1. What will make this call worthwhile and successful for you?

A good open-ended opening question that lets prospects know you are there for them—to listen to their needs rather than immediately throwing the typical sales pitch down on the table right out of the gates.

2. How do you manage your customs processes today? Why is that?

Again, such a question allows your prospect to put their minds back into their day-to-day. Up to this point, they still might be in, “Oh great, another sales call” mode. So, put them at ease and let them surface potential bottlenecks or issues your product may be able to quench.

3. What is frustrating you with your current import or export process or selling to your customers?

This could be a question asked instead of the previous, or, in addition to. If the latter, a better way to ask might be, “You mentioned frustration around XYZ. Can you elaborate?”

4. What’s working well with your current process?

Rarely is every component of a process broken or need to be replaced. Thus, there might be certain aspects your prospect doesn’t want to lose with the implementation of a new solution. You should know that.

5. What factors are limiting your process from being as effective as it could be?

Similarly, perhaps there are just a couple of things that need to be fixed with their current process. If you know this before your turn to speak, it will allow you to draw a stronger connection between your product features and the already-mentioned pain points.

6. In what ways would making this change disrupt your current processes?

This is a trust-building question, in that it allows your prospect to see someone (you) who is confident enough to be asking for holes to be poked in their product. You, in turn, can now give a crafted rebuttal addressing why those might not actually be “holes” after all.

7. What is motivating you and your company to take on this project?

One might typically ask this question like, “You said your company was struggling with XYZ, is that correct?” Even though problems may have been previously stated at some point, going the open-ended route will confirm the facts and could even give you more information with which to work.

8. How do you envision your challenges being solved? What does that solution look like?

This question may be a bit risky if your prospect starts describing a facet your solution doesn’t provide. But, if you’ve made it to this point, your product should be a good enough fit for you to capably circumvent any potential issues. Also, if your prospect ends up describing your product features, you’re in an advantageous position.

9. What has been done to fix your issues so far?

A great question that, if answered favorably, will lay out on a silver platter all the reasons your solution is superior to other available options.

10. If you have tried to solve the issue internally, what challenges have you run into?

Similar to the above, perhaps your prospect has already tried to fix their problems with internal band-aids, and just needs something bigger and better. You can expect greater buy-in if it is your prospect doing the talking about their problems, with you following-up with statements about the solution (rather than you doing all the talking).

11. Why was this method tried instead of “X”?

Again, just more discovery. It’s in your best interest to know why a certain solution was chosen previously. Why? Because how great would it be if your product was in alignment with what your prospect thought they were getting with another solution (that ultimately failed)?

12. How will you be evaluating different options? Which other vendors are you considering?

You should obviously have a good idea of your competition, and who your prospect might be considering in addition to your solution. But, if you know specifically (by hearing it directly from the prospect), you can narrow your focus and attack with depth rather than breadth.

13. What kinds of content or collateral can I send you to make the process easier?

This is a good question given our struggle to retain large chunks of information presented during a short amount of time. With so much being exchanged, sometimes it just takes your prospect seeing a benefit said alternatively, or on paper for the light bulb to illuminate.

14. How will the decision-making process work?

A mistake some sales reps might make is to ask, “when can I expect to hear from you.” Why? Because how much can you do with an answer like “in a couple of days”? There isn’t any value there. On the other hand, if you hear everything that needs to happen next, you can address anything that might help them move along towards getting a deal done.

15. If those steps include the signing of the final order too, what can I do to help that process along?

Even with above question #14, your prospect might not be factoring in the actual closing action to get the deal in place. This follow-up question just cements all activities along that precious timeline.

16. Other clients we’ve spoken with are challenged by common issues like ‘A, B, and C.’ How are these challenges affecting your business?

This type of statement/question combo can accomplish a couple of things. One, it shows you’ve done your homework, and even if you haven’t spoken with anyone challenged with those things, it allows you to surface other common problem areas your product might address. Secondly, if you have another customer in a similar industry, or even a prospect’s competitor, such a question will surely get the prospect’s attention

17. If the problem you’re facing was solved immediately, what would that look like for your business?

Think back to the times where you envisioned success for yourself; crossing that finish line in the distance…it motivates you to work that much harder, right? Similarly, this question puts your prospect in “superstar” mode, allowing them to get a quick glimpse into what it would mean for their career should they be able to solve “hot button” issues plaguing the company.

18. How do you think changing this process could make your job easier?

And to go along with the “superstar” question above, getting prospects to visualize their jobs being easier with your product has a similar positive effect.

19. What are some of the specific things stopping you from reaching your objectives?

Perhaps it’s budget, time constraints, or something else entirely. Whatever it is, you need to know it, and then feature it as a key piece when developing your perfect sales pitch.

20. What things might get in the way of this moving forward?

This might sound like the above, but the goal of asking differs slightly. For instance, while budget might be the long-term roadblock, there could be a shorter-term hurdle that must be cleared first. Perhaps you’re talking to someone who doesn’t have the authority to make the purchase, and convincing that decision maker is the immediate challenge.

21. Why do you think this challenge hasn’t been addressed yet?

Really, this is a way to ask about potential roadblocks without being so blunt. Meaning, maybe one important person in the organization really likes the current process and solution, but most others want to make a change. Well, then you’ve just uncovered an issue that needs to be addressed sooner than later.

22. What kind of budget do you have for this project?

Trick question. Asking this doesn’t really encourage additional dialogue, and can really stop any momentum previously built. So, a better approach could involve you being more transparent with pricing, stating something like, “The average spend for others in your position is $XYZ. Can you talk me through how this aligns with your expectations?”

23. What are your concerns about making a change?

This question puts resources aside, and really encourages the prospect to lay their cards out on the table. Sure, nobody has enough budget or time, but what is it that really concerns your prospect about making a change? You’d be surprised at what you might learn here. It could be something as small as your prospect being fearful of proposing a change to higher-ups.

24. What questions do you have that I haven’t answered yet?

A perfect way to end, as you can bet anyone serious about finding a solution will have more, specific questions to ask of you. If they don’t have any questions, consider it a sign that you need to be doing more to connect their problems to your solution.

25. Do I have your endorsement?

Do I have your endorsement?” is geared toward the individual’s opinion, which in this case is really what I wanted to uncover and a lot safer for them to answer. If the prospect says no or gives a noncommittal answer, I ask, “Why, what’s holding you back?” or “What would it take to get your endorsement?” Once they answer the question and their concerns is on the table, I can work on overcoming the objection.

Once buyers verbally say, “Yes, you have my endorsement,” they rarely go back on their word. They may not own the final decision authority, but you know they are definitely going to be selling internally on your behalf.