Advice To The 20-Somethings Joining Mamdani’s City Hall

What I Learned About Leadership When I Was Way Too Young to Have It

When I was 29 years old, I was very unexpectedly appointed to become the Deputy Governor of Illinois. Unlike New York City, which has half a dozen deputy mayors, there was just one deputy governor. That meant overseeing the state’s budget, operations, legislation, policy and communications. I was wildly unqualified and I knew it.

I got to Springfield about eight weeks into Rod Blagojevich’s first term. We were facing a $4.2 billion budget deficit (which was massive back in 2003). The cabinet was meeting. The governor was not there (I would soon learn he was almost never there). I was about to walk into the room. I stepped in and jumped back. Holy shit, this was a room full of grownups. Serious people. And I was supposed to tell them — all of them — what to do. I took a breath, walked in as confidently as I could and ran the meeting. And it was fine. They just wanted someone to make decisions and be responsive. I ended up working well with just about everyone there (and the people who weren’t up to the job didn’t stay long).

A lot of very young people will assume positions of real authority in Zohran Mamdani’s City Hall. That has already generated criticism and will continue to. So what? From what I learned firsthand, if you follow these rules, the stories when you leave will be the exact opposite of the criticism you faced when you came in.

(1). Be responsive.

You helped run a great campaign, but campaigns and governing are two very different things. What matters is what you actually do once you’re in the job. You cannot do that alone. This is not a tiny legislative office. This is an entity that employs over 300,000 people. That’s the size of the workforces of CVS or Apple or Lowe’s.

You are as good as the people who work for you or who work in the agencies or areas you oversee. The first way to earn their trust and get their best work is to be responsive. You’re not that busy or that important that you can’t get back to your commissioners, assistant commissioners, your own staff, councilmembers and others in that realm every day. I had a rule that the day was not complete unless every email was dealt with, every text was dealt with, every phone call was returned (or I decided affirmatively not to return or answer it) and the next day’s to-do list was written.

By getting back to people promptly, you save them a lot of time, they feel heard and respected, you know what’s going on, and even when you say no, they’re going to take it a lot better than being ignored. Yes, it’s more work for you and yes, you’re already very busy. I get it. Do it anyway.

(2). Don’t hire people just like you.

I know it’s fun to work with your friends, especially after pulling off this kind of win. And I know you feel strongly about your ideological positions and want like-minded people around you. But this is an operational job. You need people who know how to make sure clean water runs through the tap or the trash gets picked up or that the lights turn from green to red — people who know what to do when things invariably go very wrong.

At the end of the day, you want to use the relatively brief time you have at City Hall to do real things that you care about and feel proud of. Blagojevich was obviously a disaster, but I worked on issues like creating universal health care for kids, universal pre-school for all 3 and 4 year olds, and becoming the first state to tear down all the toll booths and implement open road tolling and so on. None of it would’ve happened without people around me who actually knew how to run things. I could help them come up with ideas and I could help ensure the legislation passed and the funding was appropriated — but they were the ones actually running the programs. Not me.

(3). Be nice to reporters.

Spending the term fighting with reporters doesn’t work (Adams tried it and it failed miserably). Some reporters truly are assholes. Many are really nice. They’re humans. Either way, be responsive.

Be candid. Don’t lie to them — it always comes back to hurt you and you destroy your reputation in the process. Follow the larger comms strategy of the administration, but also build relationships with reporters so when you have a big new policy idea to announce, they want to do you a favor and take it seriously.

Also, one slightly crazy idea. In Illinois, I got rid of all of the agency press offices and combined them into one big, central press office. That allowed us to remove a lot of inept people, gain total control over the messaging, improve the quality and speed of response to reporters and coordinate the message a lot better across multiple agencies. It worked really well.¹

(4). Say no.

As we just saw, corruption is no stranger to New York City government. You might face situations where you are asked to do something illegal or to look the other way. Saying yes is the beginning of the end of your career. You have a conscience. You know right and wrong. And if you know it’s wrong, say no and tell someone about it.

Do not be a good soldier and keep your mouth shut. Do not assume that the political upside for the mayor or his agenda is so great that it’s worth doing something illegal to achieve it (or that anyone will even stand behind you if you get caught). Do not assume that the upside for you — professionally, personally, economically — is ever good enough to risk your career and freedom over.

It’s very uncomfortable to say no to someone more powerful or wealthy than you. I got really lucky that one time that Blagojevich asked me to do something illegal (extort Rahm and Ari Emanuel), I was so offended by the stupidity of the request that I said no and reported it. I then had to testify about it in the grand jury, the trial and the re-trial. It was a miserable experience. But still a lot better than being one of the many people who were indicted.

(5). Do not get captured by the system.

It is so easy to exist in your own bubble and lose perspective on everything else. Bluesky is definitely not reality. It might have mattered a lot — along with TikTok, Instagram, YouTube — in the campaign. And it might be a good way to still reach some of your constituents. But a world based around likes, retweets, etc… is a world destined to fail.

You’re working in the leadership of the most diverse city in the world. You are working in a city that if it were its own country, it would have the eighth largest economy (by GDP). It’s home to many of the world’s biggest and most high profile industries — a city almost everyone on the planet is aware of.

You will probably never have a job like this again. Take full advantage of it. Meet as many people as possible. Talk to people who don’t already agree with you. Learn as much as possible. Travel around the city — don’t get stuck at City Hall or in a handful of neighborhoods you already know. Say yes to more work, more responsibility. Travel around with the mayor on the weekends just to see and do cool stuff. This is a once in a lifetime opportunity. Make the most of it.

Working at City Hall may be the most interesting, impactful and fun job you’ll ever have. Sure, you’re young and inexperienced. In some ways, that naivety is going to help you achieve things you don’t even know you’re not supposed to even try. But also try to know what you don’t know.

Congrats on your new role. You earned it. Now go make something of it.

1. Although you will have to endure a lot of grumbling first.