Jeff Smith: Do as I Say — A Political Advice Column

Today, we proudly present a new feature at The Recovering Politician.  Jeff Smith, one of our most popular contributing RPs will be answering YOUR political advice questions here and at City & State, a very popular Web site that focuses on New York politics.

Please send in your questions for Jeff to, and Jeff might answer them in subsequent columns.

My name is Jeff Smith, and I’m a recovering politician. Oh, I still love politics, and I follow it as closely as ever. But I no longer have a political future; the U.S. Attorney in Missouri’s Eastern District saw to that.

After a 2004 congressional bid in which, as a 29-year-old nobody, I lost narrowly to the scion of Missouri’s leading political dynasty, I figured I was done with politics. But thanks largely to a documentary film about our first campaign I got sucked back in, winning a State Senate seat two years later. I adored the Senate—loved crafting policy, loved helping people, loved the camaraderie with my colleagues.

Then, through an uncanny series of events involving a lie, a car bombing (in which I had no part) and my best friend’s wiretap, I spent 2010 in federal prison.

Along the way I learned about politics, policymaking and people; about friendship, temptation and betrayal. Mine is a hard-won perspective, but one I’m honored to have the opportunity to share with City & State’s readers.

One of the hardest things in politics is knowing whom to trust. That makes discretion critical, since asking a friend for advice can be akin to calling a press conference and broadcasting it.

This column aspires to be the confidant you can trust for an unvarnished opinion: a “Dear Abby” for politicos, if you will. I look forward to answering questions about all things political, and helping readers gain their wisdom more easily (and anonymously) than I did.

I’m running for office, and though I have some volunteers, most come in once, then disappear. I asked my campaign manager why and he said they were all flaky. Do you have any advice?

S.E., Webster Groves, Mo.

Dear S.E.:

First, fire your manager; he sounds flaky. Second, sit down with volunteers when they come in. Ask them why they’re volunteering and what their dream campaign job is. Then—unless their answer involves holding a press conference or sleeping with the candidate—give them a chance to do it. They may have to hit 100 doors before they get to draft a press release, design a mail piece or storyboard a TV ad, but they’ll have a reason other than cold pizza to stay engaged.

Finally, the heart of the problem: Your campaign is no fun. Make your campaign a social event. You’re the candidate; you set the tone. If you’re having fun, they will too—and you’ll attract more fun people. I used to bet my interns/volunteers on anything: One-on-one basketball, who could recruit more supporters while canvassing, which one of them could get somebody’s digits at an event. It’s possible to have a blast and be deadly serious about getting votes at the same time.

I’m a legislator who screwed up. I promised a school superintendent in my district that I’d vote against new charter schools, then told the charter-school advocates that I’d support their bill, which would allow for charter-school expansion. If I seek higher office, the public-school types and teachers’ union could get me primary votes, but the charter-school lobby donates pretty heavy. What should I do?

W.C., St. Louis

Dear W.C.:

In the future, only make promises you can keep. But since it’s too late this time, here’s what you should do. Since you appear to be agnostic about which is the best policy, call some informed constituents without a stake in the matter to feel them out. If there’s any consensus, vote that way. Then, if you must break your word, you have the one semi-acceptable excuse: “I’m sorry. I heard from my constituents and thought hard, and I decided to vote ‘No.’ This was a good lesson; next time I won’t give my word until I understand the issue better.” And tell them well before the vote so they don’t count you as a “Yes.”

Last, before running for higher office, get your views straight so you’re never again making policy calls based purely on personal political considerations. It screams “hack,” and it’s why people distrust pols.

I’m an elected official who recently found out that my female chief of staff had sex with three male interns. I’m not sure whether to talk to her or high-five them—she’s pretty hot. But seriously, should I say anything to her?

D.A., Miami

Dear D.A.:

If your male chief of staff had banged your last three female interns, would you say anything to him? (Hint: Any answer that includes the phrase “high-five” is incorrect.)

I’m running for office and I have nearly $100,000 [worth] of pledges hanging out there. I’ve tried calling people who pledged, but they won’t take my calls. How can I get my money?

S.A., Kansas City, Mo.

Dear S.A.:

Remember, it’s not your money, it’s the donors’ money. Now you’re going to have to help each of your donors keep his word to you.

Here are some possible strategies:

1) The investment approach Email the donor and ask for advice on an issue in which he has expertise. Don’t ask for money. When he replies, thank him graciously. Now he’ll feel invested. Then, a few weeks later, ask him for the money. Remember: If you want advice, ask for money. If you want money, ask for advice.

2) Peer pressure Ask a mutual friend—probably another donor with whom you are close—to invite them to an upcoming funder.

3) The meet-cute If a few pledgers work in the same building, stand in the lobby just before noon punching elevator buttons. Usually you’ll “bump into” them on the way out to lunch. Embarrassed, they’ll likely reiterate their pledge, and later that day, reminded of the embarrassment, they’ll send the money.

4) Creeping Hit their neighborhood while door knocking. Obviously, this is complicated in Manhattan, but feasible in most of New York. You canvass anyway, so why not end each quarter by canvassing pledgers?

5) Cybercreeping Email a link to people who owe pledges and get them to click on it, then follow them around online with Google ads. “Forget to donate to X? We forgive you. It’s not too late…”

I’m a public official who was recently visited by the Feds. I think I’ll be okay, but just in case I’m not…what was prison like?

Name withheld

Dear Name Withheld:

It’s a lot like politics, minus the riffraff. More on that next time.

(Cross-posted, with permission of the author, from


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