First Time in Government

“The President of the United States is going to call you in three hours to offer you the job, so I need to know in two whether you will say yes because we do not surprise the President.” That’s what Todd Park, U.S. Chief Technology Officer (CTO), said to me in August of 2014 as our family was about to head back to San Francisco for the new school year.
Todd Park, Assistant to the President and Chief Technology Officer
shows President Obama information on a tablet April 15, 2013.
Official White House Photo by Pete Souz
In those two hours, I tried to figure out if I could really make a significant positive impact in the job the President would offer me as Deputy U.S. CTO. And, if so, whether that was worth moving our family.  The ability to make a positive impact is generally my north star when trying to make job decisions, but time and again, when I am looking back on whether taking a job was the right decision, the quality of the team I got to work with is always most important. Now that I’ve had some time to reflect on my time in government, and the entire Obama team has moved on from team CTO, I know that this time was no different. While I am extremely grateful for the impact of the work I was privileged to do, I am most happy about my time in government because of the the people I got to do it with.

The Eisenhower Executive Office Building, home of the
U.S. CTO, pictured c 1907, then the State, War & Navy Building
Gall, George, Washington: The Capital of the Nation (1907).
Digitized by The Internet Archive from the Library of Congress

The impact of government work was amazing. Our purpose was clear: help make life better for and with the American people. Under President Obama, Team CTO had significant impact working together along with many others in our home at the Office of Science and Technology Policy (OSTP), elsewhere in the White House, and across the Federal Government. We supported the work done by previous CTO teams to bring tech capacity to government in the form of the Presidential Innovation Fellows, 18F, U.S. Digital Service, and revamped Office of Digital Strategy. We brought more data science and data scientists into government through the creation of the U.S. Chief Data Scientist team and role, and creating a data science cabinet. We expanded data collaborations for solutions in justice, jobs, housing, education, and more, while continuing to get more government data out to the public. The Open Government Partnership (OGP) continued to thrive and grow and we shepherded the U.S. Open Government National Action Plans while teaming up with the National Security Council and State Department to help lead the U.S. OGP. With support from the Chief of Staff, we created a new tool for tech policy making called the Tech Policy Task Force -- which added “TQ” to many policy tables, formulated a federal source code policy, moved the government forward on artificial intelligence and uncrewed aerial vehicles, accelerated open educational resources, highlighted the opportunities and challenges of big data and algorithmic decision making, and worked with the Departments of Education, Transportation, Commerce, State, Homeland Security, Justice, and others to help regulations get out of the way of innovation while protecting people’s rights and lives. We pushed for greater recognition of all American talent, including women and underrepresented minorities in STEM; catalyzing for improvements in the portrayal of STEM people in media; expanding inclusive opportunity in computer science education; ensuring outreach for jobs in innovative industries in hiring programs, such as TechHire; increasing Internet connectivity in the U.S. and around the world; championing innovative local community solutions; pushing through more diversity and inclusion in the Federal government workforce; and expanding best practices in organizations and companies in diversity, equity, and inclusion, including an implementation action grid, the Tech Inclusion Pledge, and expanded inclusive venture funding.  And, lots more. Even reading the list brings a tired smile to my face.

President Obama writes his first line of code and celebrates
with the middle school student who helped teach him, Dec. 8 2014.
Official White House Photo by Pete Souza
So, while there was no shortage of impact, I still would say that it was the people that were the most important reason why I was so glad that I had the opportunity to work government. The diversity of people in the White House and at agencies was a huge difference from Silicon Valley. That diversity was expressed in terms of the traditional lines of socio-economic, ethnicity, race, color, religion, age, disability status, gender identity, sexual orientation, and far more balanced gender representation, but also in terms of point of view, educational, geographic origin, and career background. Sometimes, I was among others like me but more frequently I was unusual along a number of dimensions such as my lack of long federal service, my lack of military service, my tech background, etc. I came away extremely impressed with the level of experience, intellect, and passion that the Obama White House was able to attract. There were people who you later discovered were Rhodes Scholars, or Supreme Court clerks, or had beaten a Scrabble world champion over the weekend. I had expected both the diversity and excellence, but it is one thing to expect something and quite another to live it for two-plus years.

President Obama talks with U.S. CTO Megan Smith, and
OSTP Director Dr. John Holdren, Oct. 8, 2014.
Official White House Photo by Pete Souza
Team CTO under U.S. CTO Megan Smith was also outstanding. I had the privilege of working with a number of people that I have admired and wanted to work for for years. I also got to meet and work with a bunch of folks that I might never have otherwise met. Over my time there, the U.S. CTO team while I was there included at different times: Puneet Ahira, Seth Andrew, Rob Bacchus, Jake Brewer, Marvin Carr, Jimmy Catania, Colleen Chien, Evan Cooke, R. David Edelman, Ed Felten, Anjali Fernandes, Brian Forde, Brianna Fugate, Dipayan Ghosh, Vivian Graubard, Renee Gregory, Dan Hammer, Natalie Evans Harris, Read Holman, Kristen Honey, Mina Hsiang, Kelly Jin, Terah Lyons, Matthew McAllister, Dawn Mielke, Lynn Overmann, Ryan Panchadsaram, DJ Patil, Tom Power, Laura Weidman Powers, Jason Schultz, Nick Sinai, Lauren Smith, Ashkan Soltani, Suhas Subramanyam, Emily Tavoulareas, Maya Uppaluru, Aden Van Noppen, Nancy Weiss, Claudia Williams, Charles Worthington, Cori Zarek, and, of course, the wonderful Megan Smith herself.

Some of the wonderful folks that made up team CTO,
Jan. 14, 2017.

That combination of a top-notch team amid a diverse broader group of excellent folks from top to bottom at OSTP, the broader White House and across the Government, made going into work both a joy and a challenging learning experience every day. I felt like I grew a ton, learned a lot about how the U.S. government functions, and picked up some really interesting management and leadership lessons from the people I got to work with. I came home mentally worn out but almost always smiling. I also made a bunch of new friends.

President Obama talks with Girl Scout White House Science
Fair participants who had designed a Lego page turner to help
people read books who may not otherwise be able, Mar. 23 2015.
Official White House Photo by Pete Souza

Now that I have been out of work for a few months, I am thankful for the opportunity to make a positive impact but I am certain that I made the right choice that August because of the amazing people I got to work with. I am still fired up that I had the privilege to serve with each and every one of them, and ready to go and work with them again!

President Obama, listens during a technology 
strategy discussion, Oct. 8, 2014.

Dense Dead

If there is some interest, I'll publish something longer on this. In the meantime, I threw together a quick script that takes a link to one of the wonderful Grateful Dead shows available to stream from the Internet Archive and edits out the least dense of Dead songs, Drums and Space, so that when I am listening to the Dead and working, I don't need to skip them.

The result is and a chrome extension that will rewrite Grateful Dead Internet Archive pages to push the m3u files through Dense Dead.

For example, to hear a slightly denser version of The Grateful Dead's last show, the Internet Archive URL would be:
the streaming URL on that page is:
and the DenseDead URL would be:
If you visit the Internet Archive URL for the show with the Dense Dead chrome extension installed, clicking on the VBR Stream Playlist link will automagically give you the denser m3u file even though the page itself still shows the full show.

If you find shows where Dense Dead doesn't work, hit me up on Twitter @amac and I'll see if I can fix it. If you want to know more about how I did this, also shoot me an @reply over on Twitter and I'll consider writing more.

Public domain image of skull from An Illustrated System of Human Anatomy: Special, General and Microscopic,
Samuel George Morton (1849) scanned by Google Books from Oxford University Library


Samuel George Morton (1849) scanned by Google Books from Oxford University Library

Chiefs of Staff: We need more in the private sector

A bunch of friends in Silicon Valley have asked some version of “what was surprising to you in govt?” or “what did you learn about govt?” This is part of a series of posts answering those questions.

One of the MANY things I learned while serving as Deputy U.S. Chief Technology Officer was just how amazing the folks are that have the title “Chief of Staff.” They are some of the unsung heroes of the White House and government as a whole. There is no true equivalent to the Chief of Staff job and it is pretty rare in the corporate world, particularly in Silicon Valley (but see Kris Cordle at Slack). Chief Operating Officer (COO) may be the closest analogy, and it is no coincidence that Sheryl Sandberg, Facebook’s extremely effective COO was Chief of Staff at the Treasury Department before moving to Google and Facebook. Read on for a bit more about what a Chief of Staff does, with some examples from President Obama’s administration.

Letterhead of the Chief of Staff to the President

First and foremost, a Chief of Staff (COS) is a manager.

Data from the Office of Personnel Management
The U.S. Federal Government is extremely large. The President of the United States is a CEO of sorts for approximately 2.6 million civilian executive branch employees engaged in a mind-bendingly diverse set of jobs (including the military, that number is over 4 million). In addition, the President’s relationship to the country makes him also responsible to the more than 300 million people that make up the United States. As a result, the President’s time, and that of other leaders in government (called “principals” in government), is precious and spent on external events, relationship calls, decision making, or getting information, and, in each case, only if the principal is not replaceable with others. An example of part of that schedule for President Obama is archived here but the schedules of other principals, from the Director of the Office of Science and Technology Policy (OSTP) to the Secretary of Commerce, are similar.

A COS's first job is making sure their principal’s vision is implemented effectively and that requires, in the first instance, managing their principal. They need to make sure that their principal is using their time effectively, for example that any issue that can be resolved at a lower level is resolved, and that they have the information necessary to make informed decisions. This part of the COS job requires an extraordinarily good relationship with the principal and almost supernatural ability to predict what the principal wants. A COS may have their own views but a significant amount of the COS power and effectiveness comes from being, in Game of Thrones vocabulary, the “Hand of the King.” This relationship balances a COS's management of their principal with their relatively egoless role as their principal’s direct report and executer. They are also truth-tellers who aren’t shy about bringing bad news to their principals. In my experience, the best COSes are both supremely loyal and trusted by their principal to make significant decisions without them. This gives them a dual role “staffing” their principal but also being principals in their own rights. Denis McDonough, who was President Obama’s COS during my time in the Executive Office of the President, is a great example. Denis was in sync with the President and his guidance could be relied upon to reflect the President’s. As much as anyone at the White House, he seemed to embody being in service to the President. At the same time, the buck frequently stopped with Denis, and, in those situations, he was a principal himself.

Chief of Staff to the President, Denis McDonough,
walking with President Obama, Sept 22, 2014.
Official White House Photo by Pete Souza
The COS is also likely to be the manager of the department. Hiring, firing, tasking, internal dispute resolution, and other managerial duties are often functions that are delegated to the COS. The principals oversee these but a ton of day-to-day management is done by the COS. For example, within OSTP where I worked, Cristin Dorgelo was the COS and would do weekly one on one meetings with each of the Director of OSTP’s reports. Cristin constantly was touching base with people across the department. She interviewed every person brought into OSTP, and she had an exit interview with everyone who left.

OSTP Chief of Staff, Cristin Dorgelo,
leading brainstorming at an NIH event, June 24, 2015
Photo by @NIH3DPrint
Similarly, Natalie Quillian, part of Denis’s COS team and a Deputy Assistant to the President, established new internal communication avenues for the White House to help spread internal communication and to create a sense that all of the employees in the Executive Office of the President were part of one team. Natalie also gave me and other White House staff regular guidance and mentoring in how to approach different processes and people within the White House.

Deputy Assistant to the President, Natalie Quillian, 
introducing her child to President Obama, Aug 27, 2014.
Process Wranglers

The Federal Government has a significant amount of process designed to improve decision making and ensure that the diverse viewpoints of departments are represented. For example, Presidential Policy Directive 1 laid out the National Security Council system for national security decision making under President Obama. A well run process can produce a good decision but, equally importantly, it will produce a decision with buy-in from the components and agencies that will need to implement the decision. While laudable, these processes are a lot of work to run and to exist within. The various COSes are the masters of them and are responsible for “shipping” a decision just as in Silicon Valley we rely on product managers to ship products.

Natalie was an expert at driving a process to completion. Understanding the type of decision that was required, she effectively figured out the right forum, the right questions, and the right type of information to get in front of the right set of principals to ensure an informed and constructive discussion that could produce a decision that would then have the buy-in to be implemented. She did everything from scrutinize an attendee list in order to add a person or two that needed to be included (or remove someone that was unnecessary to the decision); force lower level folks to more finely hone their disagreements or come to agreement on items that didn’t need higher level participation; push the conversation in the meeting towards an argument that was left unaddressed; and follow up to crisply articulate the meeting’s outcome and the mandate of each participant going forward. Each is an active task requiring a very high degree of understanding of the subject matter and emotional intelligence about people across government. I saw Natalie and many of the other COSes take this on across an incredible range of substantive areas from national security to communication to legal issues.  

The White House under President Obama was also a place that effectively used memos. As Jeff Bezos reportedly does at Amazon, the White House used memos to force the cogent development of argument and to allow components and agencies to resolve disagreements and to make decisions in a way that others across government and outside of government can see and understand. Working a document, with hundreds of other potential editors can be a recipe for committee-written prose and a huge time waster. The only thing worse would have been the potential for future disagreement if the various players didn’t have to come to agreement on paper. This paper process would have been impossible without the COSes. For example, on any given day, Cristin could be involved in a handful or more memos. Over her time at the White House, that meant that she was likely involved in thousands. She developed an expert sense of what was an important edit for OSTP and what might be better to let go. As importantly, the set of COSes within the Executive Office of the President and at the agencies were repeat players with strong relationships and a good deal of trust between them. Irreconcilable substantive policy differences that might otherwise disrupt the decision making process could often be resolved to the satisfaction of all through Cristin’s relationships and the creativity of the COSes.

Implementation Gurus

Federal government implementation of policy is almost always the responsibility of agencies. For example, while the President may determine that Federal data should be open, it is up to the Department of Transportation to release Traffic Fatality data to the public. This can leave execution of policy initiatives, particularly ones needing interagency cooperation without a central driver. Since few policies are successful without successful implementation, President Obama focused White House staff on continuing to track policy decisions through implementation and helping where needed. No-one did that better and across more important policy priorities than Kristie Canegallo, whose title was Deputy COS for Implementation. During her time in the position I saw Kristie ensure appropriate implementation across a wide range of topics including the Affordable Care Act, Precision Medicine Initiative, Cybersecurity National Action Plan, and the technology transformation of government more generally. And those were just a small percentage of her workload.

Deputy Chief of Staff for Implementation, Kristie Canegallo (center), 
with other members of the Affordable Care Act team
giving an update to President Obama, April 1, 2014.
As with any good operator, Kristie delegated effectively but sometimes got into the weeds to better understand and debug problems. She removed obstacles for the teams. She elicited and measured teams against metrics. She kept the cross-agency and cross-functional teams focused on the bigger picture and brought her own mastery of all of the tools available to our government to get the job done. Kristie is one of the better executing leaders I have ever worked with and her focus on and skill in implementation was shared by many of the COSes.

Calm, Solution Oriented, and Without Ego

A great COS is also calm, solution oriented and without ego. Yohannes Abraham, Valerie Jarrett’s COS at the Office of Public Engagement, is a great example of this COS attitude. Like part of a startup founding team, Yo has seen it all, so nothing phases him. He does not dwell on blame but moves quickly towards finding solutions. For example, I once brought him an issue that I was working on that some said might threaten one of his core implementation projects. Yo’s project was a higher Presidential priority than what I was working on. He talked through the issue calmly and saw the tensions between the two policy objectives. Together we weighed the good that would come of each and then talked through an approach to try to ensure the thing I was working on could get done in a way that would not threaten the higher priority policy project. Then he used his relationships to broaden that understanding and ensure that others could come to the same conclusion. Yo, like the other COSes, worked on thousands of individual policies and launches. His experience showed in his calmness and in the creative solutions he was able to make happen and often he was working to push someone else’s work over the finish line. Yo is exactly the kind of person you want to be working with you on the hardest problems. No ego, all drive to make a positive impact.

Chief of Staff of the Office of Public Engagement, Yohannes Abraham
Undated Government Photo

We Need More Chiefs of Staff!

While not every business is as large or complex as the Federal Government, the Chief of Staff position is underutilized in the private sector. The skills of Chief of Staffs in managing their bosses and staff, pushing through processes, and driving implementation, all with a reassuring calmness, solution orientation, and lack of ego, are very much in need in Silicon Valley.

I focused this post on the COSes that I worked with closely over the last few years but there were many others, and all were world class. And, they also ALL tendered their resignations as part of the peaceful transition of power at the White House. They would each be well suited to be CEOs or COOs in the private sector. I can’t wait to see what they do, and I would work with any of them again.


Public domain images from J.J. Thomas, Illustrated Annual Register of Rural Affairs for 1876-7-8, Luther Tucker & Son (1878) scanned by Google Books from Ohio State University Library

Basic CyberSecurity

Public domain image of fence from J.J. Thomas,
Illustrated Annual Register of Rural Affairs for 1876-7-8,
Luther Tucker & Son (1878) scanned by Google Books
from Ohio State University Library
Some former Obama Administration folks have asked for advice on what do to re: cybersecurity now that they are using non-government equipment. Since we each have a different threat model and different setups that advice should be very different, person to person. BUT, for the folks I know, no matter who you are, or what setup you have, start with:

1) Use two factor authentication. the Electronic Frontier Foundation (EFF) has handy guides to turning it on at many major services. If yours isn't listed, check this two factor resource maintained by Josh Davis.
2) Use a password manager so that using unique, hard to guess passwords is easier than using bad ones. Also use the password manager to store your fake answers to those insecure security questions, such as "what is your mother's maiden name?" EFF has a great video about password managers suggestions and Wirecutter has some suggestions about which one to use.
3) Keep your operating system and applications updated. If you are no longer using an application, consider deleting it.

The three steps above are relatively simple to do and shouldn't take more than a half hour to set up. There is no excuse for NOT doing them. They will save you from many, many, many, many types of attacks and heartache.

Public domain image of barbed wire fence from
.J. Thomas, Illustrated Annual Register of Rural Affairs
for 1876-7-8
, Luther Tucker & Son (1878) scanned
by Google Books from Ohio State University Library
One additional thing I suggest, particularly if you are involved in anything sensitive, is to think about what information about you is accessible by others, such as your friends, the places you work, and the providers of the services you use. Threats may get information from those sources, instead of you.

For more information, please take a look at the EFF's excellent Surveillance Self Defense guide (which is labelled surveillance but could really be labelled "privacy" or "security").

And, if your threat model includes the government getting access to your devices at a protest or as you cross the border, there are some other important things to consider.


Photo by Doc Searls, CC BY-SA

Alexander Macgillivray, also know as "amac," is curious about many things including law, policy, government, decision making, the Internet, algorithms, social justice, access to information, and the intersection of all of those.

He was United States Deputy Chief Technology Officer for the last two years of the Obama Administration. He was Twitter's General Counsel, and head of Corporate Development, Public Policy, Communications, and Trust and Safety. He was Deputy General Counsel at Google and created the Product Counsel team. He has served on the board of the Campaign for the Female Education (CAMFED) USA, was one of the early Berkman Klein Center folks, was certified as a First Grade Teacher by the State of New Jersey, and studied Reasoning & Decision Making as an undergraduate.

Not Working in the Trump Administration

I was asked by a reporter recently about whether I would have continued on in my job as part of the Trump Administration. I said no and for me it was not a difficult choice. I wanted to elaborate a bit on that here in case useful to others.

First though:

a) I have friends who made a different choice. Everyone's situation is different, everyone's potential job within an administration is different, and we all have our own ways of thinking about this issue. I believe that thinking about the moral and ethical implications of one’s work is important, as do all of the people that I have talked with who are staying. I would like to see more folks think about those implications, both in government and outside of government.

b) I am strongly supportive of the various indications I have heard about this Administration’s continuation of the Obama Administration’s agenda to improve government services by improving federal tech, and am optimistic about what might be done in that space with the support of the strong group of people who have offered to stay. The office of the U.S. Chief Technology Officer, the U.S. Digital Service, the Tech Transformation Service (including 18F, the Presidential Innovation Fellows, and many other parts), the agency Digital Services teams, the offices of the Chief Information Officer (CIO), Chief Information Security Officer, Director of White House IT, agency CIOs, and the rest of the digital family in government still have a ton of work to do to make government more efficient and effective on behalf of all of us. I believe in a functioning government that is effective at delivering services for people. A thriving government digital family is essential for those efforts. And, that work has been supported by Republicans and Democrats. It was hugely supported by President Obama and there are indications that President Trump’s team is also supportive.

N.B. I feel the opposite way about President Trump’s tech policy agenda, see e.g. the rumblings about Net Neutrality.
c) I am fortunate to have many privileges others do not, including the privilege to choose where and with whom I work. Those are real privileges that not everyone has. I was born lucky and got to go to excellent schools and jobs over time, which led to connections, additional privileges, and more. I am white and male. Being able to make the decision not to take a job is a privilege that is unevenly distributed. Furthermore, in talking with some career civil servants, some feel the very idea of getting to choose which administration to work for is a form of spoiled entitlement.  There are people who have been quietly serving on behalf of the American people for 40 years. People who have made life better for Americans under Presidents that they disagreed with. These are many of the folks who were critical in explaining government to me and helping me use its tools during my tenure. If our entire civil service turned over every time the Presidency changed, our government would function significantly worse, if at all.

d) It is also unclear to me how much of an administration's policies people should consider when trying to ethically evaluate being a part of an administration. Clearly, I shouldn't be involved in something I believe to be ethically wrong. To what extent am I also responsible for what the other ~2.5 million government employees do? What about the President?

Anyhow, all of the above is just to reiterate that there are many reasons others have to choose to stay. I respect and thank those that have stayed. They have important work to do, and I admire them for doing it. But it is not the right decision for me.

I told the reporter I would not continue on as Deputy U.S. CTO  for a constellation of reasons.

1) First and foremost, my job as Deputy U.S. CTO was very connected to the President's agenda. That is one of the reasons people in those types of jobs historically tender their resignations before inauguration. It does not make much sense for the President's inner circle and the circles around them to be actively opposed to the core of the President's agenda. I strongly disagree with large swaths of President Trump's agenda (at least as far as I understand it).

2) I believe I can contribute to protecting the values I care about from President Trump’s agenda (see point (c) about privileges above). I think protecting those values is important, and I think I can do that more effectively outside of the federal government. These decisions about where to work and what to do are inherently political in part because of the opportunity cost of whatever decision one makes. Working in the office of the U.S. CTO is an incredible opportunity but comes at a cost of not being able to do other things.

3) I had the opportunity to serve in an incredible job for over two years. I tried to do as much as I could during that time. There is a lot more to do, even in areas of bipartisan agreement. I believe in fresh legs and the advantage of having new perspectives and energy on those issues.

4) My work-life balance hasn't always been great. It was time for more life in that balance.

These thoughts are a bit raw and draft but hopefully they can be helpful to others as they make their own decisions.