How to Coach a Sales Rep Who Is
Not Hitting Their Number
By Jonathan “JG” Graviss | OOH Today | November 5, 2026
Most OOH sales managers coach an underperforming rep the same way. More activity. Faster follow-up. More frequent check-ins. When the rep is sending proposals and not closing, that approach usually makes the real problem harder to see.
With political inventory cleared and about eight weeks left in the year, this is when owners and sales managers take a hard look at who is on pace and who is not. Before the next coaching conversation, it is worth knowing which problem you are actually coaching.
Four Problems That Look the Same on the Scoreboard
A rep who proposes and does not close is usually stuck in one of four places: discovery, category knowledge, follow-up, or timing. On a pipeline report, all four look identical. Proposals go out, and contracts do not come back. That is not an effort problem. It is a diagnosis problem, and coaching aimed at the wrong one teaches the rep to work harder at something that was never broken.
The fastest way to tell them apart is to listen to how advertisers say no. Most operators never record loss reasons. They should. Until they do, sit down with your rep, go through every proposal since Labor Day that did not close, and have the rep repeat what each advertiser actually said.
What Each No Is Telling You
A discovery problem sounds like an advertiser saying the proposal is not really what they need. The proposal answered a question nobody asked. If your rep cannot explain, in the advertiser’s own words, what the advertiser needed to happen, start there.
A category knowledge problem sounds like an advertiser who is not sure billboards work for a business like theirs. That objection has an answer, and a rep who knows the category gives it. The tell is a pattern: results that hold in some advertiser categories and fall apart in others.
A follow-up problem produces no answer at all. The deal does not die. It goes quiet, and nobody can say when the last real conversation happened.
A timing problem sounds different from all three. Call me after the first of the year. We are not deciding until spring. Send it over and I will hold onto it. Every answer is about when.
Timing Is the Problem Most Managers Miss
Timing fails in two ways. The proposal arrives before the advertiser has a reason to decide, and it gets filed. Or it arrives after the decision was already made somewhere else. Both lose the same way, because local advertisers do not always decide on a schedule. Many decide in the moment: a new location, a slow month, a competitor’s move. When that moment comes, the operator with an open conversation is in the room. The operator with a proposal sitting in a folder is not.
Reps propose early for an understandable reason. A sent proposal feels like progress, and it gives the manager something to count. This is where the usual coaching backfires. Follow-up still matters. But following up harder on a proposal the advertiser was never ready to consider does not create urgency. It gives the advertiser one more thing to put off.
A 30-Day Plan for One Rep
For the next thirty days, no proposal goes out until your rep can answer two questions. What would make this advertiser decide, and who makes the call? The answer is rarely a date. It is an event in the advertiser’s business. If the rep cannot answer, the next conversation is discovery, not a proposal.
Review every proposal before it goes out, and make the review about timing rather than content. When an advertiser says the decision is coming later, the rep asks what will change between now and then, logs the answer in the CRM, and keeps the conversation open around that event instead of around the document.
At thirty days, the test is simple. Your rep can name the decision trigger and the decision maker on every open deal. If that is true and deals are still not closing, the problem is one of the other three, and you start the review again. If the rep cannot learn to ask the question, or will not, that tells you something about fit. Either way, the rep deserves to know which conversation they are in.
More on how we help OOH sales teams build this kind of coaching into their week at GravissMarketing.com.
Let’s elevate OOH together and make sure your company’s marketing is as strong as your locations.
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