This week on Random Access Memories, I'm reflecting on my conversation with Juan Rodriguez, co-founder and CEO of Whistic, someone I've known for years and who has probably had more influence on my leadership style than almost anyone else I've worked with.

Juan isn't your typical CEO. He's incredibly demanding, deliberately makes people uncomfortable and has a habit of challenging absolutely everything. But he's also one of the most caring leaders I've worked with. He genuinely wants people to succeed, even when that means having difficult conversations or pushing them further than they think they can go.

We talked about his childhood watching his mother sell stuffed animals door to door in Mexico, why he believes discomfort creates growth, the importance of hiring people who challenge you, and what he learnt from stepping aside as CEO of the company he founded.

But the conversation that stuck with me most was about layoffs.

Juan admitted that he cries before letting people go. Not because he doesn't understand the business decisions, but because he understands exactly what those decisions mean for the people affected.

It's not something you hear many CEOs admit publicly.

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Juan believes we spend too much time trying to make people comfortable, whether that's our children or our employees. He deliberately challenges people in interviews, encourages disagreement and believes some of the best ideas emerge when people are forced to figure things out themselves.

He even thinks children need to experience boredom because that's where creativity develops.

If everyone around you is comfortable agreeing with you, you're probably not growing.

One of the things I learnt working with Juan was that he genuinely wants people to push back. He doesn't want employees who nod along with his ideas, even when he's convinced he's right.

He's had candidates withdraw from interviews because he challenged them so aggressively. His view is that if someone can't disagree with him during an interview, they're probably not going to challenge him when it really matters.

I still carry that into my own leadership today.

If you're paying someone to agree with everything you say, what exactly are you paying them for?

When I asked Juan about the hardest moment of his professional life, he didn't hesitate. Layoffs.

He talked about how fairness is one of his strongest personal values and why making good people redundant is particularly painful. These aren't necessarily people who've performed badly. Often they've done exactly what was asked of them.

Juan admitted he cries before letting people go.

We spend plenty of time celebrating CEOs for making tough decisions. We spend far less time talking about what those decisions do to the people making them.

Being accountable for a decision doesn't mean you stop caring about the consequences.

Juan grew up watching his mother build businesses. Starting something himself never seemed particularly frightening because entrepreneurship was simply normal in his family.

He made an interesting distinction between entrepreneurs and everyone else. It's not necessarily that entrepreneurs enjoy risk more. They tend to give greater weight to the potential reward rather than focusing entirely on what might go wrong.

That resonated with me, particularly reflecting on some of my own career decisions that didn't work out.

A decision that ends badly isn't automatically a bad decision.

Towards the end of our conversation, Juan talked about reading Radical Candor and having a moment of realisation about his own leadership.

He'd previously assumed the book was essentially an excuse for people to be unpleasant. Instead, he realised that accountability only really works when people believe you genuinely care about them.

Otherwise, you're just criticising someone.

It's something Juan has always done naturally. He can be incredibly tough on people, but they know he wants them to succeed.

The ability to challenge someone is earned through the relationship you've built with them.

I've worked with plenty of leaders throughout my career, but Juan is probably one of the people who has influenced how I lead teams the most. And one of the biggest lessons I took from working with him was something we discussed again during this conversation.

If we succeed, it's because of the team. If we fail, it's my responsibility.

It sounds obvious, but I think an extraordinary number of leaders get this completely backwards. They're happy to stand in front of the company celebrating the wins, taking credit for the strategy and explaining how their vision made everything possible. But when things go wrong, suddenly it's the market, the economy, the engineering team or someone who apparently wasn't performing.

Juan approaches leadership differently. He believes in finding the intersection between what someone wants to achieve and what the business actually needs, then giving them the freedom to figure out how to get there. That doesn't mean lowering expectations. Quite the opposite. He sets incredibly high standards and expects people to challenge him, disagree with him and take ownership of their work.

I've increasingly adopted that approach myself. I don't particularly want to tell talented people how to do their jobs. I want to agree on what we're trying to achieve, understand what they need from me and then get out of their way. If they succeed, they deserve the recognition. If they fail, I need to ask whether I gave them the right environment, support and opportunity to succeed.

But the interesting thing about Juan is that he doesn't believe his approach is the only way to lead. When I asked whether every leader should behave this way, he pushed back. Different personalities and leadership styles work for different people. His approach comes from his upbringing, his experiences and the values his parents instilled in him.

I think that's an important distinction. Leadership isn't about copying someone else's personality. It's about understanding what you believe, taking responsibility for your decisions and creating an environment where other people can succeed.

And perhaps most importantly, being willing to take the blame when they don't.

Towards the end of the conversation, Juan talked about reading Radical Candor and realising something important about why people responded to his leadership style. He'd always been demanding, sometimes brutally so, but he genuinely cared about the people he worked with. Reading the book helped him understand why that combination worked.

It made me think about something Hayley and I have tried to teach Ollie and Izzy, and a quote we have on Ollie's bedroom wall from The Boy, the Mole, the Fox and the Horse by Charlie Mackesy.

"In a world where you can be anything, be kind."

It's one of Hayley's favourite sayings, and we have it in several places around the house. I think it's easy to underestimate how important that message is, particularly when we're constantly encouraging our children to achieve more, work harder, compete and succeed.

Juan and I actually have very similar approaches to parenting, particularly when it comes to football. We both push our boys to take risks, work hard and give everything they've got. We talked about how sometimes the performance you're most proud of isn't the goal or the assist, but the moment your child gets knocked down, gets back up and keeps fighting.

I remember Ollie playing against a lad who was considerably bigger than him, playing in the Sheffield United academy. He was getting absolutely battered, but he kept going. Afterwards, Ollie thought he'd played terribly. I told him it was one of the best performances I'd ever seen from him because of the determination he'd shown.

I want my kids to be ambitious. I want them to work hard, take risks and be resilient. But I also want them to understand that none of those things matter much if they don't treat people well along the way.

That's what I liked about Juan's approach. You can demand excellence from people while still caring deeply about them. You can challenge someone without humiliating them. And you can push people to become better without making them feel that they're somehow not good enough already.

Being kind doesn't mean lowering your standards. It means remembering there's a human being on the other side of them.

And if Ollie and Izzy grow up understanding that, I'll consider it a pretty good result.