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12 definitive traits of a leader: Part 8-Risk Taker

by Jeff Custer | Monday, June 13, 2022

Would you rather ask for permission or forgiveness?

That’s one of my all-time favorite interview questions.

At the root of that question, we get a glimpse at a person’s willingness to take risks.

Many leaders play it safe because they’re afraid of the potential negative consequences of a risky decision. What will people think if it goes wrong? Will I get fired for making this decision? Yet so many opportunities are lost by making safe choices.

Now, please don’t hear me advocating throwing every caution to the wind and letting the chips fall where they may. Effective leaders have the ability to weigh risk and reward. To assess the pros and cons of their potential decisions. They err on the side of taking risks while knowing the potential consequences. They confidently make decisions.

Effective leaders also have a clear understanding of the boundaries their organization has established as tolerable risk. Some organizations are very risk adverse while others have a culture that tolerates more.

I once hired a customer service consultant to train some of my employees. I’d seen his presentation and thought he was engaging, thought-provoking, and poignant. And I wanted my employees to have a chance to learn from him. However, the organization was pretty risk adverse. It was the kind of place where nearly every person asked permission for everything.

So what was I supposed to do? I knew if I asked permission there was a chance the whole idea would be turned down. Which would end up hurting employees’ ability to deliver an excellent customer service experience—which was an area that needed improvement. I also knew if the idea was approved there’d be a push to not only train my employees but the organization at large. And that would be a daunting task that likely would be unsuccessful at such a large scale.

I decided not to ask for permission. I brought the consultant in and only my employees went through the training. But I also invited my boss to attend the final session.

Did I get my hand slapped for not asking permission?

Nope. Not only did I not get my hand slapped, but my boss said we should get all of her other employees trained.

The risk in this example wasn’t really all that high. But it did go against the grain of the culture. I assessed the risk and the reward. And I made the decision I thought was best for the organization.

If you’re unsure where those boundaries are in your organization, talk about it with your boss in your next one-on-one meeting. Really try to understand the risk tolerance your boss and the organization are willing to allow. Then go out on a limb and push those limits. Test them and see what happens.

Your organization needs you to take prudent risks because that’s how you’ll continue to improve.

What opportunities are you passing on because you’re averse to taking risks?

The most effective leaders put it all on the line for what they believe needs to be done.

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Are you struggling to improve your effectiveness as a leader? Email me at for a free consultation.

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Jeff Custer is a long-time leader at both private and Fortune 500 companies where he has developed and led both high performance individuals and teams. He is passionate about developing leaders and building high impact teams. Jeff resides in the United States.

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