Going Deeper in the Sales Conversation
Remember last week’s newsletter? We talked about pain. And you, as a superstar, used our “conversation” to uncover your prospects' pain.
You and your prospect agree there’s something to work on together.
This is the moment where many sales conversations feel successful—but quietly start to fall apart.
Now it’s time to go deeper. And that means being more direct with your questions.
Have you ever left a meeting feeling great? The conversation was solid, the problem was clear, everyone seemed aligned… and yet, in future meetings, the deal never closed.
That usually doesn’t happen because of timing or pricing. It happens because some very important questions were never asked. Even when we think we asked enough, it is worth checking,
Budget: The Question Everyone Avoids
This question is almost taboo. Many sales professionals avoid it because talking about money feels awkward, intrusive, or risky. And yes—that discomfort is very human.
But asking about the budget is not about asking your prospect to open their wallet on the spot.
It’s about understanding reality.
You need to know whether a budget exists today, whether it needs to be approved, or whether it will be created in the future. Even if they don’t give you an exact number, this information helps you shape the conversation—and your solution—properly.
When you don’t ask about the budget, you’re guessing. And guessing leads to proposals that are either unrealistic or misaligned. When your prospect understands why you need this information, they’re far less likely to hold back—and far more willing to adjust expectations if needed.
Budget clarity doesn’t kill deals.
Lack of it does.
Decision-Making Is More Than Who’s Involved
The second area where deals often stall is decision-making.
Many people believe decision-making questions are only about identifying who’s involved. And while that’s important, it’s just the starting point.
You also need to understand:
- What criteria do they use to select a vendor or partner
- What their internal evaluation process looks like
- How vendors are compared and prioritized
- Whether you’re being evaluated alongside competitors
- And what, if anything, could delay or prevent a decision altogether
These questions help you understand not just who decides, but how decisions are made.
Without this clarity, you might do everything right—only to lose momentum because you didn’t anticipate an internal process, a competing priority, or an unspoken obstacle.
Timing Matters—and So Does Trust
You can’t ask these questions too early. And you can’t ask them without trust.
Budget and decision-making questions only work after you’ve had an honest, deep conversation about pain. When the prospect sees that you’re genuinely trying to understand their world—and not just push a solution—these questions feel natural, not confrontational.
If you skip them, you may find yourself going back later to fill the gaps. And by then, momentum may already be lost.
Final Thought
Strong sales conversations don’t fail because of poor presentations. They fail because of incomplete discovery.
This helps you go deeper in your conversations this week. And if you’d like support in weaving budget and decision-making questions into your process—without sounding awkward or scripted—schedule a discovery call with me. We’ll break it down and build something that works for you.
But, be ready, I will ask a ton of questions of you.
Talk soon,
Tati
