50 Questions B2B Buyers Need Answered in 2025
Why should buyers trust your product over every other option available?
Hey there!
Thanks for joining me for edit #4 of The 100.
Yesterday, the DealBook 2024 Summit took center stage, hosted by The New York Times and DealBook founder
. It’s a gathering where tech leaders often share bold predictions about the future and reflect on the societal impacts of their work.In one of the most compelling moments of the day, Andrew asked OpenAI’s CEO and co-founder, Sam Altman, a deeply personal question:
"When you have your child next year, what do you think you’ll tell them about this new world we’re about to enter?"
Altman’s response:
"There's nothing like getting ready to have a kid that makes AGI seem so irrelevant. The level of excitement I have about AGI, I thought was very high, but it's so much higher about having a kid. It really puts into perspective what really matters. We have been developing incredible new technology for a long time, and each time it's happened, people have had these conversations. 'What does this mean?' The industrial revolution comes along, machines take all of our jobs, what does this mean? The computer revolution comes along, computers take a bunch of current jobs, what does this all mean? And the answer? At least in terms of what it means to be human? Is not very much. The economy will grow. The kinds of jobs people will do will change. And people will care way more and love their kids way more than they care about AGI. And anything else any other technology can deliver. Deep human drives are so powerful, and have been here for so long. Evolutionary drift is pretty slow, that I think in some sense, my kids will grow up in a super different world, and in some sense it'll be exactly the same."
That sentiment echoes something I wrote about last week: the more things change, the more the fundamentals stay the same.
Now, let’s bring this idea closer to home.
When we talk about B2B marketing, there’s a lot of noise around tactics: warming up email addresses, scaling outreach, or orchestrating ABM strategies. But beneath the complexity of digital transformation, the essence of what drives decisions hasn’t really changed. Businesses, and the people within them, still make choices based on trust, value, and deeply human needs.
Yet, as B2B go-to-market strategies have embraced technological transformation, buyer distrust has grown alongside it. The rise of spammy advertising, misinformation, and misuse of data has left buyers skeptical of direct brand engagement. They’ve seen too many ‘3X ROI’ headlines, to take brand claims at face value. Not to mention generative AI is also making cold outreach more of a challenge than it already was 👇🏽
As a result, buyers now prefer self-service journeys that put them in control. They seek out independent research, peer reviews, and unbiased resources to inform their decisions, prioritizing transparency and credibility over polished sales pitches.
Recent McKinsey data underscores this movement. Today, one in five B2B decision-makers are willing to spend between $500,000 and $5 million in a single self-service or remote interaction. Forrester backed this up in their 2025 B2B marketing and sales predictions, by saying “as Millennials and Gen Z buyers drive purchasing decisions, more than half of large B2B transactions (US$1 million or greater) will be processed through digital self-serve channels, including the vendor’s website or marketplace.”
That means your future customers are out there right now, forming opinions, drawing comparisons, and making decisions — often before you even know they exist. If your content doesn’t provide the clear, honest answers they need, they’ll find it elsewhere.
Which brings us to today’s edit.
How do you build trust without resorting to exaggerated claims or over-polished campaign narratives? It starts with making sure your buyer experiences answer these 50 critical questions with confidence and transparency. These are the questions your buying committees are already asking as they navigate their decision-making process.
Can they clearly see the value your product experience provides?
Do you explain how it works in a way they can relate to? (role/use-case/industry-specific)
Are your claims backed by real data or existing customers?
And perhaps most importantly: does your content help them feel confident, not just informed?
Now, when buyers search for new products, they want to know they can trust you before they engage directly with your team. Answering these questions builds the foundation of that trust, showing buyers that you respect their independence while still providing the insights they need to move forward.
Now, to the questions!
Trust signals: Why should I choose you over everyone else?
Your audience begins here 🏁
Comparing options, contrasting features, and searching for clear signals of differentiation.
According to the principle of choice overload, too many options without distinct contrasts lead to decision paralysis. Clarity is essential to creating resonance. I explored this idea further in my post on the psychology of progress and how it influences B2B buying behaviors here.
Now to the critical questions executives start asking when evaluating new technology vendors.
1. What top three problems do you solve? When was the last time you critically examined your solution through the lens of your ICP's specific roles, use cases, and industry applications? For each of these, building out 2-3 solid examples can help establish a preliminary fit across multiple qualification criteria.
2. Why can't I build this myself? With generative AI and no-code tools on the rise, this question challenges the need for external investment when internal solutions seem more feasible.
3. What makes you different from [competitor]? Write down your three key differentiators. Now, could any of your competitors claim the exact same things? The "we were first" argument doesn't land like it used to.
4. What's your real experience helping companies like us? Generic case studies don't cut it anymore. Your prospects want to see themselves in your success stories e.g. same industry, similar tech stack, comparable challenges. VIDEO is a super winner here in terms of formats that increase the stickiness of the message.
5. Will this work with our tech stack? Integration anxiety should be managed by increasing trust (via your buyer experiences) in your ability to navigate their unique technical architecture without creating new headaches.
6. What security standards do you meet? Your prospects are asking this early because security issues can kill a deal before it starts, no matter how effective your solution might be. Be sure to define which standards garner the most respect and trust. eg. SOC 2 Type II, GDPR/CCPA, ISO 27001 etc.
7. How often do you ship updates? While this is the question at a broad level, this may be researched in different ways. e.g. An IT/Security focus query search could be "[Product] update notification process" but a business impact outcome could be “How often does [product] add new capabilities?
8. Do customers drive your roadmap? The hidden question: "Will we have a voice in your future direction, or are we just along for the ride?"
9. Can you grow/adapt with our team? Teams are getting leaner. They need to know you can scale both up and down with their changing needs.
10. What's your track record in our industry? Slightly different from question 4. This is your brand’s street cred on serving the industry as a whole, vs a specific type of firm e.g. employee size, niche use cases etc, location etc. P.S. using your existing discovery calls and support tickets can be the foundation of great pieces of content to power several parts of your GTM messaging e.g. product marketing, sales enablement and demand generation.
How quickly can I start seeing measurable results?
Modern B2B teams would rather have an application or service they can implement/integrate quickly rather than a perfect solution that takes forever to roll out.
Give them concrete timelines, specific milestones, and real customer implementation stories. Mapping out the first 30/60/90 days a great perspective to provide early on so they have clear expectations of your value.
11. What's day or month one like? Tell this story in visually and audio-engaging formats. Infographics, video explainers (which can make great TOFU ads) and employee-led recorded content. It has to be trustworthy and honest to hit right away.
12. How long until we're up and running? Clarity here is key. Even in the agency business, most folks won’t mind if you say this will take three months to execute but they have a massive problem if you said one month to completion and took three.
13. What team resources do we need? Beyond the basics: Your prospects have sat through too many "comprehensive onboarding programs" that turned out to be a PDF and a prayer. Show them the actual platforms, resources, and human support they'll have access to.
14. How do you train and educate/upskill our users? Showcase your enablement ecosystem. Quick demo videos, certification paths, learning hubs - make it visual. B2B buyers want to see the actual platforms and resources, not just promises of "world-class training."
15. Can we bring our existing data? Address migration anxiety head-on. Share your data migration methodology through interactive guides or workflow diagrams. Consider creating a "Migration Readiness Assessment" tool buyers can use and learn from independently.
16. What can we customize? The old "configuration vs. customization" debate isn't theoretical anymore. Teams need to know exactly how they can make your solution fit their workflows, not the other way around. Let buyers explore different setup possibilities through interactive demos or configurator tools. You can do a custom build or use dynamic tools like Navattic.
17. Who's our main contact? They're not asking about a name on a support ticket. They want to know who's invested in their success and will be there when things get complicated.
18. What wins can we expect in X days? Map out those early victories with honesty and precision. If it takes time to see impact, explain why - and what they'll see along the way.. Instead of promising quick wins across the board, set clear expectations through defined frameworks.:
For quick-value tools (e.g., communication platforms): Show 30-day impact metrics
For complex solutions (e.g., enterprise CRM): Map 30/60/90 day milestone paths
For data-driven tools: Explain the data collection period needed before value realization
19. How do we track progress? Share actual dashboard screenshots or demo videos of your reporting capabilities. Create "Metrics That Matter" guides specific to different user roles. Let them see how they'll measure success in their language, not just yours.
20. What results do similar teams see? Build interactive case studies where buyers can filter by industry, company size, or use case. Include voice-of-customer video clips focusing on measurable outcomes. Instead of generic testimonials, share specific journeys. Let them see the challenges, adjustments, and eventual victories of teams just like theirs.
What happens when I need help or something goes wrong?
Your content needs to make your support model transparent and accessible. Show them exactly what happens when they need help, backed by real metrics and customer experiences. Buyers assume something will go wrong eventually. No one is judging you on perfection but more on how you handle the opposite.
21. What support do we get? If you offer human support as a differentiator, demonstrate exactly how it works - show real SLAs, team structures, and support workflows.
22. How fast do you respond? Beyond the SLA: They don't just want to know your target response times. They want to know what happens in those critical moments when they're stuck and need help now..
23. Do we get a dedicated contact? This question is about more than account management. It's asking "Will someone understand our unique context, or are we starting from zero every time we need help?"
24. How do you handle outages? The deeper question: "When things go sideways, how transparent will you be? Will you hide behind corporate speak, or will you treat us like partners?"
25. What's your fix time average? Your prospects have been burned by pretty SLA promises before. They want real data, real examples, real stories of how you've handled past challenges.
26. Can we reach you 24/7? Even if you're not a global company, your buyers probably are. They need to understand exactly what happens when they need help outside your core hours.
27. Where do we go for help? Show clear paths for different issue types. Include preview access to help resources pre-purchase.
28. How do we request features? Showcase your feedback-to-feature pipeline. Share your product feedback process and highlight customer-requested features that made it to production ( those case studies we mention in the first section!).
29. What can we fix ourselves? Show them where self-service makes them faster and more effective, and where reaching out gets them better results.
30. Is your user community active? They're looking for signs of a healthy, engaged user base that can help them maximize value from your solution.
How will this investment drive bottom-line growth?
Your content must bridge the gap between features and financial outcomes. Give them the tools to build internal business cases and the proof points to back up their recommendations. If buyers can't clearly explain your value to their finance team, they won't buy—no matter how much they like your product.
31. What's the typical first-year ROI? Those vague "3x ROI" claims that saturate every website? They're not as convincing anymore. Your prospects need concrete, role-specific value metrics they can defend in a budget meeting.
32. How do we measure success? Build success metric frameworks for different roles. A CMO needs different metrics than a demand gen leader. Show how your product tracks and reports on each. (Always remember, role-specific, use-specific and industry-specific parameters ensures all bases are covered!)
33. What time does this save? When you say "increases efficiency," your prospect hears "prove it." Get specific: "Reduced reporting time from 5 hours to 30 minutes per week across 12 marketing analysts."
34. How does pricing work? Hidden pricing often means automatic exclusion from consideration, even from ideal customers (and generative search queries!). If you can't publish exact prices, at least provide frameworks that help buyers understand your pricing model.
35. Are there hidden costs? Own this question directly. List every cost category upfront: data storage, API calls, user seats, integrations. Better to address it now than lose trust later.
36. Do customers stick around? Break down why customers stay or upgrade. Include churn reasons for transparency - it builds credibility.
37. How do teams justify this purchase? Provide actual business case templates and ROI stories. Show successful approval patterns: "Here's how Enterprise A justified based on productivity gains, while Startup B focused on revenue impact."
38. What costs will this cut? The consolidation conversation: With tech stack bloat becoming a genuine concern, show exactly what tools or processes they can streamline or eliminate.
39. When do we break even? Create realistic breakeven scenarios based on implementation speed and use case complexity. Let them see all the variables that impact time to value.
40. Which metrics should we watch? Build metric tracking guides by role and goal. Show how successful customers monitor progress from day one.
Can your infrastructure handle our scale and security needs?
Throughout this section, maintain two layers: high-level assurance for decision-makers and detailed validation for technical evaluators.. Make the complex clear without oversimplifying the critical details. One unanswered security question can kill a deal faster than any feature gap.
41. What's your uptime record? Beyond the 9's: Stop hiding behind "99.99% uptime" claims. Show your actual status page. Let them see incident history, resolution times, and how you communicate during issues.
42. How do you back up data? Document your backup architecture and recovery processes. Show recovery time objectives (RTO) and recovery point objectives (RPO) clearly. Include backup verification procedures and testing schedules.
43. What APIs do you offer? Your technical evaluators want to see beyond document links e.g. the API playground, test real calls, understand rate limits. Show, don't tell.
44. How do you handle heavy loads? Share real numbers. "Here's what happened when Customer X ran 10,000 simultaneous processes. Here's what we learned, and here's how we've improved."
45. What auth methods work? Map out the actual authentication flows. Show SSO implementations, custom paths, every option they might need as they grow.
46. Is our data encrypted? Walk through encryption at rest, in transit, key management. Security teams need to see your thinking, not just your compliance.
47. How long do you store data? The compliance conversation: Break down retention policies, configuration options, and how you help customers meet their regulatory requirements.
48. Can we build custom reports? Showcase reporting capabilities through interactive demos. Display custom report examples and API reporting endpoints. Include report builder tutorials.
49. What powers your backend? Share architecture diagrams that speak to both technical and business audiences. Highlight reliability, scalability, and security measures without overwhelming detail.
50. How do updates work? The change management question: Document your release process, testing procedures, and most importantly - how you minimize disruption to their business.
A note on content planning in 2025
It’s safe to say we don’t always need new content. Generative AI has flooded our feeds with noisy, often impersonal material that’s easy to spot as machine-generated. But despite this abundance of information, audiences are still sometimes struggling to find trustworthy, actionable answers when they need them most.
Before you launch your next content initiative, pause to consider:
Where do some of the questions I pose above, naturally surface in your buyer's research process? Think about the silent journey they're taking before they ever reach out. Closed-won account surveys really help with validating/seeding this insight.
What questions naturally cluster together in your buyer's mind? Not in your marketing plan, but in their actual decision-making process.
Which validation points need hard data versus social proof? When does a quick video answer beat a detailed whitepaper?
How can you ensure your answers appear when your buyers are searching—not just where pushed the latest post?
Which answers need constant updates to stay relevant, and which can serve as foundational pillars?
Building distribution that informs the org and educates the audience
First-mover advantage in content distribution can yield remarkable long-term gains. A few observations worth considering:
LinkedIn's dedicated video feed. Early adopters are already seeing increased reach and engagement. Be sure to follow Jamé Jackson (Gadsden), Community Manager at LinkedIn, for workshops and tips on how to excel with this media type.
Reddit: Platforms like Notion and Figma have actively engaged on Reddit, tapping into genuine conversations to shape their roadmaps. P.S. Redditors value transparency and detest overt self-promotion. Nothing that starts with ‘Be sure to check out XYZ’, will see the light of day on the subreddit.
Rising platforms like BlueSky present early-mover advantages. Emerging platforms like BlueSky offer opportunities to build thought leadership and community before they become oversaturated. Erin McCool at HubSpot shares her insights here on whether B2B companies should consider the platform.
Your owned digital spaces remain your most valuable asset. As platform algorithms evolve and third-party data becomes less reliable, your website, email community, and other owned channels are your most consistent and controllable assets because they’re not at the mercy of a third-party algorithm. Don’t leave them neglected and underutilized (understatement of the year).
If you're already answering many of these Qs effectively and trying new distro channels in your GTM campaigns—celebrate that win.
If not, don't rush to fill gaps before Q1 25 launches.
Build thoughtfully.
Create intentionally.
Focus on buyer understanding first, content second.
Kexin Chen, Head of Executive Marketing at Salesforce and I chatted about how to approach this on The Break to Build podcast here earlier this year.
2025 belongs to the marketing and product teams who help their buyers/users find clarity in the chaos of it all. As Sam implied, while technology can be transformative, personal priorities (and I’ll add productivity in there) matter far more. Buyers lack the time or patience for journeys that feel untrustworthy, lack credible information, or are incomplete. The last thing your team wants to do is become contributive to that frustration.
Till next Thursday,