Most people view Sales as the people with “slick answers.” When a prospect asks a question, a sales team might know how to take it, turn it on its head, and convert the prospect into a customer before anyone knows what happened.
But that’s not what modern sales look like.
It’s about problem-solving and product fit. Rather than overly slick answers that pretend your solution is one-size-fits-all, you should instead ask questions that make the prospect stop and think. Because it’s in those moments that you make genuine connections.
“Questions allow us to fill in the blanks on what we couldn’t find in our prep,” says Jen Allen-Knuth, founder of Demand Jen. “They create a two-way conversation (vs. a seller presentation.”
So stop presenting like you’re alone in the room. The days of Don Draper are gone; you won’t do much selling if you’re working from presentation boards and expecting your lead to tag along like a passive observer.
It’s about communication, which is acommunication is a two-way street of deliberate problem-solving and well-framed questions.
Here we’ll break down what great sales questions sound like, why most salespeople resist using them, and how to flip your discovery process from passive to precise.
The Two Big Mistakes Salespeople Make When Asking Questions
Asking Lazy Questions that Shift the Work to the Buyer
A good rule of thumb is to avoid questions that ask your prospect to do all the work.
A question like “What are your biggest priorities?” forces the buyer to do all the cognitive heavy lifting. Suddenly, they feel like they have to come up with several answers to your question.
But what if they showed up at your business because they have one big problem they wanted to solve? Your question assumes the wrong frame from the beginning.
So stop with the open-ended questions. “Showing up to a call with ‘so, what’s the team working on?’ makes the buyer do the hard work,” says Jen. “It’s on us to come with a specific point of view, based on our research, and use questions to seek to be corrected.”
In other words, do the homework before you ask the questions. See if there are spots where your prospect might correct a faulty assumption.
Be specific with these questions. Specificity builds trust and accelerates your learning. “A correction equals new information,” adds Jen. “New information equals discovery.”
Don't start with open-ended questions if you’re thinking like a communicator and not a presenter. That’s essentially an invitation for your prospect to do your work. Lead with specifics—lead with the homework you did—and allow a prospect to correct you if your assumptions were faulty.
That’s how you get answers that are truly important to them.
Avoiding Questions Because We’re Afraid of the Unknown
We feel safer if we bring slides, stats, and case studies to our sales pitch. It’s like working with a safety net. But feeling competent is different than being competent, especially in sales.
“When presenting or sharing slides, we often feel like we’re ‘in control’ of the conversation,” says Jen. “When we ask a question, we open ourselves up to the unknown. That can be intimidating for newer sellers.”
The problem is that intimidation sometimes makes us want to shut down. And that shows up in our self-confidence. If we enter conversations expecting rejection, prospects often pick up on those vibes. A question as simple as “how can I help you today?” can begin to tank the interaction from the outset if it’s dripping with uncertainty.
Sales reps should welcome uncertainty. The customer wants to solve that uncertainty, after all. So that’s where the sale is probably hiding. Don’t think of questions as ways of opening uncertainty, but resolving it. Ultimately, that allows you to venture into the unknown with your prospect.
If it feels less like a sales pitch and more like a team attacking a problem, you’ll ask far better questions.
The Anatomy of a Great Sales Question
Use Point-of-View Questions That Invite Correction
Did you like pop quizzes in school? Probably not. Pop quizzes could fill us up with anxiety and get our palms sweating.
It’s the same in the sales process. If you approach your customer with a pop quiz—an open-ended question that invites them to deliver an impromptu essay—it can rub people the wrong way.
They’re going to say: Wait—aren’t they supposed to be the ones with answers? Why am I doing all the heavy lifting?
So if you want to come up with great sales questions, reverse it. Rather than asking vague, open-ended questions that invite them to do work, do some work yourself.
Start with a hypothesis.
Jen offers a powerful format for making this work:
“I don’t work within your four walls, but it seems like (Acme) is focused on moving upmarket with companies outside of SaaS…what did I get wrong?”
Notice a few things about this “hypothesis” format:
- It’s specific to their needs. It addresses industry-specific issues (“moving upmarket with companies outside of SaaS”) that show you’ve done your homework.
- It’s willing to be wrong. Phrases like “it seems like” allow for the possibility that your third-party perspective isn’t correct. That’s fine; communication is often about throwing darts at a board and asking if it was a hit.
- Pass the baton. Show you’re willing to be corrected with a negative question (“What did I get wrong?”). After all, that’s the point of asking probing questions.
The inherent tension of throwing out an incorrect idea is part of what makes your pitch more compelling. Either your prospect feels you “nailed it”—in which case, you’re off to the races—or they feel compelled to correct you.
Stop fishing for the “right” answer; instead, provoke a correction that reveals something you couldn’t have otherwise known.
Ask for the Roadmap, Not Just the Pain Point
Great salespeople will identify the prospect’s pain, true. But they don’t stop there. They keep digging for the process, internal politics, and company roadblocks that have made the journey so hard in the first place.
Ever hear the phrase “you can just do things”? It works in sales, too: you can just ask for things.
A few examples:
- “What’s it going to take to get this deal done?”
- “Help me out here. What am I not getting?”
- “If I said I can solve your problem with ____, what’s the obstacle you would warn me about?”
The goal is to unlock actionable next steps. Whether your prospect replies with an obstacle or a resounding “Let’s do it,” you’ve made progress. These are the kinds of questions that will also help you build alignment and speak specifically to the obstacles that are in their way.
Add Time Pressure with “Worth Solving Now?”
Maybe a prospect agrees that you’ve hit the nail on the head: you’ve figured out their problem. But maybe that problem isn’t quite urgent yet.
Without urgency, your pitch won’t be quite as compelling. It can be a pitch they bookmark for later—but they file that bookmark in their “backburner” folder.
As a result, you get ghosted. And you can’t figure out why.
To solve this, Jen recommends two of her favorite closing questions from Mor Assouline:
- “Based on what we covered today, is this a problem worth solving?”
- “Is it a problem worth solving, now?”
Notice that both questions hint at urgency. And while it’s true that the prospect may answer “no” to the latter question, Jen doesn’t mind that. She says, “If I get a ‘no’ there, it opens up the ability for me to ask deeper ‘why?’ questions.”
Avoid These Common Question Pitfalls
Yes/No Questions That Don’t Reveal Anything
Ever go to a wedding and roll your eyes as the DJ asks the crowd: “Who’s ready to dance?”
The answer is too easy. “We are. We are ready to dance. Just play the music, will you?”
You should similarly avoid yes/no questions that don’t reveal much about your customers. Don’t ask them, “Are you trying to increase revenue?” It sounds specific—revenue is a number, after all—but since everyone wants more revenue, it’s actually quite vague. Similarly, the question is, “Do you want more efficiency?” We all do.
“They’re too general,” says Jen of those yes/no questions. “What company is not trying to do those things?”
So instead of asking yes/no questions, ask “W” questions: who, what, where, when, and why. Rather than asking, “Are you the key decision-maker?” you can ask, “Who else would weigh in on this if your company were to move forward?” Now you can work with specifics and overcome those obstacles.
Fake Objections and the Lies Buyers Tell
Unfortunately, not every prospect is a perfect prospect. Some might be probing a few solutions online and aren’t ready to buy.
You should ask questions to test for authenticity. After all, most people probably won’t tell you if they’re not. They’re perfectly content to let you think there’s a potential sale there.
Some prospects throw out fake objections about why they can’t buy now. They turn to this “bag of tricks” if they know a salesperson will immediately rule them out.
To deal with these issues, you’ll want to try a couple of things:
- Build a repertoire for handling these objections. For example, build your own FAQ doc so you can ask pointed questions if you get frequent objections, like “I don’t have the budget right now.”
- Be willing to ask for the sale. If you do get that objection—low budget—then ask questions that demand a specific response. “What kinds of returns would you need to see to justify spending XYZ per month?”
Avoiding the Elephant in the Room
The scariest questions are sometimes the most necessary. Be willing to take on the “elephant in the room” if there is one. That’s where you can end up saving the most time.
“We don’t want to hear bad news,” says Jen. “But every time we let these deals fester, we run the risk of wasting time on a deal that never converts.”
It’s a self-fulfilling prophecy. In an effort to avoid our worst fears—losing the sale—we make sure we lose the sale on a longer, more painful timescale. No one wants that.
Jen offers an antidote: lean into these hard questions. Ask something like:
The faster you get to the truth, the faster you’ll protect your time.
How to Get Comfortable Asking Tougher Questions
Build Conviction First, Then Ask Better
Sales can be emotional work. You’ll get ghosted a lot, and you'll be tempted to take that personally.
Our solution? A consistent process.
If you do get ghosted, go back to your process. Log the experience and look for feedback. See what you could have done differently. Even if the lessons of the broken sale are hard, you’ll come up with better questions to ask the next time. That builds confidence and conviction until you feel that you’ve “seen it all.”
Let Buyers Teach You
You don’t have to be the know-it-all salesperson with a slick answer for everything. In fact, it’s probably better that you aren’t.
“It’s perfectly okay to admit when we don’t know a specific term or need more clarity on an answer,” says Jen. “Responding to ‘Can you help me understand…’ is far better than pretending like we know what they’re talking about.”
You don’t need a flawless reputation, after all. Those don’t exist. But you do need a reputation for honesty.
Use a Strong Opener that Connects to Business Priorities
Jen says she’ll often open with a pointed question:
It seems like your company is doing X…what did I get wrong?
This flips the focus away from the features of your product. Instead, you’re now having a business strategy session. You’re not trying to “double their revenue” or “double their efficiency.” You now sound like an internal employee who’s addressing specific problems with their company.
This helps build buy-in from your prospects. There’s something more trustworthy about someone who’s willing to dig into a problem right alongside you, getting their hands just as dirty, being willing to admit what they don’t know.
When it comes time to frame your product as part of their next company initiative, they don’t feel like they’re “buying” from you. They feel more like they’re partnering with you.
Discovery Isn’t About Your Product, But About Their Truth
The biggest misconception in sales is that the goal of a discovery call is to sell, sell, sell.
Sure, sales are important. That’s ultimately what you’re there for. But in the discovery conversation, that’s jumping the gun.
“The goal of a discovery conversation isn’t for the prospect to discover more about our solution,” says Jen. “It’s to help the prospect discover more about their own business.”
If you do that right, you can ask questions that will unlock genuinely useful insights. And when you do, the customer will already have evidence that you’re the one who can help solve it.
After all, you were the one with all the good questions.
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