Prospecting Questions That Move Deals Forward
Sales isn’t about kicking the can down the road or waiting for someone to finally make a move. It’s about qualifying fast, building trust, and uncovering what really matters to your prospects.
Too many salespeople avoid the tough questions, but those are exactly the ones that create confidence and get real answers. It’s time to lean in. Last week we covered questions 1-6. The remaining seven questions will separate buyers with intent from those just browsing.
7. What solutions have you tried up to now?
Start with what’s been done. It’s essential. When you ask, “What solutions have you tried up to now?” prospects reveal their pain points and their history. Did they attempt to fix it themselves? Did other vendors fail? As they open up, you gain insight into what works—and what doesn’t.
8. What is the risk if this issue is not solved?
Every deal has a risk. If your prospect can’t articulate a risk, the odds are good they’ll stick with the status quo.
If there’s no real pain, there’s no urgency, and probably no sale. You want answers that quantify and clarify just how critical the problem really is.
9. What is your timeframe to solve this issue?
Time matters. If there’s no pressure or timeline, your deal just landed on the back burner. Find out what their expectations are.
If they say, “It could be next quarter, or three years from now,” that changes everything. Your most valuable resource is your time; use it wisely.
10. How have you solved issues like this in the past?
History repeats itself. This question isn’t just about solutions, it’s about process. When you ask, “How have you solved issues like this in the past?” you’re looking for trials, tests, departments involved, and the flow of decision-making. Their answer gives you a roadmap for how they do business, and what you’ll need to navigate.
11. If this issue is not solved what is the impact?
Don’t hesitate to dig deeper. Once you know the risk, push to uncover the impact.
Are they going to miss their revenue targets? Lose customers? The bigger the impact, the more likely they’ll take action.
12. How will solving this issue help you?
Go personal. Deals get done when there’s a real benefit, not just for the company, but for the individual. Listen for answers that tell you how your solution improves their life, their job, their numbers. Then, look for ways to connect the dots between your solution and their personal wins.
13. How will solving this issue help you with your customers?
Every business is serving someone. Take it a step further.
This question gets your prospect thinking about downstream effects. Prove that you’re focused not just on them, but on their customers as well. When they realize your solution goes beyond their own organization, the value grows.
Push for Tough Answers—Don’t Wait
Salespeople lose deals because they hesitate. If you don’t ask tough questions early, you’ll waste countless hours with buyers who are only mildly interested. Qualify fast. Make sure you uncover intent, not just interest.
The best prospects are ready to take action. Find them, and set your sights higher to close deals that matter.
How to Defeat Sales Call Anxiety
Let’s boost your confidence and get you back on the phone.
Find episode #397 wherever you download podcasts!
What Does ‘Good’ Look Like in Sales?
w/ Jeff Bajorek
Jeff and Mark examine why repeatable, high-profit pipelines and genuine customer relationships are harder to define than most leaders think.
Episode #398 is out now!
