The Two Questions Every Restructuring Reveals

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The new organisational chart went up on a Tuesday. Twenty-three boxes, cleaner reporting lines, three fewer layers between the shop floor and the board. The CFO had modelled it for six weeks. The logic was airtight; cost synergies, faster decision-making, a structure built for where the business was going rather than where it had been.

By Thursday, the best engineer on the team had updated her CV.

Nobody had done anything wrong, exactly. The structure made sense. The targets were rational. The process was efficient. And yet something had gone missing in the gap between the org chart and the people standing on it because an organisation, however elegantly designed, is never experienced by the people inside it as a system. It's experienced as a conversation. A decision they weren't part of. A message from a manager who seemed rushed. A rumour that reached them before the announcement did. Systems live on paper. People live in moments.

This is the paradox at the centre of senior leadership. The capabilities that get you promoted - strategic thinking, operating models, metrics, accountability structures - are almost entirely systemising capabilities. And they matter enormously. But the higher you climb, the more your effectiveness depends on something the org chart can't measure: how the people inside your systems interpret and emotionally respond to them.

Two ways of seeing

The psychologist Simon Baron-Cohen drew a useful distinction, not as a leadership model but as a way of describing two different drives in how people engage with the world. Systemising is the drive to understand rules, patterns, and cause and effect - if I do this, that happens. Empathising is the capacity to recognise what another person is thinking or feeling, and to respond to it appropriately.

Most senior leaders are strong systemisers. It's a large part of how they got the job. Fewer are equally strong at empathising and fewer still have learned to hold both at once, under pressure, in the same afternoon. That combination, I'd argue, is the actual job.

Great leadership requires the ability to systemise the organisation while empathising with the people inside it.

Two ways to fail

A leader high in systemising and low in empathising will, over time, build something efficient and hollow. The restructure will be well argued. The spreadsheet will balance. But people will start to feel like variables rather than colleagues - managed, not led. Trust erodes quietly, long before performance does, because nobody feels seen.

The opposite failure is quieter but just as costly. A leader who empathises deeply but struggles to systemise builds warmth without structure. Difficult decisions get delayed out of kindness. Underperformance gets tolerated because confronting it feels unkind. Standards blur. Everyone feels cared for and nobody is quite sure what's expected of them - which, given enough time, people experience as its own kind of neglect.

Neither failure is a character flaw. Both are a leader operating on one setting when the moment demanded two.

The three questions

In practice, the two capabilities ask different things of a situation.

Systemising asks: what is happening, what's causing it, what needs to change?

Empathising asks: how are people experiencing this, what are they worried about, what meaning are they attaching to it?

Leadership asks the harder, third question: how do I make the right organisational decision in a way that people can understand, trust and act on?

That third question is where I find it useful to think in three parts a logic, empathy and authenticity. Logic makes sense of the system: it's the discipline that gets you to the right structural decision. Empathy makes sense of the people: it's what tells you how that decision will land, and where. Authenticity is what makes people believe you. You can have the logic right and the empathy right and still lose the room if people sense you're performing concern rather than feeling it. They can tell.

Back to Tuesday

Picture the same restructuring, run by a more complete leader. The structure doesn't change - twenty-three boxes, three fewer layers, the same hard commercial logic. But the sequence does. Before the chart goes up, she talks to the team leads about what's coming and why. When she announces it, she names what people stand to lose, not just what the business stands to gain - a report they built, a title they earned, a team they trusted. She explains the reasoning in plain terms, not slide language. She leaves room for people to be upset without treating their reaction as resistance to be managed. And critically, she tells them what happens next, specifically, because uncertainty is what people can't tolerate, not change itself.

Nothing about the system changed. Everything about how it was inhabited did.

That's the distinction worth thinking about. Systemising ability tells you what the right structure is. Empathising ability tells you how it will be received. Leadership is the discipline of holding both, and refusing to let the comfort of one excuse the neglect of the other.

So the next time you're about to make a major call, a restructure, a strategy shift, a decision that will ripple through people's working lives, ask it twice.

Does this make sense as a system?

And how will it feel to the people living inside it?