The Island Problem: Why Leaders Struggle to Take People With Their Ideas

Leaders struggle to take people with their ideas because they often see the destination clearly without having travelled a step by step path to it. Others stand elsewhere and hear only fragments, like listeners of tapped songs. Without a reconstructed journey, the idea stays one person's island and cannot be understood, challenged or executed.

The Island Problem: Why Leaders Struggle to Take People With Their IdeasAndrew Baker's Technology Blog Posts, 04/Nov/2026
https://andrewbaker.ninja/2026/11/04/the-island-problem-why-leaders-struggle-to-take-people-with-their-ideas/

The curse of seeing something clearly is that you quickly forget other people cannot see it yet, and that they have no obligation to make the leap simply because you have already landed.

An executive said something to me recently that I have not been able to put down. He told me that I was born on an island, while he was born on the mainland. I wasn’t entirely sure what he meant at first, but as he explained it I realised he had found a remarkably elegant way of describing something I have wrestled with for most of my career. His point was that when I have an idea, I am already standing on my island. I can see the landscape, I understand how the pieces fit together, and I usually have a fairly clear view of what is broken, what is possible and what the future could look like. Everyone else, meanwhile, is standing on the mainland, and when I try to explain the idea I am effectively giving them directions to a place I have never had to travel to myself. I know my island intimately; what I don’t know is the journey from where they are standing.

That observation was uncomfortable and genuinely useful in equal measure, because it was not a criticism of the idea at all. It was a criticism of my ability to help other people reach it.

1. The Problem With Being Born on the Island

Some people arrive at ideas through a long and deliberate process. They start with a problem, collect evidence, weigh the alternatives, work through the constraints and gradually converge on a conclusion. Their thinking is sequential, which means they can describe the journey afterwards because they actually travelled it, step by step, and they can retrace those steps for anyone who asks.

Other people seem to arrive at the destination almost immediately. They recognise patterns, connect concepts that look unrelated, and form a picture of something that doesn’t exist yet, often without consciously working through the intermediate steps. They simply see it, and sometimes they see it with extraordinary clarity. The catch is that seeing the destination is a completely different skill from getting someone else there. When somebody asks how you arrived at your conclusion you may genuinely struggle to answer, not because you haven’t thought about it and not because the idea is poorly formed, but because the reasoning that produced it was never experienced as a neat sequence. You didn’t walk across the bridge; you were born on the island, and now someone is asking you to describe a bridge you have never crossed.

2. What a Stanford Experiment With Tapping Songs Tells Us

In 1990 Elizabeth Newton, then a psychology doctoral student at Stanford, ran a deceptively simple experiment as part of her dissertation that I think captures this problem better than any slide deck ever could. She split participants into two groups, tappers and listeners. Each tapper was given a well known song, things like “Happy Birthday” or the national anthem, and asked to tap out its rhythm on a table. The listener’s only job was to name the song.

Before hearing how their listener had done, the tappers were asked to predict how often listeners would guess correctly, and they estimated about half the time. Across the 120 songs tapped in the study, listeners correctly identified roughly 2.5 percent, which is about three songs. That comparison, between the success rate tappers predicted and the rate listeners actually achieved, is the whole story, and the reason for the gap is the interesting part.

When the tapper taps, they hear the melody playing in their head. They hear the words, the harmony and the phrasing, and the knocks on the table feel like a perfectly obvious rendition of the song. The listener hears none of that. They hear a series of disconnected knocks that could be almost anything, and from inside the tapper’s head it is very hard to appreciate how little information those knocks actually carry.

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I find this experiment slightly painful to read about, because I have been the tapper in far too many meetings. I have stood in front of a room describing an architecture or a change programme, hearing the full orchestra in my own head, while the people opposite me heard only knocking. And my instinct in those moments has often been to tap louder rather than to ask what they were actually hearing.

3. Why Intelligence Doesn’t Solve This Problem

One of the more interesting aspects of the island metaphor is that it has very little to do with intelligence, and in some cases intelligence makes the problem worse. People who are particularly good at recognising patterns or making conceptual leaps tend to underestimate how much intermediate reasoning other people need, because they have never needed it themselves.

Psychologists describe a related phenomenon as the curse of knowledge, and Newton’s tappers are probably its best known illustration: once you know something, it becomes very difficult to imagine what it is like not to know it. It is worth being precise about what the experiment shows, though. It demonstrates how badly we misjudge the gap between what is in our heads and what actually reaches someone else; it says nothing about how people arrive at their ideas in the first place.

My own reading of the island problem, and it is an interpretation rather than an established psychological category, is that it may be a stranger cousin of the curse of knowledge. The usual framing assumes you learned something step by step and then forgot how hard it was to learn. The islander may never have consciously experienced those steps at all. If that is the case, the problem is not just forgetting the journey but never having had a map of it to begin with, which is much harder to fix.

Either way the consequence for leadership is the same, because leadership is not simply about having good ideas. It is about creating the conditions in which other people can understand, challenge, improve and ultimately execute those ideas. An idea that lives only in one person’s head has very limited organisational value. It might be brilliant and it might even be right, but until other people can make sense of it, it remains an island.

4. The Danger of Mistaking Disagreement for Incompetence

This is where I think the metaphor becomes genuinely important for leaders. When you can see something clearly, disagreement starts to feel irrational, and you find yourself wondering how people cannot see it, why the team is still debating something so obvious, and why everyone wants three months of analysis on something you could start tomorrow. Those questions quietly carry a dangerous assumption, which is that because the destination is obvious to you it ought to be obvious to everyone else. It shouldn’t be.

Consider a fairly ordinary example. An architect proposes collapsing a sprawl of overlapping platforms into one radically simpler architecture. From the island the case is overwhelming: fewer moving parts, fewer integration points, lower long term cost and far better resilience. Operations looks at the same proposal and sees a migration that touches every critical system they are accountable for keeping up. Finance sees a large spend this year in exchange for savings that arrive in three. The product teams see a year of roadmap disruption and a lot of explaining to do to their stakeholders. The architect presents the end state again, with better diagrams, and the room gets quieter rather than more convinced.

Nobody in that room is necessarily wrong. They are each looking at a different stretch of the journey, and the architect has only described the destination. The mainland is not populated by people who lack imagination; it is populated by people who hold information you may not have, and somebody who has spent twenty years running the existing system might know exactly why the last three attempts to reach your destination failed. If you treat resistance as evidence of limited thinking you stop listening, and you lose the very information that would have made your idea better.

5. The Bridge Is Part of the Idea

I have increasingly come to believe that there are really two separate acts of creation involved in any meaningful change. The first is imagining something that doesn’t exist, and the second is working out how other people can get there. We tend to celebrate the first one, admiring founders, architects and people who can see around corners, while treating the second as mere execution.

Organisations, however, don’t transform because someone imagined a better future. They transform because a group of people collectively worked out how to move from the present to that future, and that requires a different set of capabilities altogether: patience, empathy, the discipline to listen, the ability to explain the same thing in several different ways, and the humility to accept that the bridge you imagine may not be one anybody else can actually cross. Sometimes the bridge has to be built from the mainland side, which means letting the people standing there help design it.

6. Leadership Is Not a Guided Tour of Your Island

When you are passionate about an idea there is a strong temptation to believe that leadership means convincing everyone that your destination is worth reaching. So you prepare the presentation, explain the future state and walk through the benefits, and when people still don’t get it you explain it again, sometimes louder and usually with more slides. This is the tapper’s mistake in corporate form, because each repetition sounds richer to you and no clearer to them.

A more useful starting point is to stop talking about the island and ask people to describe the mainland. What does the world look like from where they stand, what do they believe is possible, what constraints are they working within, what assumptions would have to change before the destination made sense, and what would a sensible first step look like to them? None of these questions are concessions. They are how you map the geography between two different perspectives, and sometimes they reveal that the island isn’t quite where you thought it was, or that there is a much better island nearby that you couldn’t see from where you were standing.

7. Practical Tips for Islanders

Recognising the problem is the easy part, so here is what I have found actually helps when I catch myself tapping on the table and wondering why nobody is singing along.

Ask people to play it back before you go any further. At the end of explaining an idea, ask someone to describe it back to you in their own words, and listen to what they say rather than what you hoped they would say. This is the single fastest way to discover whether they heard the song or just the knocking, and it costs you about two minutes.

Start from their current state rather than your future state. Before you show anyone the target architecture or the new operating model, describe the world as they experience it today, including its pain points, in language they would recognise. If people cannot see themselves in your starting point, they will not trust your destination.

Write down the intermediate steps, even the ones that feel obvious. Islanders skip steps because the steps feel trivial to them, so deliberately write out every stage between today and the end state and then hand that list to someone who wasn’t in your head when you wrote it. The steps that feel too obvious to mention are usually exactly the ones the mainland is missing.

Explain the idea at least three different ways. Try a concrete example, a story about a customer or an engineer, and a picture or diagram, because different people find their way across by different routes. If you can only explain an idea one way, that is often a sign you haven’t fully worked it out yourself.

Treat objections as terrain data. When someone pushes back, resist the urge to defend the destination and instead ask what they know that you don’t. A good habit is to respond to the first objection with a question rather than a counterargument, and to keep doing that until you genuinely understand the constraint behind it.

Let the mainland design the first bridge. Describe where you want to end up, then hand the first step to the people who understand the existing environment and ask them to propose how to get there. You keep ownership of the direction, they own the route, and the plan that comes back is usually more realistic than anything you would have drawn alone.

Take the smallest crossing first. Rather than asking people to believe in the whole island, find a small, reversible step that proves part of the idea and lets people experience it for themselves. Nothing converts a sceptic as quickly as standing on a bit of the island, even briefly.

Find a translator from the mainland. Most organisations have people who are trusted by the operational teams and also understand what you are trying to do. Pair up with them early, test your explanation on them first, and let them tell you where the knocking stops sounding like a song.

8. The Responsibility of the Islander

What struck me most about the executive’s observation was that he wasn’t asking me to stop thinking the way I think, or to become more conventional or less willing to challenge assumptions. He was pointing out that the way I arrive at an idea and the way somebody else comes to understand it are two entirely different processes, and that I had been treating them as though they were the same thing. It is tempting to see communication as something that happens after the thinking is finished, but if I cannot explain how someone gets from their current reality to my proposed future, then there is something important I haven’t worked out yet, not necessarily about the destination but about the change itself.

I would go a step further than that, and it is a less comfortable step. A leader who repeatedly fails to bring people along cannot keep blaming the organisation for moving too slowly. Once or twice it might be the mainland; by the fifth time it is almost certainly you. At some point the failure to turn an idea into shared understanding simply is a failure of leadership, however good the original idea was, and being right about the destination does not earn you an exemption from that.

None of this means the islander has to design the whole crossing. If you have never lived on the mainland, it is fair to ask how well you really understand the obstacles to leaving it, and the people who know the existing terrain are usually far better equipped to plan the route. The model that works, in my experience, is the islander contributing the direction and the mainland contributing the knowledge of the ground, with both deciding together whether the destination is worth reaching. When that goes well the islander learns things about the mainland they never understood, the mainland starts to see possibilities that previously looked unimaginable, and the eventual destination becomes something neither group could have designed alone. That isn’t compromise in the negative sense; it is collective intelligence doing exactly what it is supposed to do.

9. A Final Thought

I have spent a lot of time reflecting on that conversation, partly because I recognised myself in the metaphor immediately. I have often felt the frustration of seeing something clearly and not understanding why it isn’t equally clear to everyone else, and I suspect I have sometimes mistaken my own difficulty explaining an idea for somebody else’s difficulty understanding it. Those are not the same thing, and Newton’s tappers are a fairly humbling reminder of just how wide the gap between them can be.

Perhaps the problem was never that people couldn’t see my island. Perhaps I spent too much time describing the view and not nearly enough time understanding where they were standing. The most important leadership question is probably not “can you see what I can see?” but “can I understand where you are well enough that we can find a way forward together?” A vision is valuable, but a vision nobody else can reach is just a place where you stand alone, and the real achievement isn’t getting everyone onto your island. It is building something worth travelling towards, together.

References

Newton, E. L. (1990). The rocky road from actions to intentions. Unpublished doctoral dissertation, Stanford University.

Heath, C. and Heath, D. (2007). Made to Stick: Why Some Ideas Survive and Others Die. New York: Random House. (The source of the widely retold account of the tapping study.)