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The road less traveled: 8 questions to ask to evaluate the risk

What if Bill Gates had decided not to leave Harvard and start Microsoft? How many people would not have been touched by the Bill and Melinda Gates Foundation today? How would your life have been different if [insert example here]? Obviously these are big examples, but consider that often the best work comes out of people doing what seems on the surface to be foolish or undesirable. 

Recently I heard a speaker refer to himself during his very colorful and successful career as, “a fool venturing where even angels feared to tread.”  He was talking about his natural desire and abilities to take on risks and roles that others had shied away from or would not even consider.  While there are some of us who are by nature avid risk takers and who enjoy the challenge of the unknown, regardless of personal hard-wiring or inclinations, there may be a legitimate reason for any of us to take “the road less traveled.” Here are some questions to help you evaluate risk.

  1. How interested are you?  Sincerely evaluate whether the role is really of interest to you. Can you get excited about the work and the outcomes? Does it tie to your vision for yourself, what you enjoy and your future? If not, then it’s a no-go. All of the other questions won’t be worth asking if this one is a no.
  2. How big is the risk, really?  If you are asked to take on a start-up for your company or perhaps apply your expertise to turn around a failing area of the business, why wouldn’t you? The fact is most of these situations have nothing but upside.
  3. What’s the worst that could happen?  Unless you are in the military, we are not talking life and death situations. If you find it’s not in your wheelhouse, then at least you will have learned something about business and about yourself in the process.  In most cases, given the great upside, even modest success is a great win. It’s really more about how you handle it. Of course, consider what you’re risking and take the necessary precautions.
  4. What are your strengths?  Leverage what you do well and you have won already.  You don’t have to be the smartest, boldest, loudest person in the room to get the job done.  Jim Collins makes a great case for humble, collaborative and methodical leadership in his book Good to Great. An assessment tool such as Predictive Index® can help you become more aware of your strengths.
  5. What resources will you need? If you know your strengths, then you will also be able to identify your weaknesses or gaps. Demonstrate your ability to think critically and thoughtfully about what you are being asked to do by assembling a team or leveraging the right resources to get the job done. These should complement you and each other to ensure all types of work can be handled.
  6. How committed is the organization to success?  If you can’t get what you need, then that will tell you something about how committed the organization is to ensuring success. None of us do our jobs alone, let alone those that are high-profile opportunities. Availability of the right resources will be key to your success as the leader.
  7. Are you an effective leader?  If you are asked to take on a risky or high-profile role, there is a chance you have demonstrated some solid leadership traits. However, the best way to know for sure is to ask the right questions about your competencies, measure them objectively and then use that information to grow and supplement your gaps. 360o surveys and candid, transparent conversations with your team can help.
  8. Do you have grit?  Grit is another word for perseverance, but embodies tenacity as well. Like the ancient Japanese proverb, “Get knocked down seven times, get up eight,” do you have what it takes to deal with the challenges? This cannot be taught. You will need to look to your past and evaluate where and how you have demonstrated grit. It may be that this is also the right opportunity to really test and demonstrate it.

The real message is that these questions can be applied to any role or any opportunity. Simply stated, all roles have risks and nothing is guaranteed.  If you can answer the first question affirmatively, then go through the other seven to give yourself a better chance at success.

Article by Tom Cox.

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