Nobody Warns You How Lonely the Top Floor Is

By John Roberts, CEO – Leadership Collective Australia, 5-minute read 

Think about the last time your organisation appointed someone to a senior role — CEO, CFO, CIO, COO, General Manager. Whoever it was, they got the job because everyone in the room believed they could do it.

The CV stacked up. The experience was there. The track record, the judgement, the presence in a difficult meeting — all of it checked out.

So why do so many genuinely capable leaders end up struggling?

It's rarely because they've run out of ability. Far more often, it's because they've run out of people to talk to.

The higher you go, the smaller the room gets

Here's something that doesn't come up in the interview process: the more senior you become, the fewer people you can be completely honest with.

There are things you can't say to your team, because they'd read too much into it.

Things you shouldn't say to your board, at least not before you've worked out what you actually think.

And things your family and friends will listen to kindly, but can't really help you untangle — because they've never sat where you're sitting.

So you carry it yourself. The restructure. The person who isn't working out but who everyone likes. The growth plan you're not sure about. The shareholder who keeps calling. The acquisition that looks great on paper. The nagging question about whether this is even the right job for you anymore.

None of that is unmanageable on its own. It just gets very heavy when there's nobody to put it down in front of.

The best leaders don't do it alone

Here's the thing worth noticing about the executives who seem to handle all this well: almost none of them are doing it in isolation.

They go looking for perspective. Deliberately. Not because they doubt themselves — usually quite the opposite — but because they've learned that an idea you've only ever tested inside your own head isn't really tested at all.

Sometimes a peer asks one question that flips the whole problem on its side.

Sometimes you describe a challenge and someone says, "Oh, we went through that two years ago" — and saves you six months.

And sometimes a single confidential conversation gets you further than a month of internal meetings ever could.

Good leadership isn't about having every answer ready. It's about making better calls, more often.

Your organisation is a very small sample size

The real danger of isolation is subtler than loneliness. It's that you slowly get trapped inside the logic of your own business.

Same people. Same meetings. Same assumptions, repeated until they start to sound like facts.

That's how blind spots form — not through carelessness, but through repetition.

Which is why time spent with leaders from completely different worlds tends to be so valuable. A manufacturing CEO can hand a tech business the insight it's been missing. A CIO can crack something open using a lesson from healthcare. A CFO spots the opportunity everyone else walked past, simply because they're looking from a different angle.

The wider your field of view, the better your decisions get. It's not more complicated than that.

Most organisations invest in everything except this

Companies will happily spend serious money on systems, technology and process improvement.

Far fewer put anything into making sure their most senior people have a trusted group of peers to think with.

Which is odd, because leadership quality is one of the biggest levers on how a business actually performs.

Give an executive a confidential space to talk things through and the effects show up quickly. Better decisions. Expensive mistakes avoided. Opportunities spotted earlier. And a level of confidence in their direction that's hard to manufacture on your own.

The organisation feels all of that, even if it never sees where it came from.

Curiosity doesn't retire

One more pattern worth mentioning: the strongest leaders we come across tend to be the most curious ones.

They ask for feedback they don't have to ask for. They take opposing views seriously. They're comfortable saying "I might be wrong about this" out loud, in front of people.

However far along they are, they still behave like there's more to learn — because there is.

The last word

Capability is what gets you the role.

What keeps you effective in it is something else entirely: the people around you, the perspectives you can access, and the support you're willing to ask for.

The leaders who last aren't usually the cleverest people in the room. They're the ones who built a trusted network around themselves and never got too senior to learn from it.

Because in leadership, the real risk was never capability.

It's isolation.