Bringing Compelling Stories to Life

5 keys to a compelling leader’s story


Many years ago I worked with a leader in the finance industry. She was the COO of a large bank and was leading the organisation through a complex transformation. We had the strategy story completed and I was trying to convince her that we needed to develop her story as a leader.


Anne: “Why do we need that? The stories not about me it’s about the team.”


Mark: “Yes, but you are the leader of the team. People want to know how you see the world.”


Anne: “I hate talking about myself, and I don’t want to stand in front of my people talking about how great I am. Besides, my story isn’t that interesting anyway.”


Anne later shared that she had done a version of her story during some media training and had shared it with her team and it didn’t go well. Anne had fallen into the trap that many leaders fall into of only telling a positive story, and as a result, she had been perceived as being inauthentic. I assured her that our process would be very different, and asked her a series of questions that ended revealing one of the most engaging leader stories I have ever heard.


In creating an engaging leaders’ story, there are 5 critical question to answer:


  1. How did you get into this industry and what have you experienced?

Very senior leaders are often seen as exceptional and there can be a misconception that they were always going to make it. And yet, I still haven’t met a leader that intended to end up where they are. By giving your audience context for your journey, you can show that your success wasn’t predetermined, but rather a series of choices and experiences.


  1. What is the biggest challenge you face right now and what’s at risk?

Leaders are meant to have all the answers and to tell people what they need to do. The problem is this is rarely the case. By identifying the challenge that you see and what is at risk, you force your audience to focus on the  most pressing problem at hand and create a sense of urgency. Hearing a leader talk about this also forces your audience to understand that this is also their greatest challenge.


  1. What do you love most about what you do and how do you do it?

Any successful leader I have ever met is successful for a reason, and that is because they love what they do. Whether it is leading a team, developing people or solving big problems, chances are what you love is exactly what is needed in this moment to solve the challenge you are facing. In this way you can demonstrate how you see the world and where the opportunity lies moving forward.


  1. What keeps you up at night?

Whenever I ask a leader this question they are taken aback. Too often leaders are expected to be confident and have all the answers. And yet, whenever I ask them this question the answer is always around not being able to effectively lead the team, make the change or engage the right people. In short, not being enough. Sharing this with your audience is a powerful way to show that you are human, you are vulnerable, and is a key way to connect with your audience.


  1. What is the difference can you make and what will it mean?

In great stories people don’t become something else, they just become who they really are. It is only through great challenge that they are forced to grow and step into the person (or leader) they are meant to be. This is where a leader can demonstrate their values and how they overcome adversity. They can also then create a picture of what it will mean when “we” are able to achieve the goal or deliver on the promise.


As it turned out, Anne had gone from studying archeology in the United Kingdom, digging holes next to female inmates from a local prison, to her dad telling her to “learn about those computers because they are the future”. This led to her studying computer science and ultimately becoming the COO of one of Australia’s leading banks. As it turns out, her personal transformation was exactly the experience that was needed to lead her team through their business transformation.


By asking these five questions in creating your story, you may not only be able to create an engaging leaders’ story, but you just might be able to transform your leadership.