Are you a good leader? 3 paradoxes that say otherwise

Leadership is usually discussed in terms of vision, execution or performance. But I’d say more than anything else, what defines great leadership is an understanding of human behaviour and all its paradoxes. 

We seek approval, yet lose respect by doing so. We avoid risk, yet regret not taking it. We distrust our intuition, only to find we perform better when we’re in auto-pilot. 

Each of these psychological contradictions contains a lesson that every leader would do well to understand. In this first installment of a two-part series, I’ll explore three out of six human paradoxes, and what they reveal about effective leadership. 

1. The Paradox of Pleasing: Leaders need the courage to be disliked

The more you try to be liked, the less you’re respected.

Most people are wired to seek belonging; our evolution has literally depended on social connection for its survival. 

That instinct intensifies at senior level, particularly for newly appointed leaders. They want to maintain harmony, smooth every edge, and show they’re approachable. There’s nothing wrong with a leader who wants to be liked. The risk is when it overtakes their sense of judgement.

Teams notice when tough feedback is softened to avoid upsetting someone, or when decisions bend to keep everyone happy. If a leader’s position appears contingent on how well it will be received, authority feels fragile. 

Leaders need the courage to be disliked. That doesn’t mean they have to court opposition, but they can’t be afraid of making unpopular decisions, either. The best leaders I’ve met articulate a clear rationale for decisions and hold to it, even when reactions are mixed. 

When teams see that decisions are anchored in purpose rather than popularity, they infer strength, fairness, and long-term intent. They may not agree with every call, but they trust the reasoning behind it. That’s how leaders earn genuine followership.

2. The Regret Minimisation: Leaders must encourage risk-taking

We’re more haunted by what we didn’t do than by the mistakes we made.

Many organisations still treat failure as a liability, creating cultures where people hesitate to test new approaches. Only, progress comes from learning, and learning can only happen when we make mistakes. 

It may feel safe staying entrenched in the familiar, but it stifles innovation and limits growth. In fact, the State of Innovation 2025 report proves that firms with higher innovation activity achieve “far greater” revenue growth than non-innovating firms. 

Caution is necessary in regulated sectors like banking or insurance, but without a degree of experimentation, things stagnate and the money stops flowing. If your organisation keeps postponing a digital service because it feels risky, guess where your customers will go? To your competitors who weren’t afraid to be digital-first.

Leaders must legitimise intelligent risk-taking within their teams, such as by creating space for thoughtful experimentation, allowing people to present ideas without judgement, and by asking “what are we not doing because it feels uncomfortable?”

The future won’t belong to the safest institutions. It will belong to those that explored every avenue, broke out of the box, and pursued their “what if?”

3. The Intuition Glitch: Step back and let the team run 

Overthinking simple tasks makes performance worse.

According to the conscious processing hypothesis, skilled performers do worse when they’re under pressure because it forces them to think consciously about skills that are usually performed automatically. 

Consider a pianist: normally, they can execute runs and arpeggios fluidly, but when they start thinking about each note and finger position, they break the automatic sequence, and stumble.

Likewise, when senior leaders try to control every operational detail, or insert themselves into every workflow, overall performance degrades because they’re preventing the natural, automatic flow of execution.

In financial institutions, where complexity is high and stakes are significant, the temptation to control is strong. But at the senior level, your value lies less in operating and more in creating clarity and space. Leaders must design systems and appoint people they believe in – then step back. 

The discipline of self-awareness  

Taken together, these three paradoxes challenge leaders to look inward before they look outward. The desire to be liked, the instinct to play safe, the urge to over-control – they all point to the same discipline: self-awareness. The ability to notice when approval-seeking impedes judgement, when fear narrows ambition, or when control interrupts performance. 

Leadership improves the moment that awareness is grasped. When leaders understand their own impulses, they lead with greater intention and steadiness.

In part two of this series, I’ll look at three more psychological contradictions (the Ironic Process Theory, the Socratic Paradox, and the Paradox of Happiness) and the lessons they offer about language, learning, and creating meaning at work. 

In the meantime, if your organisation is assessing the leadership behaviours required for the next phase of growth, I’d love to have a conversation.