Leading when nobody knows what comes next

This article forms part of a CN&CO series covering The Insurance Conference Western Cape 2026. Across the series, we revisit the ideas, stories and conversations shared by the conference’s speakers, highlighting the insights that are shaping insurance, business and leadership in a changing world.

Earlier this year, during the floods in the Western Cape, Stellenbosch University registrar Dr Ronel Retief was faced with a high-stakes choice: should the university close its campus? Or remain open?

Closing unnecessarily would disrupt thousands of people, cancel tests and expose the university to accusations of overreacting. Staying open, if the conditions became dangerous, could put students and staff at risk.

There was no risk-free option and no model that could make the decision for her.

While Ronel and her colleagues were studying weather reports and agonising over road safety, however, some students were outside being towed through the floodwater behind a vehicle – for fun!

It was a wonderfully human illustration of complexity. Leaders can make the most careful decision available, but people are not passive pieces in a model. They interpret decisions, work around them and occasionally ignore them entirely.

This story set the tone for Ronel’s warm, humorous and deeply thoughtful session at The Insurance Conference Western Cape 2026: a conversation about how to lead when nobody really knows what is going to happen next.

Different worlds, shared promises

Universities and insurers may appear to inhabit completely different worlds, but Ronel quickly found common ground. Both make long-term promises about a future they cannot see.

An insurer accepts a premium today for a claim that may only arise in 2050. A university welcomes an 18-year-old and promises a qualification that will still mean something decades from now.

“We are both making promises about an uncertain future,” she said. “Neither of us knows exactly what 2050 will look like, but we still have to help people prepare for it.”

The similarities go further. Insurance has a protection gap; higher education has an access gap. In both cases, the people who most need the product or service are often those least able to afford it.

Into this uncertainty steps the leader, who is expected to have direction, certainty and answers – preferably the correct answers, delivered calmly and confidently the first time.

Ronel recalled the “family meetings” of the Covid-19 pandemic, when a change in alert level would be announced on television. Within minutes, her phone would begin ringing. Would classes continue? Would residences close? Could graduation go ahead?

One message read: “In these uncertain times, surely the least the university leadership can do is give us some answers.”

The problem was that Ronel had watched the same announcement as everyone else – only four minutes earlier.

Perhaps, she suggested, leadership today is not about providing certainty. “Our job is to help people act well without it.”

The next wise action

Three frameworks have helped Ronel navigate this challenge.

Firstly, Ronald Heifetz distinguishes between technical problems, for which expertise and solutions already exist, and adaptive challenges, where the solution is not yet known and people must change how they think or work. People do not necessarily resist change, Ronel noted; they resist the loss that comes with it – the loss of a skill, status or sense of identity.

Secondy, the Cynefin framework suggests that different situations require different responses. Complicated problems can be analysed and solved. In genuinely complex situations, however, cause and effect become clear only afterwards. Leaders must try something, observe what happens and adapt.

Third is Adaptive Action, which turns this into three practical questions: What is happening? So what does it mean? Now what is the next wise action?

“A plan is not always a prediction,” Ronel said. “Sometimes it is simply a hypothesis that must change as reality changes.”

When hard work does not guarantee success

Ronel’s second story was more personal. As executive owner of SUNStudent, Stellenbosch University’s new student information system, she became the face of the largest system implementation in the institution’s history.

She had built her career on a reassuring belief: work hard and success will follow. This project did not honour that arrangement.

“There were delays, exhausted staff, functionality that did not work and high-stakes decisions about whether to proceed,” she said. “Going live too soon could threaten the institution’s academic records; delaying carried an enormous cost.”

The experience taught her to communicate precisely when she most wanted to hide, to acknowledge people’s pain rather than manage it away, and to explain the reasoning behind decisions.

“What people remember is how you behaved while the system was breaking,” she said. “That may be the only part of a crisis you can truly control.”

Five practices for uncertain times

Ronel distilled her experience into five leadership practices: collaborate, show compassion, be authentic, be honest and act.

Collaboration matters because no leader can hold all the necessary knowledge. “A team whose members all think alike simply cannot represent enough of a complex world.”

Compassion means recognising that every decision has a human cost. “The spreadsheet is not the lived experience, and understanding what someone stands to lose is not the opposite of accountability.”

Authenticity matters too. Ronel joked that her predecessor was a tall, serious, bearded man. She was none of those things. Trying to fit someone else’s leadership profile, she discovered, consumed energy she needed for the actual work.

Honesty includes having the courage to say, “I do not know.” Used properly, those words are not a retreat but an invitation: “I do not know – what do you think?”

Finally, leaders must act. They should test ideas small enough to survive being wrong, learn from the result and change course when needed. “Revising a plan is not failure; it is learning.”

Take the fork – and enjoy the journey

Ronel ended with a refreshingly undignified approach to wellness.

“Take the lunch break,” she said. “Put in the half-day’s leave. Find friends who can love the unpolished version of you. Exercise, read, garden, go to church, watch a series or spend time with a dog – what matters is finding something that restores you.”

Quoting Yogi Berra, she left the audience with one final thought: “When you come to a fork in the road, take it.”

We do not need to know everything that is coming in order to lead. We need to know who we are, what we will not compromise, whom we will listen to and what wise action we are going to take next.

And, if possible, Ronel reminded us, we should have some fun while doing it.