38 Systems Thinking Questions That Expose The True Structure of A Buying Decision

In complex B2B sales, every deal is more complex than it looks on the surface. A potential buyer contacts a salesperson and asks a few questions. Inexperienced salespeople might take the conversation at face value and assume that the person calling them knows what they want, understands the full scope of the situation, and has the full authority to make the purchasing decision.

Successful salespeople understand that the person contacting them is part of a larger system, with many moving pieces and multiple relevant stakeholders, each with their own point of view on the purchase. In order to navigate this complexity, reach the appropriate stakeholders, and win the deal, a salesperson must be able to zoom out on the larger systems affecting the purchase, and zoom in on the smaller details that matter.

Successful salespeople understand that stakeholders are part of a larger system.

Asking the right questions during the first discovery call can reveal the true structure of the deal, ensure you’re reaching all of the relevant stakeholders, and set the project up for success. Here are 38 questions to help your team zoom in and out on the deal:

What Questions

Starting with the “what” helps frame the conversation, uncover the distinctions of the problem(s) clearly, and guide the buyer to identify and name the most relevant stakeholders.

1. What exactly is the problem from your (the stakeholder’s) point of view?

2. What is the problem from the department’s point of view?

3. What is the problem from a company-wide view?

4. What other departments are impacted by this?

5. What other systems interact with this problem?

6. How do others in the industry view this problem?

7. What is the problem from your customer’s point of view?

8. What other departments are impacted by it?

9. What other systems interact with it?

10. What aspects of it affect you personally?

11. What is the downside if this doesn’t work out for you?

12. What is the downside if you do nothing?

13. What does it say about you if this succeeds? If it fails?

14. What does it say about your team, the other departments, your company?

15. What blocks do you foresee to completing the project?

16. What will need to happen before this decision can be made?

Who Questions

As the problem is being defined through “what” questions, relevant stakeholders and their relationships and perspectives on expressed problems and eachother will begin to reveal themselves. Using additional “who” questions will help your salespeople find them all.

1. Who else is interested in this problem being fixed?

2. Who else is impacted by it, at the different levels of the organization?

3. Who else needs to be involved?

4. Who would support this project?

5. Who would object?

How Questions

“How” questions help the buyer and the seller understand the impacts, risks, priorities, and urgency of the problem, at each level of the impacted systems.

1. How does this connect to everything else you’re doing?

2. How long has it been a problem?

3. How have you tried to solve it before?

4. How is this affecting you?

5. How does it impact the department?

6. How does it impact the company?

7. How does it impact other systems?

8. How does it impact your employees?

9. How does it impact your industry? What about the wider global market?

10. How will you know when you succeed?

11. How will your CEO measure success? Your boss? Other departments? Your team?

Why Questions

“Why” questions get to the heart of the problem and help connect it with what truly matters to each stakeholder.

1. Why hasn’t the problem been solved already?

2. Why does it matter to you?

3. Why does it matter to the company? To your team? To other departments? To other individuals named in the “who” questions?

When Questions

“When” questions provide a timeline framework, reveal hidden urgencies, and help the salesperson to get everyone aligned with a shared mental model for implementation.

1. When does this need to be solved to support you and your team?

2. When does it need to be solved to support the company? What about the other stakeholders identified by the “Who” questions?

   1. How critical is that timeline? To you, to the team, to the company, and to the other stakeholders?

Even beginner salespeople can better understand the systems their buyers and their decisions impact, using these questions. Along the way, they will gain the business savvy that helps them engage with stakeholders at differing levels of the buying organization. They will learn how to engage with CEOs, CIOs, department heads, peers, and employees, making them better sellers overall.

Ultimately, zoom in/zoom out questions help sellers and their buyers structure their understanding of the deal so that they can build a shared mental model that helps buyers make good decisions. And salespeople who can do that are salespeople who win.