Top 3 challenges in connecting with the new generation of B2B buyers - and how to overcome them

As discussed in last week’s episode of Beyond the Buyer, a new generation of buyers is in charge - with 67% of large B2B purchase decisions being led by Millennials and Gen Z - yet many businesses struggle to connect with these buyers who bring radically different expectations to the table. After publishing that article, I received several really thoughtful comments and messages from the linkedin community - thank you for these!

Your feedback got me thinking about the real, day-to-day challenges we face in connecting with these buyers. Inspired by your insights, I’ve shaped this article around three key challenges—and practical ways to overcome them. (and if you’re in a hurry, feel free to jump straight to the key takeaways at the end)

Challenge 1: Breaking down their wall of distrust

“When I speak with Millennials - well, younger buyers in general - I did notice they approach every interaction with caution. They question everything, including our value proposition - and they’re not easily won over.” - Director of Sales, SaaS industry

Millennials and Gen Z grew up navigating misinformation and clickbait, making them inherently skeptical. 65% of Millennial buyers distrust traditional advertising, and 71% prefer recommendations from peers or reviews over branded messaging (Forrester, The State of B2B Social Media Marketing, 2024). To stand out, businesses need to prove authenticity upfront.

Approaches to this challenge:

Show, Don’t Tell: Prioritize real, relatable stories. User-generated content (UGC), such as customer testimonials and case studies, is 2.4x more trusted than ads (Forrester, Predictions 2025: Trust, 2024). Highlight actual results to demonstrate credibility.

Be Radically Transparent: Millennials value openness—whether it’s about pricing, processes, or values. According to a Salesforce survey, 59% of Millennial buyers value upfront clarity on pricing (Salesforce, Connected Customer Report, 2023). Showcase transparency across touchpoints.

Invest in Genuine Thought Leadership: Use thought leadership, educational content, and case studies to highlight your expertise - according to CMI (Content Marketing Institute, B2B Marketing Trends, 2024), 78% of successful B2B marketers cite content that focuses on building trust as their most effective strategy. And particularly when it comes across as genuine: 87% of younger buyers trust thought leadership that educates without selling (Forrester, Predictions 2025, 2024), that properly connects with their interests. Use platforms like LinkedIn to share insights that resonate with their challenges, that help them learn.

Challenge 2: Keeping their attention in a world of infinite distractions

“Millennials aren’t waiting for us - they’re already 10 steps ahead in their research...sometimes in place we don't even think about. The challenge is staying relevant while they explore on their own.” — Enterprise Account Manager, Tech Sector

Millennials and Gen Z approach B2B buying like their personal lives: fast-paced, self-guided, and digitally enabled. Research shows 57% of the buyer’s journey is completed before engaging with sales (Forrester, Predictions 2025: Business Buyers, 2024), and most younger buyers prefer to research independently.

Approaches to this challenge:

Create Addictive Content: Use interactive formats like quizzes, calculators, and visual storytelling to make your content irresistible. Interactive content drives 2.5x more engagement from Millennial buyers than static formats (Forrester, Predictions 2025, 2024).

Personalize Interactions at Moments That Matter: Tailor your communications and content to individual buyer preferences, e.g. deliver personalized email sequences, dynamic website experiences, or product recommendations based on their behavior. 74% of buyers are more likely to choose a vendor offering personalized experiences (Forrester, The State of B2B Social Media Marketing, 2024).

Serve up Snackable Content: Millennials and Gen Z thrive on quick, digestible content that fits into their busy, always-on lifestyles. Focus on bite-sized formats like short videos, carousel posts, or concise infographics that deliver value in seconds. These snackable pieces make it easier for buyers to absorb and act on your message, especially when they’re on the go.

Challenge 3: Catering to the expanding needs of a diverse buyer group

“It’s not just about catering to different priorities anymore... it’s about how these priorities come together, or worst case: collide! One stakeholder pushes for ESG alignment while another wants immediate ROI - how do you bring them together without losing focus? That’s the real challenge.” — Marketing VP, Tech Sector

Millennial and Gen Z buyers are influencing B2B decision-making in significant ways, but this shift is also expanding the needs of buying groups across generations. Today’s buying groups consist of 6-10 stakeholders, each with their own unique concerns and priorities (Forrester, Predictions 2025: Business Buyers, 2024). Millennial and Gen Z buyers often bring fresh perspectives and expectations to the table, such as prioritizing innovation, transparency, and seamless digital interactions. This “clash of preferences” amplifies the already diverse needs within buying groups, making it difficult to create a pitch that resonates with everyone.

Develop Comprehensive Buyer Personas: Detailed buyer personas are essential for understanding and aligning with the diverse priorities within a buyer group. By mapping out stakeholder-specific personal motivators and drivers for decision making, businesses can better address the unique needs and therefore connect on a deeper level - with signficiant impact. Companies that document personas are 2.2 times more likely to exceed lead and revenue goals (Content Marketing Institute, B2B Marketing Trends, 2024). This level of insight provides a clear roadmap for tailoring communication and driving more effective engagement across the buying group.

Tailor Messaging for Diverse Buyer-Groups: Identify the generational and professional priorities of each stakeholder in your buyer group: Millennials might respond to stories about your sustainability initiatives, while Gen Z will value tools that showcase real-time performance. Addressing these nuances builds trust across the group: 70% of buyers feel more confident when vendors tailor messaging to their unique needs (Forrester, Predictions 2025, 2024).

Equip Them to Advocate Internally: Millennials and Gen Z are natural collaborators. Give them the tools they need—like visual dashboards, simple explainer videos, and interactive ROI calculators—to present your solution’s value to their peers. Internal advocacy is critical, as 70% of buying decisions are influenced by peer recommendations within the group (Forrester, Predictions 2025: Trust, 2024).

YOUR KEY TAKEAWAYS

Engaging Millennial and Gen Z buyers demands a strategic rethink of how B2B operates. These buyers bring a digital-first mindset, high expectations for personalization, and an emphasis on values like transparency and innovation. To thrive in this new B2B landscape, businesses must address these challenges head-on:

1. Trust Is Earned Through Proof, Not Promises: Millennials and Gen Z don’t trust traditional advertising or vague claims. To win them over, provide tangible proof of your credibility: Use user-generated content, authentic case studies, and thought leadership that educates without selling. Transparency about pricing, processes, and outcomes isn’t just appreciated—it’s expected.
2. Engage on Their Terms, Not Yours: These buyers are already halfway through their decision-making process before they even speak to your sales team. Meet them where they are with content that fits into their self-directed journeys. Prioritize interactive formats, bite-sized videos, and highly personalized content that aligns with key moments in their research. Relevance and immediacy are your strongest tools for keeping their attention.
3. Master the Art of Winning Over a Diverse Buyer Group: Today’s buying groups are increasingly diverse, with stakeholders pulling in different directions - ESG advocates prioritizing sustainability, CFOs focused on ROI, and IT teams demanding seamless integration. Success comes from uncovering what unites them. Build personas that highlight shared goals across generational and functional lines, then craft a value narrative that connects their priorities into one cohesive story. Alignment isn’t optional - it’s your competitive edge.

Which of these challenges do you face most often? Have any of these strategies worked for you? Share your thoughts in the comments or via DM and let’s continue the conversation!

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