Top Sales Discovery Questions to Ask in Your Outreach

Sometimes, sales can feel like guesswork. Even if you’ve identified your ideal prospect and managed to strike up a two-way conversation, it can be difficult to know if what you’re offering will be what they’re in the market to buy. 

The early stages of your outreach, also known as the discovery phase, are your prime opportunity to clear up the uncertainty around what your prospects need and how you can help them. Your prospects hold all the knowledge you need to correctly position your product or service, but to tap into that knowledge, you’ll need to guide them with the right prompts. 

“But, what are those prompts?!” We hear you cry.

We’ve got you covered. In this article, we’ve pulled together a list of our top sales discovery questions to make those initial conversations so much more efficient for you.

Need to skip ahead? We’ll cover: 

• Get to Know Your Prospect’s Business
• Identify Pain Points and Challenges
• Develop a Plan of Attack for Your Prospect

Get to Know Your Prospect’s Business

You can’t sell to your prospect if you don’t know anything about the company they work in, and the job they do. It’s best to ask these questions in your initial call to establish the nuts and bolts early on in the sales cycle. This might look like:

“Can you explain exactly what your company offers and how it differs from competitors?”

Why you should ask this: Understanding the mechanics of the company you’re selling to can help you identify where your product and service can elevate the customer experience, or help your prospect find new customers. By asking your prospect to specifically identify how they stand out from competitors, you can open a conversation around giving them a competitive edge through your product or service

“Who are your key customers and how do you reach them?”

Why you should ask this: This is one of the top sales discovery questions you can ask – but it’s often forgotten in initial calls. When you ask about a company’s customer base, you can tailor your pitch to the specific circumstance that your prospect’s organization needs.

“How does your job fit into the company structure”

Why you should ask this: Firstly, you’re opening a conversation around your prospect’s pain points. If your prospect is one member of a large team, they might feel isolated or that there are a number of hoops to jump through. While a member of a small team might be overworked and under-resourced. All of these clues are useful to you in developing the right pitch. Secondly, you are also starting to get a picture of which other stakeholders might be involved in the sign-off process for your sale.

Identify Pain Points and Challenges

It’s no secret that pain points are the crux of any sales cycle. When you understand these challenges, you can then position your product as the ideal solution, tailored to address their specific needs. By asking the right questions, you can gather valuable insights that will help you craft a compelling narrative around your offering, demonstrating its relevance and value. Some top sales discovery questions for identifying pain points include: 

“What are the biggest business blocks or challenges your team is currently facing?”

Why you should ask this: This question is a gateway to understanding the core pain points your prospect is dealing with. It allows you to identify the primary issues that are hindering their success, whether it’s inefficiencies in their workflow, gaps in their current technology stack, or other operational hurdles. Knowing these challenges helps you align your product’s features and benefits directly with their needs, making your solution not just relevant but essential.

“And how are you currently addressing these challenges? Are your current solutions successful?”

Why you should ask this: Focusing on the performance of any current solutions in place helps you identify gaps and areas where their existing tools fall short. It opens up the conversation for you to showcase how your product can bridge these gaps, offering superior functionality, better integration, or more robust support. Highlighting these differences positions your product as the more capable and comprehensive solution.

Develop a Plan of Attack for Your Prospect

As a salesperson, your job in the mind of your prospect is to stand with them side-by-side in business to help achieve their goals. When a prospect shares these goals and their strategic vision, you can tailor your pitch to show how your product can help them achieve their desired outcomes. This not only strengthens your value proposition but also builds a stronger connection with the prospect by demonstrating that you’re invested in their success – so they just might buy from you again! Our top sales discovery questions to understand a prospects goals include: 

“What are your team’s most pressing business goals for the next quarter/year?”

Why you should ask this: This question provides a clear picture of the prospect’s strategic priorities and long-term vision. Knowing their wildest business goals allows you to position your solution as a direct contributor to their success. Whether their focus is on growth, efficiency, innovation, or customer satisfaction, you can tailor your message to highlight how your product can support and accelerate these objectives, making it an integral part of their strategic plan.

“What would success look like to you?”

Why you should ask this: Asking this question helps the prospect articulate their vision of success, making their goals more tangible. It encourages them to think about specific outcomes and metrics that define success in their context. This visualization enables you to draw direct connections between your solution and their desired results, showing how your product can turn their vision into reality. By aligning your offering with their success criteria, you make it easier for them to see the value and impact of your solution.

Paint a Picture of the Process

Put down the brushes… Here, we’re talking about getting a clearer idea of your prospect’s decision-making process. Which key stakeholders need to be involved and consulted to get the deal signed off? Our top discovery questions for understanding the decision-making process are: 

“Can you walk me through your decision-making process for major purchases?”

Why you should ask this: This question is essential for mapping out the steps your prospect takes when making significant purchasing decisions. By understanding their process, you can identify key milestones, decision points, and potential bottlenecks. It also helps you anticipate any additional information or approvals required so you can keep on top of the sign-off stages and ensure the deal goes through smoothly.

“Who else will be involved in this decision?”

Why you should ask this: Knowing all the stakeholders involved in the decision-making process is vital for effective engagement. This question helps you identify key decision-makers and influencers who need to be convinced of your solution’s value. It’s also important to ask if specific teams, such as the tech team for security checks or the finance team for budget audits, need to be involved. Understanding these dynamics early on ensures you can address each stakeholder’s concerns and requirements, preventing potential roadblocks that could derail the deal.

Be Upfront With Budgets

Pursuing a prospect who doesn’t have the budget to buy from you can be a frustrating dead end. To avoid sinking countless hours into an unviable lead, you should address budgets early in the discovery process. While it might seem like an awkward conversation at first, addressing budgets head on can save you and your prospects precious time and energy. Our top discovery questions on budget are to-the-point, and give your prospect the opportunity to clearly set their expectations from the outset of the sales cycle:

“Is there a budget already allocated for this project?”

Why you should ask this: This question is fundamental for assessing the financial readiness of your prospect. Knowing whether a budget has been allocated helps you understand their commitment level and the financial parameters within which you need to operate. If a budget is already in place, you can tailor your pitch to fit within those constraints, making your proposal more attractive. If not, it may indicate the need for additional justification or ROI demonstrations to secure the necessary funds.

“How do you measure the ROI of your investments?”

Why you should ask this: Having oversight of how your prospect measures ROI allows you to frame the benefits of your solution in terms that resonate with their financial goals. This question provides insight into the metrics and benchmarks they use to evaluate success, whether it’s cost savings, revenue growth, efficiency improvements, or other key performance indicators. By aligning your value proposition with these metrics, you can demonstrate the tangible financial benefits of your solution, making a stronger case for its adoption.

Talk Through the Timelines

Getting an idea of how quickly your prospect can move in confirming a purchase helps you align their buying process with your sales cycle. While a prospect might be completely sold on your product right now, they could need more time to confirm the budget or rally the various stakeholders in their organization. Our top discovery questions to hash out the timelines are:

“How quickly do you need to implement a solution?”

Why you should ask this: Knowing a prospect’s timeline for implementing a new solution helps you prioritize follow-ups and align your sales process accordingly. If they need a quick fix, you can accelerate your efforts to meet their deadline. Or, if there’s more time to play with, you can pace your engagement and provide thorough support. Understanding their urgency ensures that your solution is positioned as a timely and relevant option, increasing its appeal.

“Why is addressing this issue a priority for you right now?”

Why you should ask this: Understanding why the issue is a priority helps you grasp the underlying motivations and pressures driving the prospect’s purchase decision. Armed with this extra insight, you can tailor your pitch to emphasize the immediate benefits of your solution. Whether it’s due to a looming deadline, competitive pressures, or internal goals, knowing the reasons behind the urgency helps you align your messaging to resonate with their current priorities.

Let’s Wrap it Up!

The discovery phase of the sales cycle can be a bit like dating. You have to find out early on whether your prospect is a good fit for what you’re selling to avoid wasting time and resource on courting them. But, with the right sales discovery questions, you can get to know your prospects and their pain points quicker, so you can focus on tailoring your outreach to meet their needs.

Frequently Asked Questions (FAQs)

What types of sales questions should I ask in discovery calls?

Use discovery calls to find out more about the prospect’s business and their role, their budgets, the sign off process and their timelines for purchasing from you.

How can I improve the questions in my discovery calls? 

Failing to prepare is preparing to fail. Make sure you’ve done your research into your prospect and their market, and ask open questions to encourage a good flow of conversation.

What are the top sales discovery questions I can ask to help me make more sales?

Ask questions that help you understand more about the viability of the lead based on their budget, the efficiency of their sign off process, their pain points and their timelines.