what I do today, even though I’m not in true sales, you know, like selling products or solutions or whatever, but I’m now customer facing. But this time the conversation is a little different. It’s about skilling and making sure organizations that do business with Microsoft are, have the resources and the skills that they need, and need to really learn our products and get comfortable with it. So it has really evolved from being like doing a lot of internal stuff in the learning development world and now I’m back to being customer facing, but in a non sales role, if you will.

Jolynn Ledgerwood:
Right. So you said you don’t do sales anymore, but I think at the root we all are always doing sales in some capacity. Right? Yeah.

Monesh Bulchandani:
So there’s definitely some truth to that.

Jolynn Ledgerwood:
Yeah, absolutely. So getting to work with our, getting to work with your customers, what are some of the ways that you encourage their attending these courses or do you bring play and fun into the courses that you use for customers?

Monesh Bulchandani:
Yeah, so I’m not really training them. What I’m doing is really a consultation. So I’m asking them lots of questions in terms of their skilling strategy. How are they approaching that within their organizations, whether they have dedicated L and D teams. So doing a consultation and based on that information gathering that I do, I will present them with the different resources and opportunities we have for them. So we have everything from self paced training to training in person. So depending on what their needs are and what gaps they’re trying to fill, you know, I’ll put a plan, if you will, in front of them.

Jolynn Ledgerwood:
That’s great, that’s great. I, I love that you have the ability to work with customers and, and the insight team to figure out what best suits them. How are you so forward thinking? How do you anticipate emerging technologies will shape employee and customer skilling initiatives?

Monesh Bulchandani:
You know, AI is the hot thing. Right. And AI is here to stay. And one thing I will say, AI cannot replicate being an authentic, empathetic human being. Yes, it can do a lot of tasks, but one thing it will not take away from us humans is the actual human element itself. So I think AI is a great thing and it can take a lot of tasks so we can focus on that relationship that AI cannot really build.

Jolynn Ledgerwood:
And I appreciate you just throwing out the elephant that’s in all of the rooms and workplace discussions nowadays. And that’s AI. And you’re right, it can’t take the human element out of what we do. There’s certain roles that, you know, we know AI is going to completely take over, but I don’t see training and development being one of those roles. Yeah, I need to just go into an AI and ask, you know what, where do you see play in the workplace moving forward and just see what that Answer comes out. Because that ought to be interesting.

Monesh Bulchandani:
So a little.

Jolynn Ledgerwood:
Yeah, a little pivot. Let’s talk about your work with the Alumni Advisory Board at USC and the mentoring you do with students. How did you get to start doing that?

Monesh Bulchandani:
Ever since I graduated from usc, I became involved as an alum almost immediately. So I would sign up to do mock interviews for graduating students. I would review resumes, I would sign up for different mentoring programs. So I was doing that for so long, about 15 years. So I really got to know folks within the Annenberg School of Communication and Journalism and had a great relationship. And then a couple years ago, they approached me and said, hey, you’re so involved. You do a lot for us. Would you like to be on the board? It just makes sense.

Monesh Bulchandani:
And I said, oh, absolutely. What an honor. Was not. That was not my goal. I was not expecting that. Did not even know the alumni board existed, but they approached me and said, oh, wow, this is great. So it’s a three year appointment. I am now in my final year of the.

Monesh Bulchandani:
So I absolutely love doing it. You know, when I went to usc, I didn’t have a lot of resources and I didn’t have a lot of support. Various reasons behind that. So I really believe in paying it forward and making sure, you know, the future generation, they’re really prepared for what’s to come after graduation, because that’s a whole different reality.

Jolynn Ledgerwood:
I think that’s so great, Manish, that you saw that need and volunteered. You weren’t asked. You just said, hey, I want to help out these students, these young adults that are entering their world. And college is new and different for so many people. So to be able to work with them, I bet that’s extremely fulfilling for you.

Monesh Bulchandani:
Yeah, it is. And it’s also a very different time, different world we’re living in. So I’m also learning a lot from this new generation. I’m like, hey, mentor you. But let’s think of it as reverse mentoring. Like, teach me something too, right? So I like the exchange of ideas that happens during those conversations.

Jolynn Ledgerwood:
That’s great. And I, you. We have a lot of similarities. One of the things I love most about learning and development is the fact that I find that I learn so much from the people that I teach and hope that they get as much from me as I’m trying to teach them. So what are some of the core values that are most important to you in the workplace environment?

Monesh Bulchandani:
I would say being authentic, bringing your full self to work. And I know we hear that a lot But I think that is critical and bringing the human element in your work because before someone gets to know me as a Microsoft employee, get to know who’s a human being first because I think that will give people a sense of, you know, who you are as a person and how you work and what are your values, what’s your mission. So get to know me on a human level before, you know, we go down the path of just business. So that’s very important to me. Being empathetic, you know, we all have a story, so making sure that we understand we, hey, we come from different backgrounds, so just being empathetic towards that. And I would say one other thing is just, you know, good leadership. I’m not in a formal leadership position and I always tell people you don’t need to have direct reports to be considered a leader. Like I’m a leader as an individual contributor.

Monesh Bulchandani:
Right. So I think good leadership, specifically when it comes to coaching, removing blockers and seeing other people progress, right. Like cheering people on, people around you. So I think that’s also important to bring to the workplace.

Jolynn Ledgerwood:
That’s great. And you’re right to be a leader doesn’t mean that we have to have direct reports. It doesn’t mean that we have to have people that report to us. It just shows that you’re setting the right example in the work that you do. You’re setting the standard high. You’re holding yourself accountable to the work that’s done. And, and, and you’re right. We all come to the table with different baggage and different stories and different paths and all those things.

Jolynn Ledgerwood:
So it’s great that you are so empathetic. And I see that in you in all the times that we’ve spoken. So that’s just great. Absolutely. So initiatives that are coming up for you at Microsoft, anything new and trending that you guys are going to try to prioritize in the near future, you.

Monesh Bulchandani:
Know, still everything AI, right? Still making sure our customers are set up for success, making sure that they have all the resources. So AI, the technology is evolving so quickly. So I really foresee lots of different programs coming in the future, not only for employees, because we want to make sure our employees are getting skilled as well, but also for customers. So I still see AI being a big part of what that’s going to look like or what the programs are going to look like. And I know we’re moving very fast because I feel like this technology is moving at such a fast speed. So trying to keep up with that, number one and number two, making sure everyone has the skills that they need in order to really have those conversations with their customers or even within them, you know, within the organization itself.

Jolynn Ledgerwood:
Yeah, you’re right. It’s. It’s coming fast. Hard and fast, I guess is the best way to say it. But you’re. My head’s even spinning on. Wow. Like this is, I feel like I’m trying to embrace it, but trying to understand it.

Jolynn Ledgerwood:
So I love that you’re actually spending time with the teams to help them understand how it can be beneficial and useful. And you’re right, it is absolutely going to be the future. There’s no turning back now. What about again, I mentioned it earlier. Like, I wonder if AI talks about fun in the workplace, but how are ways that integrating fun has enhanced collaboration and learning for you at Microsoft? Because from what I understand, Microsoft’s a pretty fun place to work.

Monesh Bulchandani:
It is a fun place to work. And I will say in terms of AI specifically, we will try different prompts and it’s not all business related, right? Prompts like, hey, describe my personal personality based on all the work that I’ve done or create an itinerary for this trip that I’m taking. So we try different prompts as an icebreaker that’s not necessarily related to Microsoft or the workplace. So that’s one way of having fun. And there’s a lot of learning happening because prompt engineering is such a big part of AI. So I think it’s also a great learning experiment at the same time, but also having fun.

Jolynn Ledgerwood:
That’s great. That’s great. And when you incorporate that type of fun, do you see better results? Do you see people more engaged? Do you see people like retaining that knowledge longer, stronger?

Monesh Bulchandani:
They’re so excited to share what they’re getting back from Copilot, which is Microsoft’s AI technology. So there’s a lot of sharing and excitement to a point where you keep going and continuing to have that conversation. But at some point I’m like, okay, now we really have to talk about business. Love the enthusiasm, but we got to move on. So I think that brings a lot of fun. And we have different AI skill skilling challenges within the company. We have hackathons, in fact, that’s coming up in a couple of weeks. So there are so many initiatives within the company that we do to have fun but also learn at the same time.

Jolynn Ledgerwood:
That’s great. I love that. Can you share a memorable experience from your mentoring at usc? Maybe a student that’s impacted you? And obviously we could keep it confidential, but can you share any stories that have really resonated with you?

Monesh Bulchandani:
Yeah. I will say the mindset of the younger, newer generation, Gen Z, you know, very different mindset in the way they think and the things that they do on the side. Like when I graduated from college a long time ago, I did not even do half of the things that they are doing on top of going to school full time. So that was very eye opening for me and that was happening with all the students that I was talking to and it gave me the sense of inspiration. Like even though, you know, I’m not in college and that phase of my life is over, I’m like, it’s still not too late. So I would say that’s memorable and I know that I’m being very general, but it has really inspired me to think about, hey, if they’re doing all these 10 different things while going to school full time, there are other passion areas of mine that I could focus on while working full time. So that has been a wonderful experience for me personally.

Jolynn Ledgerwood:
I love that. And you’re right, they’re doing so much more now than we did. Which I think is great because it speaks to. We don’t have to work all the time every day to be successful.

Monesh Bulchandani:
Exactly.

Jolynn Ledgerwood:
We don’t live to work. We should. I hate the word should, but I think we’re supposed to work to live and to have fun and to be involved outside of the workplace and places like you mentoring other students and you know, volunteering your time with that and really being involved in the world. Not just this 9 to 5 or 8 to 5, whatever work job that we have. Which.

Monesh Bulchandani:
Yeah.

Jolynn Ledgerwood:
Which I think is really great.

Monesh Bulchandani:
That’s what I would say that that should be a greater purpose. Right. So yeah.

Jolynn Ledgerwood:
I will also say growing up with this would be so challenging for me personally. I see my kids on the devices all the time and I’m just like, put it away. And now at the workplace you see people on those devices all the time. And before it was that it must be a distraction from your work. And now it’s more, it’s part of my work is to be involved and to be responsive to other business platforms and events and stuff. That’s awesome. Yeah. So speaking of fun traveling where it’s then, do you have any places on the radar for traveling soon?

Monesh Bulchandani:
Yes, I’m going down to California next week in fact. I’m going to see some family, friends, but also get time to relax and then I’m going to Vegas for a team conference. And then I’m going to New York for a leadership conference. So September, for some reason, happens to be very. A month focuses on conferences, for some reason, but I’m going to get in some RNR in between all that. So that’s coming up on the horizon. And then other trips planned after that as well.

Jolynn Ledgerwood:
Oh, that sounds. Talk about fun. That sounds great. I love conferences. Getting to meet other people in our industries, and especially team events in Vegas. You can’t go wrong there, right? I mean, yeah.

Monesh Bulchandani:
Hey, you know, and there’s gonna be a lot of time for fun and good food and, you know, interacting with people in the flesh.

Jolynn Ledgerwood:
Yeah, I love that. That’s awesome. So, personal question. When was the last time you played with LEGO bricks?

Monesh Bulchandani:
A long time ago. But lego, I grew up with lego. I played with LEGO my entire childhood, but it’s been a while. However, if I see a LEGO store in the city that I’m in, I will walk in and walk around and take a look because it brings back all those memories. So, yeah.

Jolynn Ledgerwood:
So did you. If you bought the kit, do you follow the rules or do you toss the book in? Free build.

Monesh Bulchandani:
Free build. Like, yes. That, that’s. That was always me. If I had to say, if I bought a LEGO set where you had to build a castle, I would take all the pieces and build it like a concert venue or something along those lines, you know? So I never looked at them. The book. I don’t have a lot of patience for reading instructions, so that’s just me. But I would build something and it’s such a good exercise for your brain as well.

Monesh Bulchandani:
Right. And I think, I have a creative brain. So that, to me, was how I approached lego.

Jolynn Ledgerwood:
And that’s one of the things I love most about you is you’re like, I’m tossing the book and I’m just building what I want to build. Where I am, as you can see, I have several legos behind me. I am by the book, like, and if I can’t find a piece, I’m like, stop. Find. You know, it’s. I don’t have as much of a creative mind as you, and so I, I, yes, I can build things, but it just, it doesn’t come to me as easy as actually reading the book. So I love how just like, yeah.

Monesh Bulchandani:
Are you that person that lays out all the pieces and counts them and making sure nothing’s missing?

Jolynn Ledgerwood:
What’s wrong with that?

Monesh Bulchandani:
Like, I don’t, I’m not judging.

Jolynn Ledgerwood:
I don’t count the pieces, but I do sort. So I make sure that I. How. You know, I know where to get them. Yeah, I. Yes.

Monesh Bulchandani:
Hey.

Jolynn Ledgerwood:
But no, we all. And that’s again, one of the things I love about asking that question to everybody is we all have our ways to build with LEGO bricks, and we all have our ways to do other things in the workplace. And nothing’s wrong or right. It’s just who we are as people and how we have all those differences. Yeah, exactly.

Monesh Bulchandani:
It’s how our brains work.

Jolynn Ledgerwood:
Exactly, exactly. Okay, so you have a wide. Over a huge toolbox of things that you’ve collected over your career for learning, development, mentoring students, your own upbringing. If you could offer our guests today one of those tools to take with them, what would that be?

Monesh Bulchandani:
Empathy. That’s an easy question. We’re living in a very interesting world right now, and I think we could all use empathy and kindness, whatever you want to call it, it’s much needed. It’s always been needed. But I think in the last several years, we could use that.

Jolynn Ledgerwood:
I appreciate that, and I absolutely agree. Thank you so much. So guests today, go out and be empathetic. Read the rule, read the book on Legos, or toss it and free build. Mane, it’s been so great having you. If our guests want to reach out to you, what’s the best way for them to find you?

Monesh Bulchandani:
Oh, they can find me on LinkedIn if we could paste that somewhere. But LinkedIn is a great place. And let me know you listen to this podcast so I know you are a listener.

Jolynn Ledgerwood:
Yay. I love it. And yes. So Monash, if you can’t find him, reach out to me. And he’s connected. So we’d be more than happy to connect you. It has been such a pleasure. Thank you so much.

Jolynn Ledgerwood:
Enjoy your travels and be safe.

Monesh Bulchandani:
Thank you. I really appreciate being here. Thank you for inviting me.

Jolynn Ledgerwood:
Thank you so much. Take care, everybody, and we’ll see you next time on Play for Performance.

Monesh Bulchandani:
Thanks.

Jolynn Ledgerwood:
That’s a wrap on another episode of Play for Performance. I hope today’s conversation sparked some ideas for how you can bring more joy and engagement into your workplace. Remember, transforming workplace culture doesn’t happen overnight, but every small step toward play and connection makes a difference. Try one thing we discussed today, even something small, and see what happens. If this episode resonated with you, please share it with someone who could use a little more play in their professional life. And don’t forget to subscribe so you never miss our weekly conversations with incredible guests who are changing the game of workplace engagement. Have a guest suggestion or want to share your own Play at Work story, Reach out to me at jolynnlevateyourtalent co or find me on LinkedIn. I love hearing from you.

Jolynn Ledgerwood:
Until next week, keep playing, keep performing. And remember, work doesn’t have to be taken seriously to be serious. This has been Play for Performance. I’m Jolynn Ledgerwood and I’ll see you next time.