Over prepare, then go with the flow

Posted 08.27.2008

Barack Obama keynote at the 2004 Democratic National Convention With the Democratic National Convention underway this week, media coverage of Barack Obama is in full saturation mode. Sifting through some of it in yesterday’s Washington Post, I came across an article by Eli Saslow that’s an amazing example of how a leader can let go of doubt and pick up the confidence that he or she needs to lead at the next level.

As the article relates, Obama’s breakthrough moment was the keynote speech he delivered at the 2004 Democratic convention. Here’s an extended quote from Saslow that sets up the situation back then:

Obama’s staff had worked exhaustively to secure the chance for such a life-defining moment, even though the young politician doubted his qualifications for a keynote spot… (He) approached the lectern in Boston a virtual nobody, a representative for 600,000 constituents in Illinois’ 13th District. He exited having set the course for an unprecedented political ascent, with the fortified self-confidence that he could deliver when it mattered most.

How did he do it? The same way you get to Carnegie Hall … practice, practice, practice. The same day Obama was offered the keynote spot, he started writing the speech himself. He labored over it and crafted it, even escaping at times to the restroom in the Illinois State Capitol to get some quiet time. As the convention date approached, he delivered it at least 15 times in practice. He then delivered it three more times using a teleprompter for the first time in his life. As he stepped on stage in front of thousands in Boston and millions watching at home, he was nervous for the first couple of minutes until the Kansas delegation let out at a loud cheer when he mentioned their state. From that moment, he relaxed, found his rhythm and rocked forward. The results of what happened during the next 15 minutes will be on display tomorrow night when he accepts his party’s nomination for president.

My takeaway? When the stakes are high, leaders cannot over prepare for the big moment. Preparation breeds comfort and comfort breeds confidence. That sense of grounded confidence is what people are looking for in their leaders. Because he was well prepared and ready, Obama connected with his audience that night in Boston four years ago. And you can do the same with your own core constituency, be it staff, colleagues, and other key individuals in your executive life.