The will

One of the questions I am asked most often by the founders I work with is some version of this: how much is too much?

They are not talking about budgets or strategy. They are talking about people. Specifically, about the particular exhaustion that comes from investing heavily in someone and slowly realising the investment is not being matched. The time, the mentoring, the belief, the doors opened and held open. The courses offered, the extra conversations, the moments where you put your own credibility on the line for someone who has not yet earned it on their own terms.

Most of the founders I respect are generous in this way. It is part of what makes them good leaders. They see potential before it has fully declared itself. They back people early. That instinct is not wrong. But it is not always enough. And learning that, properly, costs something.

There is a version of investment that looks like leadership but functions more like hope. And hope, without the other person moving towards you, is just distance with good intentions.

Across the founders I have worked with over the years, two kinds of people appear again and again. I want to tell you about both of them, because together they taught me something I have come to believe is one of the most important things a leader can understand.

The first ticks almost every box. Good with people, strong on relationships, visible potential in almost every direction you look. On paper, an easy decision. In practice, a familiar story. I have watched founders give generously to people like this. Time, belief, opportunity after opportunity. The investment is made with the best of intentions, because the potential looks real and the desire to help is genuine.

The second does not tick the boxes, at least not at first. Rough edges. Not quite the skill set. Does not present in the way you would ask for on day one. On paper, a risk. In practice, the first thing you notice is that they are already running. Curious, hungry, leaning forward before you have fully committed to them. They ask questions nobody taught them to ask.

They come back the next day having acted on a conversation from the day before.

One wants what the investment feels like. The other wants what it can build.

This distinction is harder to see than it sounds. The first is not cynical. They are not deliberately wasting anyone's time. They genuinely respond to the attention, the support, the sense of being believed in. And for a while, that looks like progress. There are moments where it seems like the turning point has arrived. But it never quite does. Every next step is deferred. Every opportunity to stretch is quietly declined. What looked like potential gathering itself is, in fact, potential comfortable where it is.

The second is uncomfortable almost constantly, and that discomfort is the engine. They do not always get things right. They make mistakes that someone with more polish might not have made. But they run at every mistake the same way they run at every opportunity. Without hesitation. With genuine curiosity about what it means and what comes next.

What I have watched, again and again across the founders I work with, is the same slow realisation. The investment in the first person does not build them. It props them. And the longer that continues, the more expensive the confusion becomes, for the leader and for the person being propped up. It is not kindness in the end. It is a kind of stalling, for both of them.

You can offer someone a ladder. You cannot want them to climb it more than they do.

The research, it turns out, supports what experience quietly teaches. Mark Murphy's study of more than 20,000 new hires found that 89% of the time when someone fails in a role, the reason is attitude, not skill. Technical competence accounts for just 11% of failures. The résumé, in other words, is almost never the problem. The will is.

So how do you find it before you have invested heavily in someone who does not have it? You will not find it in a polished interview. You will not find it in credentials or references. You find it in the small things that happen before anyone is watching. How a candidate treats the person who greeted them at the door. Whether they followed up after the interview, and what they said when they did. Whether they came prepared not just with answers, but with questions of their own.

And there is one question worth asking in any interview, early and simply: tell me about a time you taught yourself something nobody asked you to learn. The person with will has an answer ready, usually more than one. The person without it will struggle to find a single example that does not trace back to a requirement.

Employ for attitude. Train for skill. The will does not appear on any résumé. But you will know it when you see it, because it walks towards you before you have finished walking towards it.

The question I encourage the founders I work with to ask, earlier and more honestly than feels comfortable, is not how much should I give this person. It is simpler than that, and harder.

Are we walking towards each other?

Because the person who is already running does not need to be carried. They need room, direction, and someone who can keep up. The investment there does not feel like investment at all. It feels like momentum.

Will is not something you can give a person. You can create the conditions for it. You can model it, encourage it, reward it when you see it. But you cannot install it. And the most generous thing you can do, for yourself and for the people in your care, is to be honest about the difference between the two as early as you possibly can.

You can only truly help someone who is willing to help themselves. Everything else, however well-intentioned, is just you walking alone.

Clarity where possible. Humour where necessary.