The real magic of enterprise leadership

It’s mid-morning, and I’m standing in a café queue.

The person ahead of me asks, “What’s a Magic?”
The waiter responds, “Well, um, it’s a type of coffee, but smaller… it’s actually our most-ordered coffee right now.”
“Cool,” says the customer. “I’ll try one of those.”

I smiled for two reasons.

First, I was in Singapore, and being from Melbourne - home of the cultish Magic coffee - it felt like an inside joke going global.

The second smile came later, as I sipped my iced matcha oat latte (very Singapore, and surprisingly delicious). Because this Magic moment reminded me of another “most-ordered item” I hear all the time in my work with leaders:

Enterprise leadership.

And I sometimes wonder whether people really know what they’re asking for when they order it.

Most of the time, when I ask what people mean by enterprise leadership, the answers are polite versions of “you know… bigger picture thinking… breaking down silos… connecting dots.” All good things, but a bit like describing a Magic as “a coffee, but smaller.” Technically true, not particularly useful.

Let’s be honest. When organisations say they want enterprise leaders, what they usually mean is: can you please get our senior people to stop obsessing about their own swim lane and start thinking like they all work for the same business?

That’s rarely a skill issue. It’s an addiction issue.

Leaders have spent years mastering their craft, their team, their function. They’ve been rewarded for control and efficiency. Now we’re asking them to zoom out and make trade-offs that might not serve their local goals. That takes daily, deliberate practice - and the courage to wean themselves off a local focus.

And to make things harder, the system often works against it.

We tell leaders to “think enterprise” while measuring them on individual KPIs.
We talk about “one team” while rewarding division-level results.
We celebrate empire builders, then run workshops on collaboration.

So the system tends to pull everyone back to their swim lane.

That’s why enterprise leadership starts with courage. The courage to lead for the whole, even when the system makes it hard. Even when sticking to your patch gets you runs on the board. 

That courage comes alive through small, deliberate practices. Here are a few to get you started: 

Keep asking, “What would our customer care about in this conversation?”

Name the enterprise question or challenge. In meetings, take a moment to say out loud what’s happening across the whole business, not just your part. It helps everyone zoom out together.

Host an empty seat in your meetings. Who’s not physically here, but would want to have a say in the decision we’re making? This could be the customer, a regulator, or another part of the organisation. 

Spend time outside your own swim lane by visiting other teams’ meetings, inviting them to visit yours, or even hot-desking in different parts of the office - not just you, but everyone in your team.

Each of these nudges helps shift a team’s perspective from “me” to “we” to “us”. 

That’s enterprise leadership. 

Magic.

Until next time,
Simon