8 Killer Sales Questions

Sales have three important skills: (1) asking thoughtful questions, (3) listening, and (3) following up. If you can’t master these three skills, you will never make it. Even if you’re not a rock star at everything you do, these three skills will take you further than anything else.

Listening is a skill that you have to work on for your entire life, but asking the right questions (those thoughtful questions that drive people through the process) builds up trust and credibility and gives you the information you need to close the sale. That’s something that you have to be able to do without being salesy, without being pushy, and without being awkward. That’s something that you need to figure out, or you will watch those sales disappear.

Here are the eight killer sales questions you need to have in your back pocket to get away from the stale, repetitive, scripted conversations you’ve been having.

1. “Can you tell me a little bit about what you’re doing, looking to put together, or hoping to achieve/accomplish?”

The reason why I like to start with what your customer is thinking is that it starts to humanize the conversation. It puts you in a position where you are there to learn from the person because, truthfully, they don’t want to feel like they’re putting themselves out on a limb by sharing their ideas with you. A lot of us salespeople often forget that we are the experts and that most of our clients aren’t. Based on our reaction, we can make customers feel dumb for even thinking or considering this thing.

I like to start conversations by entering softly and putting myself in a position where I’m not judging what the other person is saying or thinking. I’d say, “I’m curious. How did you arrive at that?” or “Tell me a little bit about what you’re doing” or “Tell me a little bit about what you’re thinking for this project.” or “Tell me a little bit about why you think this purchase might be right for you.” I just ask all these general questions. That way, I’m not putting myself in a position where it seems to the prospect that I’m judging them, because I’m not.

2. “Is this something you’ve done before, or are you breaking new ground?”

You can pick your own wording for this, but all I’m trying to understand is whether or not this is something the prospect has experienced before. If the prospect has some experience in it, I’m not going to talk down to them. I’m not going to be condescending. I’m not going to explain things that they already know. I’m going to skip a few steps. I’m going to be a little bit more assumptive. I’m going to use language they know. I’m going to bring them to my level because they’ve done this, whether they are at my level or not. I’m going to use assumptive language so that we are seen as equals now.

However, if they’ve never done this before, then I’m going to become more of a guide. I’d ask, “Have you ever purchased a home before?” “Have you ever gone through the process of a mortgage or negotiation for home insurance?” “Have you ever launched a new marketing campaign before?” “Is that something that you’ve done?” So I love to ask these questions because they gauge where the prospect is in the process, and you can start to change your language based on how much they know.

3. “Do you have a clear idea of what you want and you’re simply looking for the best person to help you execute on it, or are you looking for someone to come in and work with you and do all the heavy lifting for you?”

I know that’s a really long question, but here’s why it’s important: I have given two possible options to help the prospect formulate and articulate where they think they are. They may say that they know exactly what they want, but they really don’t. But I like to ask this question because it helps me understand how they perceive themselves. Perhaps they step into your process and say, “Listen, I’ve done all the research. I know exactly what I want. I know what I need. I’ve reached out to a few different companies, and I just want to find out what the quote is.” Okay, perfect. They’re looking for someone to help them execute, and you have to make this simple, clean, and fast for them.

4. “This is a real investment of time and money, and you have a bunch of different options, ways, and approaches you could take. How did you land on this one?”

When someone is sitting across from me, I don’t assume that they’re going to want to work with me. I don’t assume that they’re gonna want to work with my competitors. I assume that they may not even want or need the very product or service I offer. They have so many options, so I’m curious what led that person to think about this. It’s just the type of question to get the dialogue going and uncover those hidden gems in terms of their motivations, their thoughts, their fears, and their desires. You want to learn as much as possible about your prospect and how they think.

So a question like this will help you qualify whether or not what you offer is right for them. And for me, in sales, there’s nothing more important than being 100 percent transparent and 100 percent ethical. Your job is to help them find the right solution for them, not simply to make a sale. Sometimes the right solution isn’t the one you have to offer, so asking this question can direct the prospect to what I do and what I sell or offer. However, there are times when it’s so glaring and obvious right away that what I’m offering is not what they need; in this case, I just have to be able to call it on the spot.

5. “You obviously have a great product/service team approach. I’m interested to know, why did you focus on that?”

When you’re sitting down and speaking to someone, there is nothing better than taking a genuine interest in what they’ve accomplished, what they have, or how they work. In every conversation, I look for an opportunity for me to get excited about the possibilities. When I’m working with entrepreneurs, I’m genuinely excited about what it is they’ve done, so it’s easy for me to say, “I can’t believe that you found this niche in the market. How did you find that?” or “You’ve been operating for 30 years, and you’re in your second generation — that is really cool! How did you find the transition from the first generation to the second generation?”

Look for the opportunity to have a genuine interest, and then ask. Not only will this help you understand how to navigate the sales conversation in the future, but it’ll also help you shape the pitch, the proposal, the quote, etc. You’re going to dig deeper. You’re going to learn more. You’re going to bring that into the conversation you’re having in the future to close those sales.

6. “What are we looking to accomplish?”

This is when I say, “You’re spending all this money. What is it that we really want to do at the end of the day?” The reason I ask is because (1) I’ve opened up enough of a rapport that they’ll be honest with me and (2) I want to know if, at the end of the day, what it is we want to accomplish actually aligns with everything they just said or if it actually contradicts everything they just said. More often than not, people don’t really know what they don’t know. They say they want to accomplish this and they want to do it this way. If you just take them at face value, you’re going to run off and produce all these quotes and all these approaches. You’re gonna sell them a product. You’re gonna hand it to them, and then they’re going to be disappointed. They’re going to get buyer’s remorse. It won’t work. It won’t match up to their expectations, and it’s not because you didn’t manage expectations — it’s because you didn’t really catch the fact that they thought they had the answer.

So you went off and delivered on that answer, but meanwhile, the answer was completely wrong. At this point, I want to say, “What is it we’re really looking to do here?” I dig deep, and I make it blunt. I want honesty. Then I want to see if it actually aligns with everything they just said. If it doesn’t, now is the time to start to be a consultant. Start to be a helper. You should be a guide. Steer them to what would really accomplish their goal.

7. “What are the timelines you’re hoping to work within?”

Assume you’re working with someone who’s buying a car. It takes three or four days for the car to be available for pickup, but they’re expecting to drive off with it that day or the next day. Naturally, you would ask, “When are you hoping to pick this vehicle up?” And then they go, “Well, I have a big party this afternoon, and I was hoping to roll in with this new vehicle to show everyone how successful I am.” And you go, “Okay, well, hmm, we need to get licensing done. We need to do all these things.” You have the ability to manage your customer’s expectations. Know their timelines. When they say, “I don’t know. We’re in the research phase. We have no timelines,” that’s not true. They have timelines. Ask them, “Is it really so? Perhaps three months? Six months? A year from now? Two years from now?” Then they might go, “Well, no, not that long. In the next few months.” Ask them their expectations for the timeline so that you can judge whether it makes sense and whether you can actually deliver. Ultimately, remember that most people don’t really know; they’re just making stuff up.

8. “What type of budget are you hoping to work within?”

We leave it to the end because it’s an important question. Most salespeople and entrepreneurs get super uncomfortable talking about budget, but budget is a reality. It’s something that you have to be able to address. You don’t want to make people uncomfortable, but it is as important as any other question that you ask. While you could start this little dance by telling them the ranges that you have, I much prefer finding out from them a general range they’re hoping to work within, and it goes two ways. First, people will be honest with you, and they’ll say, “Really, I mean, I’m not sure how much these things cost, but I’m thinking about working within this range.” Fantastic. It’s either too low, too high, or it’s right on — those are your only three options. Second, perhaps they’ll say, “I don’t really know. I have no idea what these things cost.” Then you can lead in with some highs and lows or some ranges.

Just think about buying a car. I have a Ram 1500. Well, Ram 1500s range from $30,000 to $75,000. Even if you’re selling something like a vehicle, you can easily ask, “What type of budget range are you looking at?” so that you can work with it. If you can get an indicator of what they’re thinking and where they are in terms of range, you are in a better position to steer them in the right direction. If people won’t give you the price, I literally explain to them, “These projects range in budget depending on the complexity. I want nothing more than to be able to give you the thing that you want, but it’s my job to be able to come back to you with the most efficient solution or most competitive price or most creative thing [whatever it is that they value].”

People will either give you the price range, or they don’t. If they don’t, there’s not much you can do. You can just say, “Well, our ranges work from X to Y. There are lows. There are highs. Are you somewhere in there?”

But at the end of the day, you cannot walk away from the conversation without having an understanding of the budget range therein, and most importantly, this is a question to ask late deep within the conversation. It’s not that you’ve wasted their time because you’ve asked all these other things and then there might be a miss. You don’t want to front-load the conversation with the budget because it’s not just about budget. It’s your job to understand them.

Ask these thoughtful questions so you can help guide your customers at a solution that’s right for them. If you give them exactly what it is they want and need, your close rate naturally will improve. When I say that there are three skills you have to be able to master to be good at sales (following up, listening, and asking thoughtful questions), asking thoughtful questions is most important. Nail this, and you will be a better salesperson. There are no bloopers here, folks. Got it? Yes, we got it.