Founders are often praised for vision, grit, or technical skill. Those qualities are critical to their success. But in my experience, it is when these qualities are combined with two quieter “force multipliers” that the real magic happens.
The two qualities I am talking about are curiosity and insight. The fact that they are so important to maximizing the value other “hard skills” is why I’ve put those words into my own motto.
So, let’s dig into that a bit more. The combination of curiosity and insight is not necessarily natural, at least not for most people. Although, it comes more naturally to some. But for most people until they identify the combination as being a “superpower” they probably never spend much time refining the art of asking the right questions and really listening to the answers.
Because the kind of curiosity I am talking about is not random, or incidental, it isn’t just about asking questions. It’s about asking the right ones — the ones that get behind the façade that almost everyone puts up.
Being genuinely curious means asking yourself questions like: “What is it like to be this person?,” “Or I wonder why they said that, and why they said it THAT way.” In effect it means exploring other people’s motivation – but not because you are digging for information – but because you are really interested. When someone says something unexpected, a natural response is to react with judgement. Writing the opinion off as strange, or ill-informed, or arrogant. But so what if it is any or all those things?
When someone says something that you did not expect, they are revealing that what motivates and animates them is not what you thought. At that point, don’t step back.
Lean in.
Because the key to influencing anyone – customer, investor, employee, – anyone is to understand what motivates them. AND then to appeal to that motivation. EVEN when it is not what motivates you.
As Walt Whitman is purported (by Ted Lasso) to have written – “Don’t be judgmental, be curious.”
To get to this point though you must make sure that you have conversations that explore the other person’s situation and motivation – and not just the transaction you came to talk about. With customers, that means resisting the urge to pitch immediately and instead asking how they do their job, and what they see as their real challenges. With investors, it means looking past the checkbook to understand what kind of outcome they would need to be interested in a deal. With employees, it means finding out what gives them energy, and what doesn’t.
By the way, this is another one of those pieces of advice that is easy to say and hard to do. In the dynamic world in which most founders find themselves, they are conditioned to “prove” themselves quickly at the start of any interaction. They feel the need to show how clever they are, how novel their product is, how hard they’ve worked. They are encouraged to always have their elevator pitch ready.
Genuine curiosity, though, requires a completely different approach. Being curious means forgetting what you came to sell and realizing that a successful meeting is more about what you take away not what you leave behind. It means putting your own brilliance on hold long enough to really notice what someone else is telling you — and sometimes what they’re not telling you.
In the heat of the moment this is hard because there is a difference between curiosity as a tactic and curiosity as a disposition. People can feel the difference almost instantly. If you ask questions with the intent of steering someone toward your own agenda, they will keep their guard up and you won’t learn much of value. If, on the other hand, you ask because you genuinely want to know — because you enjoy the act of discovering something new — then the conversation shifts. This is especially true if the question you ask is not a question they often hear.
Genuine curiosity is not about extracting information. It’s about entering the conversation willing to be surprised, even changed, by what you learn. That is why it works. Because suddenly you are not interested in what they can do for you. You are interested in them.
And here’s the paradox: when you stop approaching people as sources of advantage, and instead approach them as sources of learning, you unlock far more advantage than you could have engineered. Because what you gain is not just data, but engagement and trust.
Over time, that learning, when paired with insight, begins to reveal opportunities others miss. Not the shallow “opportunities” of a pitch deck, but the deep ones rooted in people’s real motivations — the things they don’t always state, but which drive their decisions.
Curiosity on its own is incomplete. You can ask a thousand questions and still miss the point. What makes curiosity powerful is when it’s paired with insight — the ability to hear an answer and see through to the stresses and constraints that are really driving it.
When a customer says, “We’re not ready to buy yet,” the surface issue sounds like timing. But the real story might be that they’re under pressure from finance to reduce sole-source contracts, or that an upcoming re-organization has frozen every spending decision. Until you understand that world, you can’t meet them where they are.
When an investor insists on another round of diligence, it’s easy to assume they’re skeptical. More often, they’re playing for time — not wanting to admit that the fund doesn’t yet have the capital in place. Or it might be a junior partner who believes in you but doesn’t fully grasp your argument, and fears being turned down by the review committee — which reflects badly on them. Their hesitation isn’t always about you; sometimes it’s about the risks they face inside their own system.
And when a public servant resists every attempt to get a clear or written answer, it may not be bureaucratic obstinacy at all. They may know that the decision is beyond their authority, and that making a promise — even informally — could be career-limiting.
In each of these situations, the surface behaviour makes perfect sense once you see the constraints beneath it. That’s the value of pairing curiosity with insight. It lets you navigate not just the words people say, but the realities they’re operating within. And that’s where influence starts — not in argument, but in understanding.
It takes patience, though because such insights can only come with time and experience. Asking good questions will allow you to discover things you did not know. But it takes insight to realize when you are seeing patterns you have seen before and make the leap to understanding the deeper meaning of what you have just seen on the surface.
Insight is what allows you to move past surface data and connect with the real drivers of human behavior. And THAT is where decisions get made.
I should admit here that founders I coach sometimes tell me they are surprised at my ability to predict how people will react, even when I’ve never met them. I don’t think of this as a talent. To me it’s simply the result of a career’s worth of practicing curiosity and working hard to develop insight. When you spend long enough trying to understand what makes people tick, you really do begin to see the patterns. At least, I certainly have.
This isn’t clairvoyance. It’s apprenticeship. The more genuinely curious you are about people — the more you’ve listened, absorbed, and reflected — the more those insights accumulate. And eventually they start to look like intuition.
A founder’s technical skills, market knowledge, or personal resilience are all important. But they will only take you so far. In complex businesses — and space is nothing if not complex — you are always dealing with people whose motivations are layered. A procurement officer responding to directions that you are not party to. An investor dealing with interactions with their limited partners that you know nothing about. An engineer afraid of being wrong, while still wanting to think “outside the box” for once.
Curiosity plus insight is what lets you meet those people where they are. It’s what turns a negotiation from a transaction into a relationship. It’s what makes someone remember you not as “the person with the widget” but “the person who understood.”
Without curiosity, founders default to projection: assuming others see the world the way they do. That leads to missed opportunities, misaligned investors, and teams that quietly disengage.
Without insight, curiosity becomes trivia: lots of questions asked, but nothing learned.
Put the two together and you have a way of continually calibrating your business against reality — not just your own assumptions.
In the end, curiosity and insight are not add-ons to a founder’s toolkit. They are the multipliers that make every other tool sharper. They don’t guarantee that you’ll always get the answer you want, but they do mean that when people answer you, you’ll actually hear what they mean and not just what they said.
And that is how trust and reputation is built — one curious question, one quiet insight, at a time.
