There have been hundreds, if not thousands, of articles that have been written about how making mistakes and learning from them, is one of the major keys to success. 

As leaders, we're often asked to be tolerant of mistakes so that we create a learning organization, rather than one that has a fear of, which can then paralyzes growth.

But this is the wrong emphasis! Here we're focusing on the outcome rather than the type culture we would like to create.

It's not mistakes that lead us to success, it's risk-taking, and as leaders, we need to be cultivating a culture of smart risk-taking. A culture where people understand what risk taking is, what's is a smart risk and then feel comfortable in proposing or even taking risks.  

When we can build this kind of culture, we will have an innovative organization which will push the limits of possibility.

Here are five ways to encourage risk taking.

Model Risk-taking Behavior

I worked for a boss who talked about risk taking all the time, and while it was true that he was tolerant and supportive in times of failure, he wasn't much of a risk taker himself and consequently the organization took very few risks, even though he actively promoted it.

Leadership defines culture, and if we want to create a culture of acceptable risk taking, then we need to display that kind of behavior.  We also need to be transparent about the risks we are taking, explain why we are taking that and any mitigation we may have in case it fails. 

People learn from watching and if they can understand our smart risk-taking approach it can help them develop better theirs.

Define Smart Risks and Set Limits

We need to define what we mean by smart risk.  The last thing we need is for the entire department to be taking big risks that jeopardize the business. We need to clearly communicate limits to risk taking and have procedures in place for review of any proposed risk that would breach these limits, a kind of risk review board.  

Identify Your Best Risk-takers And Unleash Them 

Risk taking is a behavior, not a process, so identify who your best-existing risk takers are and encourage them to take smart risks. The more people modeling smart risk-taking behavior, the quicker and easier it will be to create that culture.  It's also good to have them acting as mentors to other members of your team, helping to teach people how to take smart risks.

Create A Safe Environment For Risk Taking

We need to create a safe environment for risk-taking; this means not punishing people who take smart acceptable risks and fail but supporting them, helping them learn from their mistakes and then encouraging them to try again.  These are the kinds of mistake we should tolerate, the ones that look to move us forward.

Reward Smart Failures

Set up a structure that reviews failures and rewards the best attempts, as this will show that the organization is serious about risk-taking. 

What gets rewarded gets repeated, so we need to reward the best failures as well as success as this will send a strong message to the organization. Something like a Who Dares Wins Award, showing that it's about the smart risk taking not just about the success.


We need to bear in mind that risk-taking is a behavior and although it can be learned, there will be some that won't want to take risks, and we shouldn't look to force them. 

Risk taking needs to be encouraged, it needs to be nurtured, and if you follow the five steps outlined above it will help create a safe environment for smart risk-taking to occur.