Building ‘What If?’ Cultures

Building ‘What if?’ cultures

I’ve been reflecting on Simon Sinek’s recent conversation with Christina Tosi, and those two deceptively simple words: “What if?”

It got me thinking about the many coffees and conversations we have with sponsors and project leaders, and a theme we see again and again: in complex project environments, people hesitate to take managed risks. Too often, everyone’s waiting for someone else to give permission.

But what if we stopped waiting?

What if leaders modelled genuine curiosity, and the courage to not have all the answers, instead of performing certainty?

Where curiosity gets stuck

This reluctance to ask “what if?” usually isn’t about competence, it’s about culture. Many leadership environments still reward knowing over learning, and achieving over experimenting.

What struck me about Christina’s story is this: when her grandmother limited her access to the “safe” baking environment, she didn’t just learn to bake differently, she learned to think differently.

That’s the paradox modern leaders face too: unlocking possibility often starts with being willing to admit we don’t have all the answers.

When leaders hold certainty too Tightly

At Advance, we see this daily. The difference between teams frozen by risk-aversion and those who experiment intelligently rarely comes down to technical skill alone, it’s behavioural.

True experimentation demands psychological safety. It starts with leaders who are comfortable asking, “What if our assumptions are wrong?” or “What if our usual approach is exactly what’s holding us back?”

It’s not about reckless trial and error, it’s about building cultures where “what if?” becomes a tool for professional collaboration, not just solo creativity.

The real risk? Playing it safe

Too often, risk management drifts into risk avoidance. But real risk management is intelligent experimentation: testing, reframing, learning.

And that mindset can’t be outsourced. If leaders cling too tightly to certainty, teams protect the status quo. When leaders show they’re comfortable with uncertainty, while staying clear on outcomes, teams learn to do the same.

What if we didn’t default to ‘proven’ anymore?

One question I keep coming back to: why do so many capable professionals stick rigidly to “proven” methods, even when they’re clearly no longer working?

Part of the answer is that certainty feels safe. But teams mirror the emotional maturity of their leaders. When leaders make space for curiosity and accountability, teams do too.

Christina Tosi didn’t succeed by avoiding failure, she turned failure into fuel. That mindset shift is a muscle leaders can develop, if they’re willing to ask better questions.

Building ‘What If?’ Cultures

At Advance, we help leadership teams build exactly this capacity: the habits, trust and conditions that make “what if?” possible, and productive.

Because in our experience, the leaders who transform teams and deliver complex projects don’t always have the answers. They’re the ones brave enough to ask the questions that unlock better thinking.

So here’s one for all of us:

What if your leadership culture encouraged more curiosity than caution?

What might you achieve?

If you’d like to explore what “what if?” could look like in your team, let’s talk. Drop us a line, because the best breakthroughs often start with a simple question.