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Jennifer Byrne: [0:06] The true heroes, in my mind, are the folks who did the quiet work of ushering that transformation through a company. They get no credit. They're the note takers in the meeting, but they're the people who are the lifeblood of transformation.

Dan Saks: [0:24] That's Jennifer Byrne, the former CTO of Microsoft US, who currently leads her own firm, Digital Future Consulting. Jennifer got her start working for a small cybersecurity company that did work for government agencies.

[0:39] Since then, she's risen through the ranks to lead the US based technical organization for Microsoft, the largest software company in the world. Along the way, she has overseen large scale digital transformation projects across tens of thousands of employees.

[0:54] She's had a front row seat to the massive shift in company culture at Microsoft sparked by CEO Satya Nadella. In other words, she knows the ins and outs of how to drive change. Not only that, but she also has a passion for helping leaders prepare for the future of work and anticipate the new skills that people will need in a digital world.

[1:16] In this episode, Jennifer shares the wisdom she's gained from two decades in the technology industry, and explains why trust, clear communication, and transparency are critical for any transformation project, big or small. This is Daniel Saks, co CEO of AppDirect, and it's time to decode and apprise transformation.

[1:41] Welcome to "Decoding Digital," a podcast for innovators looking to thrive in the digital economy. I'm your host, Daniel Saks, and I'll sit down with other founders, CEOs, and change makers to decode the trends that are transforming the way we work. Let's decode.

[2:04] Jennifer, I'm so excited to have you on Decoding Digital today. To kick things off, let's talk about your background. You spent nearly two decades in the technology industry and recently served as the CTO of Microsoft here in the United States.

[2:18] How did you get your start in technology, and what's been your journey like to get where you are today?

Jennifer: [2:23] I like to say I had an unlikely path into technology, actually, like a lot of people who are in this field. When I started, I actually came to it with a background in nonprofit social services. Technology in the late '90s was the industry where there was a lot of opportunity.

[2:40] I made a very practical decision. I was much younger, had little kids, and needed a career that could help me support the kind of lifestyle that I wanted to live. I went back to school for a year and learned computer basics.

[2:53] At the time, I was living in the DC area, and at the time, there was so much demand for technical talent and so few people who were out there. This was before every university had a computer science program, and so it was easy to get in the field.

[3:08] I just happened into Avar, a small consulting firm outside of DC that was doing a lot of cybersecurity work for government agencies. I had a prior career as the director of a nonprofit, so I had a lot of business experience, and I was a warm body, obviously. [laughs]

[3:24] They put me onto projects. Before I knew it, I was installing firewalls and intrusion detection systems and writing security policies for civilian agencies, the USDA, and others. Then ultimately, in intel agencies, learning a lot about cyber warfare and the tools and techniques of both the criminals and the cybersecurity companies in that space.

[3:44] That was my start. I quickly learned that there was a lot that you could do in cybersecurity in any company, actually. I remember being an engineer and thinking, "Oh, my gosh. I'm doing the hard job." I had gotten a job at a company called Axent Technologies, which got acquired by Symantec.

[3:59] We were selling firewalls and intrusion detection systems, and I couldn't believe that I was driving a used Acura, and my sales guy was driving a Mercedes. I thought, "One of us has the wrong job here," so I went into sales.

[4:10] That was actually a really hard switch for me. I didn't think it would be nearly as complex as it was. Then from sales into sales management. Then I thought, "Well, what's next?" At that point in my career, I thought, "Well," I could either go deep.

[4:23] I could be the best cybersecurity engineer or network engineer I'd ever met, or I could go broad and leverage my domain experience, but in a bunch of different roles. I moved into alliance management, a little corp strategy, partner ecosystems, and just moved my way around.

[4:39] I thought that was really fun. What I didn't know at the time, but certainly later, was that that actually gave me a lot of really broad competency, because I'd never left behind any of the technical skills. I'd always, was very cognizant to keep that as fresh as I could.

[4:53] Then I learned a bunch of other things. I eventually landed at Microsoft as the Chief Security Officer for the public sector group, which was in 2014, which was the time when Microsoft was trying to get non US countries to adopt a friendlier stance toward public cloud.

[5:11] That was a tough thing to do, because that was the Edward Snowden days and the WikiLeaks days. No self respecting government was comfortable putting their data into a datacenter owned by a US company. I then learned the regulatory and the policy landscape in the US, but largely, in the EU and Asian countries.

[5:29] That again was a very strategy heavy job. I was working for the CTO at the time, and I ended up moving into that role. I realized that, although my technology portfolio expertise was relatively narrow, compared to all the things in the Microsoft portfolio, what I had learned was the business of technology.

[5:49] I knew enough to be able to think very strategically about how to get big customers and organizations and governments around the world to make big moves in their digital transformation journeys. That really turns out to be what a CTO, at least at Microsoft, was being asked to do.

Dan: [6:07] I know, in order to persuade the public sector and many big enterprises to adopt cloud technology, Azure, and others, Microsoft had to go through its own transformation in the way it operates.

[6:17] I've been grateful to spend time with the Microsoft execs in Redmond and also read "Hit Refresh," but can you tell us some insights as to how Satya and the team thought about that transformation, and what real life examples were from being at Microsoft in that era?

Jennifer: [6:33] Yeah. Well, the beginning of the transformation, before we ever got to the conversation with other governments, the internal transformation started with Satya himself. It was a culture change. You've read Hit Refresh, and so hopefully, you know that you can make this answer very complicated.

[6:48] In reality, it's a culture change. Satya was able to talk about a lot of the problems that every employee at Microsoft already knew existed, but they were afraid to talk about it. Like, "We know we're losing in the market. We know people don't like us. We know we have this terrible reputation from what happened in Europe, and blah, blah, blah. We don't know how to enter new markets in a friendly way."

[7:11] Everyone knew that, but nobody wanted to talk about. Then Satya all of a sudden shows up, and he talks about it. Then he not only talks about it, but he follows his words with actions. "We're going to embrace open source. We're going to have more Linux VMs and Azure VMs. We're going to get rid of our Microsoft phone, and everyone can use the iPhone. We're going to GitHub, and blah, blah, blah."

[7:32] He made that possible. Then internally, Amy Hood as the CFO started talking about customer lifetime value, as opposed to just talking about near term revenue, and changing cont plans, so that people could sign big deals with customers and not ask them for a penny upfront. It was all consumption.

[7:51] There's a lot that changed in the company, but one of the consequences of that that we were able to carry forward into our discussions with governments was this notion of total transparency. We actually got really good at talking about trust, but what trust really is.

[8:08] A big portion of trust is to be totally transparent, to show people that, when you say you are SOC compliant, well, show me all the audit controls. When you say that you meet this particular regulatory framework, and no one's ever heard of it, show me the mapping back to the controls I use internally in my own datacenter.

[8:27] If you tell me that you are going to use a key vault, show me the encryption. Give me total transparency, because if you have nothing to hide, then there's no way I can't get to a place where I can probably trust you.

[8:39] It was a big pendulum swift that way, pretty uncomfortable. You can imagine a lot of engineering leaders were rightly uncomfortable with that. Even with governments, we were sharing...With certain governments, under certain agreements, we were sharing source code.

[8:52] We had these special rooms, where you couldn't bring anything in, but they could bring whoever their designated engineers or software architects were, and we would show them our code. Just say, "Look for back doors, please. You won't find any, but please look. If you see anything that's wrong, let us know."

[9:07] There was a lot of process and procedures and programs that were designed to prove that we could be as transparent as possible, and that followed from Satya's original schtick when he started as the CEO to be himself very transparent with his employees, his partners, and his customers.

Dan: [9:26] I know transparency is something easy to espouse, but hard to live by, as is trust. It takes a long time to build, but very quick to erode. What I've found is, with trust, it comes down to how you react in the moment, in some of the intense situations.

[9:40] I'm sure there's a ton of stories that have not been public about intense situations, potentially with governments and Microsoft. What's your personal reflection or lessons on how to actually be transparent and live by the trust mantra, even when there's a lot of crazy things going on that you may not even have understood and comprehended yet?

Jennifer: [10:01] There's willingness to be wrong. This is really hard. The thing that you want to do when you are delivering software services, platform services, to market is, ideally, you can get trust done in the first conversation, right?

"[10:14] Can we just get there? I'll show you everything. Now, can you trust me?" Of course, that doesn't work that way. Trust is a function of time. I think, if you set that expectation correctly with a customer that, "Look, you're not going to trust me tomorrow, and you may not trust me fully next week."

[10:29] That's the way trust functions, not just in business partnerships, but also in our personal lives, and so that's no surprise. You can give yourself a little bit of space to not be perfect, and to understand that trust is this journey that you take together. There might be mistakes along the way.

[10:45] It's the accumulation of activity and right action over time that creates a trusting relationship. If you can keep that North Star, then hopefully, at some point, you have such a body of work between you and your customer that trust becomes implicit in what you do.

Dan: [11:02] One of the things that we're seeing increasingly is more desire to understand the technical components of security and data protection. In the past, a check box saying, "I'm PCI compliant," or, "I'm SOC compliant," had sufficed, but people really want to go many layers deeper in understanding where does the data sit?

[11:20] Let's look at the technical architecture. Whose infrastructure is it hosted on? Can it be ported? Are there back doors? You spoke to some of the ways that you can be more transparent in that regard, but what are some of the ways that a company can be proactive in really building trust around their security and data privacy?

Jennifer: [11:38] The best conversations I've ever seen are when you take a lot more time at the beginning of those meetings to explain the why of what you're doing. It's not solely specific to security, but it's something that's very prevalent in cybersecurity that you don't often find in other technical conversations.

[11:56] You have security, is an attribute, ultimately, of another technology system. Yes, technically, there are security products, and what a firewall does, but as a system, security is something that you lay on top of something else.

[12:10] It demands a conversation around why. I'm going to insert a security process onto this web service, because in order for this web service to function, it has to go out and make calls to a bunch of other third party software that I don't have control over.

[12:28] Nobody knows that unless you tell them that. That's actually really dangerous, because we know that X number of the biggest data breaches over the last five years have been because people were able to come in third party services into a web service running in your environment.

[12:43] Or authentication techniques. Why Auth0? Why you do that? Well, because last year, there was a company got hacked, because hackers were able to take advantage of a particular vulnerability. That's why. It's a context thing.

[12:55] I think, in all my years at Symantec and McAfee, and even Microsoft, talking about cybersecurity, the conversation can't happen well unless you're giving people a lot of context underneath. That's not necessarily true.

[13:08] If you're talking about Office 365, you can geek out on Office 365 and the features all day long, because everybody has the context of what the communication platform ought to do. In cybersecurity, that's not the case.

Dan: [13:19] When you were selling to CIOs and CSOs in the public sector, or at large enterprises that may have been more risk averse, how did you get them to have comfort to adopt public cloud models or other innovation, even though their risk profile might have been more conservative?

Jennifer: [13:33] Lots of little things. Obviously, there's the competitive edge of what Microsoft was able to bring to market. I would say that the game changing conversation with governments around the world in 2014 and '15 was a conversation about the relative security.

[13:46] You start the conversation with, "You can't afford to not innovate and not move forward. You can't afford to not adopt technology." People are only going to stand in line for paper driver's license for so long before you're going to need to put that stuff online.

[13:59] You're going to have to move forward. The question is which is more secure? The relative security conversation became super relevant for them, that we could say, "Maybe we're not perfect, but we're better than having your data onsite, and here are the 10 reasons why."

Dan: [14:16] Super powerful. One of the things we talk about AppDirect a lot is the concept of a digital hero, or someone who really has a certain set of characteristics, like curiosity, tenacity, vision, innovation, to be able to drive digital transformation.

[14:30] You've alluded to it in different respects, but I'm sure that, with any large transformation, especially of a government or enterprise, it comes down to the people in the room. Tell me about some of the people behind the best transformations you've seen, and what are some of the observations on how they interact and collaborate?

Jennifer: [14:48] The true heroes in my mind, the people I've kept in touch with, the people I would do any favor for it doesn't matter who you are. You need a job, you need something, I'm here. Call me are the folks who did the quiet work of ushering that transformation through a company.

[15:06] I have seen plenty of CEOs, COOs, Chief Innovation Officers put their careers on the line. They're talking to the board and promising some kind of top line revenue growth off a transformation project that's going to cost them tens of millions, or hundreds of millions, of dollars.

[15:22] They don't know that it's going to work. None of ever knew it was going to work. It's always a bet, but they knew they had to do something. There are plenty of brave executives.

[15:30] The reality is that the projects get completed, because there's somebody in a mid level role that's a procurement officer, who's going to have to tell a vendor that they've worked with for 20 years that they're not going to use their software anymore. That's not fun.

[15:44] Or it's a sys admin who's got a product that they've been using, and now, that product's going away. What's their new job going to be, and do they even know how to do it? Or it's a finance person who has to do the red yellow green chart, and all of a sudden, that chart's got a lore more red in it, because the project is going to be in a terrible state for a long time, not fun.

[16:02] Somebody has to go talk to all those people. It's not glamorous work. It's not even about the technology at that point. It's not even about the transformation, really, at that point, but somebody has to hold the hands of a lot of people who are trying to learn a new skill who are going to be adversely affected from this.

[16:17] Those are the people, in my mind, I love them all day long. They get no credit. They're the note takers in the meeting, but they're the people who are the lifeblood of transformation, in my opinion.

Dan: [16:29] We've definitely found that as well, that when we look at a digital hero, it doesn't mean the CEO. While it can be, many times, it's someone on the ground, or just has such passion for the project, and perseverance and intensity to be able to push through.

[16:43] I think we tend in the media and in the industry to highlight heroes as people at the top. I think, ultimately, there's so many people across so many different trades that are making such a big impact. I know you in particular serve on the boards of the Center for International Career Advancement and gigRonin.

[17:00] I know you were really focused on helping people through technology in their careers. What are some of the ways you think organizations can prepare their work forces for the new job skills required in a more digital world?

Jennifer: [17:13] That's one of my favorite topics, because I think that technology...Look, I've spent a whole career talking about all the wonderful things technology can do, but there is this unintended consequence that it can leave people behind.

[17:24] It requires a level of digital fluency that a lot of people don't have. That's a digital divide, just like there's a socioeconomic divide, so it's an important topic. I think the hard thing for companies is they don't actually know what jobs are going to look like.

[17:40] When I talk to Chief HR or people officers, the problem that they have is they don't know what they're training for. They don't know what that taxonomy of the new job in the more digital version of their company is going to be.

[17:52] Yeah, OK, great, I'm going to have to have X number of people who know this technology, but what's that job title, and where are they going to report to, and how do I go find them? There's some logistics around training that's pretty tough when you don't know what your future's going to look like.

[18:06] It starts with really two things. When there's a culture of learning, and where companies do it well is where executives take that to heart. I will tell you that at every big technology company I've worked at, including the most recent one, I have worked for leaders, or worked with leaders, who did not take that seriously, who did not take the time to learn the technology.

[18:28] Who did not take the time to internalize the material in order to pass the test, and employees notice. My call out to anyone who is listening is, if you are a leader, and you're expecting your people to become more technical, guess what?

[18:41] There is no shortcut. You have to do it also, because your employees will watch, and they don't want to take it, either. That's a culture of learning. Extraordinarily important. It's hard. It has to [indecipherable] . You've got to be in the boat with your people.

[18:53] Number two, you really do just need to figure out how to do training, and train, train, train, because again, you don't know what your future looks like. Over train, rather than under train. In training, there are three things that I think are incredibly important that not that many companies do.

[19:09] Number one, provide positive incentives for training. Almost always, the incentive for training is a negative incentive. "Do this, or else." I can't think of a single company that pays their employees some kind of bonus, or gives them a Starbucks gift card, or something that's predictable, reliable, and always there when they do complete training.

[19:31] Positive incentives for training. I don't know why we don't do it. I feel like we should. Number two, teach fundamentals, particularly in the technology space. For Microsoft, they want to teach Azure. AWS wants to teach AWS. Salesforce wants to teach Salesforce.

[19:48] Without the digital context that sits underneath those technologies, the training is not super helpful. If you don't understand how networking works, you're really not going to get cloud. There's a whole bunch of cloud concepts you're not going to get.

[20:02] If you don't understand apps, coding, and understand languages, you're not going to understand a lot of how to build things on Azure and microservices. What's that really going to mean to you if you don't have an understanding of infrastructure?

[20:15] I don't think companies do that very well. Get agnostic. Yes, you can teach somebody else's technology, but give people the fundamentals. Train them on that first, and then guess what? You can learn anything on top of the stack if you have your fundamentals correct.

[20:29] The third thing and final thing is that I believe companies need to encourage a lot of cross disciplinary training. I haven't seen it. It could be out there. In my experience, I haven't seen it, where you allow somebody in a tech team to take a marketing class, or somebody in a marketing class to take a tech thing.

[20:48] A lot of people say, because they get to mid level in their career, "Jennifer, what should I do? I'm thinking maybe I should go learn finance or bolster my skill set," but when they go to look internally at their company, none of that exists.

[21:01] I feel like cross disciplinary training is important. It's like taking an elective in school. It's fun. You do it, and it energizes you, and it really does build broad competency. Those are the three things that I would love to see companies do when it comes to making their work forces future ready.

Dan: [21:17] Those three are so powerful, and particularly, the power of interdisciplinary work. We've covered a wide variety of topics. It's been really, really fascinating, but one of the areas that I know surround everything we've talked about is your point on the digital divide.

[21:32] I know in the future, there's going to be a fairly significantly retooling of the economy. There's a lot of debates today around who will have jobs, who won't, and how do we manage through that. What are thoughts on what people can do today to be able to plan for, manage, and help address the digital divide?

Jennifer: [21:48] I think, within their own careers, it's time to take a hard look at what you're doing in your work space and how you think technology is going to change it. Simple things, like it's interesting, when you look at the macroeconomics of what's happening in the workforce relative to digital skills.

[22:06] You would think that it only affects the bottom rung from the pay scale perspective of the economy. That's actually not where you see a lot of shift in jobs relative to technology. It's actually the middle skills in the wage scale, if you will.

[22:22] That's because automation actually happens a lot in the kinds of jobs that sit in the middle of our economy. I say that to say that, wherever you are, whether you're a mid level manager, or an executive, you're in a construction industry, a finance industry, it doesn't matter.

[22:38] It behooves you to think about the technology that's already encroaching in your space. Think about the job that you do today. If you go to work every day and you know exactly what your day is going to look like, you have fairly automated, repeatable set of processes that you do.

[22:54] That's actually more likely to be automated than somebody who goes to work like, "Well, I have no idea how this is going to go, no idea what I'm going to do." That's a non automatable job. Those are high level trends.

[23:05] It's just a framework for people to think about. I think you have to think about yourself in your own career. The mindset shift, I like to say that I hope the word "career" goes away. I know that's a little bit provocative, but I don't think that they serve people anymore, especially people who are earlier in their career.

[23:24] This idea that you're going to have this logical, sequential thing that you do the same thing and just get better at it throughout your career, some people will. Most people won't. Most people's jobs are going to change fundamentally.

[23:34] If you have a mindset that anything less than a long career is a failure, you're not helping yourself. Rather, think of your career or your work journey as a series of adventures that can take you in a lot of different places, and that you get the opportunity to learn different skills.

"[23:53] I'm going to go take an adventure in this company, because I want to go learn how to code, because I want to go learn how this industry works. When I figure it out, I'm done. Then I can stay, if I want, or I can go onto the next thing."

[24:05] It's a mindset that allow you to think about yourself as moving on an adventure, and you'll need a lot of different skills. You get to always, at any point in your adventure, your journey, think about what it is you need to learn next. Then that ultimately makes you a super robust, agile, and hopefully happy person.

Dan: [24:25] I'm excited to continue to track your adventure and the impact you're having on so many. Jennifer, thank you so much for joining us on Decoding Digital.

Jennifer: [24:32] It was a pleasure. Thank you.

[24:33] [background music]

Dan: [24:37] On the next episode of Decoding Digital.

Gerald Kane: [24:40] For digital heroes to thrive, they really need to be in an environment that is supportive of them. Create opportunities to find those people in your organization. Find the people who want to be part of this change.

Rich Nanda: [24:54] It does come back to the right mindset, the constant willingness to experiment and understand how digital innovations will impact the company.

Dan: [25:08] Authors of "The Transformation Myth," Professor at Boston College, Gerald Kane, and US Monitor Practice Leader at Deloitte Consulting, Rich Nanda.

[25:21] Thanks for listening to Decoding Digital. Make sure you never miss an episode by subscribing to the show in your favorite podcast player. To learn more, visit decodingdigital.com. Until next time.