Here’s how you get the information you need about the “when” of the deal and how to use it to maintain momentum.
February 11, 2026
By Rachel Smith
For the last several weeks, we’ve been exploring DRIVE, Maestro’s information-gathering framework, and looking at how it compares to other sales-qualification frameworks out there. Here’s a quick recap:

We’ve made it to DRIVE’s last letter, E.
E is for Expectations
Even though we’re talking about expectations, the answers we get when we dig into E do a lot to maintain velocity in sales.

You already understand what a win means for the organization. You uncovered that when you asked questions about impact. But now we’re asking about what this deal would mean for your prospect. What do they personally want to get out of it?
Yes, you’re selling to an organization, but that organization is made up of people. There are likely many people (Forrester says an average of 13) who make up the decision-making team. The more you know about how your solution will help each person, the more champions you’ll have who can help you get your deal across the finish line.
What questions can you ask individuals to find out how this purchase could benefit them personally? Here are some options:
Your job is to sell the product or service your company provides. Your prospect’s job is NOT to buy the product or service your company provides. Their job might be in finance. They might be a CTO. They could be in HR. Their job might even be to sell the product or service that their company provides. My point is, while you’re a sales professional focused on selling, they are a something-else focused on their own role and priorities. Purchasing your solution is likely a very small part of their responsibilities.

It’s even possible that your prospect was tasked with solving this problem. They may be reluctantly exploring solutions, or even resentful of being given the assignment. When you cheerfully ask, “What does a win look like for you?” they may stare at you blankly. A win for them at this point might be getting this whole solution search over with.
That means it falls on you reframe the conversation and help guide them in uncovering their personal wins. Your questions could be:

The second layer of expectations is about what roadblocks you can expect as the deal progresses. Nobody wants to talk about everything that could go wrong, but it’s better to know about the potential pitfalls early. That way, you’re prepared for them and can ideally steer around them rather than driving into them head-on.
When you think about the questions you’ll ask to uncover roadblocks, think about all of the other DRIVE letters. Decision-makers, time constraints, resource constraints—roadblocks can come from all kinds of places.
What questions help you discover what roadblocks are lying in your path? Try these:
And if they say there are no potential roadblocks to worry about? Great! Plow ahead!
JUST KIDDING!

There are always roadblocks. Your prospect might not have a lot of experience purchasing a solution like the one you’re selling. They might not know what the roadblocks are. They might not be telling you everything. They might not have thought much about this yet. They might be the roadblock!
There are an average of 12 other decision-makers you can ask about potential roadblocks. Ask until you uncover them all. Velocity in sales is crucial. Meeting your prospect’s personal expectations keeps your foot on the gas, and avoiding roadblocks keeps you from having to brake. Keep your deal in motion with DRIVE.
Our DRIVE sales training courses onlineare FREE of charge right now. Like all of our online courses, they are developed specifically for adult learners and can be completed in small chunks when you have time.
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