B2B teams have more channels, more tools, and more “signals” than ever.
And buyers are tuning them out harder than ever.
Not because buyers hate marketing.
Because they hate being treated like a target.
This is the core problem: modern GTM systems are optimized for activity (touches, sequences, attribution) while buyers are trying to do something else entirely: reduce risk and make a safe decision.
That’s why trust and empathy aren’t “soft skills.” They’re conversion infrastructure.
In this conversation, I interviewed Steve Woods (@stevewoods), Founder & CTO at Nudge, about what it takes to build real B2B relationships in a world full of automation, hustle culture, and buyer skepticism.
Author’s note: This transcript is edited for clarity and readability.
Quick Answer: How Do You Build Trust and Empathy in B2B Sales?
You build trust and empathy by helping buyers make progress before asking them to buy.
That means: maintain context, give useful “next steps,” and trade self-promotion for perspective. Automation can support the research and timing. It cannot replace the human work of building trust.
Key Takeaways
- Trust moves deals. “Activity” does not.
- Buyers want a guide, not a pursuer.
- Automated sequences are decaying because they strip context.
- The best outreach is a give, not a disguised ask.
- Your system should surface relationship risk (lost touch, stalled progress), not just track touches.
Why Buyers Are Tuning You Out
It’s tempting to blame channels.
But the real issue is behavioral.
Buyers have learned to protect themselves from noise. They’ve been trained by years of spammy follow-up, vague “checking in,” and fake personalization.
So they do what rational people do. They ignore you until they need something specific.
Trust becomes the differentiator because it reduces buyer risk:
- Risk of wasting time
- Risk of looking foolish internally
- Risk of choosing the wrong vendor
- Risk of being pressured into the wrong timing
That’s the frame for everything below. Not “how to nurture.” Not “how to get replies.”
How to become safe to engage.
The Interview
Brian: What inspired you to start Nudge?
Steve: You and I have known each other for a long time. A few decades. My history before Nudge was Eloqua in the marketing space.
We saw marketing transition from an arts-and-crafts discipline into a measured lead generation and demand generation engine that started to connect with sales.
That was remarkable.
But looking over the fence at sales, we realized the next step was the core of getting deals done.
Steve: Building trust and relationships is the core
The core was building trust and relationships, and the breadth and depth of those relationships within our organization, that would allow the deal to move forward.
Trust and empathy had to be developed, and ultimately the deal would be closed based on those relationships.
So we decided to tackle relationship intelligence: understanding where trust is being built, where empathy is being built, and how you make a sales team more effective by focusing efforts on the right initiatives.
Brian: What growth lesson did you learn from Eloqua?
Steve: We were lucky to be part of a major change. Marketing went from unmeasured to measured.
With Nudge, we tried to be proactive: what dominant theme will shape sales for the next decade?
It became clear that relationships, trust, empathy were the core thing. And it was unmeasurable. It was intuitive.
Steve: Deal slippage is relationship slippage
Every sales leader, when you talk about deal progress and forecast and slippage, it’s about relationships and trust. But it’s not measurable. It’s self-reported by sales reps who often have happy ears.
We thought: if we can put measurement around trust, empathy, and relationships, then build tooling to steer effort, we can be part of a meaningful transition.
Why “Hustle” Collapses Trust
Brian: What inspired you to write about holding the hustle?
Steve: It stemmed from a rant.
We spent time interviewing buyers about how they buy, and salespeople about how they sell. It was Mars and Venus.
Buyers want thoughtful co-conspirators on a journey. They selectively bring in sales when they need deeper points of view.
Salespeople talked about automation, numbers, a thousand emails a day, “Did you get my last email?”
It was bizarre to realize they were describing the same animal.
Early sequences felt like diligence. Now they feel like spam.
So the rant was: “Stop. We must stop this in sales. It’s not working. It’s going downhill.”
That became the #HoldTheHustle thesis.
Buyers Don’t Need More Info. They Need Meaning
Brian: What makes a difference in the buyer journey?
The salesperson often matters more than marketing in the buyer’s lived experience.
Buyers want to know the rep is their advocate, talking straight, not pitching.
Steve: Buyers want you to journey along with them
Buyers want someone to go along with them on a journey and challenge them, educate them, and help them see the problem differently.
The facts are out there. Buyers can Google facts.
What they want is:
- So what?
- What does it mean?
- Where will this work?
- Where will it fail?
When a rep asks a question that makes the buyer pause and think, trust starts moving forward.
Steve: The trust bar moves when you create insight
“You’re probably thinking about it this way. I’m going to push you to think about it that way. Here’s why. Here’s a story. It might make you uncomfortable. But it’ll give you insight you wouldn’t get from a search.”
Empathy and Automation: Where They Actually Fit
Brian: How do empathy and automation fit together?
Steve: You can’t automate empathy. You can’t automate trust.
But you can automate the background work that makes empathy possible: understanding your world, understanding the buyer’s world, and teeing up the moments where a human can add value.
The human part is the conversation:
“Saw this, thought this, here’s a perspective you might want to consider.”
Automation can put enough on a silver platter to guide those “right moment” conversations.
3 Practical Steps to Build and Grow Relationships
Step 1: Identify where you’re losing touch
Steve: Look at your relationships and ask, “Where am I losing touch?” Most people don’t do this.
You have a first conversation. If it becomes a deal, great. But 90% don’t, and they drop off.
The best reps used to manage this manually in spreadsheets.
At minimum, put a floor under relationship building: stay in touch on a simple rhythm (for example, every 90 days) with people who matter.
Step 2: Define the next step that helps them on their journey
Now you develop the logical next step based on where they are.
You need context:
- What’s happening in their company?
- What recent events occurred?
- Executive changes?
- Where are they in their journey with your organization?
This is the evolved version of “digital body language,” but grounded in reality, not vanity engagement.
Step 3: Nudge them forward with a give, not a pitch
The next step is a nudge: “You’re probably here. You might be thinking this. If you considered this dataset, this perspective, this story, your view would evolve.”
Not a sales pitch.
Not “Let’s do a one-hour call.”
A give that builds trust first. Then, later, you’ve earned the right to ask.
The Hidden Challenge for Marketing: Do You Have Any “Gives”?
Steve: If sales doesn’t have real gives, they’re stuck with big asks: “Let’s schedule a 60-minute call.”
That’s not a give. That’s a tax.
The best orgs build actual gives:
- useful datasets
- helpful documents
- experiences that reduce buyer risk
- insight that helps internal alignment
Not traps. Not half-assets that require a call to unlock the other half.
Real gives create real trust.
Hard Truth: Trust Is Your Only Sustainable Conversion Strategy
Buyers don’t hate follow-up.
They hate follow-up that has no point.
They hate being chased with zero context.
They hate “personalization” that’s just a variable token stuffed into a template.
Trust is built when your system helps buyers think, not when it tries to make them act.
If your GTM motion is built on hustle, your buyers will experience you as risk.
And rational buyers don’t buy risk.
Bottom Line
Empathy is not soft. It’s operational.
If your system can’t preserve context, equip humans with useful gives, and support buyer progress, your “optimization” will just create more noise faster.
Stop trying to out-automate buyer skepticism.
Build trust like it’s a revenue system. Because it is.
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