Some years ago, I was racing at Key West Race Week aboard a Farr 40. All the boats in the fleet go about the same speed upwind, so the outcome hinged on what I call “geographical positioning”—where you were on the course relative to the competition. Yes, you had to have a good start, and you had to be in the right spots for the shifts and puffs, but you also had to pay a lot of attention to your position relative to the boats around you. If you had to duck a boat or you got tacked on, all of a sudden things started to snowball, and a top-10 position could quickly drop into the 30s. This was most apparent as boats started converging on the windward mark. Seeing that happen, I started playing the inside of the lead pack, something I call “leading the leaders.” In a fleet with anything more than 10 to 15 boats, apart from starts, it’s the biggest single passing lane.

Because packs develop on both laylines, boats coming in on the weather mark laylines, especially the starboard-tack layline, will slow each other down. Once on the layline, you have no option but to follow the pack into the mark. The longer you’re there, the worse off you’ll be.

To lead the leaders, position yourself toward the center of the course, relative to that pack. You may be behind most of them, but you’re eliminating one of the key variables over which you have no control: what other boats are going to do, such as tacking on you, forcing you to duck, or leebowing you, all of which might force you to the layline early. This keeps your air clear and preserves your tactical options.

If you’re on starboard tack in the correct zone below the layline, boats coming in on port won’t bother to tack on or in front of you because they don’t want to do two extra tacks. They’ll usually go straight to the starboard layline. Think about the following situation: Your competitor is on port tack, about 10 boatlengths from the weather mark, headed toward the starboard layline. He sees you approaching on starboard tack. His choices are to leebow you or dip you.

A lot of times, the conservative thing for him to do is just dip you and get to the layline. But once he dips, he’s now behind you. So, if you’re the starboard-tack boat, and you can find that perfect lane where port-tack boats will more likely dip you than lee-bow you, they’ll end up sailing down the ladder. The result? You gain.