Today I'm speaking with Karen Dunn.

Karen is one of the United States top trial lawyers and debate prep specialists for the presidential and vice presidential debates.

She's a litigating partner at Paul Weiss in New York, one of the country's most prestigious law firms.

Karen is widely recognized for her courtroom victories and is primarily known for being highly skilled at crisis management.

Her clients vary from companies, high profile individuals, and executives.

Karen went to Brown University and Yale Law School.

She then went to Washington as a judicial clerk for Judge Merrick Garland and Supreme Court Justice Stephen Breyer.

After her clerkships, Karen worked in the Obama White House as associate counsel to the president.

Karen has been the go-to person for debate prep for several leading Democrats.

She has prepared President Barack Obama, Hillary Clinton, Vice President Kamala Harris for presidential and vice presidential debates.

In private practice at Paul Weiss, Karen has been leading trial counsel for some of America's leading companies such as Apple, Uber, Amazon, and Oracle.

Karen, thank you so much for being here.

Thanks for having me.

So your mother was a lawyer and legal counsel at a public company when really very few women held such positions.

What made you want to follow her in her footsteps?

Actually, originally I decided that I didn't want to follow her because I had worked for a summer during high school at her law firm and I just thought it was really boring because my job at the law firm in the summer was very boring.

And so I just decided I was never going to be a lawyer.

And then later in life, I realized actually being a lawyer is very interesting and you get to think about interesting issues and help people solve problems.

And that was very appealing to me.

So sad to say I did not actually intend to follow my mother's footsteps, but as we all do, ultimately we turn into our mothers.

It's so true.

You turned out to be great at practicing law.

You've had many professional achievements, one of which is that you were a clerk for Judge Merrick Garland, which is an extremely coveted position.

You clerked for him when he was a U.S.

Circuit Judge for the D.C.

Judge Garland to be Attorney General.

What was your time like clerking for Judge Garland?

Well, so I love clerking for Judge Garland and I remain close to him.

He is not just a fantastic judge, but a wonderful person and a wonderful, wonderful mentor.

He has a group of former clerks who are very loyal to him and very close to each other.

And I think he really trained us to be some of the best memories of the clerkship are, you know, he had a standing desk in his office and his office overlooked the Capitol building.

So the standing desk was right at the window and you would stand him right next to him.

And he would go over every word of a draft opinion and every punctuation mark to make sure that they were exactly right and exactly what he wanted to convey.

And he really taught us not just about how to ask the important questions and think big thoughts, but also to pay an incredible amount of attention to the details and to make sure that we got everything right.

Was that something you didn't expect?

You know, I didn't know what to expect.

I mean, when you go into a clerkship with a judge, you generally don't know them beforehand.

You know, you've heard about them.

So I did have professors in law school who told me that the judge and I would become, you know, great friends and that it would be, you know, incredible learning experience to clerk for him.

And it was, but, you know, I going in, you know, as a recent law school graduate, you don't really know what to expect.

I can imagine that.

So one of the other things that you've achieved is that you have become the go-to person for presidential debate preparations.

You've led the vice presidential and presidential debate prep for figures such as president Barack Obama, vice-president Kamala Harris, Hillary Clinton.

And in an article with Politico, which I have right here, you and your partner Ron Klain were named two of the most experienced debate prep specialists in democratic politics.

Now, a presidential debate preparation is something that's quite far removed from the lives of, you know, normal people.

How do you prepare a presidential candidate for a debate like that?

I mean, it's possible that we're the leading people because nobody else wants to do it.

It's, you know, I think debate prep is sort of a niche activity.

It is very multidisciplinary.

And by that, I mean, you have to understand the substance of the entire range of policy issues that could come up at a debate.

You also have to understand communications because ultimately you're helping a candidate get out there and speak to an incredibly large audience.

Debates get the second largest audience to the Super Bowl.

So it's usually somewhere between 60 and 90 million people, which is an And you also have to know how to run a really excellent professional process to get the person prepared to ultimately stand on the stage, which involves working with the debate commission.

It involves working with other advisors.

It involves working with the campaign.

So I do view it as a pretty holistic experience and pretty intense for a period of about six weeks to two months in September and October of an election year.

And what are three essential things that a successful presidential debate preparation should include?

Well, first and most importantly is practice.

So the way that we prepare for debates is we have mock debates.

And the point of the mock debate is so the candidate gets used to being in the format, since most people don't run around in their general life, including presidential candidates debating in that kind of format.

And so you have someone play the moderator and you have somebody play the opponent.

And those people have a really important responsibility, which is they have to really be accurate predictors of what the real moderator and the real opponent are going to do and say.

So I would say the first lesson is practice, practice, practice.

The second lesson really has to do with your mindset and your demeanor.

So I really think some large portion of success at a debate is your demeanor and the mindset with which you walk on the stage, because you can be saying all the right substance, but if you're not communicating through your attitude and your presence that you are confident and capable enough to be president, then people won't feel that you are.

So I think that's also very important.

So I would say practice, demeanor, and then I think general preparation and the ability to predict what's to happen in the moment is also very important.

Okay, so those three things.

And what advice would you give to listeners at home that they could implement into debates of their own?

Do you mean if you're going to host your own home debate?

Right.

So let's say a father and daughter having a debate around the kitchen table or two friends with opposing views, what tips or advice would you give to them so they can streamline their debates?

Well, I think it's very important to listen to what the other person is saying.

And this is also a lesson that a lot of lawyers learn in, for example, in cross-examination at trial and taking depositions is you really have to listen to what the other person is saying, because that will help you understand how you're going to win.

One person just isn't listening or isn't hearing what the other person has to say.

But a debate is really different than a conversation across a kitchen table for one very important reason, which is you're not in a debate at your kitchen table.

Sometimes you're trying to persuade the other person, but in a presidential debate, you're trying to persuade the audience at home, the voters.

And it's very different to try to persuade one-on-one a person than trying to persuade people who aren't in the room with you and who are at home watching the whole thing happen.

That's a different exercise.

Of course, they're completely different animals.

So one of the people you worked with intensively over the past few years, and I mentioned this before, is Hillary Clinton.

Yes.

And I'm sure she learned a lot from you, but what are some of the things that you learned from working with Hillary Clinton?

Well, I learned an immense amount from Hillary.

I worked for her for quite some time.

And she, as has been widely reported, really has an extremely loyal group of former staff who were not just close to her, but also really close to each other and very supportive of one another.

And I think Hillary, I saw many occasions, but the occasion that comes to mind more than any others is in the aftermath of the attacks on 9-11, when she was the senator from New York.

And I just saw true, genuine, and organic leadership in how she acted.

I remember actually on the day of the attacks, the senators felt it was very important to return to the Capitol to demonstrate that the business of our democracy goes on.

And I remember being there with Senator Clinton at the time, and watching all the other senators really circle around her and gravitate towards her.

She had been the first lady, she was a senator from New York, and everybody wanted to hear what she had to say and what she thought should happen.

And it was just a moment of true, organic leadership that we don't see all the time.

So that answer actually ties into another question I wanted to ask you, which is that you've been around the world's most powerful leaders, entrepreneurs, business owners, politicians.

Is there one characteristic or quality that all these people have in common?

I think one quality they have is confidence and a belief in their own vision and in themselves.

And I think you need to have that in order to go out and lead other people.

I think another quality that all of these people have that who I've worked with is really this capacity to listen to what people are saying to them.

And sometimes it's important to listen to your advisors, who might have a different viewpoint than you do.

And sometimes it's important to listen to the public, to your constituents, to voters, and hear what's really on their mind.

And the people who I've seen be most successful are the people who really get energy and joy out of interacting with other people and hearing what they have to say and empathizing with them.

That's something I really admire in the public figures that I've gotten to work with and for.

Interesting.

So in the article with Politico, which I referenced earlier, you mentioned that one of the things that litigation and presidential debate preparation have in common is persuasion.

Now, I was wondering, how much of your work would you say is persuasion?

Well, so I am, as a litigator, an incredible amount of my own work is persuasion, both through writing and through oral advocacy.

And sometimes you're persuading your own colleagues to look at something the way that you look at it.

Sometimes you're persuading a court, a judge, or a jury.

And I think I've always been a real lover of language and how to put words together in a way that will resonate with people who you might not have anything in common with.

And that's certainly the case when I go to talk to a jury, who are people from different backgrounds.

You have to really figure out, what am I going to say that somebody will find important or interesting or memorable?

So I think a lot about that.

But so hearing that, I wonder, would you be able to effectively persuade the opposition if you weren't quite sure that your client had the better argument?

Well, I don't know.

I mean, maybe this is you just get Stockholm syndrome, but I like to think cases I'm working on, we always have the better argument.

And I do think part of it is, you have to really believe in what you're talking about.

You have to believe in what you're trying to get other people to believe in.

And I do think people can sometimes tell if you don't genuinely believe in what you're saying.

I think sometimes that comes across.

So I saw some interviews online where you talk about the Charlottesville trial.

And that definitely sounds like something that you are very passionate about and you feel very strongly about.

Can you tell us something about that trial?

So well, so for some background, along with another lawyer, we brought a lawsuit against the white supremacists and neo-Nazis responsible for the violence in Charlottesville, Virginia in 2017.

And our case goes to trial this October, begins October 25th.

And what we've alleged in this case is that the violence in Charlottesville was not an accident.

It was meticulously planned and premeditated and carried out in a way that obviously ended in the death of Heather Heyer, but also the injuries of many other people, some of whom are the people who we represent in our lawsuit.

And so I do feel very strongly about it.

I don't think planning to do racially motivated violence and then executing on that violence is something that's permitted by the laws of our country.

And I think it will be very important for us to go before a jury in the Western District of Virginia and hopefully get a jury verdict that this is not acceptable.

I hope so too.

Last question already.

What advice would you give to the next generation of women entrepreneurs and women leaders?

Mainly I'm just say, go for it.

I mean, I'm so excited to see the next generation of women entrepreneurs and leaders.

I think, you know, there are more women in leadership positions in business and in government now than there ever were, which is still not enough.

And I, you know, I think the more the better, frankly.

And, you know, I just have been, I've been really happy because at this point I'm old enough that some of the people I worked with in the government are now running for office or they've been elected to office or they're in very, you know, high appointed positions in the government.

And it's just so fantastic to see that happen.

And so I, you know, the main thing is I just want, you know, people to feel that they can do it, you know, because it's the hardest thing to do to decide to put yourself out there.

But the more people do it, the better it is for everybody.

So the main message is have confidence.

Yes, have confidence, be bold and, you know, and know that you're supporting all of us.

I mean, we, you know, I think we're, we all feel supported when women run for office and women in the boardroom and women CEOs and people who will put themselves out there.

I think it's, you know, it's not easy and sometimes very hard, but I think the benefit is it's, you know, it's supporting other women now and frankly, all the ones who come next.

On that note, thank you so much, Karen, for being a guest today.

Thank you for having me.

I love this.

It was really great to do it.

Thank you.