Cookies & privacy.

Essential cookies keep you signed in and remember your choices. Optional analytics cookies recognize returning browsers and help us understand which pages and demos people use. If you decline, we still measure anonymous visits without saving a persistent visitor ID on your device.

Privacy details
    Back to Journal
    Coaching
    Discovery
    Diagnostics
    Rep Development

    How to coach a rep who keeps losing deals in the first 5 minutes

    Cason Lamothe
    July 2, 2026
    6 min read
    Rep Diagnostics

    Discovery isn't about asking more questions. It's about asking the right ones early. A diagnostic breakdown shows you exactly where the rep's opener falls apart.

    Some reps lose deals before they even realize it. The buyer sounds polite, but the conversation is already over. The problem is almost always the first five minutes: discovery that feels like an interrogation, a pitch that starts too early, or a lack of curiosity about what the buyer actually cares about.

    You do not fix this by giving them a longer script. You fix it by showing them what they missed.

    What bad discovery looks like

    Bad discovery usually sounds like a checklist. The rep asks about budget, authority, need, and timeline in a robotic sequence. The buyer answers but does not open up. The rep gets information but not insight.

    Signal to watch for:

    The buyer gives short answers for more than a minute. That means the rep is not asking the right questions.

    The anchor questions

    Strong discovery starts with questions that invite story, not data. The goal is to learn how the buyer is currently solving the problem, what is frustrating about it, and what happens if nothing changes.

    Questions that open the conversation:

    • "Walk me through how you're handling [challenge] today."
    • "What made this worth a conversation now?"
    • "What happens if you don't solve this in the next six months?"
    • "Who else is affected by this problem?"

    Using the diagnostic

    When you review a call, look for the first question the buyer answered with energy. That is where the real conversation started. Everything before it was warm-up. Everything after it is where the deal is won or lost.

    If the rep never reaches that moment, they are pitching into a closed door. Coach them to slow down and earn the conversation. The best openers do not sell. They make the buyer want to talk.

    Found this helpful?

    Share it with your team

    Put this into practice on your next rep call.

    See how Plimsoll gives you a moment-level diagnostic after every AI buyer conversation.

    See how it works