Why the best tech leaders never graduate

In an era where AI can generate answers in seconds, the leaders pulling ahead are the ones who stay curious enough to keep on learning. 

One of the world’s most experienced cybersecurity leaders has the Japanese Kanji for ‘beginner’ tattooed on his arm. For Lance James (Founder and CEO at Unit 221b), the symbol is a reminder of a Zen concept known as shoshin, or ‘beginner’s mind’. 

As Lance told Black Hat MEA in an interview:

“The core principle of approaching everything as if it's our first time, even if we've done it a thousand times before, resonates deeply with me. It reminds us to always be fully present, open to new opportunities, and eager to learn.”

At first glance, that mindset could seem at odds with the demands of leadership today. Experience is valuable, and you gain expertise through hard work and time. Careers are (or at least, were) built on becoming the person with the answers.

Now though, the ability to keep learning may be becoming more valuable than knowledge itself.

When knowledge stops being the advantage

When we spoke to Julian Tan (Director of Corporate Strategy at BT Group), he pointed to a shift many professionals are already beginning to feel.

“Knowledge is becoming a commodity, so the differentiators over the next five years certainly won’t be about who knows the most.”

Information is increasingly abundant. AI tools can summarise reports, generate ideas, write code and answer questions in seconds. The competitive edge is moving elsewhere: towards interpretation, judgement, humility and the ability to challenge assumptions.

Research supports that shift. In a 2020 paper, Elizabeth Krumrei-Mancuso and Steven Rouse examined links between intellectual humility and learning across five studies involving 1,189 participants. They found that intellectual humility was associated with greater general knowledge and with less claiming of knowledge people did not actually have.

In other words, the people most willing to recognise the limits of what they know may be better placed to keep learning.

The expertise trap

This creates a paradox. The more successful someone becomes, the easier it is to become trapped by expertise.

• Founders can get attached to the strategies that worked during their early growth years.
• Operators can rely on playbooks that were effective in previous market conditions.
• Leaders can find themselves surrounded by people who expect them to have answers rather than questions.

The danger is subtle. Experience builds confidence, but confidence can harden into certainty.

A related study by Tenelle Porter, Karina Schumann, Diana Selmeczy and Kali Trzesniewski found that intellectual humility predicted ‘mastery behaviours’ when learning – behaviours such as pursuing challenge and engaging more deeply with learning tasks.

That is important for tech leaders because fast-moving industries punish fixed thinking. The point isn’t to abandon expertise – it’s to stop treating expertise as a finished state.

Lance told Black Hat MEA he sees a version of this challenge in cybersecurity: 

“Unfortunately, our industry often suffers from imposter syndrome, where individuals feel like frauds or believe they aren't good enough.”

But he also describes the work itself as a source of “joy and childlike wonder” when it involves tinkering, discovery and flow. That’s the beginner’s mind in practice: not pretending to know less than you do, but staying open enough to notice what you still have to learn.

Staying a student

That idea aligns closely with another point from Julian:

“While intelligence is commoditising, the core skill of interrogating it is only becoming more important. Asking the right questions and challenging assumptions are key and true curiosity unlocks these.”

For founders and operators, this has practical consequences. Staying a student might mean seeking perspectives outside your discipline. It might mean asking the newest person in the room what they see that others have missed, or learning an unfamiliar tool before you need it, or revisiting a business assumption that once felt settled.

We’ll always need experts. But more and more, we also need people who are dedicated to learning for the rest of their lives. 

Or, as Lance put it, leaders should strive to approach every challenge “as if it's our first time, even if we've done it a thousand times before.”