If you look at some of the most successful entrepreneurs of our time, one trait you’ll find in common is that they are risk takers. 

One of my favorite stories of a risk taker is inventor James Dyson.  He has said, “The key to success is failure… Success is made of 99 percent failure.” 

And he speaks from experience. In fact, Dyson failed 5, 127 times. You read that right. He designed 5,127 prototypes of his vacuum cleaner before he was successful. Talk about grit. Granted, this is an extreme example. But Dyson’s persistence paid off. As of 2018, he’s said to be worth about $5.7 billion.  

Yes, Dyson and other “gritty” entrepreneurs know a thing or two about risk and allowing for mistakes on the way to greater outcomes. The same holds true for today’s modern sellers. Modern sellers must have an entrepreneurial mindset, and part of that involves taking smart risks as the CEOs of their books of business. 

Being a smart risk taker rarely comes naturally. Through my work, I get to know clients in industries such as insurance, professional services, financial services to name a few. The theme of risk management pops up frequently in our conversations. 

It’s a logical response, given some of their industries. But what are the costs in talent, learning, innovation, and sales results if sales people don’t embrace some risk and instead mitigate the fear of making mistakes? 

There is a spectrum to risk of course, and it pays to sharpen our awareness of which risks are smart, and which ones may cause great harm in the long run. Below are some ideas to help you and your sales force succeed by taking smart risks:  

  1. Take an honest assessment of the lay of the land.Research your industry as a whole, and then look at your organization to assess risk tolerance. Compare your culture in relation to the industry. Do the same thing for your functional area, then your team, and then yourself. It’s important to know how you stack up organizationally, as well as which people in your organization are likely to embrace risk and making mistakes. A few questions to help you get started: 
  • Which companies in my industry seem to be breaking the mold with new products, services, or processes? What are the results? 
  • What are the attributes of the people making that happen? 
  • What mindsets and skills do they have? What role did learning and development play? 
  • How would I/my sales force compare with those mindsets, skills, results?
  1. Assessyour sales trainingfrom a risk perspective. This can take several angles, from both design and content. As a sales leader or training leader, some questions that can help you assess:  
  • Are my sales team members able to easily transition out of their comfort zones and  into a different perspective?  
  • Are my sales team members learning to develop their skills around smart risk and making mistakes? 
  • Are they bringing new ideas to their prospects and clients?
  1. Provide structure. This may sound counter intuitive, but a little bit of structure can raise the comfort level for risk.In Dan Pink’s Drive, he shares the story of Atlassian, an Australian software company that introduced a concept called the FedEx Day. These are one-day bursts of creativity, where employees are allowed to work on anything they would like, with two rules: it can’t relate to their day job, and they have to deliver something in a single day (hence the “FedEx” title). The results have been astounding – new innovations, creativity, and I’m betting a comfort level with mistakes – all from a single day with two simple rules.
  2. Look at failure and mistakes through a different lens. Most of us have been conditioned to see mistakes and failure as a negative, because we are a results-driven culture. And in sales, mistakes can hurt the bottom line.But what if we as sales leaders viewed mistakes differently,  acknowledging a team member’s efforts and risk-taking first, and then results? Taking smart risks and making mistakes are simply opportunities for growth.  

When we take the time to acknowledge the effort and remove the negativity, it encourages people to try again. Instead of mistakes being tagged as “failure,” they can be tagged as “stepping stones” to the desired outcome. This new lens can make your team more open, positive, loyal, and innovative.  

What have you learned from risks and failures? And are you ready to help your sales force embrace smart risk? 

For more tips on resiliency in your sales force read my post on developing a growth mindset.  

Also published on Medium.

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