Experimental with Amale Ghalbouni & Dhiraj Mukherjee | Leadership Through Uncertainty

Amale Ghalbouni & Dhiraj Mukerjee in conversation. Excerpt taken from the conversation featured in Experimental

What does good leadership look like when the market is changing faster than your plan?

That’s the question at the heart of my conversation with Dhiraj Mukherjee, co-founder of Shazam.

Dhiraj launched Shazam in 2000, shortly before the dot-com bubble burst. The investment environment collapsed, the route to market kept changing and the possibility of running out of money was never far away.

There was no neat innovation framework protecting the team from uncertainty. They had to keep adapting while building something the world hadn’t seen before.

“We had to keep learning faster than the market was changing,” Dhiraj told me.

That experience shaped his view of modern leadership. Teams don’t need leaders who pretend to know every turn in the road. They need leaders who can hold a direction, build trust and keep everyone moving as new information emerges.

These insights feature in my book Experimental.

Why leadership through uncertainty needs a different model

The traditional image of leadership is based on command.

The leader knows the destination, understands the route and gives everyone clear instructions. That model works reasonably well when the environment is predictable and the variables can be controlled.

It becomes much less useful when technology, customer expectations and wider market conditions keep shifting.

Dhiraj draws on three generations of leadership in his own family. His grandfather was Admiral of the Indian Navy and led through command. His father worked for Air India and operated more like an orchestrator, bringing different parts of a complicated system together.

Dhiraj describes the model leaders need now as expedition leadership.

An expedition leader sets a direction but doesn’t prescribe every step. They bring together people with different expertise, send scouts ahead and use what the group discovers to choose the next part of the route.

The team isn’t waiting to be told what to do. Everyone is helping to navigate.

That requires leaders to be clear about the problem and the ambition while remaining open about what they don’t yet know.

Show character rather than false clarity

One of Dhiraj’s most useful provocations is that leaders need to show character, not complete clarity.

That doesn’t mean confusing people or refusing to make decisions.

It means recognising the difference between offering enough clarity to act and inventing certainty that doesn’t exist.

A leader can say:

• We know what problem we’re trying to solve.

• We understand the direction we want to travel.

• Here’s what the current evidence suggests.

• Here’s what remains uncertain.

• Here’s how we’ll learn and adjust together.

That kind of honesty builds more useful confidence than presenting a detailed route map for a journey nobody has taken before.

It also creates room for the team to contribute.

When a leader appears to have every answer, people learn to wait. When the leader is open about what’s missing, people have permission to share what they can see.

That’s especially important in large organisations, where senior leaders often sit furthest away from the daily reality of the customer, process or product.

Curiosity begins outside the organisation

Dhiraj sees many established businesses working from the inside out.

The company decides it needs to increase sales by 10 per cent, reduce costs or launch a new technology. Everyone then focuses on delivering the internal target.

The customer hasn’t received that memo.

Customers care about the problem they’re trying to solve, not the organisation’s quarterly ambition.

Dhiraj’s advice is to work backwards from the customer. What has changed in their world? What do they need now? Where could your organisation create value?

The same applies to organisational transformation.

Before redesigning a team, introducing AI or rolling out a new way of working, spend time understanding the people expected to make the change real.

What’s making good work harder today? What might they lose? What would make the new approach valuable rather than simply disruptive?

This is where curiosity becomes a leadership discipline rather than a creative exercise.

It helps leaders find the real problem before committing everyone to a solution.

Small bets make innovation safer

Not every experiment at Shazam succeeded.

At one point, the team invested in providing more information about songs and artists. The idea seemed logical. People identifying music might also want detailed profiles.

They didn’t.

Customers came to Shazam for the experience of discovering music, not for an encyclopaedia they could find elsewhere.

“People don’t try dumb ideas,” Dhiraj said. “Ideas only look dumb in retrospect.”

The test clarified what people truly valued.

Dhiraj later applied the same small-bet mindset as Head of Innovation at Virgin Money. The setting was more regulated and risk-conscious, but the core principle still worked.

A responsible organisation doesn’t need to gamble the entire business to innovate. It can identify one important assumption and find a small, credible way to test it.

The aim isn’t to fail for the sake of it. It’s to avoid discovering the idea was wrong after months or years of expensive implementation.

Trust turns contribution into ownership

None of this works without trust.

Leaders can’t ask for input repeatedly and then ignore everything they hear. Teams quickly recognise when participation is theatre.

Trust grows when people are involved before the answer is finished. It grows when leaders explain how feedback changed the plan, or why they decided not to act on it.

Dhiraj suggests sharing your own analysis, then asking the team what it would take to go further.

“What would it take to double that?” can open a much more useful conversation than simply imposing a larger target.

The point isn’t the number. It’s discovering what assumptions, barriers and opportunities the original plan missed.

From the conversation to your organisation

Dhiraj’s experience offers a strong leadership playbook for uncertainty:

Hold onto one meaningful vision. Be honest about what you don’t know. Give people a role in navigating. Work backwards from the customer. Build trust before asking for risk. Use small bets to turn assumptions into evidence.

These are also central ideas in Experimental: The Restless Leader’s Field Guide for Building High Performing, Change Ready Teams, my bestselling business book on leadership and transformation.

The book is designed for leaders inside complex, risk-averse organisations who can see that the old route isn’t working but can’t simply abandon the expedition.

In my work as a leadership and innovation keynote speaker, I help audiences turn these ideas into practical moves they can make immediately.

Start with one live challenge.

Share what you believe. Name what you don’t yet know. Then ask your team:

What would need to be true for us to test a better route in the next 30 days?

To unlock this conversation and all the other conversations featured in the book,

Grab your copy of Experimental now →

And if you’d like to bring these themes to your audience, get in touch or connect with me on Linkedin.