We recently caught up with the excellent Caspar Craven, best-selling Bloomsbury author and authority on achieving Big Bold Goals, to discuss the qualities that make an effective leader in these uncertain times.
Q: How do great leaders navigate uncertainty?
Three things really stand out to me from working with exceptional leaders over the past decade.
First, they think big and embrace bold, uncomfortable conversations that challenge the status quo. They don’t just react to change; they actively shape it.
Second, they adopt a mindset of experimentation. As we enter a world with less certainty than ever, iterating and testing ideas—rather than waiting for perfect conditions—is one of the most effective strategies I see.
And finally, they lead with humility. The best leaders know they don’t have all the answers. Instead, they stay curious, ask better questions, and create space for new perspectives that unlock hidden opportunities.
These were the same lessons I learnt at the sharp end of huge waves on two sailing circumnavigations – once competitively and once with my family. There are so many parallels with the business world. Leaders who thrive in unpredictable environments don’t wait for certainty before acting. They focus on the right questions—the ones that unlock new perspectives, challenge assumptions, and help their teams see a path forward.
The strongest teams I’ve worked with understand that adaptability beats certainty every time. They build a culture where people aren’t paralysed by the unknown, but instead feel empowered to try, learn, and adjust. That’s what makes the difference.
Q: What’s the most overlooked skill in collaboration?
It’s the ability to drive real depth into conversations. Most teams—and even the most experienced leaders—stay at the surface. They think they’ve reached alignment when they’ve really only exchanged information.
A useful way to think about this comes from Richard Dawkins’ idea that there are two levels of understanding—one where you hear the words and think you get them, and another where you feel them in the marrow of your bones. The same applies to conversations.
There are distinct depths at which we communicate. Some conversations are exploratory, some lead to alignment, and some drive true commitment. Recognising where you are in a conversation—and knowing what’s required to go deeper—makes all the difference. The best leaders don’t just keep conversations moving; they move them forward with depth, precision, and purpose.
Q: What was the last book you read?
Patriot by Alexei Navalny. It’s a powerful and deeply personal account of courage, resistance, and the cost of standing up for what you believe in. Navalny’s story is a stark reminder of the role that conviction and resilience play in leadership.
Q: What advice would you give your younger self?
Ask better questions—especially to the people you trust—and really listen to what comes back. A great question to sit with is:
“What’s one thing I don’t seem to realise about this situation—or about myself?”
Too often, we operate inside our own blind spots, convinced we see the full picture. The best leaders—and the best decision-makers—actively seek out perspectives they might be missing. They don’t just surround themselves with smart people; they invite those people to challenge their thinking. The more you create that habit, the more you unlock deeper self-awareness, better decisions, and real breakthroughs.
For more information about Caspar Craven’s speaking topics, availability and fees, contact leo@vbqspeakers.com