The Audacity to Review

The Audacity to Win: The Inside Story and Lessons of Barack Obama’s Historic Victory The Audacity to Win: The Inside Story and Lessons of Barack Obama’s Historic Victory by David Plouffe

My rating: 3 of 5 stars

I am coming up this summer on 18 years experience in my chosen career profession — starting humbly by inventorying cabinets of RS-232 cables and BNC connectors and all kinds of leftover watchamacallits from my employer’s years of government contracting — to today where I do, um, er, I do, well, “computing things”

You know, I have the hardest time describing what I do. I say that I do “systems administration” and “software development” and “project management” or sometimes “cat herding” — but all of those are 10,000ft views of my job.

It gets even worse when I try to tell people what I know. One of my colleagues asked recently “How did you know that?” — and about the best I could say was well, “I just knew”. Sure, I could rattle off a whole list of technologies, but I’d forget to list more than I’d remember to list — and for anyone outside my profession — and likely for most of the people in my profession, it would sound like some mishmash of buzzword bingo. I’m a problem solver. I’m good at it, as you would hope to be after 18 years in multiple computing platforms and roles and tens of thousands of little computing problems, tens of thousands of little failures and hopefully a few successes day in and day out that burn in neural pathways so that you just know.

I get the feeling that David Plouffe is a bit in the the same boat. The man clearly just knows how to run a campaign. He helped engineer the successful presidential campaign of Barack Obama — where words like “breathtaking” “amazing” “historical” even themselves can’t capture the event. I’m not sure that it’s all that possible to use hyperbole to describe the win. No matter your politics — even those with crazy conspiratorial theories — could really counter just how much of an watershed event that win was, particularly as a “professional” endeavor.

With that win, Plouffe has likely cemented his place in the history books as one of the best, perhaps the best, campaign managers ever. The environment conditions were right for an Obama win, and David just knew how to build and manage an organization that worked within those conditions. But he has the hardest time telling you how.

The Audacity To Win does highlight some of the tactics used in the campaign, and it provides some mention of the strategy — but with a few exceptions — it all feels incredibly generic. I guess I was expecting more details, more stories, more insight into the day to day decision making. It all feels like a 10,000ft view “We met our metrics, our supporters got nervous, we stuck to our guns, we laughed, we cried, we won.”

I’m being a bit hyperbolic — the book is better and more detailed than that — but most of the time it feels like that. You just know that David is the best at what he does, but you don’t get enough information as to why or how. I don’t think that’s a flaw — it’s really, really hard, at least in my own experience, to do that. The only way I know how to do it is to tell stories and weave them together in illustrative ways. And I guess that is what I was looking for — I was looking for more stories like this (Chapter 5, “Win or Go Home” — in the run up to the Iowa Caucuses):

“In early December on a Saturday night…, all thoughts turned to the Des Moines Register poll, which was scheduled for release in the next day’s paper… Generally, polls are a dime a dozen in a presidential race, and the sheer number of them makes each one seem less important. But the release of the Register poll is considered an event. Time stops and waits for the results.

My first experience with the poll was in 1990 when I was working on Tom Harkin’s Senate race. This was before the Internet, so if you wanted the scoop on the poll you had to go down to the Register’s loading docks around midnight and persuade one of the truck drivers to give you a copy before he left on his route. Harkin’s campaign manager called me into his office on a Saturday afternoon and told me to stay out of the bars that night and instead to go down to the Register building at midnight, get a copy of the paper, and then call him at home (cell phones were just large, toaster-sized oddities in those days) to give him the results and read him the story—then he would call the senator.

Sounds pretty pro forma and uneventful, but to a wet-eared twenty-three-year-old kid it was a high honor; it made me believe I must be doing a good job to be trusted with such an important task. Since then I have never seen a Register poll without thinking of that night and of how seemingly insignificant moments like that can have an outsized impact on your professional trajectory. Now I got to play the old hand: I told our mostly under-thirty staff about how we used to get the Register poll down at the docks because there was no Internet, and they would roll their eyes and look at me like I had escaped from the set of Cocoon.”

More of those would have made the book a five star book.

You certainly don’t walk away from this book empty handed, I’ve bookmarked a number of pages in my Nook — because I think there are some tactics that the campaign employed that highlight strategies for the ways in which you successfully engage people these days. Hints to the answers to questions about how you take an organization, use technology and communication — and engage people “on the ground where they are” — and what you choose to focus on and what not to focus, even in the face of the conventional wisdom. By all measures, the Obama campaign was an incredible success — and one that seems to be built on more bedrock principles than normal — and there are things to learn from that.

I just wished there had been more insight into the day to day execution. More stories, more 10ft views rather than the 10,000ft views.

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