Host Intro (Gene Kim)

Last year at this conference, we heard from Peter Moore, who marveled at the performance of Microsoft pre- and post-Satya Nadella. He observed that Microsoft had the same market cap when Steve Ballmer first became CEO and when he left 14 years later. In the eight years since Satya Nadella became CEO, Microsoft's market cap has increased by more than 6X, becoming one of the world's most valuable companies.

I have long wondered whether the first seeds of this new Microsoft came from the famous Dev Division, home of all the developer tools, compilers, and runtimes that we're all likely so familiar with, such as Visual Studio, Visual Studio Code, TypeScript, the CLR, and so much more. There are some fantastic glimpses of this in the book "Customer-Driven Culture," which came out last year. Ever since reading that book, I've been wanting to interview someone who is featured so prominently, Amanda Silver, who is now Corporate Vice President of Product for Developer Tools, on how they were able to create this amazing learning dynamic within the Developer Division.

Reaching out to her has been on my to-do list for what feels like years, especially since she came up so frequently in conversations I had with other people. Then I heard her January interview that she did with Scott Hanselman, and she shared her perspectives on remote work and its impact on leadership values that she holds near and dear, which blew me away. I think she has lessons that are relevant for every technology leader, and I'm so delighted and honored that she was willing to share her thoughts with us today. Amanda, thank you so much for being here today.

Amanda Silver

Thank you so much for having me, Gene.

Gene Kim

I've introduced you in my words, but can you introduce yourself in your own words and describe what you're working on these days?

Amanda Silver

Sure. I'm Amanda Silver. I am the CVP that runs the PM, design, and user research teams for Microsoft's Developer Division. As you described, the Developer Division basically works on all of the products at Microsoft, and platforms, that target developers as the primary audience. That's Visual Studio family, .NET runtime, most recently the Azure PaaS platform as well. Basically, the application platform portion of Azure is also in the Developer Division, and we work very closely with the GitHub team on product integration.

I've been at Microsoft since 2001. I've always been working for developers, and part of the reason for that is I just love having developers as my audience. I think of them as my muse. In a way, developers are tech enthusiasts. They are early adopters. As a product person, I really live for fast feedback cycles, and I love having developers be my audience because I can ship something in the morning and know by the end of the day whether it was a hit or a dud.

Gene Kim

That's so awesome. Amanda, in the book "Customer-Driven Culture," you spoke so eloquently about how important it was for leaders to have awareness, curiosity, and courage. Can you talk about what these attributes mean to you and why you think they're so important?

Amanda Silver

These are foundational. This is what our boot camp inside of the Developer Division is really based on, and we bring everyone through a two-week boot camp and kind of bring them through awareness, curiosity, and courage.

For me, the awareness aspect is understanding that everyone is coming to everything that they do with a certain set of biases and preconceived notions. It's understanding what are the sets of data points that you have, the lived experiences that you have that are informing your point of view, and then recognizing that that might not be all of the information that you should be using to make a decision. Another dimension of awareness is also understanding how you show up, how your presence and the way that you're showing up influences other people in the room.

Curiosity is very related to growth mindset and the idea of lifelong learning. Curiosity is the idea that every opportunity is an opportunity to learn and to elevate your thinking, and even your organization's thinking, on a particular matter. That's a foundational element of everything that we do when we're working on a technical problem or trying to make a data-driven decision.

Courage is being willing to have intellectual honesty and rigor and bring that to the conversations that you have, even when it might feel scary, and it might even put your own position at risk, or it might cause you to call out someone who may be more senior than you, and make sure that we're actually having a conversation based on facts as opposed to hierarchy.

One of the things that we talk about a lot in our team is that we don't want to have decisions made by the highest-paid person in the room. We call that the HiPPO: highest-paid person in the room. We want to drive decisions based on data, based on intellectual honesty, rigor, and we want to be able to talk about that openly and share that with our team.

Gene Kim

That's so wonderful. In that interview, you also talked about your desire to make sure that everyone in the team or in the organization, in the collective hive mind, has a voice. One can hear this and think that you're just being nice, meaning you're being considerate. But I suspect that for you, it has a lot more to do with something much bigger than just being nice. Can you talk to that?

Amanda Silver

I think there's two dimensions of it. One is scale and the idea of how a leader actually scales to something that they can't personally be the expert in, in every dimension. You need to be able to empower your teams.

The next aspect is empowerment. When we think about how we actually build organizational capacity, we need to continue to invest in the next generation and trust them to make those decisions. Part of the approach that we have is to empower our team so that they can become the experts in this particular portion of the market, the competition, the technical challenges that we're faced with, and we can demonstrate that we actually trust them to make decisions.

When you suck up all of the decision-making power to the most senior people in the room or to just the leadership team, then you're not empowering your team. You're not building the next generation of leaders in your organization. You're going to have a retention challenge as people get more senior. Also, I don't think you're making the decision based on the best information.

What I want to see happen in our organization is that each one of the people that we empower actually has the best context on that particular portion of the market that we're trying to compete in, and that they have first-hand experience with the customers that we're trying to serve based on the motivations that they have. Then we can help drive a collective decision with the full view of everything that we're trying to accomplish in the organization. As senior leaders, we can bring more context to the conversation in terms of the global atmosphere of everything that we're trying to achieve, but we really want to make sure that our individual teams are empowered to execute as independently and with as much information locally as they possibly can have.

Gene Kim

That's wonderful. The phrase that really stuck with me was, "If we're not doing this, we're not getting the best out of our people."

Amanda Silver

Exactly.

Gene Kim

I absolutely love that. The other thing that really caught my attention in your interview with Scott Hanselman was how you talked about Microsoft moving from remote-friendly to remote-first, and how you've been surprised at how effective remote meetings can be, and in some cases maybe even more effective than in-person meetings. Can you talk about what you've grown to like about remote meetings and, in particular, some very surprising contexts, like the senior leadership team around OKR planning and even that famous two-week in-person boot camp?

Amanda Silver

For sure. Even before the COVID pandemic happened and we all transitioned to working from home, we already had a pretty geographically distributed team. I think we were about 40% geographically distributed, non-Microsoft campus based. We already had a team culture that was what I would call remote-friendly in those days, but looking back on it, it was really not very remote-friendly.

We wouldn't start the Zoom meeting or Teams meeting all at the same time. We might forget to add the remote attendees until later into the meeting, maybe five or 10 minutes into the conversation, which happens way too often. We wouldn't have notes from the meeting or decisions from the meeting. We wouldn't pause to make sure that the remote attendees were actually included.

Even in that era, I recognized that if we actually made our team culture better for remote employees, that would create a more inclusive environment for everyone on the team. When you think about how you actually run a remote meeting, for you to include the remote attendees, you need to create pauses in the conversation, and you need to poll the room to see if other people have contributions that they want to make. It's too easy in a remote meeting for it to become basically a two-way conversation: the most senior person in the room, and everybody who has prepared the content delivering the content for that most senior person in the room. Why do you have everybody else in that meeting? Because they're not contributing to the conversation.

By building in these pauses so that we can listen to everybody and their thoughts on the matter, we create openings for diverse viewpoints. If you don't do that, then you're really only basing it on the information that's been previously prepared for the conversation and for the HiPPO's opinion. We've found this to be really essential.

It's not just about the actual running of the meeting itself. It's also about what you do outside of meetings, and how you even approach meetings in this new remote-first workplace. The answer, to me, is in some ways you have a lot less meetings. It feels like we have video conference fatigue in this world. That caused me to want to have fewer conversations that are done via video conferencing. For you to do that, you need to have much more asynchronous communication, and it needs to be snackable. It can't be long, 25-page strategy documents or super-long recorded videos. It needs to be bite-sized, consumable bits of content that everyone can understand and that has a big impact on them.

That's been a big element of what we've done as we've transitioned to more asynchronous content: making it more personal, creating a lot more human connection in that asynchronous content, making it shorter, and being more intentional about when we actually bring people together for a meeting. What do we actually expect to get out of it?

In the old world, there was a lot of absorbing via osmosis. You would be in the room, you'd capture the gestalt of the other people in the room, and kind of create the collective hive mind by being in physical proximity with each other. There might be multiple conversations going on and whiteboards, and it's very exciting. But it's really impossible to replicate in this remote-only world.

We had examples like the boot camp that we run. The second portion of the boot camp is a customer-driven workshop where we take four days and divide into different teams of five to six people each. We assign each group to a business problem, they interview a set of customers, and they do the sense-making process.

Gene Kim

Real customers? The ones that you might be so protective about, you give them to the rookies to actually talk to directly?

Amanda Silver

Real customers, yeah. What I love about this is we actually give it to people who are straight out of college, as well as people who've joined our team who are coming from 20 years in the industry and have incredible experience.

What's fascinating is when people have that raw exposure to an actual customer that we're trying to serve, I think of it like oxygen. It's like putting light on. It's helping to infuse the conversation with reality, with the reality of the experience of the person that you're trying to serve.

This kind of meeting was really impossible to do, we thought initially, remotely. What we found is that it's actually better remotely. The reason is it's way more inclusive of our geographically distributed team than the Puget Sound-only version of this boot camp that we had been running previously. We've also transitioned to using software that facilitates brainstorming, which we weren't using previously.

In the world where we were doing this all physically, we would have little tables, little pods, Post-it notes, stickies, charts, markers, dry erase boards, and all of that. It was great, and they came up with some great ideas, but at the end it was very hard to reorganize into coherent thoughts, so the presentation itself was a little jumbled when they finally came to the pitch based on their explorations. Also, there was no way to actually capture the ideas and the insights that they had.

Just this past week, we had another one of these boot camps. I had two teams assigned to look at a business problem that we're actively doing product development on. Their insights were so good based on the eight interviews that they had total that now, on the way to doing the pitch for our senior management, we're actually going to run it by this team that's full of college hires and new hires into Microsoft, because they had such good insights from these interviews that we think they're actually great first readers of this pitch we're trying to make.

I think it's empowering. It allows the team to recognize from the get-go that they are empowered to make decisions and have these kinds of insights. It's also empowering to these geographically distributed teammates. What we're finding is that this new world feels more inclusive to many of our teammates.

Gene Kim

I love it. When I read about this in the book, I found it mind-expanding: the idea that customers are not viewed as a scarce resource to be shown with high degrees of ceremony and protectiveness, that this is actually integrated into the onboarding process. I love how remote meetings are a mind-expanding story. That's work at the edge. You had another example of how remote meetings have changed for some of the highest levels of leadership in terms of defining goals and cascading or rolling out the OKRs throughout the organization. Can you talk about how you've been tackling those?

Amanda Silver

I spoke a little bit about how everyone has video conferencing fatigue. I think that managers, in some ways, are the most stretched in this new world. The last year has been extraordinarily challenging for everyone. For anyone to be a great manager, they have to demonstrate that they care about their employees, they have to be there for their employees, and they have to coach them. The management job is easier when you're all in physical proximity because of that osmosis nature. You can have a lot of training that happens unintentionally just by people being in the office and observing what happens with other people.

In this remote-only world, a lot of the training, onboarding, coaching, and human support, the emotional support that a lot of people have needed over this past year or almost two years of this really turbulent situation, has taken a toll on a lot of managers. I was very concerned about that when it came time to our next planning cycle.

Gene Kim

I'm assuming that you didn't want to inflict the endless 17-hour planning sessions on your team.

Amanda Silver

Exactly. The way we had done this previously when we were all physically co-located was that we would book a two-day offsite. We'd expect everyone to fly out, and we'd prepare documents and reading material for them to consume, then we'd discuss it and have brainstorming meetings. It was using the power of osmosis for everyone to come to an agreed perspective on what we needed to do.

But we really couldn't afford to do a 17-hour meeting or a 16-hour meeting with everybody attending remotely. It just doesn't work. You can actually see people drop off after 90 minutes, even when it's something that really matters to them and is important to them. It's hard for people to sustain the energy in video conferencing.

What we did is we asked ourselves: what is the minimum amount of structure that we need to provide to the team, both in terms of the planning exercise itself and in terms of the output of the plan? Rather than coming with many strategy documents and many hours of meetings, we came to the conclusion that the thing that we needed to focus on most was just aligning on our OKRs.

My team is still in a learning process of OKRs and understanding how best to use them in our organization. Even now I'm starting to close Q1 and look at Q2, and there are some shifts that we'll be making in the team based on what we've learned over this last quarter. But zeroing in on the OKRs as the main thing that we need to agree upon across the organization has been clarifying, and it's allowed us to get more focused on what we absolutely need to accomplish during this next semester. Rather than speaking in platitudes of what we'd like to see happen, we have to get down to brass tacks about what are the outcomes that we actually need to see happen over this next period.

Gene Kim

That's awesome. It's bringing back memories of over a decade ago, these lifeless three-day meetings where people bloviate away about what we should do, need to do, and all the decisions have actually already been made. It's just a phenomenal waste of time.

Amanda Silver

As a writer, I'm sure you recognize that some of the hardest parts of writing is editing. It's sometimes easy to write what you think, but the hard part is, "If I had more time, I would have made it a shorter letter." I think that is an essential part of the OKR setting process: eliminating the additional extraneous, superficial metrics that are not the things that you need to focus on, and getting down to really what are the most essential things that you need to accomplish.

Gene Kim

That is so wonderful. I have some other questions about the leadership context, the culture change at Microsoft as mentioned in the book. But before we do that, you mentioned in that interview some specific tools and techniques that you use to make better use of people's time. You mentioned things like writing strategy documents, allocating reading time during meetings, specific things that you have found effective not just for you, but in your leaders. Can you talk a little bit about that?

Amanda Silver

Definitely during this period, writing has become way more essential: effective writing, compelling writing, data-informed writing. That's something that we've been working on a lot over the last couple of years, and it's become so essential.

The other dimensions of it are the humanity. Part of what happens in physical proximity is you get to know one another as humans, and you're able to connect on a personal level. In some ways, one of the things that I'm most worried about in this new world is that people feel less connection to the organization, to their colleagues.

What I've also been trying to do is to make sure that we're helping one another learn about one another as humans, in the context of the strategy that we're trying to execute on, and in their career trajectory. An example is regular podcasts internally. They're designed so that you can take them on a walk. You don't always have to be physically attached to your monitor to consume this kind of content.

The goal is to talk about the strategy, so everybody understands the strategy we're trying to execute, but also the human behind the strategy, because they might not bump into them in the hallway. How do you get to know the other people on your team, what they're working on, and their career trajectory and story? We'll talk about this person working on this element of the strategy at this point, what we want to accomplish, then they will talk about their background, what led them to make this contribution to the team at the time, and why they are so passionate about it. I'm finding this is helping our team think about how they can grow their career inside the organization, or what they think their next steps are, and make connections in ways that they might not otherwise be able to make.

Another example of the kinds of things that we've had to do in this new environment is introducing people in haphazard, random introductory calls. I think about it as an onboarding mentoring ring, where I'll take the cohort of people who've started in the team for the last month, bring them all on a call, and say, "Look, you guys are now your peer mentors in terms of supporting one another coming into the team. You need to make this connection and create this network that will support you."

Gene Kim

I have loved so many of these things that you've talked about with such conviction and passion. In our conversation, you talked about how important it is to you that leaders model, coach, and care. In the book, model is defined as set the tone for culture and leadership, act with integrity, be accountable. Coaching was defined as define team objectives and outcomes, help success across boundaries, help the team adapt and learn. Care was defined as know everyone's capabilities and aspirations, attract and retain great people, and invest in the growth of others.

This management model looks very different than what many people are familiar with and maybe grew up with, maybe even alien. It might appear to be more about being nice than about delivering results. How have you had to explain it to people who were maybe initially skeptical or resistant?

Amanda Silver

I actually had a conversation with Satya a couple of years ago about this culture shift. He said to me in that conversation that he felt he had two abilities as CEO. One is he could put the troops in different locations, he could decide to invest in this project or that project, and he had the power of helping to decide which teams he was going to fund. But then he could also be a cultural ambassador. He could recognize that the tone that he sets actually sets the tone for the entire company and the way that we operate.

That really stuck with me. When I think about what I'm doing, I'm trying to bring more people into the industry and empower them to create with technology. When I think about why people reach out to Microsoft to understand how we might be able to help, a lot of times they're reaching out not because they're looking for this particular product or that particular tool, but because they have a culture that they're aspiring to achieve, and they think Microsoft can help them achieve that culture.

When I think about the way that our own team runs, I want to make sure that we are customer obsessed, that we're talking to customers all the time. As I said, I think of them like oxygen or sunlight. It's the way that we ensure we have great products that are serving the needs of the people that we're building them for.

I want to make sure that we're intellectually honest and rigorous, and that we're all really grappling with the information that we have so that we can make the smartest decisions, and that we're making decisions based on data as opposed to hierarchy. We also have to recognize that no one can accomplish anything without fantastic team members that are committed to what we're trying to accomplish.

When I think about what it takes for myself to show up fully invested in what I'm trying to do, I need to make sure that my values are aligned with the mission of my organization. I have to make sure that I feel empowered and capable given the tools and resources that the organization has given me to get that job done. I need to make sure that I'm learning, that I have coaches, mentors, and other people that I'm working with that I can learn from, and that I'm growing and making progress.

When I think about the role of a manager, it's to do all of these things as a model, to show other people how they can show up, how they can be their authentic selves, what the values of our team are, and how we live our values every day. We recognize that, especially this next generation, but I think it's true for everyone, wants to be lifelong learners. They want to continue to grow and progress. If you're not, as a leader, coaching your people on how they can become better, and if you don't think about every one of your employees as someone who is on a learning journey, who's growing in capability, then I think you're missing out on one of their aspirations.

The other thing we have to recognize, and it's so true over the last couple of years as we've gone through this incredibly challenging period, is everyone is dealing with a lot of stuff in their personal lives. We need to acknowledge that and not pretend like there are completely separate compartments. The previous generation was very compartmentalized. You would not talk about your personal life in any dimension at work.

The reality of today is that's just impossible, for many reasons. First, we're dealing with a lot of stuff at home, but also for a lot of people, myself included, I wake up, I see my family, and then I come into this office, my home office, and interact with people through video conferencing and email and textual interactions. There is this need for human connection outside of your family as well, that I think a lot of people get through work. In a physical environment, you can have your work friends, lunch, dinner or beers after work. But in this world where we're all sequestered into our own home offices, it's hard to make that human connection.

To really connect with people and make sure that they feel like their aspirations can be achieved in the organization, we have to recognize the whole person that they are and respect that and value that, and help them understand how they can grow in the team.

Gene Kim

I love so much of what you said, and I think it's so obvious that this is right if we really want to fully enable the unleashing of everyone's creative problem-solving potential. Maybe if we can connect the dots. You've been at Microsoft for 20 years. Can you connect the dots in terms of how these changes in culture, management philosophies, what gets modeled by leaders, how do you attribute that with how teams have been better able to innovate and create things of value to your customers? How would you convey that to someone who is all about the bottom line?

Amanda Silver

The way that I think about it is we are all, in fact the entire industry is, operating with finite capacity. In my world, I focus on developers as my customers, and the entire industry is limited by the availability of developer talent. We have a massive developer shortage in the world. What we need to do in my organization, and really every organization needs to do, is figure out how do we do more with less. That's what we're always being asked to do.

To me, there are three different ways that we can help make that happen. One is we can bring more people into the industry, and to do that we need to recognize that we need to invest in new people coming into the industry overall, to mentor them, sponsor them, and support them in their learning. We need to improve developer velocity. In other words, we need to make sure that individual developers and their teams are capable and more focused on what is valuable to the customer, to the organization, and delivering that, eliminating busy work and making sure that we're focused on delivering customer value. Then we need to make sure that we can actually scale as an industry, and we do this by collaborating with other disciplines, with developers outside of the team, and so on.

When I think about what we're trying to do, we're really trying to achieve more business performance by empowering the software development teams, because it's the software development teams that are the center of innovation. They are the ones who are actually transforming all of these businesses to be digital-first companies. It's through empowering the development team and making sure that they can be as effective as possible at meeting the demands of their customers and the organization that my hope and expectation is that that will lead to better business performance.

Gene Kim

That is so great. I have told people after we last talked, I had a smile on my face for the remainder of the day. Thank you so much. It's impossible for me to overstate just how delighted I am that you were able to do this interview. Could you tell everyone how people could best reach you and what in particular you would want people to reach to you about? Is there any particular help that you're looking for these days?

Amanda Silver

Great question. First of all, you can reach me @amandaksilver on Twitter, probably easiest to access, but you can also find me on LinkedIn or any other place.

What I'm trying to do is to basically empower development teams. For a lot of people, they might think that means productivity in terms of the widgets, the output. It's the number of lines of code, or the number of check-ins that are merged, or number of releases that go out. That's not really what developer productivity means to me.

It's really more about those other metrics that indicate that the organization is empowered and that you support the team in growing their organizational capacity and the impact that they can have. It's things like time to first contribution or feature, or how long does it take to test a code change, or to see the code change show up in production, or to understand the time that it takes you to remediate an issue that has come up. Those are the kinds of metrics that really matter to empower development teams.

That's what I would love to hear stories of people: how they've improved those kinds of metrics in their organization, what culture changes they had to enact inside of their team to get that to happen, and what challenges they're seeing inside their organization to be able to enable that. That's what I'd love to help others with as well.

Also, anything that we can do to make sure that the next generation of people who are creating software is more diverse and more representative of the humanity that we're trying to create for.

Gene Kim

Wonderful. Thank you so much, Amanda.

Amanda Silver

Thank you so much, Gene. It's been great.