There is a moment in the 2011 film Moneyball that captures a leadership transition many professionals recognise.
Billy Beane knows baseball. He understands the game inside out. But when he is forced to build a competitive team with limited resources, doing what has always been done is no longer enough.
The challenge is not effort or technical knowledge. It is changing how decisions are made, often in the face of scepticism and incomplete information.
That moment resonates because leadership transitions often look like this. You are no longer rewarded simply for doing the work well. You are asked to set direction, make trade-offs and stand by your judgment when the answers are not obvious.
This is why sports films endure. They often show people who excel at execution but struggle when asked to lead, to decide under ambiguity, scrutiny and pressure.
Last week, I participated in a fireside chat on mentorship, allyship and building networks as part of the Women in Cyber Leadership Programme.
As with most fireside conversations, not every question was directed at every panellist. But the discussion surfaced a familiar pattern — one I have seen repeatedly across roles, sectors and career stages.
The hardest transition into leadership is not technical. It is the shift from doing the work to setting direction and shaping decisions.
Looking back, what I now recognise as mentorship did not feel formal at the time. I did not even have the language for it.
I remember being promoted and feeling more apprehensive than excited. What stayed with me was not the role itself, but how my boss framed the decision.
The promotion was not only about output, but responsibility, ownership and judgment.
That moment marked an important realisation. Performance may get you noticed, but leadership develops when someone signals confidence in how you think, not just in what you deliver. At the time, I did not call it leadership development. In hindsight, that is exactly what it was.
What is striking is how closely this mirrors workforce research.
The (ISC)2 Cybersecurity Workforce Study shows that while technical capability in cybersecurity continues to grow, leadership gaps persist, particularly in judgment, communication and decision-making under pressure.
The hardest part of progression is not technical mastery. It is the move from execution to leadership thinking.
This transition matters because leadership decisions, especially in high-risk and regulated environments, are rarely made with perfect information.
Representation matters here as well. Women make up only around 20 to 25 per cent of the global cybersecurity workforce, with representation falling further at senior levels.
This is not simply a diversity issue. It is a decision-quality issue. When certain perspectives are absent, some ways of assessing risk and consequence never enter the room.
This aligns with broader leadership research. Highly effective CEOs spend a significant portion of their time engaging stakeholders, because good decisions depend on hearing different perspectives.
If leadership effectiveness relies on perspective, under-representation becomes a real organisational risk.
Senior leadership remains largely male-dominated, and access to opportunity often sits with those in positions of power. Women tend to seek mentors or sponsors with organisational influence.
This is not out of preference, but because that is where pathways are shaped.
As such, mentorship and allyship matter beyond individual support. They make pathways visible and place responsibility on those who progress to open doors for others.
This leadership shift is not confined to cybersecurity or boardrooms. It appears in everyday moments.
I was reminded of this while in the car with my brother, a business owner, when he received a call from one of his staff.
She was anxious about being asked to lead a new task — not because of the work itself, but because she was unsure whether she was ready.
He did not question her capability or step in to take over. Instead, he talked through how to approach the task and reassured her that it was acceptable not to have everything figured out at the start.
She did not need more instruction. She needed confidence, perspective and someone to signal belief in her judgment.
Leadership progression is rarely an individual journey. It is shaped by who helps you think more clearly, who challenges your assumptions and who is willing to stand behind you when decisions matter.
Universities like my alma mater, the University of Leeds, invest in mentoring because many students already perform well. In the age of AI, what differentiates graduates is not output but leadership capability — perspective, judgment and the ability to make sense of complexity.
In the case of the Billy Beanes of the world, leadership is not about knowing the game better than everyone else. It is about being willing to change how decisions are made and standing by those decisions when they are uncomfortable.
Performance may open doors. But perspective, trust and relationships determine who is invited to lead.
The views expressed here are the personal opinion of the writer and do not necessarily represent that of Twentytwo13.
