The New Playbook for Selling AI: From Confusion to Confidence

How to Sell AI When Buyers Don’t Know What They Need

Artificial Intelligence has become the most urgent—and most confusing—technology purchase for B2B buyers. Companies know they need to act, but most don’t know where to start or how to evaluate solutions.

That tension creates one of the toughest challenges for sales teams: buyers are under pressure to invest in AI, but they don’t know how to buy it.

The stakes are high:

• 95% of AI pilots fail (Rand Corporation)
• More than 80% of executives plan to increase AI investment (Bain & Company)
• Yet only 28% of enterprises have embedded AI effectively (McKinsey)

This disconnect means sales leaders are watching promising opportunities stall out, forecasts slip, and competitors step in.

Why AI Deals Stall

When faced with hesitant buyers, many sellers default to old habits:

• Leading with technical jargon that overwhelms instead of clarifies
• Highlighting features without tying them to buyer challenges
• Over-promising speed and adaptability as differentiators

These approaches backfire. Buyers already feel uncertain, and feature-heavy pitches only increase their doubt.

One CRO recalled losing a major opportunity after relying on a product-centric pitch. A competitor won the deal—not with superior technology, but by asking smarter questions about process, risks, and success metrics. They taught the buyer how to buy AI.

The lesson: selling AI requires less pitching and more guiding.

The Solution: How Sellers Can Cut Through AI Confusion

The real barrier to selling AI isn’t technology—it’s buyer disorientation. The solution isn’t pitching harder or showing more demos. It’s building confidence by combining Richardson’s consultative approach with the Challenger methodology to create sellers who can both empathize with buyers and reframe their thinking.

To help buyers move forward, sales leaders must equip their teams with four essential consultative skills from Richardson’s proven playbook:

1. Adopt a Buyer-Centric Mindset

Step into the buyer’s shoes. Acknowledge the ambiguity they feel and frame the conversation around their uncertainty—not your product roadmap.

2. Use Authenticity

Replace jargon with credibility. Share stories, case studies, and examples of how others successfully navigated AI adoption.

3. Build Decisive Momentum

Ask for feedback regularly. Each small commitment helps buyers synthesize complexity and build toward larger decisions.

4. Listen Actively

Coach sellers to listen to understand, not just to respond. An open dialogue creates trust and reveals the real concerns that need addressing.

Expanding the Playbook: Where Challenger Comes In

While consultative skills reduce confusion and build trust, they’re even more powerful when combined with Challenger’s commercial teaching. This is where sellers move from clarity to action by:

• Teaching for Differentiation: Sharing insights that challenge buyer assumptions and deliver value in the conversation itself.
• Understanding Buyer Needs: Helping buyers articulate business problems—and surfacing hidden problems they haven’t considered.
• Controlling the Sale Process: Guiding buyers through an evaluation roadmap, anticipating blockers like security reviews, and making the path clear.
• Defining Outcomes and Metrics: Turning vague AI ambitions into measurable business goals such as faster decisions, improved margins, or higher customer satisfaction.
• Using Constructive Tension: Showing the true cost of inaction—lost revenue, higher operating costs, or diminished market relevance—and motivating buyers to move forward.

Examples of Constructive Tension in AI Sales

Lost Revenue

Find critical insights that impact the organization financially, then show how that compounds over time.

What this sounds like:

“Companies that delay AI-enabled analytics typically miss 5–10% of potential revenue because they can’t act on data in time. Standing still means your competitors are monetizing insights you never even see.”

Increased Costs

Identify inefficiencies or operational expenses that AI could eliminate.

What this sounds like:

“Manual processes and outdated systems typically add up to hundreds of hours of hidden labor costs each year. What feels stable is actually draining X% margin.”

Market Relevance

Show how delaying AI adoption damages reputation and competitive standing.

What this sounds like:

“Competitors who invested in AI early will already meet higher customer expectations. What feels like a safe delay now can put you in a permanent catch-up mode later.”

Risk Exposure

Highlight compliance and regulatory blind spots that legacy systems create.

What this sounds like:

“Legacy compliance processes create blind spots. Without AI-enabled audit trails, many companies don’t realize they’re exposed until regulators or customers point it out. What feels low risk today may actually be your highest area of exposure.”

Selling AI Is About Clarity, Not Code

AI is transforming how companies operate—and how sellers must sell. Traditional, feature-heavy pitches only add to the confusion. Buyers need clarity, confidence, and guidance.

That’s why the most successful sellers combine:

• Richardson’s consultative approach → building trust, listening deeply, and creating buyer confidence.
• Challenger’s commercial insight methodology → teaching for differentiation, reframing assumptions, and creating constructive tension.

Together, these approaches equip sales teams to:

• Teach buyers how to buy AI before showing them what to buy

• Translate AI complexity into clear business outcomes
• Build urgency while strengthening long-term trust

At Richardson and Challenger, we help sales organizations reframe the AI conversation, create differentiation in crowded markets, and execute consistently across every customer interaction. By combining Richardson’s consultative approach with Challenger’s methodology, sellers can both earn trust and create urgency. This dual strategy transforms uncertainty into clarity and equips sales teams to win in the AI era.

Frequently Asked Questions About Selling AI

Q. Why is selling AI so difficult?

A. Selling AI is difficult because most buyers don’t know how to evaluate it. Unlike established technologies with clear benchmarks and proven ROI models, AI is still an emerging space. Buyers struggle to define success criteria, calculate return on investment, or anticipate risks. When sellers respond by relying on jargon or feature-heavy pitches, it only deepens confusion and slows decisions.

Q. How can sales teams build buyer confidence in AI solutions?

A. Confidence comes from guidance, not features. Sales teams can build it by shifting the conversation from what the technology does to how the buyer can approach adoption successfully. This requires acknowledging uncertainty, sharing authentic case studies, listening actively, and linking AI capabilities directly to measurable business outcomes. When buyers feel understood, they gain the confidence to move forward.

Q. What skills are needed to sell AI effectively?

A. The most effective sellers rely on consultative skills that make buyers feel supported rather than sold to. They adopt a buyer-centric mindset, use authenticity to build trust, create momentum by regularly checking in for feedback, and practice active listening to uncover the concerns buyers might not voice immediately. These skills turn abstract discussions about AI into clear, buyer-led progress.

Q. How do you create urgency when selling AI?

A. Urgency is created by helping buyers see the risks of inaction. Sellers can use constructive tension to highlight the tangible costs of delay, whether that means missed revenue opportunities, mounting inefficiencies, eroding market relevance, or increased compliance risks. By showing how the status quo is actually more dangerous than change, sellers move buyers from hesitation to action without applying unhealthy pressure.

Q. What’s the advantage of combining Richardson and Challenger when selling AI?

A. The advantage lies in blending two proven approaches. Richardson’s consultative methodology builds trust and reduces confusion, giving buyers the clarity they need to feel confident. Challenger’s commercial teaching reframes assumptions, introduces new insights, and creates constructive tension that motivates change. Together, the two approaches allow sales teams to meet buyers where they are and guide them toward where they need to go, turning indecision into decisive action in the complex world of AI sales.

Q. How do you sell AI solutions when buyers don’t know how to buy?
A. The key to selling AI isn’t pitching more features—it’s guiding buyers through confusion. Sellers should use consultative skills to build confidence: adopt a buyer-centric mindset, share authentic examples, create momentum by checking in regularly, and listen actively. By teaching buyers how to buy, sales teams reduce risk, create clarity, and move deals forward.