By Abigail Abrams
January 12, 2017

As Barack Obama prepares to hand the White House, and the country, over to Donald Trump on Jan. 20, the president’s staff has spent some time looking back at their experience. TIME asked Obama White House staffers what advice they would give to their incoming counterparts about navigating the historic halls of 1600 Pennsylvania Avenue.

From funny memories to life lessons, Obama staffers recalled learning a great deal over the course of their time serving their country. Here are 13 of their best pieces of advice for Team Trump:

  1. You can prepare too much.

    Macon Phillips, former Director of Digital Strategy: We built all of WhiteHouse.gov before Inauguration Day. We built this giant site, and we tried to figure out all the things that we would need and put it out there. Then on day one, we started seeing that some of these sections weren’t interesting at all to people. Avoid over­preparing in terms of content. Put something simple out there, and pay attention to what people care about, and then develop content toward that.

  2. Learn where you’re going.

    Katie Lillie, former Director of Press Advance: My first piece of advice to Trump Admin­istration employees is to take a tour of the White House. So when the press secretary asks you to bring the press to the Map Room, or to meet at the Palm Room door, you actually know where the hell you’re going..

  3. Push for access to information that will help you do your job.

    Tommy Vietor, former National Security Spokesman: Bush’s National Security Council spokesman Gordon Johndroe wisely encouraged me to push for access to meetings about sensitive military or counterterrorism operations, even if there is no plan to ever discuss them publicly. His point was that because of advances in technology, it’s more likely than ever that these operations become public, and you’re far better positioned to manage the story and protect sensitive information if you’re briefed ahead of time. He was right.

  4. It’s probably best to make major announcements after the stock market has closed.

    Dan Pfeiffer, former Senior Adviser to the President: There was a speech that Treasury Secretary Tim Geithner gave rolling out how we were going to deal with the banking crisis that caused our stock markets to sink as it was happening. A split screen of Tim giving his speech, and the Dow tanking, was a vivid real-world lesson. When you work on Capitol Hill, or even in a campaign, and you mess something up in messaging, or rollout, it’s fine. Maybe you have a bad couple of days in the press, maybe your boss yells at you, but you don’t see billions of dollars of wealth disappearing before your eyes on live television. In hindsight, you quickly learn that it actually makes more sense to make those announcements after the market is closed.

  5. It’s okay (and even good) to say no.

    Lisa Brown, former Staff Secretary: You’re in this incredible place, and you want to recognize what an honor and privilege it is to be there. At the same time, you can’t be so cowed by being there that you don’t give your best honest advice. Sometimes as a lawyer, that means effectively saying no. “I really don’t think this is a good idea.” Or, “I really don’t think you should do it that way, but here’s what you can do.” Don’t just be a yes person. That does not serve the office. History has shown this. Ultimately, it does not even serve the individual, but it certainly doesn’t serve the institution.

  6. Help the president do his or her job.

    Rahm Emanuel, former Chief of Staff: The most important thing you can do is tell the President that you’re going to help him do his job. Like, I always used to tell everybody, you can’t go in there and tell him a problem. You better offer him a minimum of two solutions. Your job is not to throw problems at him and see if he can figure out the solution.

  7. But know when to keep problems off the president’s desk.

    Jason Furman, Chairman of the Council of Economic Advisers: There were times in 2009 when we didn’t agree on the technical design of a small-­business-­lending program. Because we couldn’t resolve it ourselves, we brought that disagreement to the President. In retrospect, it’s pretty embarrassing that we were bothering him with details as small as that. Big disagreement on philosophy on how to deal with autos? Bring that to a President. Should you do a 10% or 15% matching rate for your new tax credit for such-and-such? Probably worth figuring that out on your own.

  8. Expect the unexpected.

    Lillie: There are always people all, sort of, lurking in the White House. One day I was rushing to get from the pool spray on the South Lawn for the Easter Egg Roll, to a meeting in the Situation Room about a foreign trip, and there was this group of people who were just walking so slowly on the colonnade. I was just kind of impatiently waiting, and all of a sudden one of them turns around and I realize it’s Justin Bieber. And I thought, Where am I? I just need to get to the Situation Room for my trip call, and Justin Bieber and his entourage are slowing me down. So just always expect the unexpected.

  9. Be culturally sensitive to White House visitors.

    Katie McCormick Lelyveld, former Press Secretary for First Lady Michelle Obama: There are cultural sensitivities that come naturally to the chefs because of their training. So if we’re hosting someone from another country, what are the dietary concerns? What are the celebrated foods? What are the cultural pieces reflected in cuisine that make the visit on the level that the White House should be?

  10. Reach out to people outside your bubble.

    Valerie Jarrett, Senior Adviser to the President: Spend more time outside of Washington. There’s just no substitute for not just interacting with the American people, as we do here every day, but meeting them where they are. Not only is it helpful to inform our policies, but it also just is a great reminder of the grit, and determination, and resilience of the American people.

  11. Especially reach out to people outside of Washington.

    Brian Deese, Senior Adviser to the President: You have to make a very conscious effort to reach out, to talk and interact with and communicate with people outside of the bubble that you are entering. The intensity is so high that you can easily go for weeks or months without real meaningful contact outside. That puts you in a position where you won’t do your job as well. It can also put you in a position where you are sacrificing relationships and people that matter in a way that you’re burning the candle down to the end.

  12. Your behavior always reflects on your administration.

    Lillie: What I always tell my advance staffers is that a lot of times you are the closest someone will ever get to the President. Your behavior and what you do could wind up on the front page of the New York Times. It reflects on him and on this Administration, at every point. Whether you’re at a bar in Washington, D.C., or overseas. You also still need to have fun and live your life, but I think it’s important to remember that you can’t ever turn that off.

    Vietor: It’s not just that people might recognize you. It’s that D.C. is filled with people who will actively try to hurt you, so be mindful of talking about work in public. You will inevitably be overheard.

  13. Be authentic.

    Melissa Winter, Deputy Chief of Staff and Senior Adviser to the First Lady: Do what you like. Do what you love. Do what’s interesting to you, because I think folks know what is inauthentic.

Macon Phillips, former Director of Digital Strategy: We built all of WhiteHouse.gov before Inauguration Day. We built this giant site, and we tried to figure out all the things that we would need and put it out there. Then on day one, we started seeing that some of these sections weren’t interesting at all to people. Avoid over­preparing in terms of content. Put something simple out there, and pay attention to what people care about, and then develop content toward that.

Katie Lillie, former Director of Press Advance: My first piece of advice to Trump Admin­istration employees is to take a tour of the White House. So when the press secretary asks you to bring the press to the Map Room, or to meet at the Palm Room door, you actually know where the hell you’re going..

Tommy Vietor, former National Security Spokesman: Bush’s National Security Council spokesman Gordon Johndroe wisely encouraged me to push for access to meetings about sensitive military or counterterrorism operations, even if there is no plan to ever discuss them publicly. His point was that because of advances in technology, it’s more likely than ever that these operations become public, and you’re far better positioned to manage the story and protect sensitive information if you’re briefed ahead of time. He was right.

Dan Pfeiffer, former Senior Adviser to the President: There was a speech that Treasury Secretary Tim Geithner gave rolling out how we were going to deal with the banking crisis that caused our stock markets to sink as it was happening. A split screen of Tim giving his speech, and the Dow tanking, was a vivid real-world lesson. When you work on Capitol Hill, or even in a campaign, and you mess something up in messaging, or rollout, it’s fine. Maybe you have a bad couple of days in the press, maybe your boss yells at you, but you don’t see billions of dollars of wealth disappearing before your eyes on live television. In hindsight, you quickly learn that it actually makes more sense to make those announcements after the market is closed.

Lisa Brown, former Staff Secretary: You’re in this incredible place, and you want to recognize what an honor and privilege it is to be there. At the same time, you can’t be so cowed by being there that you don’t give your best honest advice. Sometimes as a lawyer, that means effectively saying no. “I really don’t think this is a good idea.” Or, “I really don’t think you should do it that way, but here’s what you can do.” Don’t just be a yes person. That does not serve the office. History has shown this. Ultimately, it does not even serve the individual, but it certainly doesn’t serve the institution.

Rahm Emanuel, former Chief of Staff: The most important thing you can do is tell the President that you’re going to help him do his job. Like, I always used to tell everybody, you can’t go in there and tell him a problem. You better offer him a minimum of two solutions. Your job is not to throw problems at him and see if he can figure out the solution.

Jason Furman, Chairman of the Council of Economic Advisers: There were times in 2009 when we didn’t agree on the technical design of a small-­business-­lending program. Because we couldn’t resolve it ourselves, we brought that disagreement to the President. In retrospect, it’s pretty embarrassing that we were bothering him with details as small as that. Big disagreement on philosophy on how to deal with autos? Bring that to a President. Should you do a 10% or 15% matching rate for your new tax credit for such-and-such? Probably worth figuring that out on your own.

Lillie: There are always people all, sort of, lurking in the White House. One day I was rushing to get from the pool spray on the South Lawn for the Easter Egg Roll, to a meeting in the Situation Room about a foreign trip, and there was this group of people who were just walking so slowly on the colonnade. I was just kind of impatiently waiting, and all of a sudden one of them turns around and I realize it’s Justin Bieber. And I thought, Where am I? I just need to get to the Situation Room for my trip call, and Justin Bieber and his entourage are slowing me down. So just always expect the unexpected.

Katie McCormick Lelyveld, former Press Secretary for First Lady Michelle Obama: There are cultural sensitivities that come naturally to the chefs because of their training. So if we’re hosting someone from another country, what are the dietary concerns? What are the celebrated foods? What are the cultural pieces reflected in cuisine that make the visit on the level that the White House should be?

Valerie Jarrett, Senior Adviser to the President: Spend more time outside of Washington. There’s just no substitute for not just interacting with the American people, as we do here every day, but meeting them where they are. Not only is it helpful to inform our policies, but it also just is a great reminder of the grit, and determination, and resilience of the American people.

Brian Deese, Senior Adviser to the President: You have to make a very conscious effort to reach out, to talk and interact with and communicate with people outside of the bubble that you are entering. The intensity is so high that you can easily go for weeks or months without real meaningful contact outside. That puts you in a position where you won’t do your job as well. It can also put you in a position where you are sacrificing relationships and people that matter in a way that you’re burning the candle down to the end.

Lillie: What I always tell my advance staffers is that a lot of times you are the closest someone will ever get to the President. Your behavior and what you do could wind up on the front page of the New York Times. It reflects on him and on this Administration, at every point. Whether you’re at a bar in Washington, D.C., or overseas. You also still need to have fun and live your life, but I think it’s important to remember that you can’t ever turn that off.

Vietor: It’s not just that people might recognize you. It’s that D.C. is filled with people who will actively try to hurt you, so be mindful of talking about work in public. You will inevitably be overheard.

Melissa Winter, Deputy Chief of Staff and Senior Adviser to the First Lady: Do what you like. Do what you love. Do what’s interesting to you, because I think folks know what is inauthentic.

To read more words of advice from Obama’s White House team to Donald Trump’s incoming advisers, see the full story here, or pick up a copy of the latest issue of TIME.

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