Why Your Boldest Work Should Go to Your Most Relentless People

In my years at Deloitte, Bank of America and Kotter, and in the work I do now with leadership teams, I have watched the same decision play out whenever a leader sets out to achieve something that genuinely matters. They do not begin by asking who has time. They begin by asking who has the drive to see it through. Availability comes up later, if it comes up at all.

This runs against the instinct most of us are handed early in our careers. Protect your best people. Do not overload them. When something new lands, give it to whoever has space on their plate. It sounds responsible, and it is completely backwards. The leaders who actually deliver the significant thing tend to do the opposite. They go straight to the people who are already carrying the most, and they do it on purpose.

Significant work goes to the driven, not the available

The people who move a hard plan forward are the ones with the appetite for it, not the ones with the calendar for it. Drive is the signal. Availability is only a measure of activity, and activity tells you very little about who will finish a difficult thing.

David Perell makes this point well in an essay called The Paradox of Ambition. We are taught that hard goals are hard and easy goals are easy. In practice, and especially in ambitious settings, the reverse can be true. A bold goal is often easier to accomplish than a modest one, because ambition itself attracts. It draws talent, attention and belief in a way that a safe, sensible target never will.

Stripe understood this earlier and more deliberately than most. One of its own engineers, reflecting on what made the company work, put it plainly: the strongest people are drawn to the most ambitious problems, and the pull of a big problem more than makes up for the difficulty of solving it. In their experience, the talent a bold problem attracted did more for them than the added difficulty ever took away. The size of the ambition was doing the recruiting.

There is a small piece of history that captures the appetite I am describing. Before Amazon was Amazon, Jeff Bezos nearly called it Relentless. He registered relentless.com in 1994, and to this day the address still redirects to Amazon. The name did not survive, but the quality it described ran through everything that followed. Relentless describes how much someone wants a thing. It has nothing to do with how full their week already looks.

Why failure is not an option when the plan is bold

The moment you commit to something bold in front of your people and your market, you have told everyone that you can be trusted to deliver it. That signal only holds if you actually do. A bold plan that fails does not fail quietly. It unmakes the very impression of boldness you were trying to create. Listen to how chief executives talk now and you hear the same promise everywhere, to move faster and decide more boldly.

This is why you cannot hand a visible, high-stakes plan to people who are ambling along, hoping something good happens to their careers. You reach instead for the people who have already shown, more than once, that they deliver. That is simply an honest reading of what is at stake.

Consider how Stripe began. Two brothers from a village of barely a hundred people in rural Ireland decided that the way the world moved money online was broken, and set out to build the thing that would replace it. Their goal sounded absurd for a startup with nothing to show, to increase the GDP of the internet. Here is what that ambition attracted. Peter Thiel and Elon Musk, the two men who built PayPal, wrote the seed cheques. They looked at a pair of unknowns proposing to replace what they themselves had made, and they backed them rather than defended it. Fifteen years on, Stripe's most recent valuation puts it at $159 billion, roughly three times what PayPal is worth today.

That is what a genuinely audacious goal does. It does not merely raise the stakes for the people inside the work. It reaches people who have no obligation to care, and it pulls them in. High stakes draw the relentless and send the passive looking for something quieter.

Why the stretch assignment is really a proof of talent

When you hand your best person a bold and visible job, you are not testing whether they can do it. Everyone already believes they can. You are giving them the chance to prove, in front of everyone, what is already assumed about them.

Hold that alongside the point above, because the two live in tension and both are true. A bold assignment is a genuine opportunity for a high performer to shine. And you can only offer it to someone whose success you are already willing to back, because a public failure is expensive for you as well as for them. The high performer understands this arrangement completely. So do you. Everyone is watching, and for the person who wants to be seen doing hard things well, that scrutiny is most of the appeal.

This is the part leaders tend to miss. The stakes you think might frighten your best people are the very thing that attracts them.

Why the safe target is the expensive one

Scoping a plan down to make it feel achievable does the opposite of what you intend. It lowers the stakes, and low stakes do not attract your strongest people. Make the work small and safe to protect everyone's capacity, and you will find yourself staffing it with whoever happened to be free. People are often free for a reason.

So the modest target quietly costs you twice. It repels the driven, who wanted something worth their effort, and it hands the work to the passive, who will treat it as one more task. You pay in the calibre of the team, and you pay again in the result. Decades of research into goal setting, going back to Edwin Locke and Gary Latham, point the same way: specific and difficult goals reliably produce higher performance than vague or easy ones, provided the person accepts the goal and believes it is within reach. That final condition is the whole game. The goal must be hard enough to be worth wanting, and credible enough to be won.

There is a loop in this, and it runs in both directions. Ambitious plans attract driven people. Driven people deliver. Delivering earns you the standing to be more ambitious next time. The reverse turns just as reliably. Modest plans attract whoever is free. Whoever is free delivers a modest result. And that modest result becomes the evidence for setting an even smaller target the year after. Most organisations are somewhere on one of those two loops right now, and the direction was set by the size of the last target somebody was brave enough to name.

A modest target, then, only looks like the cautious choice. This is where a great deal of ambition quietly goes to die, in a plan made so safe that nobody strong ever wanted it in the first place.

Two questions that raise the ambition

If you want to know whether your plan is ambitious enough to attract the people who could carry it, borrow two questions that Patrick Collison is said to ask at the end of his meetings at Stripe:

1. Is this the most ambitious version of this plan we could pursue?
2. What would we propose if resources were not the constraint?

Both questions do the same quiet work. They strip out the self-censoring that shrinks a plan before anyone has had the courage to argue for the larger version. Most plans are made smaller than they need to be, not through debate, but through a series of unspoken assumptions about what is realistic. These two questions drag those assumptions into the open where they can be examined.

One caution, and it matters. The talent effect only works when the ambition is real. The same Stripe engineer who described the pull of ambitious problems was careful to add that it holds for work that genuinely matters, and not for a bigger number chosen to look impressive.

I lived this. Around 2007, the practice I was part of at Deloitte Consulting set itself a target of $100 million. Not the firm, just our small part of it. I was on the team that was set to make this happen - in the New York office, close enough to the centre of it to feel every decision, and I have rarely felt more alive at work. I worked long hours and wanted to. I carried it alongside a full client load and made the rest of my life work around it, because the number meant something and I wanted to be one of the people who got us there. Nobody had to persuade me. And that is precisely what a target does when it is real. It does not extract effort from people. It attracts them.

A bold goal that serves only the leader's image will attract no one worth having. Raise the ambition, certainly, but raise it towards something worth rising to. As the economist Tyler Cowen has observed, lifting another person's aspirations costs you very little and can transform what they are willing to attempt.

So the target you set is never only a number to hit. It is the signal that decides who wants to be part of the work. Set it low to keep everyone comfortable, and you will recruit the people with time on their hands. Set it high, and make it genuinely worth the effort, and you will recruit the relentless, who were always the only people who were going to get it done. Before you make your next plan realistic, ask the second question of it, and watch closely to see who leans in. That is the work I care most about with the teams I serve, finding the conviction to set the bigger target and the discipline to deliver it.

Common questions

Do ambitious goals really attract better talent, or is that Silicon Valley folklore?

It holds up beyond the folklore. Stripe's own engineers described the effect from the inside and found that the talent an ambitious problem attracted outweighed the extra difficulty of solving it. Decades of goal-setting research from Edwin Locke and Gary Latham point the same way, that specific and difficult goals produce higher performance than vague or easy ones. The condition in both cases is the same. The goal has to be genuinely worth wanting.

Is it not irresponsible to set a target you cannot be sure you will hit?

The safe target carries its own risk, and it is simply less visible. A modest goal repels the people who would have wanted something harder, so you end up delivering it with whoever was free. The responsible position is not a smaller target. It is a bigger target staffed by people whose success you can already back.

What is the paradox of ambition?

It is David Perell's observation that a hard goal can be easier to reach than an easy one. Ambition attracts talent, capital and attention, so the bigger goal arrives with more support behind it than the modest goal ever gathers. The difficulty rises, but so do the resources, and often by more.

What are the two questions Patrick Collison used to raise ambition?

He is said to have closed meetings at Stripe by asking whether this was the most ambitious version of the plan the team could pursue, and what they would propose if resources were not the constraint. Both questions expose the quiet assumptions that shrink a plan before anyone has argued for the larger version.

Why do leaders give bold projects to people who are already busy?

Because appetite is a better predictor of delivery than capacity. The people who are already carrying the most are usually carrying it because they want the hardest work, and a visible, high-stakes job is the thing they want most. Availability measures activity. It tells you almost nothing about who will finish.