Advanced Questioning Skills: Mastering the 11 Types of Discovery Questions

This is a guest post from one of our current members Mary Grothe at Sales BQ®.

In order to be a quota crusher, you have to know how to ask the right questions. Understanding your prospect’s problem better than the next salesperson (and making sure your prospect sees that you understand) will set you apart from the competition. To get there, you need to create an advanced, structured approach to questioning. I won’t sugarcoat it: This is extra work! When you become an advanced questioner, you’re going above and beyond what most salespeople are doing—but that’s exactly why you should be doing it.

To get you there, I will walk you through the foundational steps to build your questioning skills. Read on to determine the answers you should be seeking from prospects, the different types of questions you can ask, how to customize them to make your prospect feel heard, and exactly when to ask them.

Step 1: Determine the Answers You Need

To figure out what answers you need your prospects to give you, make a list of what you need to know about your buyer. Imagine the perfect sales meeting: What kind of information would you walk away with? If you could learn everything you needed to know about whether your buyer was a viable prospect, what information would you have? Now, write out all the answers you need to know. Use the list below to get started.

1. Static Information: What do you need to know about the company? This is where you uncover the basics, like company size, geographic location, number of locations, industry, etc.
2. Demographic Information: What demographic information do you need about your buyer and their team? Do you need the names and job titles of the decision makers? Do you need to know which members of the team will be influencers and end-users?
3. Psychographic Information: What do you need to know about your buyer and decision-makers’ emotional states? What information will tell you how invested they are in solving the current problem? What emotions and behaviors do you look for from a prospect to signify that they’re ready to buy?
4. Budget & Investment Specifics: To know if your prospect is prepared and qualified to buy, what do you need to know about their financials? Do you need to know if they are prepared to make a one-time purchase, or pay a yearly recurring cost? Do you need to know the customer’s existing spend on the problem? Do you need to understand their ability to make an investment and a desire to spend money? 
5. Logistics & Timing Scenarios: This is where you find out about all the background noise going on behind the scenes that will affect the deal. Do you need to know if key decision-makers have vacations planned that will affect the timing of the close? Do you need to understand what their emotional investment is in the logistics and timing of the deal? Do you need to know why the buyer is picking the date?
6. Authority & Decision Process:  Gone are the days of sales deals with one single point of contact—now, deals happen with entire decision teams. If your contact isn’t offering a team, you should ask for the other decision-makers, influencers, and end-users whose opinions will be key. The earlier you bring them into the process, the better your buy-in will be, and the more you’ll know about their criteria.
7. Key Problems You Can Solve: What is your value proposition? Why are your current clients happy? Try to get specific with your list – is the problem you solve for manufacturing clients different from the one you solve for healthcare clients? What about SMBs vs enterprise businesses? What do you need to know about your client to understand how your solution will make their lives better? Being an expert problem-solver is key to being successful in sales. I like to think that every prospect has a radio station playing in their head called WII FM, “What’s in it for Me?”.  And if you can get on that wavelength, you can get their attention. 

Step 2: Build Your Custom Questions

Building custom questions for each prospect takes extra time, but in order to stand out and win, you need to show up differently than your competition. Writing customized questions for each buyer has a powerful effect. You’ll build instant trust and credibility because the quality of your questions will demonstrate that you’ve done your research. Your prospect will respect you for approaching them with a clear understanding that industry, market events, geography, and other nuances might affect them differently than another prospect. To start, use your answer list from the previous step, and follow the steps below to construct the questions you’ll ask your buyer to get those answers.

1. Custom build your questions for each client based on your answer list above.
2. Be sure to modify the wording for each type of buyer persona you encounter. Create variations of each question from the last step to fit for different buyers you work with, be it executives, end-users, influencers, or gatekeepers.
3. Create second and third level follow-up questions. Your first question may not get you the full answer you need. What questions will you ask as a follow up to each of the questions from Step 1? Get as granular as you need to in order to get the answers you need. 
4. Create a cheat-sheet to use in the meeting. When you prepare for your meeting, write out all of the questions, then use the same document (or sheet of paper) to take notes on the buyer’s answers. Don’t treat it as a script, though—make it conversational and allow some natural flow to happen. A barrage of 50 back-to-back questions will make any buyer feel uncomfortable.

Step 3: Master the 11 Types of Questions & When to Use Them.

Just like everyone has a love language, every prospect has a different sales language, and speaking the buyer’s language turns you from another pushy salesperson into a trusted advisor. It makes it easier for them to buy in emotionally. (If you don’t know how to speak the languages of different buyer personas, take our Buyer BQ class.You’ll get invaluable information about how to identify, speak to, and ultimately close all of the different personalities you’ll encounter in sales.) 

1. Open-Ended Questions: Start your meetings with open-ended questions. Prompt the prospect to explain to you how they got to where they are today. What have they tried in the past? What’s worked, and what hasn’t? What’s changed in the business? Ask them to give you the lay of the land. This will get them talking, and you’ll begin to gather lots of information. 
2. Yes or No Questions: These types of questions often get a bad rap, but if you use them strategically, sometimes you can uncover important things quickly, and if you can get your prospect to say yes multiple times in a row, it has a comforting psychological effect that lowers their guard. After saying yes over and over, they will be more excited, and they will feel more comfortable sharing with you. 
3. Assumptive Questions: Tread lightly when making assumptions. You never want to put words in your prospect’s mouth. If you want them to admit they have a problem, hearing themselves say it is more powerful than hearing you say it. Instead of making assumptions like, “I assume you’re running into X,” offer a scenario that helps them come to the conclusion on their own. You can say, “Some of our clients run into X. Tell me about how you handle that.” This gives them a chance to say it in their own words. One caveat to assumptive questions: They can be useful when you’re at a stage of solid understanding, you’re picking up on the buyer’s emotions, and you need to move the conversation along, and potentially progress it to a close.
4. Multiple Choice Questions: If your prospect is a C or S personality, they might be reserved, with a tendency toward one-word answers. (If you’re not sure which personality your prospect is, review Buyer BQ before your next prospect meeting!) C personalities are analytical and don’t emote much, while S personalities won’t tell you the magnitude of the problem because they don’t want to rock the boat or make anyone feel bad. Setting up a multiple choice question, using a third party as an example, can make it easier for these buyers to open up. This can go something like, “In our experience, when clients do X, they are typically feeling A, B, or C. Which are you dealing with, or are you experiencing something else?” 
5. Future Vision Questions: Study your buyer persona until you can paint a picture of a day in the buyer’s life. What challenges, pains, and problems can you solve for them? How can you make their day better? Paint them a picture of the future where the problem is solved, and ask questions about how their life will be different (and better) within the vision you’ve painted. This can be a powerful motivation for buyers to make a decision and move the conversation along. 
6. Quantifiable ROI Questions: It’s your job to help your buyer understand how much the problem is costing, how long it’s been a problem, and what the cost of doing nothing will be. This is also an important place to ask second and third-level follow up questions. Ask them specifics about lost time and opportunity. How often do they call their current provider’s customer service line? How many team hours are they using on the problem each week? What will it cost to do nothing? What other things could you work on with all that time and money saved? Asking them to quantify the problem for you allows you to build an ROI that will help you soften the blow of the cost and give you leverage in the negotiation. This also sets you up nicely to ask future vision questions, when the depth of the problem is clear.
7. Listening Questions: Sometimes, salespeople can overwhelm buyers with our excitement and questions. When that happens, it’s time to slow down, show your buyer some empathy, and assure them you’re there to listen. Take a deep breath, envision creating space, and slow down. Relax your body language, and ask questions like, “Can you give me more context? Can you help me understand better? Can you walk me through that?” When they answer, really listen, and ask follow-up questions to demonstrate that you’re invested.
8. Problem Expansion Questions: Any time your prospect shares a problem with you, ask them more about it. Eat what’s being served, and consume it until it’s gone! You need to deeply understand their problem and its magnitude. When they say something to the effect of, “Yeah, that’s a problem,” don’t just move on to your next question—instead, expand and dig deep. Ask them for details and specifics, such as, “Who else is it impacting? What are the repercussions personally and professionally? What’s changed? Why now?” Ask until there’s nothing left to uncover.
9. Hesitation or Concern Questions: If you sense concern or hesitation from a prospect, brushing it off may be your knee-jerk response, but it won’t serve you (or them). Instead, call out the hesitation and address it when you sense it. Make space for your buyer. Pause, and say, “I feel like I am picking up some hesitation. I’m wondering if there’s something we should be talking about that we’re not.” Then, pause again, and give them space to think about it and answer you. Unearthing concerns before you’re trying to close allows you to address them head-on, before it’s too late. 
10. Take Away Questions: Sometimes, when you’re sensing hesitation, you might need to stop and do a take away. This can be especially helpful when you’re asking closing questions, but you’re getting pushback. You can say, “You know, I don’t think I’ve heard enough to justify you making this change.” This tactic will absolutely blow your buyer away. Nobody expects a salesperson to do this. If the prospect really does want your solution, they start selling you. Or, if they don’t want your solution, they’ll agree, and you’ll save yourself a lot of time. Don’t waste time writing a proposal for a prospect who doesn’t want one.
11. Closing Questions: Questions like an if-then close, a timeline close, or an assumptive close are critical to the end of a sales meeting, but too many reps don’t ask these questions. Don’t let a conversation just fizzle out, and never, ever end a call on “we’ll be in touch.” Benchmark them by asking how your product or service compares to others they’ve looked at, and figure out where they are in the process. Book the next meeting or next steps and figure out the parameters and criteria necessary to close the deal. It’s easy to end a conversation on a comfortable, “So nice meeting you!” But it won’t get you anywhere in sales. It’s better to ask a tougher closing question that they may say no to, because it allows you to move on and spend your time on viable prospects if they’re not interested.

Mapping out your questions is a powerful strategy that will take you to the next level in your sales career. When you incorporate advanced questioning into your sales process, you will build implicit trust and credibility, because you’re going to sound credible, knowledgeable, and invested in solving their problems. In your buyers’ eyes, you will look like a different type of salesperson, which will help you show up differently than your competition and ultimately win more business.

Want to learn more about becoming a quota crusher? Take our Buyer BQ class, or reach out to me here to start a conversation!

Mary Grothe, CEO of Sales BQ®

linkedin.com/in/marygrothe

Twitter @MaryLGrothe

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