Think about the last person at work who genuinely impressed you. Not the one who knew the most, or had the longest resume, but the one you’d go to when something was broken and no one knew how to fix it. The one who could walk into an awkward meeting and somehow make everyone relax. The one who, when you described a vague problem, came back with three approaches you hadn’t considered. What was it, exactly, that made them that way?
We reach for words like smart, or experienced, or a good communicator. But these are descriptions of outputs, not the engine producing them. They describe what we observe, not what’s actually happening underneath. The real question is: where do those outputs come from?
I think the answer, in almost every case, is imagination.
Imagination is not what you think it is
When most people hear the word imagination, they picture children inventing worlds, or artists staring at blank canvases. It sounds like something that belongs in kindergarten or in creative fields. Charming, perhaps, but not particularly relevant to getting serious work done. This is a mistake, and a costly one.
Imagination, in its most useful form, is not the ability to dream up things that don’t exist. It is the ability to mentally construct realities that are not in front of you. To simulate, to re-arrange, to map one domain onto another and extract meaning. It is the engine that runs when a person holds a broken system in their head and asks what if we changed this one thing? It runs when someone walks into a room full of strangers and navigates it gracefully. It runs when a person says something funny, or comforting, or exactly right.
Let’s examine this more carefully.
Problem solving is imagination under a different name
When a system fails - whether it’s a production server, a supply chain, or a marriage - there is rarely a manual for the exact scenario in front of you. Experience helps, of course. But what experience actually gives you is a larger library of patterns. Wisdom is what happens when you can take those patterns and imaginatively apply them to a situation that doesn’t quite match any of them.
A person with ten years of experience and low imagination will keep reaching for the same tools regardless of fit. A person with two years of experience and high imagination will look at your problem, compare it to something apparently unrelated, something they read, something they once fixed, something they’ve only heard about and arrive at a solution that surprises you. They are not smarter in the traditional sense. They are more capable of mental simulation: of running scenarios internally before committing to any of them externally.
This is imagination doing industrial work.
Humor is imagination with perfect timing
Humor is one of the most underrated tests of raw imaginative ability, and one of the fastest ways to evaluate it in a person. To be genuinely funny - not performatively funny, not rehearsed-joke funny - you have to be able to notice an unexpected connection between two things that normally live in separate mental categories, and surface it at the right moment. That is a demanding cognitive task. It requires you to hold the current conversation in mind, scan a very large space of associations simultaneously, identify a surprising one, and deliver it before the moment passes.
Bad comedians tell jokes. Good comedians see the world slightly differently from everyone else and can’t help pointing it out. The difference is imaginative range.
When someone makes you genuinely laugh with something off-the-cuff and contextual, what they’ve shown you is not just that they’re fun to be around. They’ve shown you that their mind moves quickly across large associative distances. That is, almost by definition, the same skill that makes someone good at debugging complex systems, at navigating difficult conversations, or at proposing solutions no one else has thought of.
The person in front of you is a world you have to imagine
Every conversation you have is, in a very real sense, a negotiation between two private realities. You have your context, your mood, your history, your assumptions. The person in front of you has theirs. And none of that is visible. You cannot directly observe what someone else is thinking, what they care about right now, what they’re afraid of, what they need to hear versus what they’re bracing to defend against. You can only infer it. And inference, when done well, is imagination.
This matters enormously for decision-making, far more than we typically acknowledge. The quality of a decision is almost never just about the decision itself. It is about the person receiving it, the moment they receive it in, and the hundred invisible factors that determine whether they hear what you intended or something else entirely. A technically correct decision, communicated to the wrong person in the wrong way, will fail. An imperfect decision, delivered with precise understanding of who is sitting across from you, often succeeds anyway.
The people who navigate this well are not necessarily the most empathetic in a soft sense. They are the most imaginatively flexible. They can suspend their own perspective long enough to run a simulation: if I were this person, with their background, their pressures, their relationship to this topic, how would this land? That simulation is not guaranteed to be accurate, but the act of running it changes the quality of every decision you make in relation to another human being. You begin to choose your words differently, your timing differently, your level of directness differently. Not because you’re being strategic or manipulative, but because you are genuinely accounting for a reality beyond your own.
Think about how this plays out in a team environment. A manager who cannot imagine the inner world of the person they’re managing will give the same feedback in the same way to everyone, and wonder why it only works some of the time. A colleague who cannot step outside their own frame will push their solution without noticing that the room has already moved on emotionally, even if the argument on paper is still sound. Meanwhile, the person with high imaginative flexibility reads the room not through some mysterious social instinct, but through active, real-time modeling of the people in it. They adjust. They meet people where they are.
This is also why imagination makes you a better decision-maker in the traditional, analytical sense. Most decisions involve other people: their buy-in, their resistance, their interpretation of what you’ve decided. A decision tree that accounts only for the logic of the problem and ignores the psychology of the people it touches is an incomplete model. The imaginative person knows this intuitively. They think about the decision and then they think about the person who will receive the decision, and they treat both as part of the same problem.
Being in someone else’s shoes is not a matter of emotional sensitivity alone. It is a cognitive skill. And like all cognitive skills worth having, its engine is imagination.
So why don’t we hire for it?
If imagination underlies problem solving, humor, social intelligence, adaptability, creativity, and most other things we actually care about in talented people, why is it the thing we least systematically measure in hiring?
The honest answer is that it’s difficult to measure, and we’ve built our entire hiring infrastructure around things that are easy to measure.
Degrees are measurable. Years of experience are measurable. Technical proficiency on a specific stack is testable. The ability to answer a behavioral question using a tidy three-part narrative structure is observable. These things all have value, but they are also, to a large degree, proxies - imperfect signals pointing at underlying qualities we actually care about but can’t directly see. The problem is that over time, we’ve started treating the proxies as the destination rather than the direction.
We screen for people who have done the job before, because that feels safe. But a person who has only done the job before will, when the job changes - and the job always changes - reach into an increasingly irrelevant toolbox. The world does not stay still long enough for experience alone to carry anyone very far.
Experience is a library. Imagination is the ability to read it.
Here’s an analogy that has helped me think about this. A library is enormously valuable, but a library without a reader is just shelves. Experience accumulates books on those shelves: references, patterns, case studies from a career’s worth of situations encountered and survived. But imagination is what lets you open those books, read them laterally, combine ideas from different sections, and apply them to something new.
A person with a modest library but a voracious, restless imagination will outperform a person with a vast library and a rigid, literal mind, especially in environments that are changing quickly. And environments are always changing quickly.
This doesn’t mean experience is irrelevant. It means experience is an amplifier: it increases the raw material available to an imaginative mind. But it is not a substitute for imagination. Hiring for experience without assessing imagination is like buying an expensive instrument for someone who doesn’t know how to play.
We need a different kind of interview
The standard interview is a marvel of imagination-suppression. You sit across from someone, ask them questions they have prepared answers for, evaluate them on how cleanly those answers fit your expectations, and call it assessment. What you’ve mostly done is measure how well someone can rehearse.
The behaviors that reveal imagination, like lateral thinking, the ability to reframe a problem, the instinct to question assumptions, the capacity to generate multiple explanations for a single phenomenon, almost never surface in a structured behavioral interview. They surface in conversation. They surface in how someone reacts when they don’t know the answer. They surface when you hand someone a genuinely ambiguous problem and watch what questions they ask before they attempt to solve it.
What questions they ask is the key thing. A person with low imaginative range will ask for clarification in order to narrow the problem as quickly as possible, to make it look like a problem they’ve solved before. A person with high imaginative range will ask questions that open the problem up, that reveal its assumptions, that map its shape before committing to a direction. They are more comfortable sitting with uncertainty because their mind is busy generating possibilities rather than searching for a match to a familiar template.
Some practical things worth trying: give candidates a problem outside their domain entirely and see how they reason about it. Ask them to explain something complicated using an analogy of their own invention. Ask them what they’re currently curious about, and then actually listen. Not to the topic, but to how they talk about it. Give them something broken with no obvious answer and watch what they do with the discomfort of not knowing.
None of this is perfect. Imagination is not easy to measure, and that’s precisely the point. The things that matter most are almost always the things that resist easy measurement. That discomfort is not a reason to give up on the effort. It’s a reason to take the effort more seriously.
Hire the person who can imagine
The most valuable person you will ever bring onto your team is not the one who has done exactly what you need done before. It is the one who, confronted with something they have never encountered, can imagine their way through it. Who can hold a problem up to the light and see it from multiple angles. Who can borrow an idea from a completely different field and arrive somewhere no one else in the room would have thought to go. Who makes the work feel lighter because their mind generates options rather than dead ends.
These people exist. They are not rare, exactly, but they are easy to miss if you are only looking for what you expect to find.
Imagination is the root system of human capability. Everything else grows from it. And we are hiring for the branches.
