Math Is Your Friend
This distance between should be steering your publishing organization's behavior, down to daily decisions. This trickles down to every salesperson who owns a piece of quota. How they spend their time any given day should stand up to the question of "How will this get you closer to your numbers?"
This doesn't mean members of your team coming up short should start hocking inventory on every street corner -- not at all. But where you stand versus your quarterly quota should affect the balance kept between effort allocations against short-term opportunities versus mid- to long-term ones.
I first witnessed this transformation of quantitative focus when IGN went from a private company to a public one. The numbers were omnipresent and affected all of our decisions and how we felt as an entity. Quarters exceeded ignited conversations about investments; shaky quarters fueled speculation, and missed ones were emotionally punishing. Whichever the case, the accuracy in internally reporting these numbers was paramount.
Privately held companies tend to treat the numbers with similar respect but not as much fear. Missing a quarterly revenue goal is not the end of the world; it should just feel like that. Worse then missing a goal is not tracking this math close enough to read the signs that help direct you when numbers are missed or made.
Even if your company as a whole doesn't operate under this influence, you should. The first step is tracking and then printing a weekly spreadsheet of the business you have closed, and the business you have proposed that, if closed, will run and be recognized within the quarter. Then apply a closing ratio to the proposed dollars (no higher than 50%) and see where your projected quarter nets out.
If too close to call or under, your daily grind must consist of a higher volume of calls to previous advertisers asking for agreement to read through an impromptu proposal in case funds turn up. If your projected total lands safely, you can then turn up the faucet on organic big ideas you have been presumably grooming.
Everyone has a boss, who would like to see professional tasks planned and executed based on a plan. The best plans are grounded in math. The worst-case scenario in publishing occurs when your sales team has been set up to fail because the numbers were set incorrectly. You miss the mark on this as a company and you lose the opportunity to exercise accountability because the sales organization never believed the numbers were legitimate.
During the dot-com daze, we were handed quotas that were thousands of percentage points off from where we came in -- and our company entered a tailspin. We survived by learning lessons and operating under legitimate quotas that were placed high enough to reach by a sales team that needed to stand on their sales toes to get there.
Establishing quotas is as much art and science as it is achieving them. Doing both well as a publisher makes for a nice run with success; throwing spaghetti against the wall to see what sticks makes a mess.