Decision-Making Questions That Get You the Information You Need for the Sale

Last week, we talked about sales qualification frameworks and introduced you to DRIVE, Maestro’s own framework for gathering information from potential customers. The “D” in DRIVE stands for “Decision,” and there are two layers to the decision-making questions you need to ask:

1. Who makes this decision? and
2. How is the decision made?

WHO MAKES THE DECISION?

The average number of people involved in the B2B purchasing process continues to grow. According to a Forrester report from December 2024, there is now an average of 13 people who take part in a buying decision. Just a few years ago, we were complaining that it was seven people. Those were the good old days, and we didn’t even realize it.

Each of these decision-makers has their own motivations and considerations, and they are often at odds. Let’s say you are selling a human-resources platform that makes benefit enrollment a breeze. Pam from HR is thrilled and can’t get her hands on it soon enough. Alonzo from IT, on the other hand, is dreading having to integrate a new platform into the already-existing tech stack. 

Let’s say Pam is your initial contact. You’re counting on her to tell you about Alonzo from IT, Wayne, who’s the CHRO, and all the other people who will be involved in decision-making. When you ask Pam who makes the purchasing decision, however, she says it’s just her. You know that can’t be true. What the hell, Pam?!

Calm down. Pam isn’t intentionally lying to you. It’s more likely she doesn’t know who is involved in decision-making (and just wait until you ask her about how the decision gets made). You sell your product or service every day, but chances are that Pam has never purchased a SaaS platform. She’s not lying; she just doesn’t know.

Depending on how often people purchase a product or service like yours, as well as the level of experience of your first point of contact, getting incorrect answers to your decision-making questions is likely. Don’t wait until Alonzo finally says something three months from now and derails the whole deal. You’re the expert. It’s your job to uncover the correct information.

What kinds of “who” decision-making questions can help you get more information? We’re glad you asked.

• Who besides yourself is involved in the decision-making process?
• Who else would be interested in learning about this solution?
• Who weighed in the last time you purchased something like this?
• Most companies we’ve worked with usually get IT and legal involved. Who from those departments should we loop in?
• Who is involved in the procurement process?
• Who is involved from an IT perspective?
• Who do you partner with when making decisions like this?
• Who are you partnering with once you’ve made the decision to help you get this pushed through? Who is the largest stakeholder?

HOW IS THE DECISION MADE?

Every organization has its own buying processes, and you need to get a deep understanding of your prospect’s approach to keep your deal moving. Like the “who” question, it might be the case that you know more about how these things typically work than your contact. If that’s the case, you will need to guide them in asking the right decision-making questions of others in the organization.

Within the question of how the decision gets made is also an element of when. How and when does the prospect organization allocate its budget? There may be periods throughout the fiscal year when an organization is able to make purchases, or even a time when a department’s remaining budget must be spent quickly to avoid reallocation.

The question of “when” within the decision-making process is also important when asking about the legal-review process. Deals often slow down once they get to legal, but by asking questions about what information they need and how long they generally take, you can avoid a loss in momentum. Even asking about when certain people will be on vacation can be important to head off your deal getting stuck.

What kinds of “how” decision-making questions can help you get more information? Here you go!

• How are decisions like this made?
• The last time you purchased a solution like this, what did that process look like?
• How does this align with your internal process?
• If you decide to go with us, what are the next steps?
• In what order do other departments get involved?
• What information have other vendors provided to IT, legal, or procurement that you have found useful?
• What is your procurement process? (Follow-up: Who would know how these decisions get made?)
• The last time you purchased, what were the steps you took after you made a decision?
• What has the process looked like for similar solutions you have implemented?
• In my experience, similar clients have had legal/IT/procurement involved. How similar is this to your organization’s process?
• In what order does their involvement typically occur?
• In what ways can we parallel process (e.g., have legal and procurement review things at the same time)?
• What questions does legal/IT/procurement typically have?
• How long does it usually take for legal to review a new solution for your team?
• How does your budget cycle influence when you can look at new solutions?
• What are the key milestones in your procurement process?

One reason we refer to DRIVE as an information-gathering framework rather than simply a sales qualification framework is that it continues to be useful throughout and beyond the sale. The answers to these decision-making questions can be important when onboarding your client. They can also be useful to your customer success team.

The “who” and “how” of decision-making can change throughout the sale, too. One of the decision-makers could leave, or you might gain a new stakeholder. Asking decision-making questions like, “What changes could come up in your procurement process?” or “How have past organizational changes influenced purchasing decisions?” can help you anticipate changes and quickly adapt. Asking the right strategic decision-making questions keeps your deal in motion.

Our DRIVE sales training courses online are 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.