It's one of the few conversations from my career that I can still remember almost word for word.
Someone had recently joined my team after working for several different managers over a number of years. It became clear pretty quickly that there were performance issues. They weren't beyond improvement, but the issues were significant enough that they needed to be addressed.
When we sat down to talk, I expected the conversation to be difficult.
I didn't expect surprise.
The person sitting opposite me wasn't defensive or argumentative. They were genuinely shocked. Nobody, they told me, had ever raised these concerns before.
I believed them.
That conversation has stayed with me ever since, not because of what I had to say, but because of everything that hadn't been said before I arrived.
Someone, perhaps several people, had decided that saying nothing was the kinder option. Whether they were trying to protect the individual, preserve the relationship or simply avoid an uncomfortable conversation, the result was the same. Years had passed without this person being given the opportunity to understand what was holding them back.
I often think that the hardest part of that conversation wasn't having it.
It was knowing how much easier it could have been if someone had had it much sooner.
When kindness becomes avoidance
Kindness has become one of the defining characteristics of good leadership. As organisations place greater emphasis on wellbeing, psychological safety and inclusive cultures, leaders are rightly encouraged to be empathetic, compassionate and supportive.
Those are all qualities worth celebrating.
What concerns me is that kindness is sometimes confused with comfort.
In trying to avoid causing distress, some leaders avoid saying the very things people most need to hear. Feedback is postponed and performance issues are left unspoken.
Behaviour that affects colleagues is quietly tolerated because no one wants to upset someone or damage a relationship.
The intention is usually positive, however the consequences often aren't.
Most leaders don't avoid difficult conversations because they don't care. They avoid them because they do. Nobody enjoys telling someone they're falling short or that their behaviour is affecting others. We naturally want to preserve relationships and avoid conflict, and behavioural psychology tells us that's entirely predictable. Faced with discomfort, we're inclined to postpone it, convince ourselves the problem will resolve itself or hope that circumstances will somehow change.
Unfortunately, they rarely do.
Small issues become patterns and then patterns become habits. Habits become part of someone's professional identity, making them far harder to change than they ever needed to be.
The cost of silence
One of the greatest misconceptions about psychological safety is that it means protecting people from difficult feedback.
Amy Edmondson's research suggests something quite different. Psychological safety is about creating an environment where people feel safe enough to speak honestly, ask questions, admit mistakes and learn from them. Honest feedback isn't at odds with psychological safety; it's one of the things that makes it possible.
Kim Scott makes a similar point in Radical Candor. Great leadership depends on two things existing together - caring personally and challenging directly.
Without care, challenge becomes harsh.
Without challenge, care becomes avoidance.
Neither helps people grow.
Looking back at that conversation, what strikes me most isn't that someone eventually addressed the issue. It's that nobody had done so sooner.
Imagine discovering that something has been limiting your career for years while the people around you had noticed it all along. Imagine realising that promotion opportunities, development conversations or performance reviews had all passed without anyone giving you the information you needed to improve.
That isn't just uncomfortable, it's profoundly unfair on just on the individual but on the teams that they have been part of.
Leaders sometimes avoid honest feedback because they worry about damaging confidence. In reality, delayed feedback often has exactly that effect. Instead of helping someone correct a recent behaviour, it leaves them questioning their judgement, wondering why nobody trusted them enough to tell them earlier and asking what else they might have been getting wrong.
The psychological impact is significant, and the organisational impact is very real and very deep.
When poor performance isn't addressed, colleagues notice. High performers begin compensating for work that isn't being done well. Eventually, frustration quietly replaces trust because accountability no longer feels consistent.
Research into organisational justice repeatedly shows that people are more engaged when expectations are clear and applied fairly. If you remove that sense of fairness, commitment gradually begins to be eroded.
And that’s before we get to the financial implications.
Lower productivity. Higher turnover. Increased recruitment costs. Lost organisational knowledge. Managers spending time working around problems instead of solving them. Customer experience suffers because internal standards have slipped.
Few organisations would ever identify "avoided conversations" as a line in their accounts, but there are many that pay for them every day.
Leading with humanity
Kind leadership isn't about making work comfortable. It's about creating the conditions in which people can succeed, and sometimes that means having conversations that neither person is looking forward to.
Handled badly, those conversations damage trust. Handled well, they strengthen it. They demonstrate respect because they tell someone, clearly and honestly, "I believe you're capable of better, and I'm prepared to help you get there."
Personally, I think that's one of the biggest misunderstandings in modern leadership - compassion isn't the absence of challenge. For me, compassion is the reason I challenge in the first place.
As we prepare for this year's Leadership Live, where we'll be exploring the theme of Humanity in Leadership, I've found myself thinking about that conversation more than once. As AI and emerging technologies reshape the workplace, we'll spend a lot of time discussing what makes leadership distinctively human.
Having those challenging conversations, this is part of the answer.
Humanity isn't found in avoiding uncomfortable moments. It's found in approaching them with empathy, honesty and respect. It means caring enough to say what needs to be said while there's still time for someone to do something with it.
I still think about the person who looked across the table and said, "No one has ever told me that before."
Every leader should hope they never hear those words - not because the conversation is difficult, but because by the time they're spoken, countless opportunities to help someone succeed have already been lost.
