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Why Kind Leaders Have the Hard Conversations
There's a manager I think about sometimes – not a real individual, but a type I've met in workshops dozens of times over. Warm, well-liked, genuinely cares about their team. And quietly, slowly letting a performance problem fester for months because raising it felt unkind. By the time it finally came out, it came out as a formal process, a shock to the person involved, and a mess for everyone. Avoided for kindness. Cruel in the end.
And that's the paradox at the heart of kind leadership. The thing that feels kindest in the moment – saying nothing, keeping the peace, not making it awkward – is very often the unkindest thing you can do over any length of time. The hard conversation you didn't have doesn't disappear. It just grows.
I'm convinced that the willingness to have difficult conversations, early and well, is one of the truest tests of whether a leader is actually kind or merely nice. So why is it so hard, and how do you get better at it?
What is kind leadership?
When I ask leaders to picture a 'kind leader', I often see a slight hesitation. There's a faint anxiety in the room. People want to say the right thing, but somewhere in the back of their mind is a worry: does 'kind' mean soft? Does it mean being popular at the expense of being effective? Does it mean never pushing hard, never raising difficult things, never making the call that not everyone agrees with?
It doesn't. Kind leadership is actually one of the most demanding forms of leadership there is. Let me explain what it actually involves.
Why kindness is good for business
A few years ago, I delivered a keynote to a large investment bank in Rome. At the end, during the Q&A, someone asked me what had most helped me build a global business from scratch. 'Kindness fuels everything,' I said. 'If you're kind and people trust each other, then you win. It's as simple as that.'
The room divided almost instantly. There were people nodding vigorously, and there were people pushing back hard – 'No way! Business is all competition!', 'The ruthless always succeed!' Someone pointed at Steve Jobs and Donald Trump as proof that kindness has no place at the top.
I've been thinking about that moment ever since. And I've spent the years since gathering the evidence, the case studies and the stories that prove the opposite is true. Kindness isn't the soft option. It's the smart one.