How Great Leaders Sell Risky Propositions


Right now I’m recruiting heavily for startups.

With FinTech booming and investor cash readily available, new and innovative FinTech companies are being launched literally every day.

And with such appetite for growth comes fierce competition for talent. With endless start-ups to choose from, simply creating the image of a cool and funky company is no longer enough. Startups are risky. And so a key part in attracting the best candidates is being able to sell this risk in the most effective manner.

To explain propositions in a manner that entices excitement over fear. To be able to get high performing candidates to take the plunge. To attract the quality of people that their competitors are only able to dream about.

Risk and reward are closely linked. Most of us intellectually know that fortune really does favour the brave and that in order to reach the summit of any particular discipline, tough decisions often have to be made. That desire and success can only be achieved by taking steps that feel uncomfortable.

Yet when it comes to the real world, often fear takes over. And that’s where great leaders can often be invaluable. By having that unique ability to explain things in manner that motivates us to take action.

So how do they do it?

Here are some ways how great leaders sell risky propositions.

They’re always honest

Risk isn’t for everyone. In fact, the only person who knows how much risk they are willing to take is the individual themselves.

Whether it’s family responsibilities, personal debt or career stability often the major obstacle to taking risks that may seem enticing is our current situations and timing.

It’s all very fine being sold an amazing final vision or the promise of a career defining pay day, but it means little if it means risking the happiness and stability you have currently.

Great leaders understand this. In fact, they realise that the only well to get others to take risk is to do no “selling” at all. All they can do is present their side of the story – the facts, the current scenario, the final vision – and allow others to make their mind up. It’s the only way to build a lasting relationship that can stand the test of time. The only way to build commitment.

And with the inevitable roller coaster that comes with taking risk, commitment is essential in order to succeed.

Great leaders get commitment.

They use stop losses

Risk can seem scary.

Often very scary.

As creatures with vivid imaginations, when we step into the unknown often our minds can run wild with endless possibilities.

Could quitting my stable job to set up that business make me bankrupt? Could relocating to that new country leave me miserable and extradite me from my friends and family? Could trying to learn that new “left-field” skill leave me unemployable in the future?

With so much at stake, it’s understandable that it’s often easier just to stay risk averse and stick with the status quo.

Yet often, it’s rare that we need to go to such extremes.

Great leaders understand that rather than going “all in”, it’s often easier to use predetermined stop losses to ensure that the downside is limited. Rather than relocating permanently, you could try it for 12 months and then reassess. You could decide how long to give the new business a try before deciding whether it might be the right thing to pursue long term.

It’s much easier to take the plunge once you know the “worst case” scenario. It builds realism and comfort.

Great leaders build comfort.

They make sure they commit themselves

But there is something that’s much more powerful than simply being honest and limiting the downside.

Something that makes taking risk much easier.

And that’s following the lead of someone whose totally committed and taken risk themselves.

You see as innately social creatures, despite how much financial stability or knowledge we have, all of us are designed to feel safer in groups. It’s comforting to know there are others on the same journey. People who we can discuss progress and issues with. Individuals who have as much as stake as we do.

Great leaders understand that the easiest way to get others to commit is to lead by example. To make it clear that they have faith in a particular course of action. To let their followers know that whatever happens they’ll never be alone.

It creates a sense of trust that’s difficult to replicate.

Great leaders build trust.


Taking the plunge can be really rewarding.

But sometimes the bigger problem is getting someone to come on the ride with you.

Great leaders understand that great achievements only happen with great people. And a powerful part of any leaders artillery is being able to attract people to things that although risky, can also be life changing.

It’s how all disruptive organisations start to grow.

How does your leader sell risky propositions?

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