Why is selling AI so difficult?

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.

How can sales teams build buyer confidence in AI solutions?

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.

What skills are needed to sell AI effectively?

Effective AI selling requires a balance of consultative skills and Challenger insights. Consultative skills—like being buyer-centric, authentic, and actively listening—build trust and confidence. Challenger insights then differentiate by teaching buyers how to think differently about AI, using commercial perspective and constructive tension to move them from indecision to action.

How do you create urgency when selling AI?

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.

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

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.

How do you sell AI solutions when buyers don’t know how to buy?

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.

The New Playbook for Selling AI: From Confusion to Confidence

Selling AI

September 18, 2024

The New Playbook for Selling AI: From Confusion to Confidence

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