Leading Without a Playbook: Why Modern Leadership Requires Comfort With Not Knowing

Maybe the best leaders aren't the ones who can see the future most clearly. They are the ones who can lead when the future isn't clear at all.

The larger and more complex an organisation becomes, the less important it is for the leader to have all the answers. What matters is having people around you who see things differently, who are comfortable disagreeing, and who will tell you when you are wrong. I’ve learned this over time. Earlier in my career, I was usually closest to the problem and expected to solve it myself. As the teams and organisations I led grew, my role had to change. I don't need to be the smartest person in the room. I need to make the room smarter.

That takes a certain comfort with not knowing. Being able to say, “I don't know.” Asking for help. Listening when someone pushes back on your thinking. And being secure enough to let someone else have the better answer. The harder part comes with seniority, because people don't always tell the person running the organisation what they need to hear. Creating enough trust for people to challenge you, disagree with you and still know you have their back isn't a soft skill. It is simply how good decisions get made.

With technology and AI moving as quickly as they are, this matters even more. We are stepping into areas where there isn't always a playbook to follow, and where decisions about what to build, where to invest and how to organise cannot always wait for certainty.

Maybe leadership right now is less about pretending we know exactly where we are going, and more about building an organisation that can find its way.

What has shifted most in how you lead as your scope has grown?