Conventional vs. Entrepreneurial Leadership: the need for both
- Phil D'Adamo

- May 18
- 2 min read

Want to succeed as a leader or entrepreneur? Think MAIA.
That's what I learnt from Aaron Sansoni, Naomi Simson OAM, Nick Bell and Rhys Henderson at the Entrepreneur Summit on Friday.
I’ve often been struck by the tension between conventional leadership and entrepreneurial leadership. Years ago, I suggested to my CEO that our executive team needed more entrepreneurial capability to unlock innovation.
It didn’t land well. The assumption being that entrepreneurs took reckless risks and that their world did not translate to large, well-governed organisations.
I don’t buy that. If anything, the pace and scale of change today demand the opposite. Leaders need to think more like entrepreneurs. So how do entrepreneurs actually think?
I attended the summit to find out. Here’s what stood out.
Entrepreneurs are MAIA leaders:
They take Massive and Immediate Action.
They think big. They don't worry about rejection or having perfect information. They start at the end and move backwards.
They stretch themselves with MAIA courage daily. When things go wrong (and they do), they don’t stop. They adjust or start again.
This is where many conventional leaders get stuck. They are responsible for avoiding failure, for delivering results without things going wrong. It's possible if the result you're seeking is not massive. They therefore think incrementally.
Entrepreneurs take a different path. They accept failure as a possibility.
They build capacity through it. A few other patterns I observed:
They don’t separate “strategy” and “execution”. They happen together.
They build value obsessively. Buying, improving, integrating, scaling and sometimes selling.
They hire for mindset, not just experience.
They track performance closely and hold people to account.
Their vast network matters but only if it’s activated.
Here’s the part that I found most compelling:
Most didn’t start successful.
Many failed early. Some struggled at school. Most have lived through real hardship.
They don’t see that as a disadvantage.
They see it as training.
Their end game?
To be happy, healthy and wealthy.
And the best of them? They pair that with a strong sense of purpose using their success to create value beyond themselves.
What does this mean for conventional leadership?
MAIA isn’t a licence for chaos. It's something to embrace in conventional leadership.
Where are you overthinking instead of acting?
Where are you overly managing risk instead of building capability?
Where are you waiting for certainty that will never come?
What's the worst that can happen?
And one final observation from a great day. There were a lot of young people in the room, some as young as 19 actively learning how to build businesses.
That shift matters. We’re moving from: “study, then get a job” to “learn, create, test, build something of my own.”
Leaders who ignore that shift will struggle to attract and keep this generation. And that might be just what we need for our economy.



