<span id="hs_cos_wrapper_name" class="hs_cos_wrapper hs_cos_wrapper_meta_field hs_cos_wrapper_type_text" style="" data-hs-cos-general-type="meta_field" data-hs-cos-type="text" >The art of asking in sales</span>

The art of asking in sales

What’s up, fellow sales friends? If you’re in the B2B game, you know the grind—always dialing, always closing. But let’s be honest, sometimes we hit walls. The deal stalls, the prospect clams up, or maybe they don’t even realize there’s a better way. That’s where the art of asking the right questions comes in, not just to keep the conversation going.

Given my time around salespeople, I’ve learned that everyone has their own style, their own verbiage, and their own swag to how they pose these questions. However, the one common denominator between everyone is the need to dig deep and uncover the real gold—the hidden pain points and untapped opportunities. As Matt Bengtsson, Sales Executive at Aprimo, puts it:

“There is no sale without pain. Period. Pain drives everything. People don't buy features and functionality, they buy the solution to their pain. So in order to create value and build a business case, you need to first understand their pain points.”

Now, let’s get into the nitty-gritty of these questions and how they can light up your sales process, all while keeping those typical objections in check. Remember, it’s not just what you ask, it’s how you handle the responses and steer the conversation that turns prospects into partners.

Digging deep to discover pain points

Imagine starting your convo with, “What are the key challenges you are facing right now?” Sounds simple, right? But this question is your key to the kingdom. It’s not just about understanding their current headaches; it’s about revealing issues they’ve normalized or haven’t even noticed. When a prospect says, “We’re actually good right now,” that’s your cue to get specific. Mention a common pain point in their industry, and watch them think, “Wait, that’s a problem we have too!” It’s about making them see the problem that your product solves.

Moving along, when you ask, “Can you tell me about your current processes and how you handle [relevant topic]?” you’re doing more than making conversation. You’re sleuthing through their business model to pinpoint inefficiencies they may have overlooked. Objections might pop up like, “Why do you need to know all this?” Here’s where you play it cool and explain, “Just trying to see if there’s a way to make things smoother for you. No big deal, right?” This keeps the door open and lowers defenses.

Aligning goals and setting the timeline 

Getting into their goals with, “What are your short-term and long-term goals?” lays the groundwork for alignment. This isn’t just chit-chat; it’s strategic alignment. If they come at you with, “Our goals are evolving,” guide them gently to nail down something concrete, even if it’s broad. It shows you’re in it for the long haul, not just a quick sale.

It’s about making them feel in control while gently nudging the process forward.

Budget talks and beating the competition

Talking dollars can make folks twitch, but “What budget have you allocated for this project?” cuts to the chase. It’s about matching their budget to your solutions without underselling or overshooting. If they balk, shift the focus from cost to investment and value, emphasizing how this is not just a purchase but a growth catalyst for their business.

And let’s not forget the competition. Asking, “Have you considered any other solutions or vendors?” isn’t nosy; it’s necessary. Here, you’re setting the stage to differentiate yourself. When they play coy, lean in with, “Totally get wanting to keep cards close to your chest. Just want to make sure we provide something that truly stands out for you.”

Prioritizing decision factors and impact analysis

When you pop the question, “What are the most important factors you will consider when making this decision?” you’re essentially asking them to reveal their decision playbook. If they go vague, dig deeper. It’s your chance to customize your pitch to hit right where it matters. This is where Matt Bengtsson says: 

“...you need to understand pain very well in your discovery call to ultimately build value, then build a business case. This way, after you win over the team and they are pitching to leadership for budget approval, you can directly tie an ROI with your product.”

Lastly, tying it all together, “How will this purchase decision impact your general business operations?” shifts the discussion from theoretical to practical. It’s about painting a picture where your solution is already in their world, enhancing, improving, and revolutionizing. If they struggle to visualize, help them. Outline scenarios where your solution changes their day-to-day for the better.

Wrapping it up like a pro

There you have it—asking the right questions isn’t just about filling silence; it’s about filling gaps in understanding, aligning your pitch, and ultimately, closing deals that last. Objections aren’t roadblocks; they’re just detours on the path to “yes.” Each question you ask opens a new door. And remember, every answer, every objection is a stepping stone to deeper insight and stronger connections.

So, gear up, use these insights, and let’s get those deals flowing. You’re not just selling; you’re partnering, solving, and revolutionizing businesses one question at a time. 

What strategies have you found effective in your sales conversations?

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