think civic
think civic: season one
Marina Nitze and Nick Sinai: Hack Your Bureaucracy
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Marina Nitze and Nick Sinai: Hack Your Bureaucracy

In this episode of think civic, Evan and Ajay spoke with Marina Nitze and Nick Sinai to discuss their new book, Hack Your Bureaucracy: Get Things Done No Matter What Your Role on Any Team.

Marina is currently a Partner at Layer Aleph, a crisis response firm that specializes in restoring complex software systems to service. Before that role, she was the US Department of Veterans Affairs Chief Technology Officer during the Obama Administration.

Nick is currently a Senior Advisor at Insight Partners, a venture capital and private equity firm. He is also adjunct faculty at the Havard Kennedy School and a Senior Fellow at the Belfer Center for Science and International Affairs. Prior to those roles, he served as a Deputy Chief Technology Officer in the Obama White House.

Episode Credits: Hosted by Evan and Ajay

Cover art created by modifying Abstract Shapes © Nathan Covert (Licensed under CC BY 4.0)

References mentioned in this episode:

  • Nick and Marina’s book, Hack Your Bureaucracy, is available to order. Here is the link to the book’s website to allow you to place your order with your preferred retailer.

  • As referenced in the episode, the Veterans Affairs website has come a long way since Marina first started at the VA. If you or someone you know needs to access resources from the VA, or perhaps you would like to check out their website, you can find that at va.gov.

  • Nick mentioned at the end of the episode that access projects and curriculum from his Kennedy School class online, you can view them at the Tech and Innovation in Government website.


[00:00:00] Ajay Jain: Hello, y'all. Welcome back to think civic. I know it is a little bit after Halloween, but we have a treat for y'all. A new episode of our podcast. Evan, who are we talking to today?

[00:00:28] Evan DeBroux: So today, uh, we are talking with Marina Nitze and Nick Sinai. Marina was the Chief Technology Officer at the Department of Veterans Affairs under President Obama and is currently a partner at Layer Aleph.

[00:00:42] Uh, Nick was the Deputy Chief Technology Officer in the Obama Administration and is currently a senior advisor at Insight Partners, adjunct faculty at the Harvard Kennedy School, and a senior fellow at the Belfer Center for Science and International Affairs.

[00:00:59] Ajay Jain: Marina and Nick recently released a book called Hack Your Bureaucracy. As authors, the two write about their experiences in the Obama administration, as well as their other roles to demonstrate how to be impactful in your organization, in Tahoe bureaucracy, whether in a government role or in your day-to-day life. And Marina and Nick are coming on our podcast today to discuss what they write about in their book.

[00:01:22] Evan DeBroux: Well, uh, without further ado, uh, let's get this episode rolling. Here are Marina and Nick.

[00:01:32] Ajay Jain: Alright, well, welcome to the podcast, Marina and Nick. Thank you so much for coming on today. Thanks for having us. So let's start with some intro questions for our audience. Marina, you were the Chief Technology Officer at the Department of Veterans Affairs during the Obama administration. What was the career path you took to get into that role, and what was your day to day work like as CTO?

[00:01:54] Marina Nitze: It was pretty circuitous. I think if you had asked even six months before this happened, if this is where my life would've gone, I would've laughed at you. I was a business process re-engineer. I started making websites professionally when I was like 12 years old. And so I had a pretty robust website business by the time I went to college.

[00:02:11] Ended up being too busy to do both, so I dropped outta college. Thought I'd go back six months later that still hasn't happened. Maybe if I have free time in the future. And then I was living in Seattle, kind of minding my own business, doing a lot of Salesforce integration for small companies; when I saw this call for some tech savvy entrepreneurs to come into government and just come to DC for just six months for the Presidential Innovation Fellows program.

[00:02:33] And it sounded just crazy enough that I sent in my resume having absolutely zero belief that I would ever even be considered right? Cuz I'm an entrepreneur; I don't have a college degree; I'm a libertarian, right; going into a democratic administration. And then I ended up being selected as one of the first class of Innovation Fellows and then a year to the date of starting that, I became the CTO of the VA.

[00:02:52] I think we can talk a little bit about what my role was like through the course of this podcast, but it was a lot about reimagining the art of the possible for how America honors and serves its veterans. That was my job description. Uh, and uh, it was a lot about like looking at the veteran experience and how we could make the VA more veteran-centric and not VA-centric.

[00:03:11] Evan DeBroux: Similar question for you, Nick. You were the deputy CTO in the Obama administration. What was your career path that you took to get to that role and what was your day-to-day work like as Deputy CTO?

[00:03:24] Nick Sinai: Thanks for the question, Evan. So I started management consulting, business school, and then venture capital mostly in the, in the Boston area.

[00:03:32] And so I was on my honeymoon, open up the newspaper. This is in 2008, and sure enough, it says that Lehman Brothers goes. The only problem is I just joined Lehman Brothers Venture Partners, the venture capital arm out in Menlo Park nine months prior. And so I, I, I told my wife, I was like, "uh honey, you thought you married a venture capitalist, but maybe not so much."

[00:03:53] But we enjoyed the honeymoon in Italy for a couple weeks and came back. And I decided to do a bit of a, a career pivot in my early thirties and wanted to go get a job in Obama Administration. And I was quite naive about what that entailed and, and how to break in, but with some elbow grease, some mentorship and, and some, some good experiences in the business world, I was able to talk my way into the FCC.

[00:04:14] The National Broadband Plan was one of those blue ribbon task forces, and from there I got hired in the Office of Science and Technology Policy, OSTP, and specifically the, uh, CTO's Office. Uh, initially as a senior advisor and then became one of the Deputy US Chief Technology Officers, which was great fun.

[00:04:30] And, you know, we'll talk a little bit more throughout the podcast about what, what we actually did, but day to day was essentially middle management, meaning, you know, there's a lot of really great folks like the Marinas of the world, and so how do you attract them and work on problems that matter to the American people? How do you empower them? How do you kind of get roadblocks out of their way and ultimately how do you get stuff done in. The listeners may not appreciate it, but the presidency is a bureaucracy of its own, right?

[00:04:57] It's several thousand people, policy councils, but then, you know, that's a small percent of the entire presidency. There's, there's so much other things going on there, and so figuring out how to be effective is ultimately why we ended up writing this book, Hack Your Bureaucracy.

[00:05:11] Ajay Jain: So let's dive into the book and talk about hacking your bureaucracy. One of the most fascinating chapters in y'all's book is about finding your paperclip. In Marina's case, this entailed developing internal and external projects at the Department of Veterans Affairs that save time and money and provided ease to public servants and veterans who use VA resources. By solving these problems at the VA, Marina was able to quote, "develop genuine relationships with colleagues who in turn would yield their capabilities to provide Marina with additional resources to implement and design her projects."

[00:05:43] So this question's two-fold, the first part is directly at Marina, but the second part is for both of y'all to answer. So Marina, tell us the story behind finding your paperclip, and for the both of y'all, how can this story's lessons be applied to solving problems in the civic tech space?

[00:05:57] Marina Nitze: Yeah, so I think your listeners may hear,” Oh, Marina was the Chief Technology Officer of the VA. That must be a really big, important job that comes with lots of resources and people.” But when I started it, I was 28 years old. I had $0 of budget and I had zero employees. And yet, as I mentioned a moment ago, my job description was to redefine the art of the possible for how America honors and serves its veterans.

[00:06:18] So it felt like there was a little bit of a disconnect there, between what I had, but I, I really, as I sat in my office, my empty office, I was trying to get a dry erase board as one of the first things I did. And I turned out I didn't have enough money for that either cuz government dry erase boards cost $105 and I had a $99 office budget.

[00:06:35] I was like, "okay, well what do I have?" And I literally had a drawer of paperclips and it reminded me of the story of a blogger who had traded through a succession of barters, had traded a red paper clip for a house. And so I thought like, "ooh, how can I, what can I literally do with these paper clips?" It wasn't literally the paperclips, but as I was having that thought, a member of the executive secretary pool popped her head into my office and said, "Hey Marina, have you seen Green Pack 42?"

[00:06:59] And I was like, "I don't know what that is, but I don't have anything else to do. I'll, I'll help you come find it." And so we wander around this 12 story huge office building, looking for Green Pack 42. Green packs are just a green file folder that when members of Congress would write letters to the VA, it would go in this folder, and then anybody that wanted to weigh in on our official response would literally with like a pen, edit the response, then it would get typed up at the end.

[00:07:20] And so I realized that incredibly important, people at the VA were spending a lot of time wandering around looking for green folders, and I wrote a little Ruby on Rails app that afternoon that printed a barcode on the front of the folders so that when it landed on someone's desk, they would scan it. And then you would know who had the folder last.

[00:07:37] And so I called this folder finder because I like alliteration and they called it M-boop, M for Marina and Boop for the sound that the scanner made . And you'd hear the little boop sound going on around the office. And I had unwittingly just made best friends and earned a lot of political capital with some of the most important people at any organization, which is the executive secretary pool. Right?

[00:07:57] They then, You know, kind of, and thanks. Helped me get really primo spots on other executives calendars so I could start pitching them on my idea for what a 21st century VA looked like. And then I had a, a succession of barters that I talk about in the book. And at the end I ended up with a headcount over 75 people, a multimillion dollar budget, and had some pretty amazing projects like vets.gov, which is now va.gov, which consolidated VA's 1500 different websites into one, easy to use, veteran centric place to manage and access benefits.

[00:08:29] It really all started with doing what I could, with what I had, which was not very much. And in terms of a lesson for how other people can do it, we've all got some skill. Maybe you're amazing at planning events. Maybe you can write an inspiring speech. Maybe you could help someone just with some drudgery that they're trying to work through. Like look around your area for something that you can do with what you have. Even if it's not money, maybe you have time. You certainly have skills of some. And you never know how that will barter up to a house or a multimillion dollar budget.

[00:08:57] Nick Sinai: Marina couldn't have said it any better. And, and it really is about, you may have grand ambitions about what you wanna get done and, and how you wanna change an organization, and that's great, but you gotta start somewhere starting small and, and helping people. Even in Marin's case, what, you know, many executives would say, well, The administrative staff was not my job description, but she actually took the flip approach of, Hey, you know, these are people who I can help.

[00:09:23] And you know, my ability to write a small Ruby on on Rails app is incredibly powerful for them. That's going to build relationships and friendships and and trust. That's ultimately really important as as you start to navigate your.

[00:09:37] Evan DeBroux: Having zero resources really stuck with me, like not even enough of a budget to buy a whiteboard as a son of public school teachers from not a well funded public school, and now as a government employee, it's kind of something that I'm like, "Oh, yeah, I know what you're talking about there."

[00:09:52] You know, it does bring us to our next question. You talk about in your chapter on Think at the end, at the beginning, how Kumar Garg and Amazon have a strategy of writing mock press releases, visualizing success, demonstrating why your project matters prior to actually creating the project. It is a topic that is well applied in sports as well.

[00:10:13] You know, Michael Jordan would mentally practice shots, uh, he would take in a game. How have you employed this strategy to government even when, you know, you can't see what success really is like because you just feel that immense pressure and perhaps a lack of support. And how can our listeners utilize envisioning success to tackle bureau?

[00:10:36] Nick Sinai: For the listeners, Kumar Garg is one of our friends and he has this tip that he would recommend to new colleagues in the Office of Science and Technology Policy, and that is to to write a press release and ultimately a news article about that particular press release on the initiative that you want to work on or the initiative that you wanna start. Because so many people come in, especially into the White House, with this idea of like, Oh, we wanna do this, this, and this. And it's like, okay, well what would that look like?

[00:11:02] Assume that you've, that you've been successful running the traps, building all of the consensus inside, not just the presidency, but inside the agency that's responsible for executing and outside stakeholders, imagine the President announcing this, the White House announcing this, What does that look like? I've employed that technique because it forces you to be very specific on the what, right? Cause you can say, "Well, I wanna do this big thing around this, this, and this." But if you, if you can't articulate how it's going to be written down, what the exact changes are going to be, how you're gonna talk about in context of, you know, what the organization has been doing prior.

[00:11:38] And then if you can't put a critical lens on it and say, "Okay, well, you know, how, how would, how would the outside world, like what would they say about this?" If, if they were to give you some of the benefit of the doubt, but also kind of put it in contact kind of past, past initiatives. And so that's why we're, we're fans of this technique.

[00:11:54] I don't think we had realized when we were working in the White House, that that, uh, Amazon had this, had this similar technique that is product managers and now others in Amazon actually have to write a launch document where they talk about, you know, a particular product they wanna launch, they have to write the FAQs, uh, about it.

[00:12:13] They have to write a whole thing, kind of envisioning a particular launch. And there's a difference between talking about something generically with your friend or your colleague, and actually writing down what that looks like, because it lets you get feedback, very specific feedback. When you have a conversation with someone, they'll be like, "Oh yeah, that sounds great!" you know, and maybe they, they'll give you a little, say, "Well, maybe you missed this little detail, or that kind of thing."

[00:12:35] When you write something down that really forces, forces or, or, or, it gives you the opportunity to share it with people. And if you ask for their feedback and you really want it back, that can help you understand. Whether you're shooting for the right thing. And it also helps you visualize all of the, the, the support or the changes that you'd have to make. Right? And so that, I think that can be a very helpful, uh, technique as well.

[00:12:58] Marina Nitze: Yeah. My first paperclip trade after M-Boop actually was laying out, started with Post-it notes, what was a, what would a 21st century VA look like?

[00:13:07] And I would point out, this was 2013, so 21st century, we were already like well into it. Turn these post-it notes with the help of a couple of Presidential Innovation Fellows into a really beautiful, glossy booklet and used that calendar time to share this vision of like, "Hey, this is what the 21st century VA could be like" to my fellow senior execs at the VA to get their buy-in, to get their edits, incorporated, their edits, and then by the time that it got to the Secretary of the agency, all the senior executives had read it, had weighed in, had added their points, and that tra created a tremendous amount of like buy-in and excitement.

[00:13:41] And honestly, the fact that it was blue and like had a nice glossy cover, which cost literally $2,000 at Kinko's, but is the best money I've ever spent in my entire life because it really stood out among the piles of, you know, Microsoft Word Times New Roman size 12 font white papers that everybody else had, and you'd see though like the pops of blue sticking out of all the execs, uh, briefing binders. And that was a really cool, a really cool moment.

[00:14:08] Ajay Jain: Yeah. And this honestly segues into our next question as well. The first part of this, when Evan had just asked about envisioning success, this is kind of envisioning about your mission, and you mentioned that setting a North Star in order to implement a vision for guiding an organization or product trajectory is necessary for seeing projects to completion and that failing to do so increases bureaucracy. Is the lack of setting a North Star something that y'all experienced working in government, and how did setting a North Star decrease bureaucracy?

[00:14:34] Marina Nitze: Oh yeah, it's, See, I see lack of a North Star a lot. I think we both do. Really, You just have to look at almost any government procurement. If you look at like the healthcare.gov debacle? Did anybody have a requirement that the website be up? No. Did anybody have the requirement to enroll, you know, X number or millions of Americans? No, it was all about like, you know, will the website have, you know, this color button in the upper, upper right hand corner? And I think that's a huge area of procurement where you can see that there are not North Stars.

[00:15:03] I don't know that I'd say a North Star decreases bureaucracy as much as it can help prioritize your changes within a bureaucracy. So I mentioned, you know, our 21st century VA document at the VA. Um, that didn't get me around any rules, right? But it did get the priority attention of senior executives. So whereas maybe nobody, maybe it would've gotten in the secretary's pool to make a decision about giving me a head count six months later, it got there in weeks.

[00:15:30] And so I think having a North Star can inspire people to read your paper first, to act on it first, to give you advice versus never responding to your email. But ultimately, some parts of the bureaucracy are still gonna be there.

[00:15:41] Nick Sinai: I would add that, you know, my job for, for four years in the, in the White House was about helping set North Stars with agencies, right? And ultimately everybody wants everything to be a presidential priority, but not everything can be, because then of course, nothing would get would get done. And there's that give and take between federal agencies about what they think is important, and then of course, what the, the President thinks important.

[00:16:04] And, and that's, that's not a singular process by any stretch, but it, it's one that I think of great importance. And in fact, there's a whole process, uh, that culminates in something called the President's Management Agenda. And it's really tries to say, "for the several million workforce, what are the things that we're going to focus on not only as individual agencies, but actually across agency?"

[00:16:26] So one of the things that I worked on was this idea of open data, and we actually turned that into a cross agency priority goal. To encourage all agencies to make data more accessible via bulk download via API. How do you make that accessible to the broader immunity, while respecting privacy if there's PII, personally identifiable information, that kind of thing.

[00:16:47] And so, you know, it's one thing to have this kind of North Star, but then the question was, "How are we going to execute on it?" That's where bringing in Presidential Innovation Fellows, where bring bringing in talented civil servants who are excited to execute on this. That's what really made that that goal of opening up government data for innovation and economic growth a reality.

[00:17:07] Ajay Jain: When dealing with implementing impactful projects, at a lot of times the snails pace in government, What are common problems that slow down the design process and what can people do, whether it's government staffers or presidential innovation fellows or civil servants who have a technical background? What can these people do within these organizations to build momentum on these projects?

[00:17:27] Marina Nitze: I'd say something that we see slow people down all the time is not understanding why there's a particular step, so many so-called water cooler rules, which is like, we do this because we've always done it this way. And we always do these 17 steps because we've always done the 17 steps and understanding the source, you know, law, policy, guidance, whatever it may be, can be a really powerful tool for cutting through a lot of that.

[00:17:47] We did that a lot in hiring in the government where we just could not get good technologists through the pipeline. And it turned out one of the key challenges was a longstanding belief that HR professionals were the only people that could do resume reviews. While they meant well, they had great intentions, they tried their hardest, they weren't qualified to review the resumes of technologists and understand which ones should, should make the cut, just as I'm not qualified to review, you know, an HR professional's resume, frankly.

[00:18:17] And so when we questioned, you know, why is this required, it turned out it wasn't required at all, and that it was actually completely allowed for technologists to review other technologists’ resumes. And that ended up unlocking a tremendous amount of opportunity for us. And then in terms of like, what can people do? One tactic I'd love to recommend is doing the work outside the meeting. I think there's a really pervasive belief that a lot happens in a meeting, right? You're gonna show up with your talking points, you're gonna pitch everybody. You're gonna win them over to your way of thinking. You're gonna get the votes in the moment. That is generally not how it works, and absolutely not how we'd recommend approaching the work.

[00:18:50] If you're gonna go to a meeting and present, you know, a new idea, that idea should not be new to anybody. In that meeting, you should get the one-on-one briefings. You should understand exactly how people are gonna vote ahead of time. You should set people up with like the questions that you need them to ask. Make sure they have the talking points to support you. If you have a detractors, you should make sure that they understand the fine points of your proposal and you understand where they're gonna disagree with you, and then you can really leverage that meeting, instead to build momentum, have a senior leader show excitement for your idea. And get the vote that you maybe need, but don't show up cold thinking that your persuasive speech is going to get things done. That's a really dangerous but really, really common error that we see people make.

[00:19:28] Nick Sinai: Yeah, I'm a big fan of how can you have a small thing and get feedback on that thing, and so in the policy context that's, that's often a one pager. Where, and we talk about this in the book of writing a one pager, getting feedback on it and building consensus so that you really understand where the organization is on a particular idea, and you're incorporating feedback.

[00:19:49] But in the, in the product and civic tech world, oftentimes that's a prototype. And so I'm, I'm big fans of, well, sometimes you, if you show what you're talking about, that actually really pivots the conversation to, well, okay, well then what is early feedback from real users? And I think that just dramatically shifts the question of, "are we doing the right thing here and should we scale this thing?" As opposed to all of the bureaucratic impediments to saying yes to this hypothetical.

[00:20:16] So we have a whole chapter on pilot is the password. I'm a big fan of prototyping and getting kind of early user feedback, and in fact, I, I taught a class for five years where student teams would do this in the context of partnering with, uh, City of Boston, Commonwealth Massachusetts, VA, Census, Center for Medicaid Medicare Services.

[00:20:34] So government clients with real problems would partner with student teams, uh, both graduate and undergraduate. They've go out in the community, do the design work to really understand the problem space, come back, brainstorm some ideas, prototypes, some products, even paper, uh, prototypes, test those again with users and use that to kind of build their idea base about what should be changed and when you're, when you're rooting it in the actual the user need. I think it's super powerful. You're able to show a prototype and an actual user feedback. Marina did this famously at the VA, where they built a better website, a basic form, but showed that to unhoused veteran who is struggling to get, uh, benefits and, and care from the VA. That really was a game changer. Those kinds of, uh, showing rather than just telling can be really powerful.

[00:21:21] Evan DeBroux: You know, it kind of nested into that thought process. Let's say we've built momentum on a project. You started to work around those water cooler rules, but you kind of run into the, one of the next issues that you may face is sort of like you have these resource constraints when you're working on a project within the government or any sort of civic tech organization.

[00:21:42] How can we find ways to like increase the number of people and resources working on these projects? Once we've started building this momentum, even when there are pretty strict constraints on who we can hire, if we can hire anybody in the first place, or we're constrained on the platforms and resources we can use?

[00:22:03] Nick Sinai: I think it's about building momentum on your particular thing, but also doing the, the hard work on the budget and the, the hiring and the things that are more systemic to your actual thing. Right? And so that, that's, that's always the challenge. And we, we talk about this tension, in our book, which is, you may be so focused on a particular project or product or, or initiative, but there's this question of, well, what systemic changes can you advocate for in that context?

[00:22:31] And Evan, to your, to your point, it, it may be funding, but that you may be in a multi-year budget cycle where the funding isn't gonna show up for next year. It may be permission to use a more modern tool, but that's gonna require, you know, uh, a six month, uh, paperwork process. It, it may be hiring a particular individual who you then wanna focus on trying to get them through the, the hiring gauntlet.

[00:22:53] And all of those feel like, well wait a second, those are diversions from the actual product or, or initiative that you're working. But if you're, if you really want to be a world class bureaucracy hacker, I think you have to think about making some of those systemic changes while you are advancing your particular, uh, initiative.

[00:23:10] And it's that that initiative is what gets people excited. It's a tangible thing. It's, it's the kind of thing that people want to put money and people behind. And fundamentally what we're talking about is, is essentially entrepreneurship, but inside of organizations, right?

[00:23:23] Great entrepreneurs, they are selling a vision. They are attracting people on capital and building a team over time, and they start with nothing. And over time they gain more. And it doesn't have to be a linear thing, like a, uh, in many cases you may be empowering other organizations rather, rather than that, you know, building, uh, a lot of people under your direct control.

[00:23:43] But it is that question of are you able to attract capital or other stakeholders or other partners who are excited about this particular vision that you have and, and are are excited to join with you and make real progress.

[00:23:55] Evan DeBroux: I did want to take the chance to pivot here from this discussion on building momentum because one of the things that stuck with me as someone who sees himself, especially in his work life as extremely risk averse, is that, you know, some of the tactics mention in the book do come with certain risks in their approaches.

[00:24:14] You know, I, I do. A certain example of the White House Science Fair and Nick you had a temporary pass to be there, but then you kind of got kicked outta the room. How can people within organizations sort of mitigate these risks of some of these hacks that you're using or you're suggesting in the book? I guess the second question is, is there a point where risks are unavoidable and people just need to be aware of the potential fallout if the tactics fail?

[00:24:47] Marina Nitze: Yeah, so I think a key that we really encourage through the book and have a lot of tips around how to do, is to understand exactly how your organization works and what the exact risks and incentives are. We have a chapter called Understand the Consequences. If you, you know, fill out a form slightly off because you need it to approve cloud computing, are you going to go to prison or is it just gonna be that like your boss might be a little bit upset with you on Friday? And you know, is that okay? And what's that acceptable risk?

[00:25:14] And it's a really great exercise to run on yourself because that can help develop empathy for all the other people that you're asking to make changes or to do work and understand how what you're asking fits into their risk and incentive framework. Because something that seems very low risk, for example, to me, might be career ending for someone else. And I, if I don't appreciate that, like I'm never gonna find that middle ground.

[00:25:36] And I, I think different tactics are gonna work in different situations. By no means are we promising that one of our 56 tactics will definitely solve your problem. Sometimes it's gonna be you just, you miss the budget window and you gotta wait till next year. Or you absolutely need the vote of that senior exec who is absolutely not on, not on page and not gonna be there. But it could be a really interesting thought exercise and usually pretty successful to think strategically about what you're trying to accomplish. And if there is some way to get something done.

[00:26:04] And I'll tell a quick story here that might be relevant. When I was first launching what was then vets.gov and is now va.gov. We as a agency, we historically updated websites every quarter, so once every three months, uh, which was not fast enough for us. We wanted to do daily deployments and updates and edit, and the change management team in IT was absolutely not on board for that.

[00:26:27] They were like, "Nope, we can't, um, approve and review your changes every day. We don't trust your automated tooling, like we're totally not on board for this." And so every time I tried to deploy something, this team would take two weeks, and they would write back and vote no. And I tried a lot of other tactics. I tried befriending them, like doing lunch and learns, finding different ways that I could accommodate their, their needs.

[00:26:51] And I was coming up short. And then right about when I was about to give up, I realized something, someone pointed out to me I needed this team to vote. I did not need them to vote yes. So, I offered to them if we could automate their no vote as part of our deploy process, so they would automatically vote no every time we deployed code.

[00:27:14] And this team was like, "Absolutely! That aligns with my risk and incentive framework. I want it documented for the future Inspector General that I never, ever, ever voted yes on this even one time." And so I was now able to deploy code daily, achieving my goal, and I was able to achieve their goal of not being on the hook if this went sideways, right? Through sort of a creative understanding of what the decision making process was, so that hopefully that inspires maybe a listener to find a creative solution to their problem.

[00:27:42] Nick Sinai: The thing about risk on my mind is that we tend to do a pretty lousy job as human beings of really understanding risk. We tend to be a little too focused on what is, uh, a fixed constraint rather than seeing things as as opportunities. And so we would encourage all, all of your listeners to really think about being ambitious.

[00:28:03] And yes, you may fail, but you tend to, if you are being transparent and authentic and ethical, you tend to actually succeed more in your failures longer in your career. Because if you're honest about what you know and what you don't know, what you're trying to get done, if you're taking the time to listen and respect people who have the expertise and who have tried things, so there's a difference between taking unnecessary risks and you know, being headstrong and stupid versus taking risks, but being ambitious for the right mission.

[00:28:35] Right for the right goal. And I, and I think thinking, thinking big and wanting to change your organization to, uh, benefit, you know, the veteran or the student or whoever your particular organization is, is focused on, I think that's great. And look, yeah, you, you may fail, probably will fail, but you'll probably learn more doing that.

[00:28:54] And it'll ultimately be better for your organization, for your career, uh, and so forth. I mean, I, I, I look back at those failures and yes, getting thrown out of the White House Science Fair is in the book because I, I was frankly, being a tourist, you know, that's kind of a, a cardinal sin or a near cardinal sin as a White House staffer is you're there to, to do stuff. Not to just gawk at the President, uh, as he goes by.

[00:29:16] And, uh, you know, had I been authentically someone who had been helping, uh, uh, set up and, and prepare, then I probably would've been invited to be in a room like that. But as it was, I, I traded on some of some of the, uh, access that I had to be in that room, and, and, and thankfully someone threw me out of it.

[00:29:35] Ajay Jain: So let's segue to another one of the concepts in your book. As an Italian American, I'm a very big Frank Sinatra fan. It just goes generation and generation of loving Frank Sinatra. Although I might be an even bigger fan of Evan DeBroux's Frank Sinatra performances at karaoke night, uh, he sent me a video last night. It was absolutely incredible. I will recommend to him that he should sing "Chicago" because as a Wisconsinite, Chicago is obviously better than Wisconsin.

[00:29:58] But regardless, I was quite amused to see that one of your principles for hacking bureaucracy was called the Sinatra Test. So describe to us what the Sinatra test is and how y'all have applied it to solve problems in government.

[00:30:11] Marina Nitze: Yeah, so the Sinatra test comes from "My Way" (Marina meant "New York, New York") and it's the idea that if I made it here in New York City, I can make it anywhere. This applies to our bureaucracy hacking cuz these tactics worked in the White House. They worked in the Department of Defense, they worked at the VA, which is the largest civilian agency.

[00:30:25] And then we've since found, you know, they, Nick is in venture capital and teaching at Harvard. They keep working. I am, uh, I do it crisis consulting at, uh, large corporations and also work with state and local governments on foster care forum. They keep working and oftentimes that feeds into one of our tactics that's called go second, which is bureaucracies tend to be risk averse.

[00:30:47] But if you can line up a change to show like, "Oh no, no, you're not doing this first, you're doing it second. Someone else took the risk of going first, you're now going second." That really, really helps. And at the VA for example, it was regularly if I was like, “Oh, well DOD did this, the Department of Defense did this.”

[00:31:03] Often people would be much more bought in. They'd be like, “Oh, well a Department of Defense did it then maybe we could do it.” And that works all the time in foster care now too, where I'm like, "Oh, well Hawaii did this and other states are suddenly like, Ooh, this seemingly risky thing. Like someone else already did it. We now we're behind. Right?" It really changes the the framework.

[00:31:19] And so we just tried to set up the book that while many of the stories. In the White House or the VA or the DOD where not everybody maybe works. We hope we've made the argument that if they worked there, they will work also in your local government, in your PTA and your homeowners association and elsewhere.

[00:31:36] Ajay Jain: During my undergraduate career, I initially majored in statistics and computer science before adding on a political science double major during my sophomore year because I wanted the technology that I would interact with after college to mean something, and preferably it would mean something either in politics or in government in order to help create a more level playing field in our society in fields.

[00:31:58] I'm quite frankly, very passionate about, and as a result, I've orbited between a mix of purely technical jobs, political gigs and jobs that combine civic duty and technology. For example, when I was a Coding It Forward, I was a fellow at the Department of Health and Human Services working on COVID-19 Analytics a couple years ago, which is really, really fun as one of the coolest jobs that I've ever had.

[00:32:18] But I found the retelling of Kumar Garg's groups at the White House, to put it succinctly, the semi-policy wonks and the politicians comes in, strategist hacks to be very insightful, and I think it's a really important concept that we have not talked about that much on the podcast. Obviously, a vast majority of our listeners would probably fall in the wonks category, but when it comes to collaborating with hacks in order to create projects that benefit the organizations that we both work in, how do we as wonks pitch and sell meaningful and impactful ideas to groups with different backgrounds than us, but still share a common goal and mission in?

[00:32:54] Nick Sinai: It's a great question. I love that experience at Coding It Forward. The whole origin story of, of Coding It Forward is, is in the book. Uh, it was a handful of my students partnering with a former Presidential Innovation Fellow at Census, basically coming together to help kind of create the, the first class of Coding It Forward Fellows.

[00:33:13] And it's a great program that has now expanded to also be at the the state and local side of getting talented technologists into government for a summer. And so, you know, I'm a, I'm a big fan of those kinds of, uh, of movements. But I also love the question, um, because it, it, it basically says, "Hey, let's, let's think about the other person and the other guild. They may come from a very different set of lived experiences."

[00:33:38] And so we, we talk about that hacked versus wonks. There's a story in the book where I insulted David Gurgen to his face, and I, I called him a hack, uh, and it was the uncomfortable silence for about 10 seconds because I was describing the, the hacks versus wonks, the different set of, of guilds and inside the White House.

[00:33:56] And after that uncomfortable pause, he said, "You know, you're absolutely right." I wish, And this is a guy who had, uh, who's worked in four white houses. He said, "You know, I wish I had really learned this because this is something that I didn't understand."

[00:34:09] And so, one of the things I would encourage all the civic tech, uh, listener base of your podcast is to recognize that you may be engaging with people who don't know or care what civic tech is, and they may be of a different generation. And so how are you going to build a authentic relationship where you, you understand where they're coming from? And so I've never worked on a campaign and yet for me to be successful in a place like the White House, I had to make sure that I understood how to communicate in their world because there were just, frankly, more of them, and they were gatekeepers to getting big things done for administration.

[00:34:45] And so just very practically, what did that mean? What did that mean? That meant pitching in terms of visuals. So rather than saying, Hey, we're gonna have a White House science fair where we're gonna be able to release a lot of policy documents around STEM policy and the NIH can release this about cancer funding, et cetera.

[00:35:04] They didn't care about that. They cared about the visual about the President with kids and and Lego robots. And so if you could talk about that and you could talk about a White House Science Fair, you could name it in a way that everyone kind of gets. You know, the details of like, we're not really having a competition, but this visual of different science booths and the President going around and interacting with that was a visual that the, the hacks, and we said that very, um, it's not a derogatory term, it's actually a term of affection because they, they're people who are actually telling the story and putting policy decisions in the context that everyday Americans can understand.

[00:35:40] And so being able to, to, to say, "Hey science is important." We wanna have the White House celebrate science, and here's how we're thinking about it in terms of a White House science fair pitching in terms of, of visuals and analogs. That's kind of what we encouraged e every policy staffer to do.

[00:35:56] Marina Nitze: Yeah, and a related tactic here is cultivating the karass. Karass is a concept from Kat's Cradle by Kurt Vonnegut, and in the book, it's a collection of people that God has hidden on earth to accomplish a goal together. Our version is a little more secular, but I think people are often in bureaucracies and especially in civic tech, frankly, and they believe that there's all these people that are just around to stop you. They're there to block you. They're there to get in your way. They're there to stop your progress.

[00:36:21] And that has not actually been true in my experience. I think a healthier way to approach it is that there are people hidden around your agency or your organization that are there to help you, and your job is to find them. One of my early paperclip trades that got me my first substantial budget at the VA was actually, there was this website that was very, very expensive and it had hundreds of pages of HTML content, so just written words. That was to help veterans get find employment when they first separated from the military.

[00:36:51] And we could recoup some of the cost savings if we were able to help end this expensive contract. But first we had to move all those hundreds of pages of content to the new website. And I did not have any team at that point and, and no capacity to myself personally, recode a thousand pages of HTML.

[00:37:08] But I looked around and like, I was like, well, the security guards have computers and they're very nice and they have a little time on their hands. And so we taught HTML at lunch to the security guards and they, you know, while they absolutely focused on their first priority of keeping the building secure in between visitors, they would help code and move these pages over to the new website.

[00:37:28] And so I got millions of dollars of budget as a result. And perhaps, unfortunately for the VA, all the security guards then left for IT jobs pretty shortly thereafter. But it was a really powerful example to me that at that point, you know, my karass was the executive secretary pool and the security guards, and I will never forget that lesson, right?

[00:37:45] Those are not people that maybe in your first top 10 of people to like work alongside, but you never know how those kinds of unexpected relationships can really forge and, and help you accomplish things together.

[00:37:58] Ajay Jain: Yeah, and I completely agree with that. I mean, going to Nick's point of like navigating hacks versus wonks, for example, as someone who's kind of always been a little bit in the middle, it is very important to understand like the viewpoints of both hacks and wonks in order to have an effective government and to navigate bureaucracy.

[00:38:12] And in terms of Marina's point, just knowing the resources that you have and the people that you have and how they can help you and essentially the cards that you can play in order to get further along in your goal is also extremely, I. But I wanna talk about now getting to that place in the first place in terms of getting to the organization that you wanna be at.

[00:38:30] One of the tips that y'all bring up is this line go where you are rare. It is a line that former US CTO, Megan Smith, has stated multiple times. I believe it was also something, and Evan, you might have heard this too at our Coding It Forward farewell ceremony at the end of the summer, this was also a line that was told to us.

[00:38:47] And it's something that I've taken to heart during my career. So for example, post-Coding It Forward, I took my role at the Texas Democratic Party during the 2020 general election. In part because I knew that I would be the only technologist on the finance team. I would be the first time this position had ever been formed.

[00:39:04] I would be the person being able to. Have an impact technologically speaking, data, analytically speaking, and kind of forge this role for the future. Once I had, you know, left the Texas Democratic Party after the election, and even in my current role, it was rare for a software engineer with such a civic and government background to join it at entry level.

[00:39:21] Even though the work that we were doing was, you know, impacting local newspapers and local governments. And so my question here is, what advice do you have for young technologists to go where you are rare and carve out opportunities in their career?

[00:39:35] Marina Nitze: I think my advice would be if you are a young technologist in particular, to find problems that don't necessarily look like technology problems at first.

[00:39:43] So whatever you're passionate about, whether it be climate change or um, people struggling with housing or whatever the problem may be, find opportunities to get to know the real people that are experiencing the problem. The real flow and your viewpoint as a technologist will by itself provides some really unique insights that you'll be able to contribute, and then there may or may not be a technology problem to solve that you can bring to the table, but it's really about the diverse perspectives.

[00:40:10] And then once you know that you could, you know, potentially jump into, say, a technology team, but now you'll be rare because as you just shared in your story, now you're the rare technologist who served, you know, on the finance committee. So now that's your rarity, you're in a technology team, but you have a different rare skill set that you're gonna bring to the table.

[00:40:30] Nick Sinai: Yeah, I, I like to think about this balance between building your technology skills and working with other, more skilled or more senior technologists, so you continue to, to learn versus going in places where you're outside of your comfort zone and outside of your guild. That could be a, a, a finance team in, in a, a political party.

[00:40:52] You know, it, it could be in a non-profit, it could be in a government agency, what have you. And just finding ways to kind of continue tho… those, those threads or those loops over time, because I think that ultimately is what builds a diverse set of, of experiences and differentiates you a, as a technologist. Uh, completely agree with Marina, of course, that understanding the problem space rather than leading with the technology or the solution, uh, is a really powerful way to kind of up your game, not just as an individual technologist, but as someone who is, is able to contribute to managing or solving the solution.

[00:41:30] I would say too often in technology, we get so solution-oriented, and so rather than realizing some, sometimes some of these challenges are multidimensional, multi-generational, multifaceted, and, and they are sometimes problems to be managed, uh, um, uh, you know, to, to help millions of Americans, uh, materially, but that they cannot be solved, uh, necessarily overnight.

[00:41:53] And that technology has a, has an important role to play. I think all elements of both public and private sector, you know, have technology increasingly playing a valuable piece. And so there's so many other places to work besides big tech or startup tech. I think those are both great places to work. I have, uh, some of my former students and good friends that work in both of those ecosystems.

[00:42:16] And look, I, I'm in venture capital and so I, I work with startups and scale ups. Uh, um, every day. But I think there's also opportunities to, to, to work in corporate America, in nonprofits and, and especially in government. I'm hopeful for all the technologists that wanna serve a tour of duty or make that their career.

[00:42:34] Marina Nitze: Nick's story reminds me of one other quick tactic, which, uh, is play the newbie card. I mean, when you are a senior executive in an agency, you cannot ask basic questions. It impacts your, the respect of your peers. Like it's a very scary thing to do when you're the newer technologist on the team or not.

[00:42:51] When you're the newer person on the team, you can ask questions like, Well, wait a minute, why do we do that again? Or, where does that come from? And you can uncover like tremendous insights and opportunities. By playing your newbie card that everyone else that's there just cannot. And so I would really encourage anyone listening to play that card early and often.

[00:43:08] Evan DeBroux: You know, I think when we were writing our closing question, we kind of had the early technologists who may have another semester of struggle, uh, in college in mind here. So the book makes reference to Nick's time after the Obama administration. Nick taught a class at Harvard Kennedy School on Tech and Innovation in Government his students spent time interviewing and collaborating with government employees in Boston and as, as well as constituents who utilize government resources.

[00:43:38] This class is also well known in the civic tech community because it's sprouted the next generation of civic technologists. So final question. How can students who are not in the Boston area, uh, use some of the concepts from your class and this book to impact their own communities and organizations?

[00:43:58] Nick Sinai: Yeah. Well that's one of the reasons we wrote the book is, is to try and take some of those lessons from the class and from our experiences and make them accessible to everyone. So encourage folks to go out and buy, Hack Your Bureaucracy. Buy anywhere books are sold or listened to it on, on Audible or Kindle or, or what have you.

[00:44:14] Second, you know, there, there's the rise of a number of technology and innovation in in government types of classes across Georgetown and CMU, and frankly across the country. So it's not just at Harvard and you know, we're big fans of students being able to precipitate that kind of. So if you don't see it being taught, find your favorite design or technology or product or, or even public policy professor who wants to work, work in this field.

[00:44:43] And, you know, the, my entire class is, is open. It's at innovategovernment.org. So, you know, they can see a lot of the projects and, and curriculum there, but frankly, there's, there's a lot of great professors who are part of the civic tech community who are, are working on these types of topics. And so encourage them to, to teach you as well.

[00:45:02] Ajay Jain: Awesome, well, thank you so much Nick and Marina for coming onto our podcast today. It was really great to have this opportunity and to talk about your book. Like you, Nick just said earlier, go ahead and buy Hack Your Bureaucracy at your favorite bookstore, or check out the audio book on Audible. Thanks you all.

[00:45:16] Marina Nitze: Thanks so much for having us.

[00:45:18] Nick Sinai: Thank you Ajay and Evan.

[00:45:41] Ajay Jain: Thank you again for taking the time to tune into this episode of think civic. Nick and Marina's book, Hack Your Bureaucracy, is available at your local bookstore and online.

[00:45:50] Evan DeBroux: As always, please make sure you're following us on our Twitter handle @thinkcivicpod. To join in the conversation after this episode, be sure to hit subscribe at thinkcivic.substack.com.

[00:46:02] Ajay Jain: Bye for now.

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think civic: season one
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