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Expectations in Sales: The Personal and the Problematic

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:

D is for Decision

Maintain velocity in sales with the DRIVE information gathering framework.
  • Who makes the decision?
  • How is the decision made?

R is for Resources

  • What is your budget?
  • What human capital has been dedicated to solving this problem?

I is for Impact

  • Why are you doing this?
  • What happens if you don’t?

V is for Velocity

  • What date are we driving toward?
  • Why this date?

We’ve made it to DRIVE’s last letter, E.

E is for Expectations

  • What is a win (for the individual)?
  • What are the roadblocks we might run into?

Even though we’re talking about expectations, the answers we get when we dig into E do a lot to maintain velocity in sales.

PERSONAL WINS INCREASE VELOCITY IN SALES

Knowing what a win means for your prospect can help 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:

  • What does a win look like for you?
  • How are you measuring success?
  • What would you like to see happen?
  • How will solving this problem make things easier for you?
  • What’s in it for you, personally?
  • What have you been asked to deliver?
  • If we solve for X, what does that mean for you?

WHAT IF YOUR PROSPECT DOESN’T HAVE A PERSONAL WIN?

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.

What is a personal win for your prospect?

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:

  • What’s something you’ll gain from this that will make your job easier?
  • How could this help you spend less time on day-to-day tasks and more time on X?
  • How do you see this solution making a real difference in your role?
  • What would make it worth your time and effort?

AVOIDING ROADBLOCKS TO MAINTAIN VELOCITY IN SALES

Ask about expected roadblocks in your sale.

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:

  • What department could potentially slow down this process?
  • At what part of the decision-making process do you anticipate we’ll meet a sticking point?
  • Of the people who need to be involved, whose calendar is the tightest?
  • What obstacles are preventing you from moving forward?
  • In the past, what got in the way of you getting something you thought would get approved?
  • What didn’t you see today that you wish you had seen?
  • What vacations are coming up?
  • When you’ve purchased something like this in the past, what have other vendors provided you with that was helpful?

And if they say there are no potential roadblocks to worry about? Great! Plow ahead!

JUST KIDDING!

Knowing about potential roadblocks early can help you plan ahead and avoid them.

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.