Memo 3: So, you want to be a Supervisor
The Burton machine when choosing which ambitious neophyte candidate to back, would usually decide on a single factor: “Which one will knock doors in the rain?”.
If you obsessively follow San Francisco political news or Twitter, you could be susceptible to incorrect notions about what it takes to win a Supervisor race. As volunteer who racked up 1,500 live voter conversations in a single district told me, “The ‘experts’ on Twitter don’t understand my district.” The San Francisco Chronicle’s poll, conducted via online survey, was of 802 likely voters across 11 districts. It was a solid poll. But having 1,000s of human conversations with residents in your district will make you a much deeper expert in what citizens want and who they will choose.
This is an important, underappreciated implication—those investing in Independent Expenditures, advising candidates, and debating San Francisco politics on the Internet are not grounded in the same understanding and conviction that comes from having 1,000s of live conversations with district voters. The truth is in the field.
For example, there was a belief this cycle that the overriding issue for voters would be public safety. Given the polling, a compelling case by campaign strategists was made to this effect. But in reality, the campaigns built overridingly on Public Safety—Marjan Philhour, Trevor Chandler, Matt Buscetto—lost, and Danny Sauter, Bilal Mahmood, and Myrna Melgar, who included urbanist issues such as housing and transportation, and were more nuanced on crime and safety won. It’s not practical to reduce races down to simple assumptions such as ‘public safety trumps everything.’
Relatedly, one wish I have for the next cycle is that moderate funders worry more about capital allocation than the political strategy of the races. Moderates should have picked up D11 and D1, but we were outspent badly. It is inexcusable that only 5-10% of the ~$40M spent this cycle by moderates went towards Supervisor races—about $25M went to the Mayoral race. If we repeat this pattern, the moderate faction will undoubtedly lose a governing majority for a lack of basic planning. When Aaron Peskin, after losing his Mayoral bid promises to put his energies behind removing the Moderate faction from power, we should take him seriously.
Another fallacy people on the Internet fall prey to is the assumption that if voters disagree with you on a single high-salience issue, they won’t vote for you. District 7 voted against Ocean Beach Park (Prop K) but re-elected Myrna Melgar, a co-sponsor of Prop K, by 11pts. Voters contain multitudes; they vote more on the basis of affinity and trust of a leader, than by specific policy issues. “I may not agree with you on everything, but I trust you to do the job well.” is a common and quite rational voter sentiment.
So, what do voters really care about? As Supervisor-elect Jackie Fielder summed it up:
“[P]eople want potholes filled. They want repavements done on time. They want extra trash cans that were, for some reason, taken away. It’s this bread-and-butter politics that I think gets lost. That was really a fresh perspective for me to hear. If we’re not addressing those rudimentary expectations of city services, [voters] deserve an explanation as to why.”
Knock 500 doors a day X 7-days a week X 7-months
Winning a Supervisor campaign is pretty brutal. The races are the epitome of retail politics. The real race starts a year before you announce your campaign. It takes a year to lock in endorsements, understand the concerns of your district from community leaders, and line up donors. If you wait to do that when the campaigns are announced, it will be too late. You can try to learn on the job while campaigning, but you will more than likely lose.
It took Danny Sauter the better part of six years of grinding nearly 7 days a week. If you speak with winning Supervisors, they will almost uniformly insist the deciding factor in winning or losing their race came down to how many doors they knocked, e.g., how many families living in their district they visited personally. Comms and advertising in their district certainly matter, but personal interactions carry the most weight, and given the size of the district (10-20k voters), it’s actually possible to interact with a decent number of them. In a Supervisor race, the candidate—selling their ability to govern—is the product, and the paid and social media campaign is the marketing.
This is why the Burton machine when choosing which ambitious neophyte to back, would usually decide on a single factor: “Which one will knock doors in the rain?”. It turns out that the best candidates love knocking doors in the rain because (a) more people stay inside at home when it’s raining and (b) they are often impressed to see you out there working this hard to get their vote, and are much more likely to invite you inside. The best candidates pray for rain.
There are about 30,000 to 40,000 homes per district; ideally, your campaign hits them at least 3x. So you and your team are knocking on an average of 500 doors daily if you work 7 days a week over a 7-month campaign. Winning candidates get very comfortable with these numbers and reduce their campaign to a daily/weekly/monthly burn-down of fieldwork, knowing that if they put in this work, they have a path to victory. “Nobody will outwork me.” is the mindset of a winning Supervisor.
What about other standard campaign activities like events, community meetings, etc.? Senator Scott Wiener was District 8 Supervisor from 2011 to 2016 and has advised dozens of hopefuls, including Joel Engardio, Matt Dorsey, and Danny Sauter. This is what he told me:
“When I ran for supervisor, both the Democratic Party and Labor Council supported a different candidate. I personally knocked on 15,000 doors, and at some point, I stopped attending events in order to single-mindedly focus on door-knocking.
I wasn’t supposed to win the race — there was too much stacked against me — but I did, handily. When I evaluate how Supervisor candidates are doing now, I look at their shoes. I wore out the soles on two pair of shoes during my Supervisor race. That seems like a decent benchmark — are you destroying at least two pair of shoes?
Organizing your way to a victory is possible because the numbers that decide these races just aren’t that big: in 2022, Joel beat Gordon Mar by 500 votes, and in 2020, Dean Preston beat Vallie Brown by 170 votes, and Connie Chan beat Marjan Philhour by 134 votes.
But you must do all of this fieldwork while simultaneously engaging in the proverbial ‘knife fight in a phone booth’ that’s been typical of San Francisco political campaigns. And you will still probably lose. Bilal lost his Assembly race, Danny, like Michael Lai, lost his first Supervisor race, and Joel lost three times before coming back in grand style, being the first to defeat an incumbent since modern district elections.
But then, one day, the election is over, and you suddenly win—and you become ‘the dog that caught the bus.’
Being a Supervisor
Why would you want to be a Supervisor? With benefits, you get paid a little over $170,000 or about $34 an hour if you work the 100-hour weeks required to do the job well.
The answer is Power.
Proportional to 1/11th of San Francisco Government, you control or influence a budget of $1.45B, a city workforce of 3,100+, and the rules that govern a district GDP of $23B, 100 miles of streets, 300 acres of parkland, and the land-use rules that govern a built environment of 10,000+ homes and commercial buildings in your district.
With a board majority, you write the ordinances (laws) that govern the City and County of San Francisco. Failing a majority, you can stuff an ordinance on the ballot with just three other votes, and with six votes, you can put a charter amendment on the ballot to change the city’s constitution.
The Board has a high degree of influence over key commissions that hire/fire department heads, including the San Francisco Police Commission and the SFMTA and PUC, which manage the city's streets, transportation, water, sewer, and power services.
The Board has a bully pulpit which they can use to shape the public agenda; press releases, press conferences, and op-eds to focus and frame public attention towards their policy goals. When the public and advocates are keyed in on the right thing, their pressure forces change.
The Board also has the power of oversight. They can hold hearings to ask probing questions of department heads about what is or is not happening within the City government. Supervisors make clear that if changes do not occur, there will be repercussions in future budget negotiations and ordinances.
The job also comes with material prestige: Willie Brown, Dianne Feinstein, Gavin Newsom, and Mayor London Breed all came up as city Supervisors.
Then there is the less obvious stuff. Much of the power a Supervisor wields has been hidden from view.
Supervisor’s hidden power over building housing
A Supervisor’s power over the built environment underwent an easy-to-miss but substantial curtailment when Senator Scott Wiener and the YIMBY coalition passed SB-423, ushering in a new era of ministerial or “by-right” housing approvals. Until SB-423, a local supervisor often had a veto over any new housing built in their district.
How this worked in practice is interesting; the Board has had a norm of ‘deference’ where Supervisors would band together in a majority vote to back each other on housing approvals in one another’s district, no matter the merits. This norm resulted in an amazing amount of power wielded by Supervisors over building approvals in their district, as they could look a builder in the eye and say, “you are not building this building unless I am on board.” The supervisor would then broker exactions for the builder that would satisfy their constituents. Some argue persuasively that this power over building in their district was the most significant share of the overall political power a Supervisor wielded.
This power is being taken away, which is no small thing. SB-423 creates a ‘by-right’ or ‘ministerial’ housing approval process for market-rate housing, which means that if a builder follows all of the rules, they can just go build their housing ‘by right.’ And there is nothing Supervisor, the Building Trades Union, or NIMBYs can do to stop them:
“But, under state laws meant to streamline housing approvals and take away neighbors’ ability to block or delay projects, none among the city planners, commissioners, and members of the Board of Supervisors have any power to reject the project or force the developer to change it.”
Why can you be confident SB-423 will lead to ‘cranes in the sky?’ SB-423 simply extends the by-right process SB-35 has already established in San Francisco, which has been used to build over 2,000 deed-restricted houses in San Francisco. YIMBYs expect upwards of 80% of market rate homes will be built via this streamlined process, as it becomes the defacto route to build new homes in San Francisco.
Supervisor’s hidden power over San Francisco Municipal Transportation Agency (SFMTA)
The ways by which Supervisorial politics drives SFMTA decision-making are also interesting and quite hidden. For example, the Board of Supervisors controls via the SFCTA much of the capital budget expenditures of SFMTA.
When we pass funding bonds—put on the ballot by the board—we often empower the SFCTA to disburse the money. This forces SFMTA staff to spend a ton of internal time making grant proposals to themselves, which are approved or rejected by the SFCTA, which in turn is controlled by the Board of Supervisors.
This is one of the main mechanisms by which a Supervisor can leverage SFMTA to get what they want. This dysfunction will become material as SFMTA grapples with a budget deficit threatening San Francisco's basic transportation infrastructure.
Constituent services are the taproot of Supervisorial power
With all of this talk of power, you may not realize that a Supervisor will personally spend about half of their time on the in-district blocking and tackling of ‘constituent services.’
What are constituent services? Well, if there is a fire in your district at 2 AM, you get a call from the closest Fire Station, and then you head over to where the fire is. That pothole or parking spot on that person who helped you get elected’s street needs your attention; you’re on that. Some industrious supervisorial offices have 311 route all relevant issues to their inbox so they can help ensure the required minor and medium-sized wheels of the San Francisco Government spin into action for their constituents.
Navigating the bureaucracy of the San Francisco Government for constituents is highly valuable. Things that make you great at constituent services:
Being on friendly terms with the sub-sub department heads who can deal with removing a downed tree, trash or litter, homeless encampments, etc.
Being in constant contact with the local precinct police chief
Being seen as a constructive, level-headed Supervisor by bureaucratic leaders v.s. vindictive, mean, and performative.
If you are an effective Supervisor, your staff and your systems are taking care of most of this blocking and tackling, freeing you up for the bigger tickets—being a peacemaker of sorts for the major, divisive issues that may crop up in your district.
The city wants to put a Navigation center in your district—you have to land that plane.
The rezoning is stirring up lots of strong feelings—you’re going to be in the middle of that.
A family of four is killed waiting for a bus—you help broker street safety improvements.
A great supervisor is proactive and brings the right civic leaders to the table to resolve the stickiest questions of government in their district. They help wrangle San Francisco Government to avoid blunders and implement solutions most effectively. They do this because they care more than anyone else about tangible outcomes by the Government of San Francisco for their constituents, which is, after all, why they won the election.
Quiz time: Who is known as the ablest, hardest working, and most effective Supervisor at constituent service?
Answer: Aaron Peskin. He’s a total workhorse, knows the San Francisco Government better than anyone, and intimately understands his hard and soft power and how to wield it. D3 is also known as the most complex district in the city with Downtown, Ports, Fisherman Warf, tourism, Chinatown, North Beach, etc.
Residents have myriad issues with the Government, and Supervisors who are good at constituent services are very responsive and effective at helping get them resolved. These constituent interactions are one of the main incumbent advantages you have as a Supervisor. As citizens of your district you help have a positive interaction with you, and their affinity with you increases, and so does the chance that they will be there for you in your next election. If you are bad at constituent services, civic leaders in your district who are used to good constituent service will become grumpy with you, which can spell deep trouble in the next election.
Constituent services are a lot of work, but they are the simplest part of the job. What about the work of Governing San Francisco?
Governing San Francisco
Here is a practical tip from someone who would know on how to set up your Supervisor's office: specialize.
You pull the levers of the San Francisco Government with a staff of four. Collectively, Supervisors and their teams constitute roughly one tenth of one percent of the workforce of San Francisoco Government.
So high-functioning Boards of Supervisors have to work like a team. It’s the only practical way to govern effectively. For the team to work, Supervisors must trust one another's political and policy judgment. They push one another. And they, as individual legislators, specialize.
Fentanyl is tough, but if you did dig in with your staff and made it your overwhelming priority for several years, you absolutely could change outcomes at scale.
In a high-functioning board:
One of the Supervisors would become the domain expert in fentanyl.
Another would tackle Technology Procurement and Implementation.
Another would dig in on public safety and disorder, and another on Homelessness and Mental Health.
Etc
Each would become close not just with the Department Heads but with the Sub Department Heads. They would dedicate one of their four key staff to a single issue for years. They would help Department leaders manage their commission. They would interface with the State Legislature and even help with federal agencies. They would be operators, traversing the complexity of government, to steer the ships of agencies towards an outcome deliberately, carefully, and forcefully over time.
In an ideal world, there is so much trust between the team of Supervisors that they defer to one another in their subject matter. So, everyone is pushing in unison behind a shared vision.
Obviously, this is not how we’ve been governing San Francisco for the past two decades. Instead, we have had divisive factionalism, grandstanding, performativeness, a press corps that is generally unable or unwilling to explain the mechanics of governing—journalism that does not distinguish between a press release and a meaningful government action—and with much reform energy sucked into broadly uninformed food fights on the Twitter.
But, when the voters voted for change, teamwork is what they had in mind. Coming together to push for clarity, accountability, and outcomes are the requirements for great government.
San Francisco is home to so many world experts. It is the global nexus of the AI and Software revolution and the crown jewel of our dynamic American economy. Voters are demanding this potential energy of our prosperity and knowledge be translated by capable government leaders into the kinetic force required to power the machinery of our municipal government in the 21st century.
40 days until Inauguration Day
This is where things need to head, but it’s not where things stand right now, 40 days until January 8th, inauguration day. Races have been decided, and the lucky elected dogs who caught the bus must learn the basics, which are extensive, complicated, and mostly undocumented. The Board President is being decided, along with its committee assignments. Core mayoral staff are being assembled.
Meanwhile, a calendar of city-shaping decisions looms in early 2025: a gigantic budget deficit, SFMTA funding crisis, and a once-in-a-generation rezoning. In the San Francisco Government, “what you want to make happen” is distinct from “what will happen to you.” It can be overwhelming for those who know the worn-out, cantankerous machine of our municipal government well. Anyone new to the job should be suitably intimidated.
You are also swimming against a tide of broken incentives we, the voters, are complicit in. An ambitious supervisor with an eye on higher office knows they must distinguish themselves from their colleagues by building a press profile. The press we have in San Francisco loves covering a food fight and is generally uninterested in covering substance it considers mundane: repaving schedules, budget mechanics, city contracts, etc.
This incentive—editors chasing social media attention—produces a stream of clickbait articles that divide voters and stall progress in the place of journalism that educates citizens and civic leaders, enabling them to solve public problems. As city hall veteran explained to me:
“The best way to get attention is to spend less time on the nuts and bolts stuff and instead focus on the things that draw attention. If everyone works together nicely, that will get a great editorial from the Chronicle that no one will read.
After Mayor Breed's first year in office, a reporter asked me what I thought her major accomplishments were, and I started by saying, well, she delivered a balanced budget with a Board of Supervisors that was aligned against her without any real drama or fighting. The response was, yeah, sure, but she's supposed to do that. So, what were the real wins?Muni was not a factor in the most recent election because it's mostly running on time and well. We could barely get anyone to cover it. But street projects were because there's controversy and attention there.”
The most essential thing for us to get right—the best way to help—is to dispel incorrect notions. Chief among them is that now that campaigns are won, the hard part is done, and everything in the San Francisco Government will get better quickly. That is naive.
The moderate faction has had the balance of power to govern San Francisco for the past 20 years. When the city budget quadrupled, the outcomes were uneven at best. Elections have consequences, but politics is 10-20% of the work required to govern successfully. To remain incurious and unhelpful in the strenuous job of governing is to abdicate. If we abdicate this time, do not expect better results.
Delighted to see you tackling this crucial work. Thank you!