Debate Night in Boston for Tom and Mike

Tonight, live on WCVB, it’s the first real debate of Boston’s first “real” mayoral race in years as Councilor Michael Flaherty faces off against Mayor Tom Menino.

Waiting in the wings will be the only non-candidate to get more press than any candidate, Flaherty’s choice for deputy mayor, Councilor Sam Yoon. And hovering over the proceedings all night will be the mystery email flap which the Boston Globe revealed right before the preliminary and is now slowly, but not too decidedly, dogging the mayor.

While the decision by Flaherty to try to run with Yoon as a quasi dual ticket has been an interesting sideshow, it has little real impact on the race. Yoon’s supporters weren’t going to vote for Menino and the pairing probably won’t change a lot where the votes really are – among city workers and in the bellwethers of Jamaica Plain and West Roxbury.

It is looking like Flaherty needs another game changer, and tonight might well be one of his few remaining chances. For tonight, it’s all about communicating well and, while taking some chances, not looking for that knock-out punch that probably won’t come.

What can he do, absent a Flutie miracle toss?

• First Five and the Last Five. Menino is going to be expecting Flaherty to be aggressive and that’s ok. But Flaherty needs to focus on the first five minutes and the last five minutes. That’s when the press is going to be most paying attention and he needs to get a strong zinger in early and one late to really make an impact.

• Listen and Pounce. The best debate lines aren’t developed in the prep room, they are spontaneous – or at least look spontaneous to the press and public. So have some ideas but take time to listen carefully to what is being said. Too many candidates don’t listen to their opponent (worried too much about what they will say next). Listen and, if the time is right, pounce. Those unscripted moments can change the course of a campaign.

• Emails, what emails? Sorry, Councilor, this doesn’t yet smell like the controversy that toppled Menino. Unless emails to be released by City Hall show that top mayoral aide Michael Kineavy was plotting murder under Menino’s watchful eye, this controversy probably won’t be determinative for a lot of voters. The media and questioners will spend a lot of time on it. It’s your job as the candidate to react, yes, but then show voters you are ready to lead – not dwell.

• Articulate a Vision. This piece of advice is last for a reason – it should be first but hasn’t happened yet. To most voters, Flaherty hasn’t done that yet. Perhaps it’s the media, perhaps it is people being unwilling or uninterested in listening, but his message isn’t getting through. Don’t assume voters have heard it all – that three-month echo chamber of a preliminary doesn’t count. Tonight, it’s the playoffs. Hit the reset button, start from scratch and tell Boston why you deserve to be mayor.