What can we learn from the 2016 transition? With Ann O’Leary and Rich Bagger 

Valerie Boyd: On this episode of Transition Lab, we’re pleased to welcome two impressive guests, Ann O’Leary, the co-executive director of the 2016 Clinton transition, and Rich Bagger, who helped lead the 2016 Trump transition. 

Today, they discuss their respective experiences leading transitions and how their experience might inform this year’s candidates.  

Ann O’Leary is a longtime Democratic political figure and a self-described policy wonk. She’s held a wide variety of roles over the past 30 years, beginning with serving on the Domestic Policy Council in Bill Clinton’s White House in the late 1990s. 

She then became legislative director for Hillary Clinton’s Senate office before spending more than a decade at the Center for American Progress. She returned to politics with Clinton’s 2016 presidential campaign, first as a senior policy advisor, and then as the co-lead of her transition team. Since then, Ann has worked outside national politics, practicing law and serving for two years as chief of staff to California Governor Gavin Newsom, during which she guided his transition into office. 

She now leads the government controversies and public policy litigation practice at the law firm Jenner & Block.  

Rich Bagger is a born and raised New Jersey corporate executive, politician, and government leader. A lawyer by profession, he spent the 1990s and early 2000s as a New Jersey state legislature. 

From 2010 to 2012, he served as Governor Chris Christie’s chief of staff, using meticulous planning and political savvy to spearhead several legislative successes. Rich briefly returned to the private sector until 2016, when Christie, chairman of the Trump Transition Team, appointed him to run its operations. 

Ann and Rich, thank you both so much for being here today.  

Ann O’Leary: Thank you for having us.  

Rich Bagger: It’s great to be with you.  

Valerie Boyd: So, let’s start off broadly going back to 2016. Could you share how each of you got involved with your respective transition projects and what relationships did you have with the candidate? 

Ann O’Leary: So, as you mentioned in my bio, I’ve worked for Hillary Clinton for many years both in the White House and in the Senate and had the opportunity to work with her on her 2016 campaign, starting early when she first started thinking about it in 2014. And, so I think when she was thinking about her transition, she really wanted to build a team of people who deeply understood her agenda, also really knew her very deeply, and could really help her with the most important parts of the transition, which is how do we build a team of people who can, on day one, help her do everything she needs to be to be the most effective president. 

And how do we turn the campaign promises that she has made in terms of policy into practice? And so, she asked me and my colleague Ed Meyer, who had worked with her in the State Department to come together. And then she appointed a stellar group of chair people, including Ken Salazar, who played the role that Governor Christie was playing on the Trump team as a chair. 

And so, we got to work immediately after the convention in early August starting at that time. 

Rich Bagger: 2016, eight years ago, hard to, hard to believe I had met Donald Trump then but did not know him. I came to the transition because of my relationship with the governor, Chris Christie, who, as you noted, I had served as chief of staff. Governor Christie had just completed his own presidential primary run in 2016, and I had not worked full time on his campaign, but I knew as soon as it was, as it was announced that he would be serving as chair of the Trump transition planning team, that that was right up my alley and I knew the call was coming. 

As a matter of fact, the call came when I was in Japan on business, when the governor’s appointment had been announced. So, I signed up from half a world away to serve as executive director for the transition. And I immediately learned one of the lessons of serving on a transition, which is that your work on a transition should not be seen and should not be heard publicly. And that is because I remember telling somebody who I was speaking with in Japan that I had taken this call and I was going to be working on this and before I knew it, a Japanese politician from the LDP party sidled up to me, took a picture with me. And about three days later, it appeared in a Japanese newspaper with a photo caption that said Trump’s man in Tokyo. 

Fortunately, it was a Japanese language newspaper and nobody other than I saw it. But that was the first announcement of my role occurred in, occurred in Tokyo.  

Valerie Boyd: Yeah, you both knew what to expect. And yet it did happen half a world away. 

And I appreciate how both of you kind of touched on important transition themes in just this first interaction where you talked about how Secretary Clinton was looking for people who understood her and her agenda, that was so important. And Rich, you talked about how the transition should be seen and not heard and the tension that happens when you find yourself in the public eye. 

So, with that in mind, let me ask, as you got your transitions up and running, where did you start? What were the first items on your to do lists?  

Rich Bagger: Well, for us, literally the first thing we did, was I read two books. I read, the Romney team from 2012 had published a book that they called the Romney Readiness Project that focused on the pre-election phase of the transition. 

And then the Center for Presidential Transition’s® Presidential Transitions Guide, which is updated and comes out each cycle. So not to give a plug here, but, you know, read both of those books in painstaking detail, taking notes, highlighting and then had two meetings. We had a daylong meeting. 

Governor Christie and I did and some of the other folks would form part of our core team with the core team from the Romney transition to just go like, you know, step by step through the whole process. And then we spent a day at the Partnership for Public Service. Again, you know, just learning as much as we could and taking on as much information as possible. 

Because for me it was a key lesson. We were working on behalf of a candidate. And the campaign who had policies that wanted to shake things up, wanted to bring change to the federal government. However, a theme in our work was that to be successful, the actual methodologies of building an administration are very well established. 

Right. And to you, candidates and parties may have different policy preferences and outcomes that are intended, but the nuts and bolts of how to do things are pretty well traveled path, pretty proven, success. And so, we didn’t really want to reinvent the wheel in the process. 

Sort of followed the Romney experience, followed the guidance from the Center for Presidential Transition® and got off to work. It’s a really auspicious moment when someone says, okay, you’re to do this. Now start an enormous task, but a very important and exciting one. 

Ann O’Leary: You know, it’s interesting because the way Rich just described what he did is very similar to me, and I think that speaks to both the public. 

You know, Partnership for Public Service, as well as the bipartisan and nonpartisan nature of what you’re intended to do. And so, I think at this moment in time, in which, you know, as Rich said, eight years later, it feels like we’re in a more divided country in which sometimes maybe people forget the importance of what the transition is about. 

It’s about our national security. It’s about the efficacy of government. It’s about making sure that when California is hit by wildfires or New Jersey is hit by floods or some other state in between is hit by a tornado, that we are able to immediately respond or if something happens with regard to foreign policy in a war, that there’s not a moment in time in which there’s a pause because of the transition. 

So, I think, like Rich, I took it very seriously in terms of my duty to understand that responsibility, my duty to understand the Presidential Transition Act and what it meant for us. I was very grateful for the Partnership and for Max Stier and for all of you there to help us and, frankly, we didn’t do things much differently in terms of our education. 

We also were looking to the Romney transition. We also were looking to, you know, previous transitions. You know, I called my friends who had led the Obama transition and immediately took them out to dinner to brainstorm with them and to understand what they were doing. I think the only thing that I would add to what Rich said is that I also was trying to understand kind of who was out there mapping out what may be happening with regard to the transition.  

So, one challenge that we had that I think was, you know, different than what the Trump team would have been pacing is that Hillary Clinton had been served in government and in politics and obviously her husband for many, many years. And so, one of the challenges that was at the very forefront of what we were dealing was the fact that if we were going to win, it was going to be a Democrat-to-Democrat transition. 

And it also was going to be a situation in which, you know, there’s about 4,000 political appointees. You know, we could have closed our eyes and picked 4,000 people who knew the Clintons out of the hat. And we did not want to do that. And so, one of the things that we were really intentional at the beginning was thinking about how are we going to source new ideas, new energy, new vision, from not just in DC, but from around the country. 

So, we were really looking to state and local governments and other sources that we could make sure to get the generational leadership and change that we wanted to see with the Hillary Clinton administration. So that was one of the first things I was really focused on.  

Valerie Boyd: You’re previewing so many things I want to ask you about.  

First, as you talk about the importance of bipartisan network working together, the fact that both of you are here today, taping this interview together is meaningful in the first place. I want to come back to that in a little bit. And, as you just discussed, I think there’s a lot to learn in the current cycle about how a Democratic candidate thinking about taking over from a Democratic administration can think about the personnel choices in front of them. 

I want to ask a few more questions about the big picture of your operations before we get there. First, just the unusual nature of a transition and the fact that you are staffing up from just a few people to several hundred in a matter of months and then scaling back down to, you know, nothing all in a year. 

It’s a very unusual life cycle for any organization. So, can I ask what was your driving spirit and your unifying factor? What kind of culture and mentality did you create on the teams to keep everyone committed to the work? 

Ann O’Leary: Well, I’ll just say, you know, we worked extremely hard. So, I remember at the time, I know I slept from midnight until 6am. 

I tried to like force myself to sleep six hours, but sometimes it was maybe 5am. And other than that, I would take a morning run and then, you know, really get into the office. And I think, it was a small team when you’re, you know, we obviously only did the pre-election phase, and so I think we had about 25 people who are paid staff and another 25 volunteers by the end of it. 

So about 50 people. And there was so much to do because you really are trying to really source the best ideas and personnel and really make sure you’re prepared on the policy front. And so, we really tried to have a really unified team, you know. Something that I personally did that became a thing was at three o’clock in the afternoon, I would say like, don’t schedule any calls between three and 3:15.  

And I made the entire office do seven-minute workouts and we would run around the office and, apparently, the Biden transition did, in my honor, did this as they went forward too. But it was a great way of like having a little fun and a little camaraderie as we, as we moved forward. But I think, you know, the most important thing to know for whoever is doing it this time is just the intensity I think of it. 

And I know we’re going to talk soon about unexpected things that happen. And, that, you know, that was one of the things is just being prepared for the unprepared, you know, things that you wouldn’t prepare for. But I think having a cohesive team, the other thing I would say is, of course there’s some elbowing and drama and who’s going to be where and who wants what job. 

And so, one thing that we did that I, that I really credit, I’m going to say Jake Sullivan and others who were still back on the, on the campaign, is that we made a rule that the, nobody on the campaign was allowed to call me or my colleague and ask us for a job or talk to us about jobs. And we were very focused on keeping the campaign staff focused on winning. 

And that was really important. And so, we put kind of rules in place that, you know, once a week we may have at the senior leadership, some, you know, conversations about the transition in terms of what happens right after the election with regard to the campaign staff. But we really tried to get the staff not to think about what job they wanted, after the day after the election. 

Rich Bagger: Yeah, that’s an important, that’s an important issue. But first, let me say it’s an amazing professional and personal experience to have the opportunity to work on something so important for our country as a presidential transition. And to be in the, in the position of sort of starting from, you know, the very beginning of a, of a team of a couple of people to build the team of 10 people, that then becomes the team of a hundred people. One of the various best professional experiences of my lifetime. And, as maybe we’ll discuss later, like, and I only worked on the pre-election portion, you know, we had handed off our work somewhat unceremoniously a few days, a few days after the election, building a culture and a team among a group of people brought together for such an important, relatively short term project in the, you know, in the milieu of, you know, a campaign and, and politics, having that strong culture is vitally important. I personally onboarded everyone who joined the transition effort.  

We had about 130 people with badges to get into the office space by election day, and maybe a total of 250 to 300 volunteers for landing teams and the like who had been recruited and, and embedded. And, I remember, you know, sort of personally onboarding everyone, trying to help create that culture, you know, get people excited, but then also to emphasize what I called, the, the three rules of the transition. 

Right. And the three rules of the transition were first, the campaign’s the most important thing, the campaign is separate, but to not get in the way of the campaign, not to distract the campaign, people in the campaign are working about on job one, which is the, you know, the candidate’s election. 

The second rule was that the transition didn’t make policy. We developed plans to implement policy, but we were not, you know, sort of feeding back to, you know, create the policy positions for the candidate. So, a little bit of a challenge for us because the campaign didn’t have a lot of policy positions. 

So, if we’re going to take the campaign website, the campaign’s policy positions as our starting point for policy implementation plans that, you know, that could be a little tricky, but we didn’t want to be freelancing on policy. And the first is what I referred to, you know, before is that, you know, we were, we were not going to keep things from the transition and inside the transition, not talk to the media, not, you know, so that we did not become a distraction, you know, because public focus on, on, you know, our work before the election becomes a, becomes a distraction. 

And, once everyone was onboarded with those three things and joined the team, I gave everybody a Make America Great Again hat eight years ago. It feels like a long time ago, but gave them, but gave them a campaign hat that, you know, that showed that they were a part of the team. 

Valerie Boyd: Those, those are truly great examples from both of you, because it is a really powerful and all-consuming feeling to have some responsibility for helping a candidate put their promises into action. So, I know the culture within a transition is very dedicated, very ferociously committed to that work. 

And, for both of your examples, Rich, you meeting with, every person as they were onboarding so that they had that sense of a team and, and knowing that it’s such all-consuming work and still like finding some shred of managing to take care of ourselves and each other with just like a little daily work out. I think those are just great examples of setting a culture in that kind of environment.  

You’ve both alluded to some challenging dynamics. I’m going to ask one more kind of basic question about milestones and mechanics because we’re talking right before the Democratic National Convention, and that’s a major milestone in the transition process this year. 

It’s the second and final convention. And three days after the second convention is when the General Services Administration support to the major candidates starts. So, do you remember when that milestone hit? Did that change the atmosphere for either of you? Did the workflow and pace of planning change? 

Rich Bagger: Yeah, we, in terms of planning, and I think this is fairly common, sort of divided the transition into three time periods. The first time period was sort of inception through the conventions, you know, I forget what we called it, but I mean, that was really just sort of scoping out the basic planning. 

And then the pre-election phase from the transitions, from when we moved into the GSA space through the election day. And then the third phase would be the sort of the real transition, where the, you know, the successful transition team moves into the space that the government has set up specifically for the, you know, the official presidential transition. 

And so it very much felt to me like a milestone when we moved into, you know, the offices that we were at in together, both teams in 1717 Pennsylvania. You know, that’s when it really feels real and the office space that we had there was fairly sparse when we moved in, but by election day, was really hopping. 

I still have a, a picture Ann of maybe half a dozen or ten of us, you know, together when we, visited that building, together with the GSA, to look at the– 

Ann O’Leary: Oh, that’s great. I’ll have to get the photo from you. That’s great.  

Rich Bagger: To look at the, the space that was available, that the teams, you know, we sort of like flipped the coin or something for, which floor– 

Ann O’Leary: I remember that. 

Rich Bagger: would be on, but it was just an example of how like a lot of the mechanics throughout the process. 

So, each team is working in parallel, right? There’s not collaboration between the teams, but they’re working in parallel in a non-competitive way, you know, in, with cooperation to both teams from the incumbent team, from the incumbent administration.  

Ann O’Leary: Yeah, I’ll just pick up on where Rich left off because I do think, once you hit the convention and then it becomes real with regard to federal funding kicking in and with the GSA being able to provide both the building and the support, but then the other piece, and this goes both to your previous question with regard to culture, as well as this question, which is that there were moments in time and Rich, I can’t remember how many, but I remember at least two and maybe three times at which Rich, myself, and then of course, Governor Christie and Ken Salazar at the White House and met with Denis McDonough, the chief of staff to President Obama and the senior leaders at the White House to provide critical briefings and understanding of what was happening. And I think that just goes to this seriousness of this duty, and I think that it’s important. 

You know, I gained great respect of, I already had great respect for Governor Christie. I didn’t know Rich, but I really gained great respect for what they were trying to do. Very great respect for Dennis McDonough and the team at the Obama White House.  

And I think that it was people who came together who cared deeply about effective government and about making sure that we were doing everything we possibly could to understand the challenges that the Obama administration were facing that would become ours, you know, if we were to win, and so I think it’s just important to say out loud that I hope, that this transition coming up in the year 2024, can learn some lessons of what we did, you know, obviously since that time, so much volatility and partisanship and anger has occurred in the country, but if I look at the, you know, kind of months right before 2016, I had some hope and I will say that I was very dispirited, you know, at that point, just a private citizen to see Governor Christie and Rich not being asked to, to continue on, because I had seen their work up close and knew that they were doing this in a way that was really about our country. And so, I just will add that.  

Valerie Boyd: You both have raised a few things to follow up on, and I’ll start with the Cohabitation in the same building is the easiest place to start. It’s also the question that I get asked the most that people are very surprised to find out that both teams would occupy office space in the same building. 

And they ask, how could that even be possible? And it leads into a little bit more of what Ann was just saying about, you know, the 2016 election was pretty tough by all accounts, with both candidates fighting hard to win, but you both managed to cooperate with the Obama White House, cohabitate in the same building, and generally kind of work in the same direction for the good of the country. 

And as you said, things feel even more partisan and intense than they did, or they feel even more partisan intense today. Do you think it’s possible for the two transition teams to cooperate in this election cycle in the way that you did? 

Ann O’Leary: Right. Well, I can only hope that they do. I, you know, I think the cohabitating is really not such a big deal. 

You’re on different floors. The only thing that you gain, and I’ll now tell Rich that I was spying on him, but you basically see who’s coming up and down the elevator. So, then you go upstairs and say, I just saw so and so from the Bush administration going up in the elevator, wonder what they’re doing or, you know, what it might be. 

But the people we saw going up in the elevator gave us great confidence, which is they were people we knew who had served in previous Republican administrations. Now they all got fired, right after Trump came in. And so, we don’t know who ended up. Well, I don’t know. I, I mean, I do from reading in the newspaper, we didn’t see those people going in and out of the building. 

So, you get a little bit of a window into how they’re kind of conducting themselves, but you don’t really interact so much with each other. It’s really about the White House. And so here, this is about, Jeff Zients, who’s an extreme professional, the current chief of staff to Joe Biden, he’ll be responsible for convening the meetings. And of course that will, you know, obviously the Harris side, that’s easy. 

It’s the vice president. But I think, you know, I do think there’s a question mark right now with regard to whether or not the Trump team will participate in this transition in a way that is about effective governance and I, you know, no offense to you Rich, cause this is not on you, but, I don’t have any faith that the Trump people want to participate in the effective transition of government.  

Rich Bagger: Well, then hearkening back to something that you said we were, we were sort of in like, inverse positions in 2016 in terms of that your team could have like, you know, easily staffed the entire administration with people from the Obama or Clinton administrations who were standing by, probably ready to pick up the baton and continue government.  

And you were making an effort to make sure that, like, sort of the net was spread wider than that to, you know, bring in additional people into the process. We were supporting a campaign that was so skeptical of people with actual government experience that we had to work hard to make sure that people who had served in the actual departments that we were preparing transitions for were part of our efforts. 

You know, to recruit people from say the Bush administration, to be part of the effort so that we had the benefit of the experience in, in all of, all of the departments. Again, I have to say that I was so impressed with the professionalism and even handedness of the Obama administration in 2016 in terms of handling the transition out. 

There were moments at which I, I felt that the president or the chief of staff had like set certain milestones for it. And I would get, I would get calls from like, you know, a deputy chief of staff to push our work along. You need to be submitting the clearances for people to go into the, and this is like before the election, right? 

Ann O’Leary: Right. Right. Remember that. 

Rich Bagger: Assuming we would not be successful, they’d be like, we haven’t gotten enough of the pre-clearance for the people. The landing teams that we want, we got to have them all by Friday. I think they were, they were really, committed to a seamless and successful. 

And I can imagine, I don’t know, but I can imagine, you know, Obama wanting to pay it forward because I think he, you know, admired the work that President Bush had done eight years earlier. I share the concern about this year, because even a former president and people who’ve served in a prior administration, I mean, have a lot of work to do and should know they have a lot of work to do. 

And the, you know, the controversy about Project 2025 and the America Policy First Institute and these sort of like outsourced transitions, but then they’re not official and they’re operating very publicly, which opens them up to, you know, criticism and becoming a part of the campaign themselves. 

I’ll be watching closely, but it’s definitely time to start seeing the signs of an official transition taking shape. It’s obviously it’s past time. 

Valerie Boyd: Let me ask one more question before we get there, because you both have been talking about the excellent example of the Obama White House and how Dennis McDonough did all of the right things to help both teams prepare. 

And you, you touched on this a little bit earlier, but Jeff Zients is well positioned to continue that trend. What kinds of things can he be doing to make the transition planning task easier for both candidates?  

Ann O’Leary: You know, I think Rich has already spoken well to it, which is, I think it is so critical that you’re even-handed and that you have everything ready because, even though the Christie team did not continue, I imagine that a lot of the work did enable the agency, you know, landing review teams to be able to go in. 

And so, all of the work that they did to say, you know, it could very well, you know, this election, we just do not know what’s going to happen. Everybody who cares about politics is every day clicking on to see what’s happening with the polls in Wisconsin or all the various swing states. But I think this is, you know, it’s anybody’s bet at this very moment. 

And so, I think that, you know, it’s just critical for the safety of our country that our democracy, that this is taken seriously. Jeff Zients is going to do the right thing. You know, again, it’s really a very big question about whether Trump is, and I, while he’s disavowing Project 2025, every indication is that the people who worked on that project are very likely going to be walking into, if he does do a federal transition, that those people are going to walk in and they’re just going to carry their ideas over to the formal presidential transition team. 

And I think there’s just, you know, a very big question hanging over or not, you know, how this is going to work. I mean, they’re talking about completely transforming the civil servants in our country and making it much more politicized and much more partisan. And I think it’s quite scary and dangerous, and I think it’s very unpredictable as to what’s going to occur. 

So I don’t think it’s in Jeff Zients control, but I will be watching as I know many people will about who he appoints to the positions that Governor Christie and Rich held in 2016. And I don’t know what’s going to happen.  

Rich Bagger: Because regardless of the individual policy initiatives and regardless of their positive ones or harmful ones. 

The official transition is needed to actually prepare for the transfer of power and the things that need to be done and the really intricate mechanics of what needs to happen cannot be done outside of the official transition.  

Ann O’Leary: I was just going to build on what you said. 

You know, I, for those listeners who haven’t read or listened to Michael Lewis’s book, The Fifth Risk, it’s a fascinating read about presidential transitions. And it goes to, you know, some of the work that Rich had been doing, which is to say that, prior to the election, all of us were working on these policy books to make sure that people understood what was happening in each agency, what the priorities were, what the risks were, what the most important matters were. 

Michael Lewis wrote this fascinating book about the, he did a deeper dive into the U.S. Department of Energy and what happened to those transition books and basically the long and the short of it is that they weren’t read and they weren’t taken seriously. And there was a lot of people who came in who did not have either respect for government or experience in government to know how important those books were. 

So I think, you know, if I was to implore anybody, it’s to take this as a, as a very serious continuance of governance situation, because if you think about, you know, whether Homeland Security and, our energy assets, we should want somebody who matter of matter, no matter of their party, to be able to understand what the risks are and what the dangers are and be able to go in and, I worry that that when they let go, you know, the Governor Christie enriched that some of that got lost in a really, really important way. 

Rich Bagger: Yeah, it’s obviously, it’s, important for both campaigns and both candidates, but it’s, but it’s so different, right? Obviously, you know, Vice President Harris needs to be preparing for her administration and it’s a party-to-party change and it’s right. It shouldn’t just be assumed that it’s a, you know, that it’s a continuation. 

However, that has sort of like the default position of the government will continue, and with the change in party I mean, obviously, the career staff and the institutions of government continue, but for all the political appointees, the incoming administration of the opposite party has so much work to do on appointments to get the get people ready for their confirmations, but then to get, you know, non-confirmed positions lined up so people can join the government as close to January 20th as possible. Obviously, the risk is greater with an ill-prepared, opposite party transition.  

Valerie: You’re offering so many threads to follow. 

So let me start first with the compressed timeline and what that means. And then, ask a little bit more about the inter party transfer of power, intra party and how that might affect power, personnel planning. So, on the compressed timeline, you’ve both referred to the decision by candidate Trump in 2016 to change course dramatically after the election and remove Governor Christie and Rich from their positions in the planning that they’d been doing since the spring of that year. 

And I think it’s kind of well-known and well-established by this time that there was a real factor in the low number of nominations and confirmations that they were able to make at the beginning of their administration preparedness for executive orders and preparedness overall, Rich. You talked about the outside organizations to the fact that yes, Project 2025 and America First Policy Institute have been doing really aggressive planning. 

And I think, as you said, that might not mean anything unless they actually represent the candidate. And you referred to this too, that, that the candidate is disavowing Project 2025 at the time.  

Opinions are divided on how well the lessons have been learned since 2016. Some people believe that the people around the candidate are determined for that not to happen again. Some people believe that the candidate will kind of create chaos, no matter how much good planning has happened. 

But for both candidates, we’re now in August in 2016. Both the Clinton and Trump campaigns had started planning in the spring. What does this compressed timeline mean for both candidates now? Is it possible to start an operation now and still be prepared to govern in January? What might they be sacrificing? 

Ann O’Leary: Well, I think that this is really unique because you have somebody who has served as president and somebody who’s currently serving as vice president. So, there is this time, you know, kind of a really different situation I think with Harris, because she could make decisions. And when I was Governor Newsom’s chief of staff, just before, you know, before becoming his when he was governor, I was his transition lead and then his chief of staff. 

And we were, you know, Democratic, Democrat Jerry Brown to Gavin Newsom. So, when you have that situation, you do have a bit of luxury because you’re able to ask people, would you serve a few more months while we get organized with regard to appointing personnel. So, I think that there’s a little bit more wiggle room on the Harris side, with regard to personnel. 

But I do want to go back to something that you said, just in terms of the compressed timeline you were just talking about, you know, this kind of creation of chaos and you were talking about it with regard to Trump. And I will say, you know, just how much impact that creation of chaos had on not just the Hillary campaign in 2016, but our transition. 

And so, if you remember, we were dealing with the fact that the WikiLeaks with the Podesta emails went out in August, right, as we were starting to transition, which included, personal information, my personal cell phone number, information about me. And so, what that meant is that my personal cell phone was being traded around the dark web, and I was getting phone calls regularly, harassing me, telling me death threats, talking about the candidate. One could ask why didn’t I change my cell phone number, but I think it’s hard when you had a cell phone number for a long time, and that’s how everybody contacts you to, you know, kind of move forward. 

But it was extremely disorienting. And there was also like people with Russian accents would call or speaking Russian. And so, there was just a tremendous amount of chaos happening to me personally during that time as a result of the chaos that was being created by, you know, whether it was foreign interference or the Trump campaign, but a lot of work going on.  

And then I remember the day that, you know, Comey made his announcement. And, that actually happens to be the same day, but I believe we had one of those meetings at the White House and we finished the meeting and we were, I remember, because I don’t know if you remember this Rich, but we were sitting in the West Wing lobby and we were kind of chatting and being polite with each other. And I think one, I don’t know if you or one of your colleagues said, well, all likelihood we’ll be sitting on a beach somewhere and you guys will be running the money, the transition, because at that point it looked like Hillary was going to win. 

We go into the meeting, we have this very professional, good meeting. We walk out and I was walking back. It was a very hot day. And I was walking back to the transition office when the Comey situation hit with the emails and the chaos just got worse. And I think it was this, oh my God, how bad is this? 

And what’s the situation and how do we think about it? And it was trying to get the team to focus on, you know, staying focused on what we needed to do, and the campaign would deal with that. But. I just think it’s, especially right now, I mean, you look at the chaos that’s already ensuing with the vitriol that’s coming from Trump accusing, you know, Kamala Harris of not understanding her racial identity, whatever it might be, there is going to be a tremendous amount of chaos that not only impacts the campaign, but impacts the transition. 

And so, I think it’s, how do you keep your head down, keep the noise away and keep trying to do the work of the country when all of this is going on. 

Rich Bagger: That’s an enormously important point. And I certainly didn’t have the personal impacts and that you were describing, but in a tumultuous campaign where there were moments when it appeared that the likelihood of a Trump victory was extremely low, and part of the culture that I think we successfully built was that our job was to hit our deliverables by election day, where we had, we had defined a number of specific deliverables for election day that we’d, you know, sort of developed a plan over a couple of months, you know, to be able to be at that point. 

And success was delivering our, you know, our work product being on each of the other work streams where we felt we needed to be to sort of hand off to the day after the election and brief the president elect a list and it became our job to be ready regardless of the outcome, you know, so that like our, if it was looking highly unlikely that there was going to be a Trump victory, our job still was to get the work done and complete our work, which was a good thing as it later, you know, proved to be necessary just on the timing, you know, the dynamic is that the acceleration of the work is geometric, not arithmetic. So, like where you need to be in August is a multiple of times farther than where you need to be in June and where you need to be in October is another multiple set of where you need to be in August. 

And if you’re behind at any of those milestones, it makes it extremely difficult to be on time in November, December, January and February, because the scope of the work is growing so enormously. So even when you have 10 people working on something in June, if you’re not hitting your marks and getting done what needs to get done, you’re building a problem that’s going to be difficult to overcome in November. 

And the fact that in 2016, you know, there was terribly a month lost by the decision that was made to sort of go back and reassess everything. You know, losing a month at the most important time, you know, translates into half a year or the better part of a year later. And so the lesson from that, it is the importance of even in earlier, less intense phases to not lose momentum, you know, to keep on track. 

And so that means that I think the pressure’s on both teams. Again, you know, with the vice president of the United States, and the former president, you know, they do have a head start. But there’s a lot of, there’s a lot of work to do and it’s August. 

Valerie Boyd: You’ve made that point very well, Rich, that they need to be exponentially farther along by August than they would be in June. 

And it is so important to have these operations stood up now. You’ve mentioned that there is an expectation, perhaps that the vice president is part of the incumbent administration, and she might have a head start, but there’s also the perspective that if she wins, she would be her own president with her own vision and her own need to hire personnel to execute, to match that vision, and I promised to follow up on this topic.  

So, the closest precedent that we have is George H. W. Bush when he ran in one in 1988. And, as I know, you both know, the Reagan presidential personnel office asked for blanket resignations of all of the political appointees so that the new candidate or president could have a, a blank slate. 

And what we’ve heard from Andy Card and his colleagues is that caused some anxiety, of course, among many people that ultimately were asked back and potentially some, some resentment among people who were asked back as well. So, I should ask Ann first, because you were in more of a similar situation in 2016. 

Secretary Clinton was not in the government at the time, but it was more of a friendly transfer. You’ve touched on this a bit already, but how did you think about coordinating with the outgoing personnel team and identifying the right personnel who might, who might need to stay? 

Ann O’Leary: Yeah, well, you know, we had also probably through, gotten that advice from Andy Card about just being careful with regard to the, the blanket resignations. But we were so worried about this issue with regard to this perception that it was just kind of a ongoing Clinton’s last Obama administration and how do we, deal with that? 

So we were, you know, kind of, optioning out a version of a blanket resignation, in which we would have had some exceptions. I can’t say where we landed because I can’t, I can’t remember how it all worked in the end, but I know that we were very seriously considering that I think that, you know, when I was with Newsom in California, we didn’t, we very purposely did not do that. 

And I think there were pros and cons. I mean, the fact of the matter is, you know, we couldn’t as easily, it’s hard to ask people who are in your same party, will you please step aside now because we want to bring somebody else in. And so, it did make it slower for us and that transition and that administration to be able to kind of get people in place. 

With regard to Kamala Harris, I think, there’s going to be a huge expectations on two fronts, which is one, the generational change issue. A lot of people around Biden have been around Biden for decades. And so, part of it is how does she create a team where people begin to know her people? You know, a real generational team, very diverse team. 

And so, I think that there’s going to be expectations on that front. And then there’s already, and you’re seeing it in the news. And I, of course, practice law out in Silicon Valley, so see it even more so, a lot of questions about whether or not some of the kind of progressive folks who have served in the Biden administration that really came out of the kind of Bernie Sanders, Elizabeth Warren wing of the party, will those people continue to be serving and what will that look like? 

So, let’s see. You know, they’re going to be all eyes on the Harris transition in terms of what signaling she gives, not just to the party writ large, but to the business community and others. And so, I think that there is a lot of work to do to really think through those issues. And again, if we were giving advice to our friends and the Harris team, it would be what Rich said, which is keep everything as quiet and under wraps as possible so that you have the space to think about it and to really figure out what to do. 

And then of course, you’ll start making public announcements after the election, but it’s going to be a really critical time 

Valerie Boyd: Based on the sort of enthusiasm and momentum that she’s experienced upon this change. I feel like a lot of people will be excited by your point about generational change and the opportunity to show something new with the people that she surrounds herself with. 

Rich Bagger: I was going to say. I’ve never had the opportunity to work on a same party, the same party transition. The only other transition I worked on was Governor Christie’s transition in New Jersey, which was from a Democratic administration. But I did want to comment that something that’s really valuable that the Partnership for Public Service Center for Presidential Transition® does is it, you know, creates a safe space for people who’ve had leadership roles and transitions from both parties to be available for people working on transitions from both parties. 

So, it takes away like the, the awkwardness of like a Republican transition, reaching out to somebody who’s worked on the Democratic transition to ask for advice or vice versa. And it creates it, it makes it easier for Andy Card to provide, you know, advice to Ann O’Leary. 

And that, I’ve found that to be not only be fascinating personally, but extremely valuable.  

Ann O’Leary: Yeah, I think the best advice I got was from Governor Leavitt from Utah, who had been the head of the Romney transition, and he gave me this great advice that I sadly did not follow, but he said, whatever you do, don’t make and don’t tell anybody your personnel choices. 

Like, you’re going to be really wanting to tell somebody the day before the election that they did not get the job that they want, like, don’t do that because you don’t know what’s going to happen. Well, I’ll admit that we were so confident going into election day that I told one person that they weren’t going to get the job that they wanted. 

And I’m certain that person has never forgiven me. So, I would say that that was very good advice, but I did not follow. 

Valerie Boyd: Well, thank you both for those compliments and you’re both sharing tidbits that I think were not known before, that now Governor Leavitt does know about whether you followed his advice. 

It’s a good story and a good lesson. Rich, even though you didn’t experience an intraparty transition, I might still ask, because you mentioned that the Trump campaign was focused on bringing in people from outside government who had not served in administrations before. 

That seems like it made your job very challenging. Did you feel that you were out looking for new talent across the country?  

Rich Bagger: So, yes, and that’s a, I mean, that’s a good thing, right? Obviously, it’s a good thing to reach out for new talent that sort of represents the country more broadly. And a lot of the ways we did that was through state governments, with the recommendations of governors and state attorney generals and, for, you know, from people outside of Washington, D.C. from around the country. And I think we did that effectively, but also doing the work of a transition requires having people for each department who know how that department works. 

And we had a number of people who had no interest in going back into government, but volunteer their time to provide advice about particular departments and that’s invaluable. And so, for us, it was because we’ve added every person who volunteered on the transition, and we produced lists that were sort of run by the sort of campaign inner circle of everyone who was part of the effort. 

And I would go to Trump Tower in New York City on Monday afternoons and go through these lists and explain why we needed a deputy secretary from the Bush administration or someone else in a Senate-confirmed position in the department from the Bush administration because they actually know how the department works. 

And even if your agenda is to change some things in the department, if you want to be successful in that, you need to know how it works. And we did success to recruit a number of such people, and I’m glad Ann saw them in the elevator.  

Valerie Boyd: Ann, and I didn’t mean to suggest that you were not also looking for new talent across the country. 

I think, I think you said earlier in this conversation, that was a priority for you too.  

Ann O’Leary: Absolutely. Yes. 

Valerie Boyd: So, I must say, I am leaving this conversation feeling incredibly energized just by, I knew I would getting the chance to talk to either of you is a pleasure. Getting the chance to talk to you together is exponentially better because it is reassurance that in these times of a lot of fighting that, behind the scenes, we really are in the hands of good people who are doing dedicated planning on behalf of leaders and teams who are trying to do the right thing.  

So, I am very grateful to hear your lessons. I feel like you’ve shared some things that you learned from the Partnership, but I think you have taken them to the next step and made them even better and sharing your advice with our audience today. 

So are you optimistic that both candidates will be prepared to govern in January? And what gives you hope for a smooth transfer of power?  

Rich Bagger: Well, I think what gives me hope is its importance, its necessity, and that the machinery of government is designed to be successful in this effort. 

The fact that there’s a law that governs this so clearly, the fact that the, you know, executive branch of the federal government has career people who work on this, you know, for at least a year leading up to an election, that there are NGOs like the Partnership for Public Service who are dedicated to the effort, that there is a strong band of us transition nerds who hope to pay it forward by, you know, continue volunteer to offer advice. So, notwithstanding the tumult of the, of the current political environment, I think there’s so many things in place. And so many people who understand how important this is and are dedicated to its success that leaves me hopeful even in the face of headwinds. 

Ann O’Leary: Yeah, that’s a nice way to put it. I think that if I look back on it and I, I got the opportunity to serve as Governor Newsom’s chief of staff when Trump was the president and COVID hit. And so, I was in the unique position of working very closely with the Trump administration and with civil servants of the Trump administration. 

And while there’s a lot of criticism we can all give each other about how one handled COVID, the fact of the matter is that we were working with limited facts on both sides of the aisle. And we found really good people to work with in government to figure out how we got supplies to California, a blue state, how we, you know, dealt with really complicated issues. 

We were actually the state that, when they were repatriating planes of people from China to come back to the U.S., it was a federal government working with the state of California to land those planes. So, I’ve seen government work even in this Trump administration. I think what I would say is that I have entire faith and hope in the Harris administration to run a successful transition. 

I’m holding my breath about Trump and whether he does it or not, and I would say that I would implore anybody in the Republican party who knows of government and who respects government to stand up and volunteer, and I think that’s a very hard thing to do because I think there are many people who, like me, are really, are very concerned about the concerns about Trump. 

The way that Trump conducts himself, what happened on January 6th, his comments about, you know, democracy, his lack of respect for the rule of law, but I think we really need people to step up. I think the fact that we have a really good civil service and hopefully that civil service will stay in place through this era. 

And we also have a military that respects the rule of law and understands how to move forward and we may need that. And so, I think that it’s a very scary time, but I think that there are really good people on both sides of the aisle. And I hope that they will stand up and serve to make sure that we do have an effective transition of government. 

Valerie: Well said. Well, Anne and Rich, thank you both so much for being part of that bipartisan network of experts that are taking your hard-earned experience and wisdom and sharing it with the current candidates and future leaders. I have a feeling that we will be calling on you more often this year.  

Ann O’Leary: Thank you for having us. And nice to see you, Rich. 

Rich Bagger: Great seeing you. 

Valerie Boyd: Thanks very much.