No Squirrels!

Lessons Learned as a Campaign Field Organizer

Jordan Phillips
18 min readDec 4, 2016

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I left my job as a product manager in San Francisco and became a field organizer for the Hillary Clinton campaign from September 2016 through the election. I was responsible for three-and-a-bit rural counties in the Michigan Thumb.

Here are the lessons I’m taking away from the experience.

Two bits of preface:

First, this is not a political post. My politics are obvious, I’m exhausted repeating them, and I want to participate in some conversation besides “Let’s all freak out about Trump.” I don’t have anything to add there.

Second, this is not a campaign post-mortem. I’m not an expert on anything more than the the stuff that was in front of my nose this election. Hillary Clinton won the popular vote by a wide margin and lost the relevant battleground states by slim margins. My honest, loosely-informed opinion is that we lost because of a perfect storm, so changing almost anything might have changed the outcome — or might not have.

Rather, I’m reflecting on what I got out of the choice to jump on the campaign, preserving it for my own future reference, and sharing it with folks who might be interested in the same.

What is a Field Organizer?

The core function of the field organizers on a campaign is to build a volunteer corps to achieve two objectives: (1) register new voters and (2) get supporters to vote.

Two out of three ain’t bad.

An organizer accomplishes that job by plugging into existing social and civil society groups and by making lots and lots of phone calls to lists of likely supporters to recruit volunteers.

A campaign is, as one of my colleagues was fond of putting it, basically a pyramid scheme: you recruit your first volunteers yourself, and then get their help to recruit the next wave of volunteers, and then get their help to recruit the next wave of volunteers, and so on, until you have a large enough corps of volunteers to make a difference in achieving your two goals. As a result, starting early and carefully tending to your volunteer base is essential to scaling up a team.

The daily routine of organizing is a grind. The key question is always, “What can I do right now that will get me the most votes on Election Day?” Because of the exponential growth effect, the correct answer is almost always volunteer recruitment, the vast majority of which happens by phone. In six weeks, I made about 5000 phone calls personally, and even that was below my goal.

Lessons About Campaigns

Political parties are not monoliths. There’s much less of a singular “The Democratic Party” than I had thought. Instead, there’s a hodgepodge of officials, candidates, campaigns, and national, state, and local organizations. They have some shared interests and some competing interests. Then there’s the constellation of labor unions and PACs and everything else, which are even more mysterious to me. The power relationships are complex and only occasionally hierarchical. There’s very little telling anyone else what to do. It’s held together by good will and (mostly) shared interests.

Legally, I was employed by the Michigan Democratic Party — most of the staff you see in ground game are state party employees rather than actual national campaign staff. But in most senses, organizers like me thought of ourselves as working for Hillary Clinton.

It’s all just people like us. The candidates and staff on campaigns are hard-working and intelligent people with good intentions. But I had implicitly assumed there was something more than that, that those people were somehow intrinsically a cut above little people like me. I’ve had a similar assumption a few times in my professional life, and I’ve always gone through a similar process of disillusionment. Behind every curtain, it’s always been more regular (albeit talented and dedicated) folks.

The people who win elections and run countries don’t have a secret sauce more special than experience and a willingness to do the work. Don’t let thinking otherwise hold you back.

The backbone of campaigns is women over age 50. They’re the ones who most consistently show up and do the work.

Some of the wonderful people of the Sanilac and Huron County Democratic Parties. Photo credit to a volunteer whose name I didn’t note.

Political campaigning has its own micro-celebrities that no one else cares about. Say “Steph” to a basketball fan or “Travis” to someone in startup tech, and they’ll immediately know who you’re talking about and have an opinion about them. There exists a class of people who have the same devotion to campaign staff.

“You heard they’re sending Jim to Florida?
“That makes sense. I think we all remember what he pulled off in Minnesota.”
“Maybe, but he’s no Melissa.”
“Can you imagine what Melissa and Jim together on a campaign would be like? I’d pay good money to see that!”

I’m making up the names and places (I’m not someone who cares about this stuff), but some of my colleagues got very excited about the campaign gossip. It took me a while before I realized that they weren’t talking about people they knew personally; they were talking about senior figures in the Democratic firmament.

You could probably make a little money selling trading cards of senior advisers to low-level campaign staff.

Presidential campaigns are big weird pop-up corporations. Thousands of people were on payroll in some capacity, in at least a dozen departments across fifty states. There’s HR, training, marketing, IT, and everything else. At least at the organizer level, roles are built to be easy to slot someone into, most especially because time is so precious that staff need to get up and running fast. To compensate for the constant sprint and brief tenure of employees, there’s a lot more “process” than one might expect an organization with high-skilled workers to have.

Despite the specialization — just like the mess hall cooks in a Heinlein novel — everyone fights. In the final days, the HR guy grabs his clipboard and heads into the field to knocks on doors just like everybody else.

Election predictions are the enemy. Clinton was consistently the 80% or more favorite for winning Michigan according to FiveThirtyEight, Upshot, and others. If every prospective volunteer who’d said, “Nate Silver says you’re going to win, you don’t need my help” had actually come in and done the work, it would have grown our volunteer corps by maybe 10%. Ten percent more canvassers could have made a margin-flipping difference.

Lessons About Communication

Subvert expectations to get through resistance. In every cold call I made, as soon as I said “and I’m with the Clinton campaign,” the expectation became that I was asking for money. I could feel my counterpart’s defenses going up through the phone line. They were cursing themselves for picking up an unfamiliar number and bracing themselves for the predictable request for cash as the only way to forestall the apocalypse.

I quickly learned how important it was to break away from the script they were expecting if I was going to get through to people. When I was just starting out, it was a blunt “I’m calling from the Clinton campaign; I’m not asking for money.” Over time, it got more sophisticated. I’d ask how they were doing — I’ve never heard a fundraiser do that. I’d throw in a joke. I’d emphasize that I was local, mentioning the weather or how I’d driven through their town recently to show I was actually in their area. The more I did to distance myself from the interaction they were expecting to have, the more likely I was to get a real conversation that could lead to results.

Don’t be a jerk on the phone. Whether it’s a campaign volunteer or a customer service rep for the cable company, the person you’re talking to on the phone has little to no influence over whatever might be upsetting you. Being rude or throwing snark won’t change that.

These are nice people who do not deserve to be treated poorly.

The worst confrontational experience I was aware of anyone having during the campaign was not politically motivated — it was about phone etiquette. Someone raged at one of our wonderful volunteers over the phone one night, calling her a “cunt” and driving her to tears, all because she had dared to call his phone during the same evening that some other Democrat-aligned organization had also called him. I guess we were supposed to feel intimidated by his machismo, such that we’d call an urgent summit of every Democrat with a phone to make sure we never bothered him again. That didn’t happen.

Our phone lines are not special sacred kingdoms where we hold court. Telephony is a public communications protocol. Don’t be a jerk about it.

When you mean No, say No. A tour of duty as an organizer is a crash-course in the full range of human excuses. “I’d love to help, but…” I’m busy. I’m old. I’m young. I work. I’m retired. I’ve got a health thing. I take care of my grandkids. That’s a long drive from my place. By my third day on the job, I’d gone from sympathy for the struggles of all these people to realizing most of them had to be untrue, by virtue of either being totally imaginary or wildly overstated. No doubt, we’ve all got our struggles. But that’s the thing — we’ve all got our struggles, and yet we all figure out our ways to move through the world anyway.

After the Comey fiasco, when polls were tight and I feared the race might not go our way, I found myself absolutely furious at these people. We had an important and urgent mission to accomplish, and I was still getting evasive answers. Some excuses were obviously contrived; many more were impossible to evaluate. But in any case, I was spending lots of time negotiating with people, trying to find a work-around to their excuse so that I could get their help, because that negotiation paid off just-barely-often-enough to justify pushing as opposed to hanging up. I would have much rather heard the following than another lame excuse:

“No, I don’t want to help.”
“Are you sure I can’t get you in here for an hour or two in the coming weeks?”
“No, it’s not something I care about.”
“All right, sorry to hear that. You have my number if you change your mind.”

It’s worse than a “Yes,” but at least I could write someone off and focus my efforts elsewhere. “I’d like to, but…” is about making ourselves feel less bad about our choices, and that’s a waste of the other party’s time.

About 15% of people will pick up a phone call from an unfamiliar local number. Local numbers do better than out-of-state numbers.

The second-hottest place in hell is reserved for those who have trick voicemail greetings.

You know the ones I mean.

“Hello! [pause] Sorry, who’s this? [pause] Oh, I can’t hear you. What was that? [pause] Just kidding! You got my voicemail, leave a message!”

It’s really not as cute as you think it is.

Alexander Macomb, Jr., hero of the War of 1812 who went on to become Commanding General of the United States Army, is the namesake of Macomb County. He has no time for misleading voicemail greetings.

Lessons About Commitment

We care about things to the extent we’ll act in service of them. I no longer understand what “I care a lot about X, but I won’t do anything” means. I’m sure I’ve used that line myself many times before. I now think it’s a nonsensical thing to say.

I care about the environment enough to throw waste in the trash bin, recycle most of the time, buy the occasional carbon offset, and generally accept modest inconveniences for the sake of being green. I do not care enough about the environment to give up eating cows or flying on airplanes, despite knowing both of these things are indisputably bad for the planet.

Registering voters at the Mount Clemens Columbus Day Parade.

Of course, there’s an accounting for means. A poor person who gives $20 to a charity gets a lot more “caring credit” than a rich person who gives the same amount. But in all but the most extenuating circumstances, if you can’t make a two-hour hole in your calendar over two months to help out on a campaign, you probably just don’t care about it very much.

And that’s fine — there are lots of worthy things that we each won’t act in service of. But the time we spend feigning care and coming up with excuses is a ritual to console ourselves that wastes the resources of the people doing the work. Defensive self-pity and excuse-making are material drains on the very cause we purport to care about.

Feelings don’t matter. Being right doesn’t matter. All that matters is doing the work.

It feels good to go to the mat for something you care about. As upset as I am about this outcome, I’d be much more upset if I’d had this opportunity to do something and I’d let it let pass me by. I couldn’t do it all the time — it’s unhealthy and unsustainable on all kinds of levels — but every once in a while you’ve got to go all-in standing by your values.

The hottest place in hell is reserved for those who ghost. Plans are made and resources allocated assuming you will do what you say you will. Don’t say yes because it’s what you think someone wants to hear if you won’t follow through. It’s not being nice; it’s just a different flavor of being selfish.

My maximum sustained output is about 72 hours per week. I can push past it for a burst here and there, but six 12-hour days each week is the most I can maintain. I was struck that even on a project I cared deeply for, I really needed those last two or three hours each day to unwind and put my brain on something besides work.

We worked seven days a week, but that was only doable because housing was provided and the duration was short enough that I could get by without doing any life maintenance tasks.

Lessons About Work

Important work is often not glamorous. One of the most valuable thing a volunteer could do for us was call 200 phone numbers and discover that half of them are disconnected. Why? Because she just doubled the efficiency of the next volunteer when he comes in and calls the live numbers from that list.

There’s nothing fun or sexy in calling numbers from an old voter file and discovering which half are disconnected. It’s an unambiguous drag. But it’s work that matters, and people who step up and do the boring ugly work are amazing.

Important, boring work.

As a corollary, making people feel good about doing un-glamorous work is an invaluable skill. One of my colleagues stands out in my mind for being incredible at this. She could welcome people, connect with them about their personal story, keep up their morale through a long boring shift, convince them at the end that what they’d just done was valuable, and then book them to come back and do the same thing next week. It’s a core skill of an effective organizer — and, I suspect, of an effective boss in a more conventional workplace. These people had plenty of options for how else they could spend their time, but they spent it with us, doing something objectively unpleasant.

The candidate got the volunteer in the door the first time, but it takes an effective organizer supporting and nurturing the volunteer to get them to come back.

No squirrels. I learned this campaign mantra as soon as I arrived. In the Pixar film Up, the dog Dug is easily distracted whenever he sees a squirrel. Campaigns are full of distractions that suck attention but do nothing to advance the cause. FiveThirtyEight’s new forecast is a squirrel. Talking about how much Donald Trump sucks is a squirrel. Even pretty big things like the Comey fiasco are mostly puffed up squirrels. Before and after any bit of news, what we had to do remained the same: Reach and activate every volunteer and voter we possibly can. Everything that takes us away from doing that is setting us behind.

As I slide back into life in the tech industry, I’m struck by how dominated by squirrels it is. Why should it matter to me who bought whom, or who is investing in whom, or what some minor tech celebrity said at the latest conference? Does any of this news affect the core game plan of delivering products and experiences customers want?

If it doesn’t help you do what you set out to do better, it’s a squirrel. Tune it out.

Big things are little things stacked on top of each other. The voting margin in the deciding states this year was measured in handfuls of votes per precinct. It was just two votes per precinct in Michigan and eight votes per precinct in Wisconsin. Influencing 11,000 more voters is hard. Influencing two more voters in a single neighborhood and then doing it again 5500 more times is a totally achievable matter of efficiency, best practices, and putting in the work.

Little things, stacked on top of each other.

Good tools matter. Some of the tools we had were great. Some were really lacking. In an information-management-driven project, the difference in output that between a worker with good software and a worker with middling software is a big deal. Don’t cut corners on tooling.

People want to feel that they contributed. Volunteers do (and should) feel a sense of ownership in campaigns. As a result, they’ll often contact organizers to offer advice. I had a volunteer, whom I’ll pseudonymously call Fatima, who called me every few days to share her most recent idea for the campaign:

“I think you should get Bernie Sanders to come here. People would really connect with him.”
“Is the campaign spending enough on radio? I heard Trump ads but no Clinton ads on the radio this morning.”
“I hear a lot about the Twitter. Does the campaign do enough Twitter?”

My favorite came from another volunteer: “I think Hillary looks best in white. You should tell her to wear more white.”

In my role, I had no influence on any of the above. Indeed, I was far less likely to meet the candidate than a random civilian (organizers have to work all day, we can’t take time off to go to candidate events!). But folks like Fatima wanted to know that their emotional and intellectual engagement was valued. It was frustrating at first to get these requests that I could do nothing about, but I came to see them as a sign of the investment people felt in the campaign. The job isn’t to quash that impulse; it’s to tap the enthusiasm underneath it and direct it toward something productive. “That’s a good thought, I’ll pass that along. Now, when can I get you back in here to help us knock some doors?”

The related lesson that I need to remember, given my own tendencies, is that in most circumstances showing up and saying, “What’s the plan? How can I help?” is a lot more useful than showing up with ideas on how to do everything better.

People want to feel comforted. Starting after FBI Director Comey’s bogus letter about emails from the Wiener investigation, volunteers started calling organizers to express their fears. “Do you think this is real? What will they do next? Can we still win? What does our internal polling say?” I had no inside information — all I knew came from the same public sources everyone else used, and I had been trying hard to tune out election news anyway so I could focus on the work.

My answer then was the same as it is now as people wonder about the next election: “All that matters is doing the work.” But on election night, when there was nothing left to do and people became more and more anxious about the outcome, all we could do was worry together and tell our volunteers that life would go on and things will get better.

When things get bad, acknowledge the bad, do what you can to be productive, and remember that life goes on.

Weak links are really expensive. Everyone has their highs and lows. But when someone on the team is consistently underperforming or bringing a bad attitude to work, it’s not just a question of the value of their output weighed against the price of their paycheck. The negativity they bring and the resentment their underperformance can create in others can be really costly and contagious.

Put another way, ten solid people plus one flake is worse than ten solid people. Making a painful choice now is probably better than accepting the extended drain of keeping them around.

Make time for fun together. It’s tempting to treat an important undertaking as demanding 100% focus from the team all the time. But that leads to burn out and festering animosities. My team took a late-night trip to a famous haunted house a couple weeks before the election, and experiencing something besides work with my colleagues improved our morale, empathy, and ability to communicate with each other. (Re)discovering that you’re all likable, well-rounded people is a worthy use of a few hours, even when time is a dwindling commodity.

The closest I’ve come to elected office: I was a write-in candidate in an uncontested county surveyor race in a remote corner of America. I didn’t win.

Other Stuff

I’m really looking forward to having a female president. While I understood why it energized some folks, I was pretty ambivalent about Clinton’s gender until late in the campaign. I think it was the debates that converted me: Hillary outmaneuvered Trump in a way I think few men could have managed. All the ugliest parts of conventional masculinity were on full display in this year’s election, and I’ve had enough of it. Among comparably qualified candidates, I’d earnestly prefer to see a woman as President for a while. I’m eager to see what she’d do differently.

Everyone lives in a bubble, and that screws up our thinking. Coming from San Francisco, of course I knew as an intellectual fact that I hail from a particularly mono-color political enclave. But spending the election season in red-leaning battleground turf drove home just how far removed my experience is from Purple and Red America’s experience.

My local McDonald’s restaurant had a large memorial to stock car racer Dale Earnhardt in the dining room. As far as I can tell, he had no particular connection to the area.

The divide isn’t just political. We watch different media, use different apps, eat different foods, enjoy different leisure activities, have different life plans, and so on. We point this out a lot on the Left as part of our routine self-flagellation. And we deserve some of that self-flagellation; Lefties do need to get in touch with middle America. But just as urgently, folks on the Right should spend some time in deep Blue turf and discover how we really live and why we like living in the ways we do. Watching some TV shows set in New York doesn’t count as understanding the other half .

They’re all “Real America.” But there are many places where we’re so far apart, and where our mental shortcuts have so commandeered our thinking, that we’re not really part of the same community anymore.

I’m reminded of my host family in Michigan. They’re gracious, intelligent, warm people who generously shared their home with a stranger, and they’re Democratic activists to boot. But one of my first reactions to meeting them was driven by the baggage I had brought from my culture bubble. The teenage son in the family had a taxidermied deer head mounted on his wall, which he proudly explained came from a hunting trip with his grandfather. By plenty of measures, that implies a heart-warming story of intergenerational family bonding, dedication, hard work, and so on. But my visceral internal reaction was, I don’t like guns, I’m uncomfortable.

My generally anti-gun attitudes are well-considered and sincerely held; I earnestly think gun ownership should be more closely regulated and that most people should choose not to have firearms. Living with nice folks who enjoy sport-shooting for a while did not turn my basic policy preference on its head. But I realized that in my social community at home, I know no one whose lifestyle provides a counterpoint. Without that counterpoint, it’s seductively easy for a legitimate but moderated disagreement to turn into calcified and reflexive opposition. I brought baggage that said “There’s something normatively bad about living this way,” and that’s a lazy and counter-productive way to think. I would take someone on the Right to task for making a similar judgment; I shouldn’t let myself off easy.

That’s What I’ve Got

I was only on the campaign for six weeks and change, but they were weeks intense and hard-fought, and they gave me a lot. I am grateful for the experience, the relationships built, and the reinvigoration of my conscience.

If the call comes, I don’t know if I’ll be able to say “yes” to going full-time again next cycle, but I might be persuaded: There’s a lot we need to do. Whatever your politics, when your conscience is nagging you and the opportunity presents itself to step-up, I hope you’ll do what you can.

After all, as President Kennedy observed, “Things don’t just happen, they are made to happen.”

An outsized bust of John F. Kennedy stands outside the Macomb County courthouse in Mount Clemens, Michigan.

Except as noted, all photos are by the author.

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Jordan Phillips

Lawful good positivist. Product manager. Tokyo, San Francisco, and occasionally Shanghai. If today I made the world an ounce less annoying, it was a good day.