B2B Bevelroom Consulting Team brainstorming data customer insights

Unlock B2B Sales Growth in 2024 With Data-Driven AI Questions [With Examples]

Since this article is about questions, let’s start with a question:

Do you know what the most in-demand business skills will be over the next 5 years?

According to the World Economic Forum’s latest Future of Jobs report, most of the top 10 skills are related to asking better questions. Those skills include analytical and creative thinking, curiosity, and leadership.

We believe that asking better questions of your teams, data and the world around you are beneficial, no matter what business you’re in. In particular, asking better questions, and asking them earlier than your competitors, helps you to ‘punch above your weight’ competitively.

The answers to those questions are what you need to boost your team’s Customer IQ, develop more differentiated value propositions, and keep customers happy. These are some of your best sources of competitive advantage.

The best questions can help you reframe problems in unexpected ways. They encourage fresh viewpoints and diversity of thought which leads to better solutions. Well-crafted questions have the power to inspire the exchange of ideas and fuel innovation.

Here we discuss some of the ways to ask better questions in your business to gain advantage and boost performance.

What's Covered in This Guide

Asking ‘Why’ to Explain Behaviors and Discover ‘What Could Be’

One of our favorite experts in the psychology of business is Rory Sutherland, Vice-Chairman of Ogilvy UK, one of the largest and most respected advertising agencies in the world. Sutherland co-founded a behavioral science practice at Ogilvy that applies behavioral economics and psychology to solve problems that traditional advertising agencies haven’t been able to solve. He is also the author of Alchemy: The Surprising Power Of Ideas That Don’t Make Sense.

In one of Sutherland’s many presentations, titled Billion Dollar Behaviors, he makes a compelling case for why businesses should put more emphasis on understanding the ‘why’ behind customer behavior, rather than just relying on the ‘what’ from analytics.

In the presentation, Sutherland discusses an idea from behavioral scientist, John Kenny, that the results of the most successful organizations can be likely attributed to behavioral vs. technological explanations.

Most businesses spend a great deal of time measure results, the ‘what’ of business performance in KPI dashboards. The problem is that they usually stop there and fail to consider ‘why’ those results are occurring.

As Sutherland summarizes, the problem is that in business and institutions today, there’s “too much Taylorism and not enough Druckerism.” In other words, there is too much reliance on hard data and “quantification of what already is” without creative exploration and experimentation to find “interesting causation” and “what could be.”

Asking “why” something occurs generates far more valuable insights and creative ideas than simply compiling data about “what” is happening.

What Would Be Best for Our Customers?


“We’re not competitor obsessed, we’re customer obsessed. We start with what the customer needs and we work backwards.”
– Jeff Bezos

We love this quote because it sums up the customer-centric approach to business.

There are many reasons behind the growth of Amazon over the years. That said, there is good reason why ‘Customer Obsession’ is at the top of their list of leadership principles.

Being customer obsessed can be a source of competitive advantage in a lot of ways across a mammoth enterprise such as Amazon, a B2B service business with just a few employees, or just about any type of organization in between.

It starts with continually asking one question:

what would be best for our customers?


There are lots of scenarios where this question can help anchor all decisions and behaviors in your business to a focus on the customer, such as:

  • Expanding a product line, or launching a new service

  • Designing a website or app

  • Choosing the best sales and service channels

  • Growing or right-sizing your people strategy

  • Planning a merger or acquisition


Recently, we were working with a client on the best approach for a website redesign. After much deliberation without a clear decision, we asked the team: “Okay, put yourself in the shoes of the customer. What would they want to see here? What content would be helpful, and what would they want to do next?

It was really helpful to identify and agree on the right moves to make in everyone’s minds. It also would serve as a strategic filter on future decisions.

Amazon’s ex-CEO Jeff Bezos was famous for having an empty chair at company meetings. The chair represented the customer, “the most important person in the room.”

This practice is a powerful way to remind teams that even though the customer isn’t in the room, they still matter, and it’s everyone’s job to make sure the customer’s voice is heard and accounted for. Just about every decision made inside the business potentially impacts the customer in some way or another.


Customer-Centric Strategies Tailored for B2B Service Businesses

Get our step-by-step approach for developing a B2B demand generation strategy and system for growing service-based businesses that is customer-centric, insight-driven, digitally enabled and adaptable for future growth.

Defining Your Ideal Customers and Target Markets

Do you know ‘who’ your ideal customer is, ‘what’ triggers their search for solutions like yours, and ‘why’, ‘how’ and ‘when’ they go about selecting them?

Defining ideal customers tends to be really hard for some service businesses because they want to do everything, they can to grow the business.

It’s understandable to want to grow anyway you can. But can you really afford to spend on go-to-market efforts that don’t match your best customers for growth? Do you have unlimited budget?

This lack of focus on the best customers for your business translates to dull value propositions and vaguely targeted, ineffective demand generation. In short, you end up burning cash and team effort in areas that don’t benefit the business or customers.

So how do you find out who your ideal customers are, and how to target and convert them? 

Your sales and customer success teams and your CRM systems are goldmines of knowledge as to which industries and company profiles fit best with your offering. Dig into these sources to choose who you should target.

Find your 80/20 customers

Not all customers are equal. If the 80/20 rule is playing out in your business, 20% of your customers produce 80% of your value. Your goal should be to zero in on these 20% of customers who are essential for your business’ prosperity.

Ideal customers that represent the biggest chunk of business value usually share some common ‘fit’ characteristics, some of which are more important than others, depending on your business model.

Look for patterns that indicate why some customers represent a disproportionate share of your business results. Examine your current customers and identify the common characteristics that they share. This includes factors such as company size, industry, location, and revenue.

Start with evaluating current engagements to define common characteristics of high-value clients. Value = the cumulative direct (engagements) and indirect (referrals) profit that each customer can generate over their lifetime as a client. This can be hard to calculate, so use your best estimate.

Questions to define your ideal customer profile (ICP)

We suggest starting by answering these fundamental questions to begin visualizing your ideal customers:

  • Which customer types are most important for future growth?

  • Which one or two types of deals have generated the most business value?

  • What do we need to know more about to get more of these customers and deals?


Read more:

A Customer-Centric Approach to Creating a B2B Ideal Customer Profile (ICP)


Generating More Explanations and Strategic Opportunities

There is no shortage of research and best practices around fostering data-driven organizational cultures. The benefits are well documented: faster, better decision making, boosted productivity, top talent acquisition, enhanced innovation and customer-focus to name a few.


But what about curiosity?

Simon Brown, Partner, Talent, with EY and Author ‘The Curious Advantage’ & Podcast Host

says that in the era of AI, “nurturing curiosity will be crucial not only for our professional success but also for our ability to adapt and thrive in an uncertain world.”

Curiosity encourages asking “why” and exploring unanswered questions. This can lead to uncovering hidden trends, unexpected correlations, and entirely new avenues for investigation within the data itself.

Asking those ‘why’ questions dramatically increases the likelihood of generating completely new solutions. Without that curiosity, it’s easy to get to stuck into a rhythm of defaulting to the first sufficient explanation that data may show. Failing to question data can lead to wasted effort and misdirected investments into the wrong strategies.

Businesses that dig deeper beyond the surface level of what, how, where, when, are the ones that generate differentiated, un-considered explanations for what’s happening in the world.

Unpacking and Predicting Customer Behaviors

Understanding your customer’s true motivations for buying your services is a very useful insight that most businesses don’t fully appreciate. This includes the problems they’re trying to solve, the goals they’re trying to achieve, and the pain points they’re experiencing. This also includes what’s holding back buying decisions.

The B2B customer journey for business buyers has been evolving for a number of years and tends to be a lot less predictable than your sales process. Why? Because by the time a buyer decides to contact your company, they have already completed at least two-thirds of their buying decision process.

The modern B2B buyer is very self-reliant with access to more information than ever before. They are doing a lot of self-research and vendor comparison before their first interaction with your brand. Their expectations are shaped by best-in-class experiences they enjoy as consumers.  They expect answers to their questions easily, immediately and on their terms.

They expect a personalized approach to understanding their business and delivering tailored services that caters to their unique needs and challenges.

They have considerable choices of media and information, and so many ways to learn, long before a sales contact. Their behaviors and decisions are influenced more by their expectations and social proof, vs. your advertising and sales pitches.


Consider the following:

  • At least two-thirds of a B2B buyer’s journey is completed prior to them contacting the company.

  • 7 out of 10 of potential customers aren’t ready to buy and 8 out of 10 marketing leads don’t convert into sales.

  • Even when they are ready to buy, 40% of qualified deals won’t close, usually because of a mis-match between problem and solution.


These are very positive trends, and opportunities for progressive service businesses that know how to use customer-centricity for advantage.

You’re not able to influence the majority of your buyer’s process – until you know the right questions to ask.

A great place to start is by asking prospects and customers questions designed to reveal and unpack their unique bundle of motivations and the context that shapes their behaviors. Then, align your entire business model – market selection, solution design, go-to-market, sales processes — to match it as closely as possible.  


Buyer context is as important as motivations

Most solution providers don’t fully appreciate the personal stakes involved and the emotional factors at play in business buying decisions. This is especially the case for buyers with low problem and solution awareness.

Think about the last time you shopped for something you knew very little about. How did it feel? Was it hard to find trustworthy information that guided you to the right purchase decision? Were you confused by all the solutions and claims that were hard to compare?

Now imagine that the success of your department, or even the entire company, depended upon you making the right purchase decision. The consequences of these series of small decisions might last years and cost $ millions. The stakes can be pretty high for your buyer and the buying team.

When you deeply understand customer context and motivations, you can create more compelling offerings and personalized experiences that buyers will appreciate. You may need to change how your sales team relates to customers. Have them shift into a more consultative, sense making advisor role.

Keep in mind that buying decisions in B2B, as in consumer markets, can be influenced by a variety of factors, including practical needs, emotional desires, and social pressures, and these can evolve over time. Use this knowledge to enhance your marketing efforts, improve customer satisfaction, and gain a competitive edge.

Combine Customer Intelligence and Digital Analytics to Unpack the ‘Why’ Behind Motivations and Behaviors

Digital analytics are great for determining the ‘what’, ‘where’, ‘when’ and ‘how’ of customer behaviors. However, quantitative analytics methods usually fall short on explaining ‘why’ people do what they do.

Clicks alone cannot explain a person’s motivation and intent, and they don’t provide a lot of context about their lives, work and drivers of behavior.

Combine digital analytics with VOC

Answering questions of surface analytics with qualitative customer behavioral research can present opportunities to generate some very powerful predictive and strategic business planning insights such as:

  • Developing and delivering more compelling offers
  • Understanding why prospects are not yet customers and how to better convert them
  • Determining the best services and features to launch
  • Forecasting business performance based on motivational factors and sales pipelines

In a recent client engagement, we helped a cross-functional group in healthcare combine quantitative data (clinical visits) and qualitative (patient feedback) insights in a way so they can reinforce one another.

We started with digital analytics to uncover clues that led to a hypothesis that we then further explored and tested by talking to customers. We later explored and tested new solutions informed from persona and journey research that we then verified through digital analytics post launch.

The Power of Open-Ended Questions

Mastering the art of asking open-ended questions is a cornerstone of successful selling. They spark conversations, uncover needs, and ultimately build stronger client relationships.

Here are some scenarios where open-end questions can be a game changer for your selling process.

Pre-Sale Discovery: Unveiling Known Needs and Un-Considered Factors

  • Understanding Pain Points: Closed-ended questions confirm basic needs, but open-ended ones delve deeper. Asking “What are your biggest challenges with [current process]?” exposes underlying pain points and frustrations the prospect might not readily volunteer.
  • Identifying Opportunities: By asking “How would an ideal solution look for you?” you go beyond features and explore the prospect’s vision for success. This unveils opportunities to tailor your product or service to their specific needs.
  • Identifying Un-Considered Factors: The right questions open the door to new insights into un-considered, un-met needs or a new way of framing challenges that helps the buyer realize that their situation is different than previously assumed.
  • Building Trust: Open-ended questions show genuine interest in the prospect’s situation, fostering trust and rapport. They create a collaborative environment where the prospect feels heard and valued.


Presentation and Negotiation: Addressing Concerns and Building Value

  • Clarifying Needs: Open-ended questions like “Can you elaborate on what you mean by [specific concern]?” help clarify objections and ensure your solution truly addresses them. This avoids misunderstandings and strengthens the value proposition.
  • Tailoring Solutions: Asking “What are your priorities when considering a solution?” allows you to highlight features that align with their specific needs. This demonstrates a customized approach and increases the perceived value of your offering.
  • Collaborative Problem-Solving: Phrases like “How can we work together to overcome [obstacle]?” transform the negotiation into a collaborative effort. This fosters a sense of partnership and positions you as a trusted advisor, not just a salesperson.


Post-Sale and Client Relationship Management: Building Loyalty

  • Understanding Satisfaction: Don’t settle for “Yes” when asking “Are you happy with our product/service?” Instead, ask “What aspects of our solution have been most beneficial to your business?” This provides valuable feedback and allows you to continue exceeding expectations.
  • Identifying New Needs: Asking “Have any new challenges emerged since we last spoke?” shows proactiveness and opens doors to identify new opportunities to serve the client. This fosters a long-term, mutually beneficial relationship.
  • Ensuring Value Delivery: Open-ended questions like “How can we further optimize our solution to meet your evolving needs?” demonstrate your commitment to their success. This builds loyalty and increases the likelihood of recurring business and positive referrals.


Asking Better Questions of AI Tools

Going back to the top of this article, another increasingly important skill in business will be knowing how to use generative AI tools. Generative AI is transforming marketing and sales processes across industries to disrupt business models and generate value for businesses and customers alike.

Getting the most out of these tools requires you to supply well-defined prompts and ‘questions’ for the AI bot.

In this sense, working with a generative AI bot is a lot like working with people to brainstorm or solve a problem. The better your questions in a team setting, the quicker and better suited the new ideas will be to the objective.

Likewise, a poorly defined AI prompt leads to ambiguous or irrelevant outputs.

Well defined prompts should include context about your business, target market, competitors, and current challenges. Propose ideas and ask the AI what it thinks, or how it can improve on the ideas.

For a guide to writing better generative AI prompts, we recommend these resources:


How to Practice Asking Better Questions

Look for opportunities to practice asking questions in your business.

Here are a few methods we like to use.


5 Whys

The 5 whys method originated in Japanese auto manufacturing and is now widely popular in design thinking. Asking ‘why’ in a structured way can be an incredibly effective and versatile method to uncover root causes of problems, to dig deeper into underlying motivations in consumer behavior, or even to build collaboration or bring about creative solutions within teams.

The 5 whys method doesn’t really require any sophisticated tools or documentation. It just requires an open-minded approach to problem solving, and benefits from the same rules as brainstorming.

Here’s an example of using 5 Whys to diagnose poor sales performance in a B2B services business:


  1. Start with the problem. Be clear and specific about the issue you’re facing.

  2. Ask “Why?” five times. Don’t settle for surface-level answers. Keep questioning the “why” behind each response to peel back the layers. Keep track of all the responses for synthesizing them later.

  3. Example: Problem: Sales are down. Why? Team Response: Customers aren’t converting. Why? Response: Leads aren’t qualified. Why? Responses: Target audience isn’t well-defined, not talking to the right people. Why? Don’t know who’s in market, how to find best contacts. Why? Responses: We’ve never done this, we don’t have a process or tools to do it, no budget. Why? Response: not a priority.

  4. Identify the root cause. In this case, the root cause is probably that the business hasn’t committed priority and resources to what is needed to improve sales. This in turn might have more root causes, but this should be enough to develop a solution.

  5. Develop solutions. Now that you know the root cause, you can address it directly vs. fixing symptoms. In this case, reprioritize resources and develop a strategy and process for what is needed to improve sales, including target market definition, buyer identification, lead qualification and conversion.


‘What If’ Questions

Asking ‘what if…’ is a great way to stimulate creative solutions to problems, or to break a team out of a cognitive logjam.

In our approach to customer-centric B2B demand generation, we ask a lot of what-if style questions to help clients mentally simulate a desired future or scenario before dedicating resources to execution.

This exercise basically follows the same rules of brainstorming – generate ideas while deferring judgement. The only limit is the team’s imagination.

Here are some example what-if questions:

  • What if we had ‘x’ vs. ‘y’

  • What if we did not have ‘x’

  • What if that had gone this way

  • What would be the doomsday scenario- what could go wrong?


Proactive Questions (Pre-Mortem)

A pre-mortem allows you to work backwards and look at the individual factors that could lead to failure as well as the actions to take in order to pre-empt failure. Once you’ve identified these factors, you can start thinking about how to best avoid or mitigate these risks from occurring.

For instance, you could think upfront about what could go wrong with your product’s go-to-market strategy and the marketing channels that you’re looking to use. Or you could begin to imagine what might happen if customers don’t respond to your product as expected.

Or you could market test a new product with a small segment, then use those learnings to inform future pre-mortems before scaling.

Here are some good questions to ask during a pre-mortem.

  • What would be the impact be if product messaging fails to resonate with your target audience?

  • What if customers don’t want to pay for our product? What if we’re addressing the wrong customer segment? What if we’ve got customer needs wrong?

  • What would happen if our technology program wasn’t adopted? Or what would be the downstream risks of a data breach?

  • What if our costs exceed budget halfway through the project?


Pause and Reflect

When someone comes to you with a problem, don’t immediately respond with a solution; instead reflect on the situation using questions to dive deeper.

Try this next time someone responds to your idea with a reason why it cannot work: first pause and reflect on the situation. Then respond with a thoughtful question or two that moves you both to a reasonable solution. Ask the kinds of questions that will spark more creativity among the team, and that will unlock new insights.

Checklist: 10 Steps to Customer-Centric Demand Generation

Get the accompanying checklist for developing a modern demand generation strategy and system that is customer-centric, insight-driven and digitally enabled, so you can work smarter and build the business of your dreams more confidently.

Good Strategy Starts with Good Questions

Simply asking better questions is one of the most efficient ways of generating better insights, upon which great ideas, products, experiences and strategies are built.

Getting better at critical inquiry really doesn’t cost you any more, nor does it take a great deal more time to practice. Asking good questions as part of a healthy business planning exercise can save any organization a lot of costly misfires down the road.

By moving beyond a superficial understanding of results and delving into the underlying reasons for those results, businesses can unlock new opportunities for growth and success.

A deeper understanding of motivations and what we don’t know about customers, is fuel for developing successful business strategies and durable competitive advantage.

Need Help Asking Better Questions?

At Bevelroom Consulting, we believe that good strategy starts with good questions.

We use this method in our demand generation diagnostic and other services.

In our diagnostic, we assess current strategy, identify root causes of obstacles to desired outcomes, test the biggest levers for change, and develop a roadmapped action plan to improve demand generation / go-to-market.

What you get:

  • Optimize measurement and reporting
  • Deploy new marketing programs
  • Align teammates and executives
  • Analyze performance and improve ROI
  • Improve forecasting and strategic planning

Get started with your demand generation diagnostic today.



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