HIPPOs, Steve Jobs, and the Tech Reality Check

In tech, we’re often told to be wary of the HIPPO — the Highest Paid Person’s Opinion, a term popularised by Avinash Kaushik in his 2007 book on web analytics.

The warning is simple: when decisions are made top-down without input from the people actually building the thing, things tend to go sideways. Fast. We’ve all seen it. The exec who saw a demo at a conference and now wants the entire platform rewritten in whatever technology was on the slide. The board member who read an article about AI and now every project needs an AI component, regardless of whether it makes sense.

But then there’s Steve Jobs.

He was the ultimate HIPPO. And often, he was right. So what gives?

The Jobs exception

Here’s how I look at it — from the tech side.

Jobs understood the technology. He didn’t just throw out wild ideas from a boardroom. He was involved in the guts of the product. He knew what was possible, what was nearly possible, and what was fantasy. When he pushed his team to do something that seemed impossible, he usually had a reasonable intuition about whether it was actually achievable with enough effort.

He also had taste — that overused word that people throw around when they can’t articulate why something is good. But in Jobs’ case, “taste” meant a deep, obsessive understanding of how people interact with products. That’s not a mystical gift. It’s the result of decades of paying attention.

And he was lucky. Great timing, a great team, and a few near-death experiences for Apple that forced clarity of focus. Survivorship bias is real — for every Jobs, there are a thousand executives whose “visionary” product ideas cratered their companies. We just don’t write books about them.

The real problem with HIPPOs

The issue isn’t the HIPPO’s opinion itself. Sometimes the highest paid person in the room has the best idea. They might have context that the rest of the team doesn’t — market intelligence, customer conversations, strategic constraints. Their input is valuable.

The problem is when their idea becomes law without a reality check.

I’ve been in rooms where a senior leader proposes a technical direction and everyone nods along, not because it’s a good idea, but because nobody wants to be the person who pushes back. The architecture gets designed around the opinion rather than the problem. Timelines get set based on what the leader wants to hear rather than what’s actually achievable. And six months later, everyone’s wondering why the project is over budget, behind schedule, and delivering something nobody asked for.

This happens more often than anyone admits. And it’s not because the leaders are stupid — it’s because the organisation doesn’t have a culture that makes it safe to say “that won’t work, and here’s why.”

What I’ve seen work

The best organisations I’ve worked in — and I’ve been inside everything from startups to HSBC — share a common trait: they make space for technical reality checks at decision time, not after the decision has been made.

The architect in the room. When strategic decisions are being made about technology, there’s someone present who can translate between business intent and technical reality. Not to say no to everything, but to say “yes, and here’s what that actually involves” or “here’s a simpler way to achieve the same outcome.”

Prototypes over PowerPoint. The fastest way to test a HIPPO’s idea is to build a thin slice of it. Not a six-month project — a week-long spike that answers the key technical questions. This depersonalises the debate. It’s no longer “I disagree with the CEO” — it’s “we tried it and here’s what we learned.”

Decisions with expiry dates. The best technical leaders I’ve worked with make decisions explicitly reversible. “We’re going to try this approach for the next sprint. If it doesn’t work, we’ll pivot.” This takes the ego out of it. Nobody has to admit they were wrong — the experiment just produced a result.

Earned authority, not positional authority. Jobs could be the HIPPO because he’d earned the right. He’d been deep in the product for years. He understood the constraints. Most HIPPOs haven’t done that work. They’re making calls based on a conference talk, a vendor demo, or an article in Harvard Business Review. That’s not vision — that’s pattern matching on incomplete information.

The “cool idea, but…” culture

The healthiest engineering cultures I’ve seen are the ones where someone can say “cool idea, but here’s how that actually works” without it being a career-limiting move.

This doesn’t mean engineers get to veto business decisions. It means there’s a feedback loop between the people who set direction and the people who build things. The ideas still flow from the top — but they get stress-tested on the way down.

Unless your HIPPO is secretly a product visionary with genuine technical depth who surrounds themselves with people who can tell them “no” — maybe don’t build your entire technical strategy around their opinions.

Let the best ideas win. Validate them. Stress test them. And make sure someone in the room can say, “cool idea, but here’s how that actually works.”