Your product is a great fit for the prospect. It’s in the right price range for their budget. And you can even get them a discount based on the size of the purchase. But even though this should be a slam dunk, I can tell you they won’t buy unless there’s urgency. Urgency gives people a reason to move forward. When it comes down to it, companies always have more needs than resources -- so unless they must buy your solution in the short term, the deal will probably stall. So if there’s no urgency, you should create some. Right?
Wrong. Sales strategist David Weinhaus, who works with HubSpot partner agencies, has a strong view on “creating” urgency. Instead of manufacturing a cause to act -- which isn’t helpful to your prospect and will ultimately backfire -- either uncover an existing reason they’re not aware of, or back off. With the right questions, you can get your prospect to realize they’re unhappy or dissatisfied. And if your questions don’t lead them to those conclusions, accept they’re still in education mode and let your marketing department nurture them until the time is right.
It’s also worth pointing out there are a ton of questions on this list (40, to be exact). I don’t want you to use all of them with every buyer. That would be crazy. The key is picking the most applicable, relevant ones for each prospect.
1) How big is the company today in terms of annual revenue, approximate customer number, and employee headcount?
This question helps you qualify them and start a discussion about how big they’d like to be in the future (and what’s currently standing in the way).
2) Is the business struggling, in a steady state, or in growth mode? Is [company] growing faster than the industry average?
Remind the buyer of their overarching business goals. This is a good tie-in to how your product would play into their strategy.
3) Many of the people in your role I talk to don’t know [surprising fact]. Did you?
I like the Challenger Sale method of teaching your prospect something new -- not only will your credibility and authority go up, but you’ll naturally uncover urgency. The buyer will want to act on this information ASAP.
4) What is the problem you’re looking to solve?
The buyer might be focused on a different pain point than you. Use this question to figure out if they’re on the right track. Sometimes, prospects try to address the symptoms rather than the cause by mistake.
5) Is the problem clearly defined?
Learn how much time they’ve spent investigating the issue. Hint: The more clearly they’ve isolated it, the more invested they probably are in fixing it.
6) Have you had this problem before?
Figure out just how persistent your prospect’s pain point is.
7) Is the problem easy or hard to address?
Chances are, the prospect will say it’s the latter. If it was easy to solve, they would have tackled it by now.
8) How does this problem affect the revenue, profitability, culture, or product cycle of the business?
This question highlights the larger implications of what’s going wrong.
9) Does this problem affect a lot of people?
Get your prospect thinking about how widespread the effects are.
10) Are you tasked with solving this problem as part of your regular job, or is this a special assignment?
If your prospect says, “It’s part of my job,” then make sure you tie their overall performance to fixing this issue. If they say, “It’s a special assignment,” then there’s already genuine urgency: They need to identify an answer before a certain date.
11) What happens if you address the problem? What happens if you don’t?
This naturally leads the buyer to compare life with your product and life without. The second is usually much less appealing.
12) When do you need to start seeing the results of implementing the solution?
The prospect would probably love to see results right away. Their answer will help them realize why time is of the essence.
13) What is the one thing that, if we could help solve it quickly, would have the most meaningful impact on the company?
Once you’ve pinpointed a major opportunity to help, urgency will spring up naturally.
14) How would solving this problem affect you personally?
Knowing the buyer’s individual motivators can make or break the deal.
15) How does this affect your boss?
When the prospect’s boss is happy, they’re happy. Connect the dots between your solution and their supervisor.
16) What happens if you keep doing what you are doing?
It’s far easier to stick with the status quo than make a change, even if the long-term ramifications could sink the prospect’s business. With this question, you’ll get them to come to terms with the dangers of ignoring the issue.
17) How can we make you look like a star?
This question turns you into the prospect’s partner, instead of just their rep. It also helps you pinpoint how your product can help them look great at the office.
18) What do you need to do/what objectives must you reach to get a promotion?
Along similar lines as #17, this question reveals why the buyer is personally invested in finding a solution.
19) How does this problem affect you on a day-to-day basis?
Most professionals put up with annoying or deleterious pain points. As soon as you show the prospect there’s a better, easier way, they’ll be more eager to buy.
20) How does this problem affect [department]?
Get them to zoom out and visualize the impact on the wider team.
21) If you weren’t experiencing this pain anymore, which projects/priorities could you focus on?
This question makes the buyer envision a world where they have time, energy, and resources for the tasks or initiatives they’re interested in.
22) What’s the most frustrating aspect of this problem?
Once you learn what’s driving your prospect up the wall, you can position your product accordingly.
23) What [projects, campaigns, initiatives] are you currently working on? How does [challenge] impact your plans?
This is another way of learning how the pain point is interfering with or obstructing their day-to-day work.
24) What problems come up most frequently at executive meetings?
If the CEO cares about an issue, your prospect will too.
25) Which problems keep you at the office late?
Figure out which issues the buyer doesn’t have an easy answer to.
26) Which themes are coming up again and again on [Slack, Hipchat, your knowledge base/wiki]?
While not every company uses internal chat or a wiki, asking those who do about the most common themes can help you pinpoint the most exciting, visible, or challenging things they’re facing.
27) Is your industry getting more competitive?
Most industries are. Capitalize on your prospect’s awareness that they need to act to maintain their edge -- or gain one in the first place.
28) Are you worried about [specific competitor]?
Figure out who’s nipping at your prospect’s heels, then show them how your solution will widen the gap in their favor.
29) Do you ever get the sense that [people in prospect’s department] are wasting [time, effort, leads, budget]?
Mitigating (or even eliminating) the inefficiencies in the buyer’s department would be a huge win. Open their eyes to the possibility of a fix.
30) Have you ever lost a major customer unexpectedly?
Whether the answer is yes or no, this question works. If your prospect has, they’ll be eager to take precautions so it doesn’t happen again. If your prospect hasn’t, the wheels will start turning: Wow, it would be really bad if 20% of our business vanished in one stroke.
31) How [did, would] losing that customer affect the business?
Get the buyer to vocalize the negative effects, which will drive their desire to avoid the catastrophe even higher.
32) How do you avoid getting caught in a pricing war?
Chances are, your prospect would love to find a differentiator that would save them from race-to-the-bottom pricing. You just need to explain why your product is that differentiator.
33) Would you be interested in talking to [Customer], who saw a [X%] return on our [solution, service]?
Hearing from someone who got fantastic results will spur your prospect to the finish line.
34) Maybe it would be helpful for you to talk to someone who’s [made this journey recently, faced X similar challenge, resolved the same issue]. What do you think?
If it’s too early in the sales process for references, suggest a knowledge-sharing conversation instead. You’re still connecting the buyer with a satisfied customer -- but their shared experiences is the focus, not your product.
The nice thing about this technique? Not only is it helpful for the prospect and your customer, but at some point during the conversation they’re bound to bring up your solution.
35) 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]?
Test your prospect’s commitment to act with this question. If they say they’re not ready, don’t be pushy -- instead, ask what else they’d need to make a decision.
36) If I send over the contract when we hang up, can you return it to me in [six days from the current date]?
Sales consultant Jeff Hoffman encourages reps to close this way. Normally, the buyer says they’ll need more time -- at which point you say, “Okay, can you do [preliminary step] by that date?” They’ll say yes, and now you’ve gotten a concrete agreement to make progress on the deal within the week. Boom.
(Adjust the date based on your sales cycle. If it usually lasts two weeks, ask if they can sign the proposal that day. If it lasts 10 to 12 months, ask if they can sign the proposal in three weeks.)
37) Define your timeline for solving the problem and getting the right results.
Make sure your prospect’s expectations align with reality. You may need to accelerate the sales process to meet their timeline.
38) When must this problem be solved to avoid negative impact on the business?
Get a firm deadline for the purchase. Explain to the prospect you should shoot for a few weeks or months before this deadline to protect against delays.
39) Is there seasonality in your business? Do you have a busy or slow season? Do you need to address this problem before the busy or slow season hits?
For prospects affected by seasonality (like education, tourism, and entertainment), it can be critical to get a solution in place while business is relatively quieter.
40) If we can work out a solution sooner, how does that help you?
Fixing a problem earlier rather than later is almost always a good thing. The best part about this question is that the buyer puts those benefits in their own words.