Although you, I and every other normal human being spend most of August thinking as little as possible about anything not related to the relaxation arts (swimming, sailing, eating lobster, drinking beer), candidates for first selectman are not like you or I.

At this very moment, as you and I slather on sunscreen and skim the pool, they sit in dark rooms. Surrounded by highly paid political consultants, they plan focus groups. They compile lists of possible donors, potential voters, and people upon whose property they can foist lawn signs.

Oh, wait. This is not the presidential campaign. It's not the race for mayor of New York City or even Bridgeport. This is for first selectman of Westport. So while the candidates do all those things, they are not surrounded by political consultants. They do them themselves, perhaps with help from their second selectman running mate, and respective spouses.

It seems waaay too early to focus on the first selectman campaign, yet in the tradition of our great American democracy, we must. In a few short weeks, school starts. The next day is Rosh Hashanah, then Yom Kippur, followed immediately by Columbus Day and the traditional Halloween snowstorm. We will lack electricity for weeks, yet we will trudge to the polls and elect the man or woman who will lead us for the next four years.

So the window of opportunity is tight, and it begins today.

If past campaigns are any indication, this year's race will focus on a few questions. We will ask the candidates what they plan to do about taxes. ("Keep them low!" they will say in unison.) We will wonder about the candidates' stances on the municipal budget. ("We must examine every item closely!" they will respond. "We must keep services high, but not spend a penny more than we have to!") We will ask about things like pension obligations. ("It is very important to examine this issue closely!")

Just once, I want a candidate to say:

1) It is inevitable that taxes will rise.

2) It's impossible to look at every item closely, and even if we could, every department moves money around like a three-card monte game.

3) You can have great services, but you'll have to pay for them -- that's the way the world works.

4) "I really have no clue about pension obligations. It's a mystery to me! Just like it was to the previous eight administrations!"

But the odds of that happening are the same as me walking to the planet Zork, so I will have to come up with my own questions for our first selectman candidates.

For example: How long will it take, once you're in office, to get someone from the state Department of Transportation to come down and fix our traffic mess? Sometimes the Post Road traffic backs so far up in both directions, a theoretical Westport News columnist living in the condominiums behind the post office can't even get out of Playhouse Square. And don't even get that theoretical columnist started on the light at the Post Road, Riverside and Wilton.

My next question would be: Are you for or against Downtown 2020? If you're for it, what will you do to make it happen? Your predecessor appointed a committee to plan Westport's downtown in the year 2020. They've made some progress, solved their turf tiff, and now the deadline is just a bit more than six years away. Using the full powers of your office, how will you ensure (if you believe it's important) that we reclaim our river, reroute our traffic, and return some energy and night life to this sleeping giant?

The candidates for first selectman will be asked -- often -- what they think about proposed senior housing on Baron's South. I'd broaden the question: What do they think about seniors in general? What can be done to keep them in Westport? To pass their wisdom on to younger Westporters, to introduce them to some of the new families in town, to create an environment in which seniors don't mind paying taxes to support our school system, while families with schoolchildren help subsidize men and women whose main -- maybe only -- asset is the home they've lived in and loved all their lives?

Those are big questions. There are no easy answers. But Westport is not an easy town to govern. We demand a lot of our leaders, and we seldom thank them enough.

Of course, maybe the time for "first selectman" is over. So here's one last question: What do you think about hiring a professional town manager to handle many of the duties we traditionally heap on a non-professional?

If my first three questions don't get them thinking, that one sure will.

Dan Woog is a Westport writer, and his "Woog's World" appears each Friday. He can be reached at His personal blog is www.danwoog06880.