36 Sales Questions to Create a Sense of Urgency Without Being Pushy

Over the last few years, thousands of salespeople have adopted the inbound sales methodology to close more deals, close the right deals, and build their pipeline. Selling can’t be pushy. It has to be helpful, and the salespeople who adopt this philosophy will win in the short and long term.

When teaching inbound sales methodologies, one of the most frequently asked questions is, “How do you get people to make a decision without being pushy?”

Creating a sense of urgency without being aggressive is a learned skill based on conducting good discovery, understanding the needs of the prospect, and asking the right questions of the right people in the sales process.

Remember that most customers buy a product or service for emotional reasons. Even if your product or service is relatively undifferentiated and your prospects are price sensitive, many will still make a decision based on their overall relationship with the company and the salesperson. Especially if you’re working with SMBs, a purchase may not be an insignificant decision. Often, it comes directly out of the partners’ pocketbooks and will affect their paycheck and bottom line.

Customers rarely understand the extent of your product's value when they engage at the top of the funnel. One of the most important parts of your job is to identify through discovery what problem the prospect is looking to solve, the extent of the problem, the timing of the solution, how the company wants to purchase, what the key decision criteria are going to be, and how you can make it easy for them to purchase.

Of course, salespeople can’t -- and shouldn’t -- try to spur every prospect toward a quick close. We see dozens of examples every month of prospects in virtually every industry who need more nurturing before they’re ready to pull the trigger. Some of these are just bad fits. Some shouldn’t be talking to Sales at all because they’re still in Awareness mode (Sales should let Marketing handle these leads and make sure you are not engaging too early). But many are a good fit, and are definitely moving through Consideration and toward a close with you or someone else -- it will just take a little longer.

When your prospects are good fits and far enough along in the process that they should be ready to buy, here are 36 questions you can ask which convey that moving forward earlier rather than later is in their best interest.

How to Create a Sense of Urgency in Your Prospects Without Being Pushy

1. How big is the company today in terms of annual revenue, approximate customer number, and employee headcount?
2. Is the business struggling, steady-state, or in growth mode? Is the prospect growing faster than the industry average?
3. What is the problem that the prospect is looking to solve?
4. Is the problem clearly defined?
5. Have you had this problem before?
6. Do you have written decision requirements for the solution?
7. Is the problem easy or hard to address?
8. Is this a nagging pain that has been around for years or a new issue that has increased in intensity?
9. If it’s new, what brought it on and when did it appear?
10. Is there a formal plan to address the need that has executive visibility?
11. What is the plan and who is involved in executing the plan?
12. Does the plan include a prospective Return on Investment formula or do we have to build one?
13. Is there budget for the plan?
14. Who owns that budget?
15. Is this a competitive deal or have you already picked a vendor to implement?
16. How does this problem affect the revenue, profitability, culture, or product cycle of the business?
17. Does it affect a lot of people?
18. Have you thought through the implementation timeline and process?
19. Are you tasked with solving this problem as part of your regular job or is this a special assignment?
20. What happens to it if you address the problem? What happens if you don’t?
21. When do you need to start seeing the results of implementing the solution?
22. What is the one thing that, if we could help solve it quickly, would have the most meaningful impact on the company?
23. If we are able to help and get the right results how does this affect you personally?
24. How does this affect your boss?
25. What happens if you keep doing what you are doing?
26. Do you need to accelerate your current plan or do you need a new way of dealing with this problem?
27. If we identify a solution that works, can you get started today/this week/this month?
28. If we supply all the information you need in the next 24 hours, will you have time to review it and get started by [date in the near future]?
29. Please describe a recent product acquisition process that was super-efficient for your company.
30. Define your timeline for solving the problem and getting the right results?
31. What is the drop-dead date that this problem must be solved to avoid negative impact on the business?
32. Is there seasonality in your business? Do you have a busy or slow season?
33. Do you need to address this problem before the busy or slow season hits?
34. If we can work out a solution sooner, how does that help you?
35. Do you anticipate any curveballs in the process?
36. How can we make you look like a star?