Azure for Executives

Executive Leadership During Digital Transformation with Merrie Williamson

Episode Summary

We are discussing what it means for technology executives to lead their companies through true digital transformations, both from technology and cultural change perspectives. We’ve mentioned digital transformation several times over various episodes. Today, we’ll be making digital transformation very tangible and providing guidance for leaders looking to revamp their organizations with technically driven initiatives with our guest Merrie Williamson, the Corporate Vice President of Azure Infrastructure, Digital and App Innovation, and Azure IoT at Microsoft.

Episode Notes

We are discussing what it means for technology executives to lead their companies through true digital transformations, both from technology and cultural change perspectives. We’ve mentioned digital transformation several times over various episodes. 

Today, we’ll be making digital transformation very tangible and providing guidance for leaders looking to revamp their organizations with technically driven initiatives with our guest Merrie Williamson, the Corporate Vice President of Azure Infrastructure, Digital and App Innovation, and Azure IoT at Microsoft.

Episode Links:

Episode Transcript
Digital Transformation with Microsoft
Microsoft Learn course - Enabling Digital Transformation 
Microsoft Industry digital transformation blog
Satya Nadella on Digital Transformation for Microsoft (Video)


Merrie Williamson is the Corporate Vice President of Azure Infrastructure, Digital and App Innovation, and Azure IoT at Microsoft.

She is responsible for global commercial sales, strategy, and execution for the core multi-billion-dollar Azure business. She has a strong background in leading engineering and product teams and in marrying sales to engineering.

Follow her on LinkedIn.


Paul Maher is General Manager of the Industry Experiences Team at Microsoft. He was formerly CTO at Milliman.

Follow him on LinkedIn and Twitter.

David Starr is a Principal Azure Solutions Architect in the Marketplace Onboarding, Enablement, and Growth team at Microsoft. 

Follow him on LinkedIn and Twitter.

Episode Transcription

Executive leadership during digital transformation with Microsoft's Merrie Williamson.

DAVID: Welcome to the Azure for Executives Podcast, the show for technology leaders. This podcast covers trends and technologies in industries and how Microsoft Azure is enabling them. Here you'll hear from thought leaders in various industries and technologies on topics important to you. You'll also learn how to partner with Microsoft to enable your organization and your customers with Microsoft Azure.  

Today we're discussing what it means for technology executives to lead their companies through digital transformations, both from technology and from cultural change perspectives. And we've mentioned digital transformation many times on many episodes of the show. And today we'll be making digital transformation very tangible, not just a buzzword, and providing guidance for leaders to revamp their organizations with technically driven initiatives.  

So joining us today to talk about digital transformation and leadership for it is Merrie Williamson. And Merrie is the Corporate Vice President of Azure Infrastructure, Digital and App Innovation, and Azure IoT at Microsoft. She's responsible for global commercial sales, strategy, and execution for the core multi-billion-dollar Azure business. She has a strong background in leading engineering and product teams and in marrying sales to engineering. Merrie, welcome to the show. It's an absolute pleasure to have you here.  

MERRIE: Thank you, David, and thank you, Paul, for both having me.  

DAVID: You bet. And I'll kick us right off where we described starting and that is that digital transformation is a term we hear a lot, as we've said, and we've mentioned on the show from time to time. And it seems that true change like this needs strong leadership. What does it really mean to lead through digital transformation?  

MERRIE: I think there's no one answer. There's a business strategy element where I think that's where it really always has to start. But those business strategies are not cookie cutter. Some strategies start with an IT-driven digital transformation. Some are very top-down business-driven. Some are looking at the priority of understanding internal insights, you know, how is our company operating? How do we optimize it? Some are looking at customer experiences, and how do they get more insights into what their customers are doing and thus providing better service to those customers? Some are talking about modernization as the key of the business strategy, taking what you have and really modernizing and optimizing it. Some are looking at innovation. Some are looking at all of those in macro multinational organizations. So I think leading through digital transformation really is getting your arms around what are the finite priorities for your organization? Writing that down, getting consensus, and then moving forward. So that's a tough first step.  

And then the second tough step is the human element. How do you as an IT leader...and most of the time I'm talking to CTOs, CIOs, and IT leaders. But this is a once in a generation maybe twice in a generation transitional lead through because this goes beyond adding a mobile device to your IT environment or adding a new security capability. You're really moving your whole company to a modern era; this concept that every company is a software company. And I think the eyes are on the central technical organization to really help usher that through. Yet, there's still this kind of impatience that you have teams popping up all over doing what they feel compelled to go do with the speed of their business. So to do that, it's a huge human element of leadership. You have to be bold, lead, learn, be vulnerable, break through silos. Talk to peers you might not have never talked to before. So that's the second part I think of digital transformation. That's pretty consistent.  

And the third is retooling leaders, and this isn't just the senior leaders but leaders all up and down the organization. I think we're in an era where this concept of lifelong learning is coming to hit us in between the eyes of not just the technology (because I think that's important to understand the macro trends in technology) but how do you watch innovation outside of your company and inside of your market? Who are you looking at that you want to mimic? Who are you looking at that you want to learn from? And then you have to look at what are those tools and challenges inside that you want to lead through?  

And some of the interesting things I've worked on with my team is this human change management tooling. As a technical person, as an engineer, this concept of change management is one that's not super comfortable with me, [chuckles] but I'm learning. And I think it's going to be a big part of making things like digital transformation real because it's about setting the vision and explaining to people why they should make that personal change and then reiterating it, and buying into it, and getting that feedback and program managing it like anything else. So it's been interesting to hear all these common concepts.  

DAVID: You said a lot of things there that covered a lot of ground. Two of them jumped out at me. [laughs] One is just kind of fun. You said write down what you're going to do, and then go do it basically. And I couldn't help but note that when you said that, it's almost like I could see you writing it down. You must be a very analog person. [laughs]

MERRIE: I am. And it's interesting because I think in the intro you mentioned I have a product and engineering background, but I'm in sales. And I feel like I try to imprint these things I learned in technology leadership, product management, going through software agile transition from waterfall a decade or two ago, and say okay, how would I do that now that I'm working with customers? And how do I do it with sales organizations? And how do I use templates to drive change? So yeah, I think it's something that I'm finding works because it keeps all these very complex moving parts moving. But a big part of the new balls in the air is that human part, which I don't think I appreciated before as much as I do now.  

DAVID: Oh, that's neat. So one of the things you mentioned is the idea of teams breaking out on their own, pursuing their own goal out of necessity. And I'm just wondering does that tend to be more valuable or costly?

MERRIE: I think it's a reality of how we have to manage a new normal. I think there needs to be space for innovation and independence. But there has to be a common layer of consistency especially when you look at things like identity, and security, and management, and all those tried and true concepts of a central IT group. Most of the IT leaders I talk about their role isn't necessarily to stifle teams and whether we want to call them shadow IT organizations or line business technical leadership. What it is is to make their jobs easier, to give them a consistent platform to make sure that there's an open API model so they can get what they need. But also, that they're not hacking things together in a way that leads to a bad business corner that it's hard to re-engineer in the future or leave the company exposed especially from a security policy.  

And so I think there's a new way of thinking where it's not IT or not IT. It's IT with modular teams that are going to pop up here and there. I think it's also important for a lot of big companies or companies that are growing. M&A is a big part of my conversations. What do I do in integrating a company that has a completely different set of expectations? And I think this has always been true. But I think it's even more top of mind now as people are making choices on their new cloud architectures, or the ways of working, or their skills and capabilities. And so I think that modular, almost a hub and spoke commitment, is really important.  

PAUL: That's awesome, Merrie, and welcome to the show. And I’m just going to replay it back. I spend a lot of time and I have conversations around this word called digital transformation. And you've done an excellent job of providing really practical guidance on what we mean by digital transformation. And there are a couple of points I'll call out that I loved that you mentioned, which was you're coming from a product and an engineering background, but you're now in sales. And I think a key thing for digital transformation is that osmosis of moving of skills and mind share into different roles.  

And you talked about lifelong learning and learning from others. I think that's another key point for our listeners, which is you're not in this alone. You can really learn from others and really leapfrog and accelerate the learnings but also take the failings and the best practices and move that forward. So great dialogue. That digital transformation word means lots to many. But really, I think you've grounded us in terms of some practical guidance which will help us for the rest of the show.  

So with that, COVID obviously has really brought about the need for change for all of us change in mindset. And of course, rapidly advancing cloud technologies are accelerating the ability to drive digital transformation. And so there are no more really requirements, if you will, of IT thinking about what's my five-year plan? What's my capital expenditure? It's much more about agile IT, if you will, and having that agile mindset and being adaptable. And so from your perspective, how do technology executives manage in a world where the speed of cloud and rapidly changing markets can change their direction in months instead of years? What are your thoughts, Merrie?  

MERRIE: I go back to, again, my roots. I went to school and studied manufacturing engineering. And in the pre-'80s, manufacturing lines were defined by someone sitting in an office telling middle management what to go do and middle management telling the line workers what they were doing for their eight-hour shift. And it was very top-down. And when I look at modern IT, it has to flip that pyramid. That's my most simplistic way of looking at what's going on. And sometimes you're in the middle of those shifts. Some companies are going through accelerated transitions but with that shift it forces, I think, the power of innovation to sit instead of the top of the pyramid, the bottom of the pyramid.  

So you have to have great team structures that are modular, and multifaceted, multitalented, inclusive of hearing the marketing problem, the business problem, the technical problem. It can't just have one set of technology knowledge subject matter experts. And they have to understand the overall priorities for their organization or team.  

But I think that's where middle management becomes more of a coach than looking at a checklist of what you should be doing on a daily, weekly, monthly basis. And how does that middle management then tap into the innovation that can come out of those teams yet still keep them on track to hit the goals of the organization? And then at the leadership level, how do you set goals that are ambitious but flexible enough to change because the market might change? Your hybrid work requirements might change. An M&A is announced and you have to shift priorities or add priorities and look at adding capabilities.  

And so I look at this new way of thinking about leading teams in these modular ways isn't even limited to IT. I think this is a new way of thinking about how to empower people because I think we all know that the people doing their day jobs are the subject matter experts in their day job. How do you make sure that you're hearing from them the best ideas and then giving them space to try, fail, succeed, and move ahead? And I think this is always this big company aspiration to tap into innovation and speed of a small company. And so I think that's the thing that we've all got to start learning how to do well because I don't know if a lot of us were trained at that over the last 20 and 30 years. So it's a new skill and a new set of expectations. And you have to have a lot of trust in the system. Because a lot of people are like, "Are you sure you're going to trust me to make those decisions?" [chuckles] And you got to prove it.

PAUL: That's great. So with that, I'm going to use the word culture. And so when we think about leading digital transformation, you can't ignore that creating a new culture is required to fit the new business and the culture that evolves and matures with the digital transformation. And so what does it mean to build a culture from your perspective?  

MERRIE: I think the last two and a half years at Microsoft have been eye-opening to me in how to think about building culture. I thought about it as more of a soft word before. But entering Microsoft we were going through some cultural transformation in and around the way we were building our organization but even the bigger organization of sales in this Azure space of building bridges with engineering, increasing your technical capability, which we can talk a little bit more about later. But in that new culture building really sitting down and taking an assessment of where we were, the good and the bad, or the strengths and the weaknesses, and then where we wanted to be. And then putting in a tremendous amount of time on structuring that, talking about that with leaders, affirming that what I thought or more people thought was true, which often it isn't because my lived experience isn't necessarily theirs, especially coming in with new eyes.  

But then I think what's really fun and interesting learning from the last few years is we started engineering a plan. And my Chief of Staff, Javier Nino, is probably the best architect of this I could have partnered with. But we said we see these things that we want to move towards, risk aversion, fear of being singled out for good things or bad things. How do you engineer a plan to show people that's not the way we want to behave here, that it's okay to take risks? It's okay to raise your hand. It's okay. And so we made specific plans, some of them small teams meeting together, giving feedback, some of them training and getting people together and have training moments. Some of them were specific communications. Whatever it was, we could go on and on. But we had things we wanted to progress towards. We had plans and a diversity of actions when we ran the plan.  

And then once we got through the first year, we analyzed how we thought we did. We asked how we thought we did with different surveys, and then we made a new plan. And so I think that this building of a culture is more a muscle versus a moment that leaders...I don't remember in many of my business trainings or technical trainings spending time on this. And I feel like it’s something we should be spending more time on because I'm sure we keep learning more every year about the different types of things people need, to learn, to listen, to build their own teams, their own kind of personal take on what's okay and what Microsoft supports for them, and the way they need to work, the way they need to live, the way they need to develop new intellectual property, the way they need to serve customers.  

So we know and feel good about...I say this for the bigger Microsoft and in my team that that investment reaps rewards. And we know that people are feeling that psychological safety when you make that investment. And that psychological safety in a time like COVID is super important from what they can do with their work and their output but also how committed they are to staying with their team, staying with the company, affirming their lifelong learning here, and advancing their careers.  

PAUL: And, Merrie, I'd be remiss if I didn't ask the question for our listeners. And so culture I think about growth mindset. I think about evolution. As you said already several times, it's about having that learning mentality. And so looking back on your journey around really thinking about the culture that you want and then driving that cultural change, what would be the one or two learnings for our listeners who are perhaps starting this journey? If you were to look back on your personal journey, maybe what worked well, what didn't, to fast track some of the thinking, or share some of your learning so they can really capitalize on the experience that you have.

MERRIE: I think in threes. [laughs] So what pops into my mind I think that the tips would be --

PAUL: [laughs] You can have three then. That's good.

MERRIE: All three.

PAUL: I'll take three.

MERRIE: I think one is to be honest. If you come in or take a pause as a leader and say, "Hey, this is what I see in all honesty," and don't pull punches. And make some space for people to say, "You're wrong," or "You're totally right, and I'm glad you called that out." You have to start with that core of honesty. And I think the second is to be vulnerable and say, "Hey, if I'm the leader that's been here, I might not do a good job to get us to that. If we're in a bad place, that's on me. It's on me. It's on all of us. There's just maybe it's something I'm learning, or it's my blind spot personally. But I'm in it with you, and I'm committed to improving myself for learning too. It's not at you."  

And then the third is being comfortable with truthful updates like, hey, I see us progressing here, and this is great. And here are some examples. And I see us still struggling here, and here's what I'm personally going to do to do more role modeling or ask others to come in and spend some more time with us on this particular topic. But we're just acknowledging maybe this is a really, really hard thing, and that's okay. And we're going to still commit to it. If it's not those things, if you come in with...and I shouldn't say this in a bad way but an outside consultant who says, "Here are your principles, and here's your culture," it's just never going to stick. It has to be really authentic like a family. You're not going to go to someone's family and say, "Here's how you should operate, and here's what you should care about." So you have to think about their community, and what they need, and what's the real deal. It's a tough time in the world. And if you don't acknowledge that and you're just pretending that everything's normal, I think you lose people off the bat.  

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DAVID: All right. We're back talking about cultural change. And before we dive into this a little bit more deeply, I have to mention Microsoft has an amazing set of diversity and inclusivity initiatives that have played a large role in changing our culture at Microsoft. And I think many of us are proud of those programs, the results they've delivered inside the company. But I'm wondering about outside of our organization. Merrie, you speak to countless Microsoft customers and partners. How is Microsoft helping executives drive global cultural transformation in their orgs? What are we doing?  

MERRIE: Oh, that's a great question. I think there's the structured and the unstructured things. I think unstructured there's a lot of openness for Microsoft to come into companies who say, "Hey, we want to learn from you. Will you show us how you made a transition really specifically? How did you make a sales transition? How did you make a transition and think about your business differently?" And we'll come in and give partners and customers access to our CFO teams and our HR teams. And we'll go and walk you through what we've done.  

And we try to be generous because we think this is...we think our culture is one that has a lot of positive elements not just for ourselves but communities at large, being more inclusive, leading in sustainability, taking things like ability and disability at the forefront of product design. This shouldn't just be us. We want to have others enroll in this. And we want to be generous with how we structure that and how we've gone through those changes.  

And I think the other piece that is more structural is in my day job, we've put a lot of time and effort into making things easy for customers to lead through change. And we create repeatable frameworks and tooling, and we increasingly invest in our automation to help our customers so they don't start from scratch. If you're making your first move to the cloud, or you're modernizing your application, or you're looking at a new edge scenario in your smart buildings, we can bring repeatable templates, partners to help you invest in your innovation. And so I think there's a lot of ways we show up and bring our culture elements out into the world. And I think there's just a hunger for it. And there are a lot of things that we're doing that are really appealing to others.  

PAUL: Thanks, Merrie. And so I'm thinking aloud here. In a world of digital transformation, sales models and even engineering needs are emerging in industry and even at Microsoft. What are some of the things that you're seeing?  

MERRIE: A few things that we've invested in and seen in the last few years at Microsoft, and it's probably something others see as well, is that agility, that engineering mindset of agility and agile teams really as a sales culture and a practice. How do you make sure you're not just checking in on your business every quarter but you're really checking in every day? We brought concepts like scrumming into our field teams so that we were really looking deeply into our systems and data sets but also to the humans in the field saying, "How can we help you today unblock? How can we look at urgent new elements of challenges that customers, or a technology, or the market is needing us to respond to?" And so I think bringing that mentality to sales has been...I think we're at the start of that journey, and it's really been fun to see these two worlds come together.  

We also are increasing our technical capabilities in our field teams. And we have quite a large field organization. And when I say increase our technical capabilities is we've had technical resources in the field for many, many years. But what we want is a technical competency for everyone talking to our customers. And we've invested in that both in the capabilities in our businesses, whether that's our business applications, Modern Work, Teams, Azure, data, AI, but it's also industry. And really what is the depth in understanding how Microsoft's vast portfolio applies to me as a financial institution, or a hospital system, or an oil and gas company really specifically. And so that depth I think has been really critical for us to help lead these digital transformation conversations versus bringing just a portfolio of amazing products. But there are a lot of them, and you want to put that context around them.

DAVID: There is a great set of things that are changing out there that we're addressing. And speaking of changing sales models and engineering integration with that, we have a bias on this show for helping our partners bring solutions that they build to the Microsoft commercial marketplace and sell through that different channel. So I have to ask you about that on this show. What does it mean for partners and customers to sell and buy solutions in Microsoft commercial marketplace?  

MERRIE: I actually spend a tremendous amount of time with partners in my role, a lot of them are larger partners in infrastructure on-prem and increasingly, more in our application innovation and IoT space. But I think totally hear what you hear which is partners want Microsoft as their go-to-market expansion engine. And they want to co-sell their products with us, which is why marketplace is just brilliant as a scale engine for our customers, our partners, and especially our field teams.

Marketplace can scale faster than any enterprise on its own can. And I've heard numerous times from field teams that a customer, any large customer, has up to 100-plus partners they're working with. So it's really something that we want to make easy for that customer to see how they engage with us and that partner through marketplace, how to ease that procurement process and make it really focused on how to drive to innovation versus how to mechanically get everything connected.  

And then we also want to make sure that the companies are looking at not just the marketplace but also innovation through marketplace. I think it is really really important as well because we have a lot of...I think for me, I spent a lot of time in what I think of as large, existing ISVs. But we also want to see and connect our customers to the innovation partners in the marketplace or even the portfolio of very large customers who are constantly innovating and adding to the marketplace.  

But I definitely think that we are on the cusp of making everything more automated. And I'd love to see our marketplace, our partners continue to work with us on how we make this just a seamless process and make it automated in recommendation engine, and really understanding that whole picture of digital transformation and how the marketplace can be an easy way to drive some of those really high priority strategies for the customer.  

PAUL: So as we get close to the end of the show, I'm going to wrap up with one final question, Merrie, for you, which is around designing workplaces for the future. So Microsoft Azure is the leader in cloud solutions and building digital workplaces. But what are some of the reasons clients continue to trust you, your team, and Microsoft when designing workplaces for the future?  

MERRIE: Yeah, we spend a lot of time in I think our side of the business talking about the cloud back end. But we are spending more time in this new COVID-aware era in hybrid work to talk about not just the role of IT providing a new set of tools and almost user experiences for hybrid work but also developers. And so I think there's this trust that Microsoft understands where enterprises have been in collaboration applications, obviously, their experience in designing for employee connectivity and collaboration. But I think there's getting more nuance to that, so understanding how those teams can utilize a platform like Teams to be better integrated in their supply chain planning where you use things like Power Apps to do something that highly simplifies non-automated almost old school systems and make people's lives easier.  

And I think that innovation and the low bar for things like low code to expand the reach of technology to make a specific team's life easier. There's a high energy and demand for that, whether that's data scientists really sharing ways to use more simple technology UX to go test drug trials, or it is your developers that are now distributed across the world. What are the developer resources that they can use? Whether it's GitHub integrated with Teams, whether it's the whole Microsoft experience including Surface on app. I think that's why customers trust us because we can meet them where they are in their specific scenarios.  

And then we understand what those customers are using, again, in the backend, and with their applications, and with their ISVs. So we get to see their end to end. And I think that's that customer empathy and customer technical depth that they tap into versus one piece of the puzzle, which I think makes it a little more challenging for a customer. If they have another alternative partner who's only coming in with one piece, it's a lot of work to go then figure out the rest of the model on your own.  

DAVID: Well, this has been an absolute learning dialogue for me, and I love this conversation that we're having. Of course, we could go on all day, but unfortunately, it's time to call it a show. And thank you so much, Merrie, for bringing your experience and insights into the conversation today. It's just been an absolute pleasure speaking with you.  

MERRIE: Thank you, David. Thank you, Paul Maher.  

DAVID: Thank you for joining us for this episode of the Azure For Executives Podcast. We love hearing from you. And if you have suggestions for topics, questions about issues discussed on the show, or other feedback, contact the show host, David Starr or Paul Maher through the social media links included in the show notes for each episode. We look forward to hearing from you.