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100 Discovery Questions


We listen to a lot of phone calls here at Balto, and we wanted to take some time to compile some of the common questions we hear during phone conversations. A few things we’ve noticed:


1) Many questions force the prospect to identify product solutions or features that they don’t actually like. While many salespeople are scared of asking these types of questions, we found that getting prospects to open up about this early in the sales process allows the salesperson to address the problem early on as well, as opposed to having the prospect’s problems or concerns sneak up at the end of the sales process when it’s too late to fix.


2) Many questions try to quantify the challenges and pains the prospect is facing, in terms of lost time, money, legitimacy, or simply on a 1-10 scale. By quantifying their challenges, buyers are more likely to realistically think about fixing them. Further, it allows salespeople to adjust their offerings if prospects don’t identify closely with a given value proposition.


3) Getting group buying consensus early on was particularly valuable. In many cases, the actual decision-maker wasn’t the individual the salesperson was talking too, and understanding that earlier in the conversation allowed the salesperson to better prepare for and identify the conversation and individual that had the final say.


4) Open-ended questions early on in the sales process win deals. Salespeople who came in with a static value proposition almost always failed to understand their prospect needs, while reps who asked a serious of effective, organized, and specific open-ended questions were able to adjust their value proposition to the needs of the prospect.


There are many additional insights you can identify from these questions. Should you have any questions, please feel free to reach out in the comments and we will be happy to discuss.


What questions:


  1. What is the single biggest problem you face in your job today?
  2. What problems are you facing right now?
  3. What solutions have you tried in the past?
  4. What does fixing this problem do for you and your organization?
  5. What makes you unhappy with your current solution or situation?
  6. What interests you about our solution?
  7. What additional organizational questions need to take place for this solution to be implemented properly?
  8. What kind of ROI would you need to see a solution like ours provide in order to move forward?
  9. What types of documentation or materials do you need in order to build consensus within your organization?
  10. What would you actually use our solution for? Is it something we discussed, or do you have another idea for it?
  11. What limitations do you think our solution has?
  12. What have I missed or failed to explain clearly?
  13. What keeps you up at night?
  14. What challenges take up most of your time?
  15. What type of solutions does your organization usually purchase?
  16. What does your buying process look like?
  17. What concerns could I answer upfront to save you time in the future?

How Questions:


  1. How many times have you tried to fix this problem?
  2. How do you currently go about addressing this challenge?
  3. How involved are you in buying and implementing solutions like these?
  4. How much experience do you have with this type of solution?
  5. How much money is this problem costing you?
  6. How much internal legitimacy is this problem costing you?
  7. How much external legitimacy is this problem costing you?
  8. How can we help improve this situation for you?
  9. How does your organization usually pay for these types of solutions?
  10. How much time is this problem costing you?
  11. How do you think fixing this problem would improve your organization?
  12. How do you envision others fixing the problem?
  13. How often do you think this problem presents itself within {timeframe}?
  14. How does that affect your ability to hit your goals?
  15. How do you think this problem manifests itself when you aren’t monitoring it?
  16. How does your legal process for vetting new solutions or vendors work?

Why Questions:


  1. Why?
  2. Why do you think this is a problem?
  3. Why might you cancel your order in the future?  
  4. Why haven’t previous solutions worked for you?
  5. Why do you think is a larger priority than your other challenges?
  6. Why do you think you are underperforming in this area?
  7. Why isn’t your current solution working?
  8. Why do you say that?
  9. Why haven’t you tried {possible easy/obvious solution}?
  10. Why do you believe we can fix this problem as opposed to another vendor?
  11. Why have you elected to fix this problem now?
  12. Why are you taking this meeting?
  13. Why haven’t you fixed this problem sooner?
  14. Why is this not a priority for you?
  15. Why are you not happy with your current vendor?
  16. Why do you plan to use this solution for that particular reason?
  17. Why did you reach out to us?

If Questions:


  1. If money were no object, what is one thing you would you change immediately?
  2. If {particular situation} were to change, would you still be considering a solution like ours?
  3. If a competitor reduced their price substantially, would you go with them instead?
  4. If you could only fix one thing, what would it be?
  5. If we could accomplish one thing with our solution, what would that be?
  6. If we could get one thing out of this meeting, what would that be?
  7. If we could eliminate {insert prospect objection here}, is the remaining business case strong enough to move forward?
  8. If we could fix the problem, how much would you value the solution?
  9. If you had to put compare our solution to another you are familiar with, what would you compare it to?
  10. If you had to imagine this solution working perfectly, what would that environment look like?
  11. If we offered {benefit or solution}, would you consider moving forward?
  12. If you didn’t fix this problem, would it really be that big of a deal?
  13. If we implemented this solution tomorrow, what is the first thing you would do with it?

Could Questions:


  1. Could you tell me more about that?
  2. Could you elaborate?
  3. Could you explain why you’ve mentioned that particular point (as opposed to something else)?
  4. Could you fix this problem without our help?
  5. Could you identify the factors might hinder this deal from going through?
  6. Could you identify the other decision makers we might need to talk to in order to facilitate this deal or agreement?
  7. Could you think of any potential uses for our solution that we haven’t discussed so far?
  8. Could you identify a few of the features or benefits you dislike most about our solution?
  9. Could you, on a scale of 1-10, rank your need for a solution to this problem?
  10. Could you, on a scale of 1-10, rank your belief that our solution can fix your problem?

Do Questions:


  1. Do you believe this problem is worth fixing?
  2. Do you think others have figured out how to fix this problem?
  3. Do you think morale is being negatively affected by not have a solution for this problem?
  4. Do you think {user} will be eager to use this solution?
  5. Do you believe this problem can even be fixed?
  6. Do you think your competitors either use or are considering using a solution like this?
  7. Do you believe that you can fix this problem on your own?
  8. Do you think more problems will arise as a result of fixing this one?
  9. Do you think fixing this problem will be worth the investment?
  10. Do you think this is something you could implement in the next {timeframe}?
  11. Do you believe your current concerns with our solution have been satisfied?
  12. Do you believe that we have skipped any important steps in your buying process?

Who Questions:


  1. Who actually signs this type of contract?
  2. Who is involved in reviewing these types of agreements?
  3. Who actually needs to approve the budget for this type of purchase?
  4. Who within your organization do you expect to oppose this type of purchase?
  5. Who benefits most if this problem is fixed?
  6. Who usually takes the blame when this problem manifests itself?
  7. Who will get the credit for fixing the problem if our solution works out?
  8. Who will actually be responsible for implementing this solution should you move ahead with a purchase?

Where Questions:


  1. Where will the budget for this purchase come from?
  2. Where do you envision our solution fitting into the bigger strategic vision of your organization?
  3. Who in your organization tends to offer the best feedback for these types of solutions?
  4. Where in your process does this problem become most obvious?
  5. Where do you see our solution being the most helpful?
  6. Where do you see our solution being the least helpful?
  7. Where do deals usually fall apart in your process?


Have questions? What to contact us directly. Please message us on our contact page! 



Further Readings:


1) How to Keep Your Sales Meetings From Going Off The Rails

2) This is a Tough Job: Make Sure to Respect Yourself

3) Why Staying Humble is the Key to Success in Sales and Customer Service