Otis White

The skills and strategies of civic leadership

The Art of the Ask

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There are probably many reasons to be fascinated by John F. Kennedy’s life and brief time in the White House. Here’s mine: I’ve long wondered how this one-time high-society party boy ever got to be such a good politician.

Chris Matthews, the TV commentator, may have finally answered my question. In his book, “Jack Kennedy: Elusive Hero,” Matthews said World War II changed Kennedy by placing him in charge of men not at all like him, mechanics and farmers, factory workers and truck drivers, Southerners and Midwesterners. That taught him empathy, which is a key to leadership. And somewhere along the line, Kennedy picked up a second skill: He learned how to ask people to do things.

This came in handy when Kennedy ran for office, and, Matthews writes, “realized that the key to forging loyalty within his (campaign) organization was the invitation itself. The mere act of asking someone to become a Kennedy person was the step that mattered.”

You may never run for public office, and if you do you may not need the political skills of John F. Kennedy. But asking people to do things—and getting them to do them—is a skill every civic leader and government manager needs to master, now more than ever.

Why? Because big urban problems can’t be solved by organizations acting alone; they can only be solved by collaborations. And collaborations—which are, after all, joint efforts by interests not compelled to work together—don’t come about on their own. They exist because someone brought the participants together. Simply stated, somebody made “the ask” and did so successfully.

So what’s an effective ask? It has three parts. First is finding the right person to ask. Second is asking the right way, so the person accepts the task. And third is asking again—the “second ask.”

If there’s an art to asking, it’s in that first part. That’s because finding the right person is a mixture of strategy, knowledge, and judgment. You have to know the objective (the task the collaboration will undertake), the organizations or interests that can best contribute to the objective, and the right person to work with inside those organizations and interests. (Hint: It may not be the person whose name is first on the letterhead.)

Then there’s the ask itself. Here again, it’s a mixture, usually including an appeal to altruism (imagine the good we can do) and self-interest (here’s what’s in it for you and your organization). But it has to go beyond artful phrasing because few will say yes to likely failure. So you have to show that you have a roadmap to success. That might mean facilitating meetings and offering other resources; at the very least it means deciding the number of meetings and what each will address.

And that brings us to the final part, the second ask, and back to JFK. Kennedy didn’t ask people to do things once. He asked them again and again. That’s how he built the intense loyalty that characterized his campaigns and his presidency.

There’s a bit of psychology here: When people say yes to an ask, no matter how little you’ve asked of them, they’ve investing in you. If the task is successful, your value rises in their eyes. By asking a second (or third or fourth) time, you are deepening your value . . . and building support. There’s also a bit of economics: You’ll spend much less time finding and asking people to join you a second or third time, so there is what economists might call a marginal efficiency in the second ask.

These benefits accumulate over time. But the first step, as JFK might remind us, is to ask—and ask well.

A version of this posting appeared on the Governing website.

Photo by Andreas Klinke Johannsen licensed under Creative Commons.

Civic Work and the Importance of Relationships

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In early 2008, New York Mayor Michael Bloomberg made an all-out effort to deal with his city’s traffic problems by proposing that the city charge drivers who entered the most congested areas. Mayors don’t have that kind of authority, so he asked the New York State Legislature to give it to him. Over a week’s time, Bloomberg turned on the charm, with dinners for legislators at the mayor’s residence, a team of lobbyists working in Albany, and elaborate presentations showing lawmakers how their districts would be affected by the changes.

Didn’t work. Legislators barely considered Bloomberg’s proposal, and some seemed to enjoy snubbing the mayor. Why? One reason was the hurry-up nature of Bloomberg request; legislators thought the mayor was being disrespectful by asking for a quick vote. But another reason was Bloomberg himself. As one legislator, generally considered a friend of the mayor’s, told the New York Times, “All politics is relationships, and if he hasn’t built the relationships over time, he can’t suddenly create those relationships with 48 hours to go in the process. It just shows that six and a half years into his term, the mayor just does not know how to approach the legislature.”

Ouch. And, yet, unquestionably true—both about Bloomberg, who clearly isn’t comfortable rubbing elbows with politicians, and politics in general. All politics are relationships, but then again so are most human endeavors. And nowhere is that more true than in civic work, as I’ll explain shortly.

But, first, a word about relationships in general. It goes almost without saying that we need other people to have productive and meaningful lives, but we sometimes don’t appreciate how much. Here’s a hint: Academics who’ve studied natural disasters, like hurricanes along the Gulf Coast, earthquakes in Italy, and tsunamis in Asia, have found that the people most likely to survive and later restore their lives are those with the greatest number of relationships. Partly it’s because they have support systems that others don’t, and in times of great trauma, being surrounded by those who care about you makes you want to go on. But it’s not just psychological, researchers have learned; the well-connected have access to a storehouse of knowledge about getting things done. One researcher who had studied a tsunami’s aftermath in India explained it this way: “Those individuals who had been more involved in local festivals, funerals, and weddings, those were the individuals who were tied into the community. They knew who to go to, they knew how to find someone who could help them get aid.”

And it’s not just during disasters. Researchers who’ve studied corporate CEOs have consistently found that those promoted from within companies do better, on average, than those hired from outside. This isn’t true in every case, of course, but it’s true in the aggregate: Those hired from within last longer in their jobs than those recruited from other companies. There are many explanations for this, but one that researchers point to again and again is that home-grown executives know from day one how the company really works—what academics call “private knowledge” (unlike information you could get about the company from looking at its financial statements and organizational charts or looking things up on Google). And private knowledge—about how decisions are made, who is reliable, where and why initiatives have failed in the past—can be decisive in a CEO’s career.

Or in a civic leader’s career. Why is it so important to have a big and diverse network in civic work? Two reasons:

  • Power and resources are diffuse in cities. You can’t make major changes in cities by having one or two people, or even a small group, say yes; you have to get large groups to agree. The only way to do that is by knowing the decision makers well enough to win their commitments at the right time. And that takes long-established relationships. (Are you listening, Mayor Bloomberg?)
  • Communities are incredibly diverse: economically, politically, religiously, ethnically, in educational attainment, in years spent in the community, and on and on. As a result, you have to work harder at building relationships in communities than in companies or most other human activities, for the simple reason that the people whose help you’ll need won’t always run in your circles. The first task of community relationship building, then, is to consciously seek out people who aren’t like you.

But on the other side of these obstacles is a big reward for those who overcome them: Because communities are so diverse and power so diffuse, there’s a great deal of private knowledge in cities—basically, information about getting things done that isn’t widely known. The result is that the person with the best relationships—deep in trust and broad in diversity—is the one best positioned to accomplish things. If a project is stalled, she’ll know how to get it back on track. If a crisis blows up, she’ll know the critical constituencies who’ll need to be reassured and how to do it. If there’s financing problem in an important project, she’ll know those most likely to step in with resources.

This leads us to the next big question: If relationships are so important to civic work and the benefits so great, how do you form them? How do you meet people and turn acquaintances into friends? And once you’ve deepened your relationships, how do you use them to benefit your civic work and the city?

Sociologists who’ve studied the connections between people say there are four things that strengthen relationships: the time people spend together, their sense of identification with one another, the trust that’s formed between the two (especially how free they feel in sharing confidences), and how they reciprocate, which is an academic’s way of saying trading favors.

When you look at this list, you can see how things work pretty much in that order: First, people spend time together, then they see things in the other person they identify with (even if, on the surface, the other person seems different), they begin confiding in one another, and finally they help each other out. By the time you get to that final stage, trading favors, you have a deep relationship.

As a side note, don’t let the term “trading favors” turn you off. It’s one of the oldest and most beneficial human instincts. If someone helped you move from a dorm room to an apartment in college, and you later helped him move, you’ve traded favors. If you swapped turns driving the carpool to soccer practice, you’ve traded favors. If a civic leader helped you raise money for your project and you did the same for hers, you’ve traded favors. Trading favors becomes a bad thing only when it involves trading things you don’t actually own, such as government resources.

Still, I haven’t actually answered the question. It’s important to understand the stages of relationships, but knowing them doesn’t explain how to move through them. Here’s where civic work becomes the answer to its own problem: You do it through volunteering. It’s the best way—maybe the only sure way—of meeting large numbers of people and working alongside them. Want to know who’s reliable? Work on a Habitat for Humanity project. Want to know who’s wise? Serve on a nonprofit board. Want to know who truly knows their parts of the community? Raise money with them.

And this brings us, finally, to the reasons for the relationships. For friendship, sure. To be a more civically engaged and culturally aware person, of course. But the reason you set out to build those civic relationships was to get things done in your community. And for that you have to ask people to do things: to serve on a committee, donate money, or turn out their friends for an important event.

I understand why some are reluctant to ask; they fear it makes them seem pushy. In fact, just the opposite. It makes you look like a leader. Rather than thinking less of you, people will think more of you when you ask for their help. And when they agree, they’ve invested in your success. And that may be the ultimate stage of a relationship.

Chris Matthews, the television commentator, wrote not long ago that this was something John F. Kennedy learned early in his political career: You have to ask. Matthews says it’s what has been missing from President Obama’s administration. Yes, he raised enormous hopes (and donations) among his followers in 2008. But once in office Obama didn’t ask them to do anything other than cheer for him. (Unlike, say, the Tea Party, which has continuously asked its followers to do things in opposition to President Obama.) “There are certain basics to becoming a leader,” Matthews wrote in an essay for Time magazine. “The first is asking people to follow you. Kennedy asked. Obama used people to get elected.” Matthews supports Obama, but, he adds, “He needs to start asking.”

So do you. If you want to create loyalty, which is the deepest level of relationship you can have in public or private life, you need to ask people to do things for you. But first, be prepared to spend time with people who aren’t much like you. And be quick to help them with their projects.

Photo by United Way of Greater St. Louis licensed under Creative Commons.

Why You Should Learn to Think like a Politician

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In his engrossing new biography of John F. Kennedy, Chris Matthews tells us that, in 1958, after he won re-election to the U.S. Senate and was preparing to run for president, Kennedy dropped by Congressman Tip O’Neill’s office. He wasn’t there to talk about public policy; he wanted to know from the congressman’s political aide, Tommy Mullen, precisely how neighborhoods in O’Neill’s Boston district had voted.

Together, Kennedy and Mullen went over the vote totals from Irish, Italian, and Jewish neighborhoods, precinct by precinct. Years later, O’Neill was still amazed by the sight of the future president and his own aide combing through the numbers. “I’d never seen anybody study the voting patterns of ethnic and religious groups in a systematic way before,” O’Neill told Matthews, “and I don’t think that most people realized then, or appreciate now, that Jack Kennedy was a very sophisticated student of politics.”

The key word is “student,” because Kennedy wasn’t a natural politician the way that, say, Bill Clinton was. Before running for office in 1946, Kennedy’s social world was pretty much confined to Harvard, Palm Beach, Hyannis Port, and London. He knew little of working class Boston and, surprisingly, not much about Irish Americans. He also knew next to nothing about how people got elected to office. So he set about learning by visiting local politicians and asking their advice.

Along the way, Kennedy wrote what he heard in a notebook. Here are some of the things he jotted down:

  • “In politics, you don’t have friends, you have confederates.”
  • “You can buy brains but you can’t buy loyalty.”
  • “One day they feed you honey, the next (you) will find fish caught in your throat.”
  • “The best politician is the man who does not think too much of the political consequences of his every act.”

Of all of the things that made John Kennedy a compelling figure, perhaps the least appreciated was his devotion to the craft of politics, something that became, in Matthews’ words, “an essential part of him.”

What does this have to do with cities and leadership? Just this: As we’ve grown in recent decades in our knowledge of urban economies, street-level planning, city design, the value of diversity, government finance and management, we’ve lost an essential leadership skill—the craft of city politics. Put another way, we now have a great storehouse of what ought to be done, but less and less knowledge of how to do it.

We’ve tried to fill in for that missing knowledge with citizen engagement, by asking citizens what they want, and how they’d like it delivered. (I know. I’ve been part of a number of citizen-engagement projects.) But while engaging citizens is helpful, it’s not enough. That’s because, at the end of the day, we still need someone—elected officials, mostly—to put together specific initiatives, explain these proposals to the public, sell the initiatives to other decision makers, work through the details with bureaucrats, make compromises, get the initiatives enacted, and oversee their implementation. You can use any term you want, but I’m pretty sure that JFK would have called this “politics.”

I’ll offer some ideas about dealing with our political knowledge deficit, but let me begin with two caveats. First, city government is not the same as a city. Cities are complex human environments made up of many dynamic parts, from economics and demographics to technology and culture. And cities are themselves nodes in much larger environments—regional, national, and global.

But if local government isn’t the sum of a city, it is surely the most influential part. That’s because only government has the mandate, platform, and most easily mobilized resources for addressing the issues facing a community. Think of government, then, as the rudder of the ship and some of the sails. And politics? That’s how we decide who gets to be helmsman . . . along with a good portion of the crew.

My second caveat is that politics is about two things. First, it’s about electoral politics, which is what brought Jack Kennedy to Tip O’Neill’s office in 1958. In other words, how people get elected. But second, politics is about legislation, which is how groups of elected officials, government regulators, and other decision makers come to consensus (or don’t) about what to do.

Everyone who wants to be a serious civic leader at the neighborhood, city, or regional levels needs to know both kinds of politics: How people get elected, and how government decisions are made. And not in a textbook way. You need to know how your current mayor ran for office, how she put together a winning coalition, and who was part of the coalition. And you need to know how your city’s most important ordinances were crafted, who was part of the discussions, and how the proposals changed as they moved through the process.

Why is this knowledge important? Because you need to be involved in picking the right helmsman to steer your city. And if you’re going to serve on the crew—along with people from government—you better know how they work so you can do your part.

But how can you learn about the two kinds of politics in your city? First, you can learn it as JFK did, by visiting politicians and asking them. (You’ll be surprised by how candid they’ll be if they trust you.) Second, you can hope for more media attention to the craft of politics. This probably won’t come from the traditional media but it might from new media, such as civic websites, podcasts, or even some alternative weekly newspapers.

Finally, you can create your own discussions. I have some experience with this. For a number of years, I moderated a panel of mayors for the annual International Downtown Association conference called “Everything You Ever Wanted to Know about Politics But Were Afraid to Ask Your Mayor.” We got together three or four mayors from around the country and let downtown executives ask them difficult questions.

My favorite came from a woman in Iowa who said, “Our new mayor ran on a platform of putting our organization out of business. How should we deal with that?” I was amazed by how candid the mayors were, offering advice for dealing with politicians, advancing ideas, talking with the public, and a hundred other practical tips on politics. They were so candid that I worried a little about how it might affect their careers. (I’m happy to report that, of the 20 or so mayors who appeared on my panels over the years, two are now governors, one is a U.S. senator, and several are still mayors. To my knowledge, no one suffered from participating.)

Every civic organization could do something like this—put together panels that teach politics to people who don’t want to run for office but want to be effective in their communities. And let me make a distinction here. This is not the same as candidate forums at election time or issue forums at other times. These forums are more like seminars in practical politics, where three or four elected officials talk about how politics really works—and civic leaders learn how they can work better with their elected officials. (If your current political leaders are too cautious, invite some former politicians.)

And it’s not just civic leaders who need to know how politics work. So do people who work in city halls, many of whom are surprisingly uninformed about their mayor and city council. Every college planning department and government management school ought to have seminars with politicians who explain how they got elected and how they put together legislation. And every government professional organization (yes, I’m talking about you, American Planning Association) needs to offer refresher courses at its annual conferences.

Finally, it would be a good idea if politicians talked more about politics among themselves. The thing I noticed about the mayors on my panels was how attentive they were to each other’s stories and advice; it was as if they were taking notes. This kind of peer learning is important because, if we had better politicians, we’d have better cities. And it’s particularly needed on the legislative side of politics because it’s hard to get big things done in communities. Many well-intended politicians aim too high and fail—or too low and accomplish little. Get the politicians together, let them talk about what worked and what didn’t, and they’ll improve each other’s winning percentages—and that of their cities.

John Kennedy would have understood the value of peer learning. For all his eloquence and glamour, JFK was a cautious politician who left little to chance. If someone said he’d vote with Kennedy on a major bill, JFK wanted to be absolutely sure he could depend on it. Apparently, this was something he had learned early in his career from talking with Boston politicians. Something about being fed honey but winding up with a fish in your throat.

About Otis White

Otis White is president of Civic Strategies, Inc., a collaborative and strategic planning firm for local governments and civic organizations. He has written about cities and their leaders for more than 30 years. For more information about Otis and his work, please visit www.civic-strategies.com.

The Great Project

Otis White's multimedia book, "The Great Project," is available on Apple iTunes for reading on an iPad. The book is about how a single civic project changed a city and offers important lessons for civic leaders considering their own "great projects" . . . and for students in college planning and political science programs.

For more information about the book, please visit the iTunes Great Project page.

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