Audible Sales Podcast is my favorite one in the sales canon.
It’s from the team that created Command of Message which is my favorite methodology and is ran exclusively through leaders who have lived in sales for decades.
The content is exact, precise, and dialed. Most episodes delivering within 20 minutes.
Context:
The team covers how to surface metrics and PBOs throughout the sales process. Two principles anchor the whole thing: ask early, and be comfortable with the discomfort. These questions are awkward. So is walking into a leadership meeting with no proof points asking to approve new software.
At its simplest, prospects should be grateful you’re putting them through this. It’s how they figure out whether the problem is actually big enough to warrant an evaluation, and if it is, how they build the internal case to get budget released.
My notes:
The best reps have quietly retired “Always Be Closing” and replaced it with something harder: Always Be Curious. Closing is a moment. Curiosity is a methodology. One happens at the end of a deal, the other runs underneath every call from the first discovery question to the final signature.
Curiosity means you’re genuinely trying to understand what’s happening inside someone’s business, not just qualifying them for your pipeline. It means you’re asking questions you don’t already know the answer to, and actually listening when they respond.
Most reps avoid the hard questions because they’re afraid of disrupting call flow. That fear is the thing disrupting their deals. A prospect who never gets challenged never builds conviction. They arrive at the end of the process unsure, and unsure people don’t sign. Asking difficult questions isn’t confrontational, it’s the service. You’re helping them think through something they probably haven’t fully thought through yet.
If a prospect can’t answer a hard question, that’s not a problem. That’s information. It tells you where the deal actually is.
The most underrated thing a rep can do is help a prospect build their own business case. Not hand them one, help them build it. Walk them through the back of the napkin math. Do you know what your current system is costing you in time? In money? In errors? Most people haven’t done that calculation and they need someone to show them how. Once they’ve done it themselves, the ROI isn’t yours anymore, it’s theirs. That’s a completely different conversation.
And if they push back on the ROI exercise, the question is simple: how will you make a decision without it? If there’s no number attached to the problem, there’s no urgency to solve it.
The questions that open this up are diagnostic, not interrogative. How do you know this is a problem? Is something driving this internally? Did something happen recently that brought this to the surface? Is it getting worse? Where’s the pressure coming from to solve this?
These questions do two things simultaneously. They give you signal, and they help the prospect articulate something they may have only felt but never said out loud. When someone hears themselves explain a problem clearly for the first time, the problem becomes more real to them.
After you have the pain, connect it upward. Most people at the operational level don’t instinctively know how what they do connects to what the executive team cares about. That’s where a good rep becomes genuinely valuable, not just as a vendor but as a thinking partner. Help them draw the line from their day-to-day problem to the revenue goal, to the strategic initiative, to whatever the CEO said on the all-hands last quarter. When they can make that connection, they become your internal champion, because now they have a story to tell upstairs.
Get all of this early. The closer you get to signature, the higher the guard goes. People get cautious, committees expand, and suddenly everyone needs to re-examine everything. The information you gather in the first two calls is what you’ll be living on at the end. Collect it like it’s scarce, because by the time you need it, it will be.
cullaways 
Leave a comment