Hi Reader,
After 2 decades of corporates, startups & founding businesses, the most common misconception about leadership is that it’s the title (or designation) that grants you command. But if you’ve ever worked with real leaders, you know that true authority is rarely assigned. It is inferred. It is felt. And it is almost always earned through conduct.
This was the singular insight that resonated deeply with me when I interviewed Dulles Krishnan on Brain Box - The Leadership Podcast, voted 9th pan-India by Spotify in 2022. He's been at the helm of some of the most influential tech companies of our times - like IBM, AWS, Salesforce, Coursera and now heads GTM at Avalara.
His journey has been audaciously un-linear: from travel and tourism to Chief of Staff at IBM’s $50 billion software group. He’s moved across domains, geographies, and leadership layers with an ease that doesn’t scream “corporate ambition” - but rather, quiet capability. And in our conversation, it became obvious why.
Adaptability: The Earliest Trait of Leadership
Dulles grew up as an Air Force kid, moving every two years. While most children would struggle with that kind of instability, he saw it as a gift. Each relocation brought novelty: new towns, new schools, new people. It gave him a high tolerance for change and a healthy disrespect for comfort zones.
But the real story began with his father, a humble airman, who despite not holding formal authority, would often take charge of difficult situations. Dulles saw this growing up.
“Authority was not something that was given to him. It was implied in the way he conducted himself.”
That one sentence captures the kind of leadership most of us only recognize in hindsight. It’s the kind that doesn’t come from role clarity or job descriptions. It comes from who you are when no one’s watching. From how you show up — even when you aren’t the one in charge.
Are Leaders Born or Made?
This is the timeless riddle. And I posed it to Dulles. His answer was nuanced.
He didn’t claim to be born with a leadership halo. Instead, he believes it was partly environment (growing up watching his father), and partly a set of internal values that crystallized over time: the willingness to take ownership, the refusal to pass the blame, and the courage to be in the spotlight even when things go wrong.
As he put it, “Whether we were up to mischief or building something constructive, I somehow ended up leading the gang.” A natural ability to take charge and a willingness to be accountable.
That’s a compelling lens to see leadership through. It’s not just about driving results. It’s also about being comfortable with consequences.
The Human Behind the Role
This is where Dulles really stood out - and I speak from personal experience. Back when we were in sales together at IBM, one of my earliest memories was him asking about me. Not my funnel, not my forecast - but what I enjoyed, what drove me, who I was. In a corporate context obsessed with numbers, this stood out. Turns out, that wasn’t incidental. It was intentional.
Dulles believes that leadership is about understanding the individual behind the role, not just the role itself. He doesn’t try to clone his approach across teams. Instead, he actively looks for what makes each person tick, what’s their rhythm of success.
“Don’t look for your reflection in your people,” he was once told by his manager. And he’s lived that advice ever since.
When hiring, his first lens is functional alignment. Can the person do the job? But right after that, he focuses on something far more elusive: Will this person gel with the culture of the team? Can we collaborate authentically? Can we disagree without derailing?
Because in Dulles’ world, conflict isn’t toxic. It’s essential. But only if there’s openness. Which brings me to one of the most powerful moments in the conversation.
Disagree. Then Commit.
Dulles borrowed this from his Amazon playbook. The idea that leadership isn’t about conformity. It’s about backbone. The ability to speak up, hold your position, and then once a decision is made, have the humility to commit to it.
This is rare. In most teams, people either don’t speak up (to be politically safe), or they fight until everything is dysfunctional. The elegant middle is what Dulles aims for: honest dialogue, clear dissent and finally aligned execution.
“Conflict is healthy, if there’s transparency and no personal agenda.”
It’s a simple sentence. But it has profound implications on how you hire, build culture, and drive growth.
Career Advice, By Not Giving Any
Here’s what I loved most about Dulles’ approach: he doesn’t give career advice in the conventional sense. He doesn’t prescribe a formula. He shares how he thinks. And that becomes the lesson.
He didn’t “plan” his career. He failed NDA exams twice. Got rejected due to hearing loss. Missed entrance exams. Ended up in travel and tourism. And from there, carved a path through curiosity, adaptability, and consistently showing up.
His advice to professionals?
Don’t obsess over whether it’s B2B or B2C. Don’t box yourself into linear career planning. Instead: follow your curiosity. Learn fast. And treat every industry like it’s your canvas.
Leadership in 2025 and Beyond
When asked about the future of leadership in a tech-saturated world, Dulles didn’t throw buzzwords. He offered something far more grounded: the belief that technology won’t lead education. Educators will, by leveraging technology. That’s a bold reframing. Especially in a world chasing AI-led everything.
Tech is an enabler. People drive value.
🎧 If this resonated, you’ll enjoy the 25-minute audio episode with Dulles Krishnan.
And we are proud to announce Dulles is one of the 10 "Gurus" in Brain Box Gurukul, which would be launching for DIY lovers very soon.
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