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The discovery phase: 10 questions every sales rep should ask at the start of the sales process

September 13, 2021
B2B sales organizations have been through the ringer these past 18 months. Tried and true sales processes were turned upside down as sales organizations struggled to navigate entirely new working environments. 

“What worked yesterday may not work today or tomorrow,” wrote Harvard Business Review co-authors Andris A. Zoltners, PK Sinha, and Sally E. Lorimar in a column discussing how the pandemic had disrupted the linearity of sales process execution. “A more organic, flexible, and creative approach to customer engagement is needed.”

Early conversations within the sales process have always been potentially awkward, but now with so much uncertainty on so many levels, it’s difficult to know which creative sales approach will best work with any given prospect. 

Even as working environments have begun to settle, and sales consultants have become better equipped to manage the challenges of this new normal, it’s clear the discovery phase is still crucial to the sales experience, moving prospects further into the sales funnel, and giving sales teams the information they need to negotiate terms, and, most importantly, close the deal. 

The questions you ask during the discovery phase enable you to design a tailored sales experience and build personalized demos that shorten the sales cycle, increase win rates, and accelerate revenue.


Why the discovery phase is key to solution-based selling

Discovery phase questions are core to a solution-based selling approach, a sales model that, according to McKinsey, separates the outperformers from the laggards: “Companies strongly or moderately effective at solution selling are 1.5-times more likely to be outperformers.”  

According to McKinsey, separates the outperformers from the laggards: “Companies strongly or moderately effective at solution selling are 1.5-times more likely to be outperformers.”

Why are solution-based sales methods so successful? Solution sellers focus on the customer versus focusing on the product. 

But to be successful, a solution-based sales approach relies on the sales team having a deep understanding of the prospect — their role within their organization, the challenges they face, and their industry at large. This is where the discovery phase becomes integral to the overall sales process. 

By asking the right questions during the discovery phase, you can unearth the very details that enable a solution-based sales experience tailored to each prospect. 

So how do you build an effective discovery phase that allows you to identify your prospect’s primary struggles?

It starts with asking better questions. 

10 questions every sales consultant should ask at the start of the sales process

1. "Can you tell me more about your role and the biggest challenges your team is currently facing?" 

Goal: To determine the prospect’s decision powers and level of authority when it comes to signing contracts, as well as gain insight into the company’s evaluation process when purchasing software.

Asking someone to share more about their role and the issues they face day-to-day immediately puts the focus on the customer and sets the stage for a solution-based sales process. 

Not only does it open the door to a deeper conversation about the prospect’s primary challenges, it offers you the chance to embrace a service-oriented mindset. 

There is always the possibility that certain challenges they may have are something you can speak to, giving you the opportunity to instantly add value to the relationship. 


2. "How are you addressing your primary challenges right now?" 

Goal: To learn more about the organization’s current technology maturity level and ability to implement software solutions: Is this an organization that has a full tech stack? Or, are they just beginning to build out their technology architecture?  

Be sure to take notes because this can be the most insightful question you ask. 

Knowing how a customer responds to challenges enables you to tailor your product demo so that it fits into their existing workflows. 

It also helps you better understand the bigger picture, offering a glimpse into how the prospect’s business unit is structured and who the other stakeholders may be. 

The goal is to identify exactly how your solution will save the prospect time and money, but there is also the possibility that you could turn a problem they may have into a major value prop depending on their current work processes. 

3. "How familiar are you with our product and company — was there a specific feature or function that caught your attention?" 

Goal: To quickly identify how your software can address the prospect’s needs, while also gaining a high-level overview of the prospect’s knowledge about your software’s capabilities. 

This question allows you to jump right to what matters most to the prospect. 

No one wants a ten-minute talk to hear details they already know. In fact, Gartner’s research found that B2B buyers spend only 17% of their time evaluating a product with the seller. 

Gartner’s research found that B2B buyers spend only 17% of their time evaluating a product with the seller. 

“The ready availability of quality information through digital channels has made it far easier for buyers to gather information independently, meaning sellers have less access and fewer opportunities to influence customer decisions,” reports Gartner. 

“The ready availability of quality information through digital channels has made it far easier for buyers to gather information independently, meaning sellers have less access and fewer opportunities to influence customer decisions,” reports Gartner. 


By asking your prospect what they know about your product and company, you maximize the limited time you have with them and springboard over the minutiae, as well as correct any product information they may have wrong. 

4. "If you could create a dream solution, what would it be?" 

Goal: To capture a clear view of the prospect’s primary need so that you can build a sales demo that perfectly aligns with their expectations. 

By asking prospects to define their dream solution, you initiate a larger conversation about how your product alleviates a specific pain point and could positively impact the prospect’s role, responsibilities and broader business outcomes. 

If you know from the start your product can solve their problem than you have a blueprint for building a tailored product demo, narrowing the scope on the features that speak directly to the prospect’s “dream” solution.

5. "What are your primary roadblocks right now?"

Goal: To identify any potential obstacles you may face during future conversations and address them before they interfere with or stall the sales process. 

Every sale has its own unique challenges, and many are connected to the roadblocks your prospect is already facing. 

Lack of budget, lack of employees to manage workflow processes, or lack of skills among the current workforce are all roadblocks you may be able to address during your sales demo. By identifying these issues during the discovery phase, you have an opportunity to better personalize the sales experience and create a frictionless sales process.  

6. "What happens if you don’t fix the problem?"

Goal: To find out how much the problem is costing — or could cost — the prospect and their team, and how much of an impact your solution will have on the organization.

Everyone wants to be the hero within their team or organization at large. If you can identify not only the problem your prospect is facing, but it’s potential cost to the company, you have the information you need to demonstrate the long term value your solution offers.

It’s always good to have an immediate impact. But when you can show how you can save the prospect time and money, you’re offering them the chance to be the employee who saved the day, or quarter (maybe even the year). 

7. "How many other people will be involved in the purchasing decision?" 

Goal: To determine how many people you will need to win over during the sales process, and, most importantly, who will have the final say when signing the contract. 

A 2021 B2B Buying Study by Forrester surveying more than 950 respondents from around the world found that 63% of B2B purchases included more than four buyers total, with roles ranging from, “Champions, influencers, decision-makers, users, or ratifiers — from multiple departments.” 

Gartner found that 63% of B2B purchases included more than four buyers total, with roles ranging from, “Champions, influencers, decision-makers, users, or ratifiers — from multiple departments.” 


“Despite most buyers working remotely, this year has catapulted the buying group to the forefront,” writes Forrester VP, principal analyst Beth Caplow. 

The reality is, you rarely sell to a single person within an organization, and the sooner you know how many people will be involved within the sales process, the better you will be able to manage the sales experience.

(Did you know Demostack allows you to share your demo after the call and captures the email of everyone who uses it?) 


8. "Where are you in the decision making process?" 

Goal: To ascertain how critical of an issue the prospect’s problem may be, and how rapidly your sales organization will have to act to win the deal. 

Before the discovery phase, it’s difficult to know how close the prospect is to making a decision. Having this insight early on in the sales conversation helps you build a timeline that aligns with the prospect’s schedule. 

According to Sales Hacker, enterprise sales cycles for six-figure deals typically last seven or more months, and takes a concerted effort on both the seller’s and buyer’s side to negotiate and close the deal. 

According to Sales Hacker, enterprise sales cycles for six-figure deals typically last seven or more months, and takes a concerted effort on both the seller’s and buyer’s side to negotiate and close the deal. 


“The emphasis on process becomes more important as the odds of closing the deal diminish,” writes Miles Varghese on SalesHacker.com

When you are managing a seven-month long sales process, it is imperative you know how close the prospect is to making a decision in order to keep the conversation moving forward. Even if your solution does not necessitate a seven-month sales cycle, this insight is still a critical detail to help expedite the deal.  

There’s a chance your prospect may be in dire need of a solution, and ready to make a decision now instead of later. You could beat out the competition simply by making sure the sales cycle moves forward as efficiently and as quickly as possible. 

9. "When do you hope to have this solution up and running?" 

Goal: To create a “low-effort” buying experience based on the prospect’s timeline and objectives. 

According to a recent Gartner report on revving up B2B sales growth this year, sales teams need to overcome any organizational complexity on their part by creating a “low-effort” buying experience. 

Gartner’s research found that 77% of B2B buyers said their latest purchase was “very complex” or “difficult.”

Gartner’s research found that 77% of B2B buyers said their latest purchase was “very complex” or “difficult.”


“As hard as it has become to sell in today’s world, it has become that much more difficult to buy. The single biggest challenge of selling today is not selling, it is actually our customers’ struggle to buy,” writes Gartner distinguished VP, Advisory Brent Adamson.

A quote from Brent Adamson, distinguished VP at Advisory: "As hard as it has become to sell in today’s world, it has become that much more difficult to buy. The single biggest challenge of selling today is not selling, it is actually our customers’ struggle to buy."


If you know the customer’s expected timeline, you can develop a Mutual Action Plan that helps set expectations for the sales journey, making the sales experience as low-effort as possible on the buyer’s side. 

10. "Is there anything I didn’t cover today that you hoped to hear?" 

Goal: To make sure the prospect has all the information they need so that they’re ready to move to the next step of the sales cycle. 

All too often a discovery call ends without the prospect having all the information they need to take back to other stakeholders and move further into the sales funnel. A simple question that could be answered in seconds over a phone call leads to multiple back-and-forth emails that can span over weeks, stalling the sales process.

Worse, there’s a chance a prospect will simply fall out of the sales funnel because they don’t have what they need to make an informed decision and move further into the sales cycle. 

Asking a prospect if you have covered all of their questions enables you to end the call on a high-note, and address any issues that you may have missed during the conversation.  

Building a winning discovery phase: a quick-start action plan   

Remember, discovery phase questions are meant to pull the curtain back on all the ways you can show value to your prospects. 

The information you garner from the prospect should help you personalize the sales experience and build product demos that directly address your prospect’s individual needs and primary challenges. 

Today’s sales consultants and account executives face so many challenges. 

Initial sales conversations that used to be an afterthought are steeped in time-consuming tasks: Identifying the right stakeholders, connecting with the right prospect on the right channel, bringing all the decision makers together on the same Zoom call, all while managing the technical difficulty du jour —  it is A LOT. 

An effective discovery phase helps eliminate challenges, giving you insights you need to craft product stories that resonate with your prospect and win deals faster.


Tips for building a successful discovery phase: 3 steps you can take today  

  • Begin building a list of “Discovery Phase” questions so that you have a starting point whenever you kick-off a sales conversation.
  • Use social media polls to keep a pulse on what’s going on in your industry and how the market is responding so that your Discovery Phase questions are not only relevant, but timely.
  • Start an archive of reports, studies and news articles that give you a deeper understanding of your target industries to better speak their language and ask more relevant questions.  

Schedule a call with Demostack now to see who we’re helping B2B enterprise organizations build tailored demos that boost productivity and accelerate revenue.