From map readers to explorers: How HubSpot is redefining leadership development in the age of AI

Ben Putterman has a hot take: leadership development has actually gotten worse over the last two decades, not better.

"We've just gotten very, very messy and have taken our eye off of the fundamental role of leadership," says Putterman. His diagnosis? The rise of employee engagement surveys quietly shifted the goal of management from performance to popularity.

Senior leaders consistently see one reality: gaps in coaching, lack of accountability, performance ratings clustered suspiciously at the top of the scale. 

Engagement surveys, meanwhile, tell a rosier story. The disconnect isn’t accidental. Managers have learned to optimize for survey scores rather than outcomes.

He calls the result the “Friday night beer leader”: the manager everyone loves to socialize with, but who is not pushing anyone to grow. “Your job as a leader is not inherently to be liked,” Putterman says. “You’re subverting the learning experience.”

The explorer framework: Leading when there is no destination

Fixing the likability problem, Putterman argues, requires a more fundamental rethink of what leadership even means today. Working alongside HubSpot CEO Yamini Rangan, his team developed a framework built not around giving leaders better maps, but turning them into explorers.

“How do you thrive in a world where you don’t know where the destination is?” That question sits at the heart of five leadership shifts HubSpot is building into its culture:

• Riding the change: Not managing or minimizing change, but becoming “best friends with uncertainty.” This means making fast decisions even without complete information and leaning into present-moment awareness.
• The scientist mindset: Borrowed from Adam Grant, this centers on hypothesizing, testing, and being genuinely okay with being wrong.
  
  The word “hypothesis” is now heard constantly across HubSpot, and Putterman says it has unlocked a new quality of feedback: “It’s a lot easier for people to give and receive feedback when all you’re giving feedback on is a hypothesis.”
• Getting close to the work: Building deep empathy through proximity, not surveillance. Leaders are expected to periodically step into frontline roles to see what employees and customers actually experience.
• We over me: In a world with no clear answers, no single leader can possibly navigate alone. This pillar drives a strong cultural premium on humility, curiosity, and coaching.
• Leading with context: Always anchoring on the “why.” Even when leaders don’t have all the answers, they own the message. “You don’t get the right as a leader to say, well, I don’t know what this is. Somebody else made this decision.”

How HubSpot scaled AI adoption without losing employee trust

According to internal survey data, 98% of employees are using AI tools and 84% feel comfortable with AI in their daily work, yet engagement has remained high.

The approach was built on permission and agency.

HubSpot opened access to AI tools across all employees without bifurcating who got what. They created informal weekly sharing forums where people could surface what they’d built or learned. 

They framed the whole initiative not as a threat but as support: “This AI transformation is coming into the world. What we’re going to do as an employer is help you navigate what we call the AI turn.”

The results were surprising even to Putterman. In fact, some of the most creative AI use cases didn’t come from engineers. They came from non-technical employees who had never been expected to build anything. “The creativity has been off the charts.”

Putterman sees the AI success as inseparable from the explorer mindset. An organization already comfortable with hypothesizing, failing fast, and experimenting without a map will naturally extend that posture to AI.

Culture as a strategic differentiator: how HubSpot evolved it

HubSpot’s culture code is legendary in the industry, often cited as one of the most influential documents in modern company-building. But Putterman is candid about the risk that comes with beloved cultural artifacts: they can become static.

“Where I think you can get into problems is when things become just static and unadaptable into a new world,” he says. HubSpot’s evolution preserved what was still working, the humanistic “lead with heart” principle, while layering in language that reflected the new era: adaptability, boldness, the ability to align and go.

Critically, hundreds of employees co-created the next chapter. The result doesn’t feel like a hard pivot. “It’s a very, very embedded part of the way that we work,” Putterman notes. “If anybody doubts the power of culture, it is a strategic differentiator for our company.”

The advice Putterman would give his younger self

Asked what he would tell the version of himself just starting out, Putterman resisted the easy answer.

“There is a tyranny of being right,” he says. “Some of the most amazing learning experiences are going to happen when you’re not right. It’s taken my whole career to get to that point. But boy, is it liberating when you stop worrying about how right you are.”

It’s the explorer mindset, applied to an entire career.

Resources

• Connect with Ben Putterman on LinkedIn
• Learn more about HubSpot
• Explore Growthspace for precision skill development at scale

Chapters

• 00:00 — Introduction to Ben Putterman and his career journey
• 03:07 — Why leadership development has regressed over 20 years
• 09:38 — The “Friday night beer leader” and the disconnect between surveys and performance
• 12:36 — From map readers to explorers: the framework HubSpot built
• 22:00 — How HubSpot scaled the explorer mindset across 10,000+ employees
• 27:28 — Evolving HubSpot’s culture code for the age of AI
• 32:34 — How HubSpot achieved 98% AI usage while maintaining high engagement
• 40:54 — Leadership reflection: the tyranny of being right