Learning to Lead: Part 3, Taking Risks

I’ve not ceased being fearful.  I’ve gone ahead despite the pounding in my heart that says: turn back, turn back, you’ll die if you go too far.

Erica Jong, Author

We’ve tackled authenticity and optimism as the first two traits in our leadership series pulled from the soon to release Learning to Lead.  Now on to one of those critical leadership tools that I struggle with: Taking Risks.  This is one of the most oft-cited characteristics of a great leader.  But what does it really mean?  How do you differentiate good risks from just making a stupid move?  And when is the right time to take a risk – anytime?  Knowing how to hone your “risk-taking” skill set is critical if you want to lead successfully.

Risk-taking requires a certain frame of mind.  Certain of us are intrinsically designed to feel more comfortable taking risks.  Those risk-takers could be just as comfortable bungee-jumping as starting a new venture while others are terrified.  To take risks, you have to be willing to step outside your comfort zone.  I read in How Remarkable Women Lead that, “Learning to face your fears is actually the best part of accepting opportunity.  When you do, you’ll find they are far less powerful than they seemed.  You’ll also experience the lightness of being that comes with getting back in control.” Don’t you love that turn of phrase?  It’s not “risk-taking;” it’s accepting opportunity! 

In order to be capable of taking savvy risks, you also have to be confident.  In addition to confidence in yourself and your capability, you have to be able to exude confidence to those around you in order to lead them in the risk.  You may know that the risk is a smart one, but unless you can communicate why, then no one will support you in taking the risk.  This is tough – risk-taking would not be a distinguishing characteristic of great leaders if it meant a simple path that anyone could follow.

Shona Brown, a Senior Vice President at Google, highlights the confidence-risk partnership:  I don’t think that I’m a thrill-seeker.  I’ll use skiing as the analogy because I like to jump off cliffs.  But I generally jump off cliffs that I’m relatively confident I’m going to land and that if I don’t, it’s not dangerous.  There are people who like to jump off cliffs who think their skill is better than it really is.  They hurt themselves.  There are people who are quite skilled but are afraid to jump.  I like to be at that point where you’re about to jump and your stomach is going, woo!

That is a perfect analogy of the kinds of risks you should take.  You have researched and studied and investigated (though not become immobilized by analysis paralysis), and you feel relatively confident that you are going to land on your feet.  And if you don’t land on your feet, you will not bring everyone down around you. 

Since some of us are more risk averse than others, we have to build our risk muscles.  We all know that the more we exercise, the stronger we get. Similarly, as you build your risk muscles, you’ll find yourself getting into a cycle in which your sense of self-confidence and ability to take risks improves.  Several studies note that women in certain situations tend to have a lower risk threshold because of extenuating circumstances like having young children and/or being the primary breadwinner in the family.  Understandably, those circumstances can make you wary of change that could impact those around you that rely upon you.  However, you must still begin to take on risk selectively.  The benefit of taking on smaller risks before taking on large-scale risks is it not only builds your risk muscles, but it also begins to develop your reputation for someone capable of taking “smart” risks.  It also equips you with the skills necessary to analyze risky situations so that you can distinguish a “smart” risk from a bad risk. Note, these risks don’t have to all be career risks.  Take a language course.  Plan an event.  Sign up to be on the board of a charity you love.  Take a practical step that requires you step out a little.  Sometimes practicing outside of work allows you the freedom to feel more comfortable if the risk doesn’t pay off. 

The authors of How Remarkable Women Lead asked leading women how they identified an opportunity.  The women didn’t have greater luck than the average woman, but they had prepared minds where they could assess risk and opportunity.  The recommendation that came out of those interviews was, “Start with the upside.  Most of us approach risk-assessment by listing what can possibly go wrong.  We’re pros at filling out that list.  Flip this around.  First imagine the very best that could happen.  Write it down and make it tangible – what you will learn, what skills you will build, what options you will have, what new people you will meet.”

Another step to moving you toward a more risk/opportunity taking mindset is to acknowledge risks you have taken.  Every time we embrace taking a chance and try something new, we’re becoming leaders. You have taken a risk if you’ve:

• Applied for a new position or taken on an assignment that’s a stretch from what you currently do;
• Moved to a new company;
• Spoken up in a meeting, especially with an opinion that may not be popular;
• Advocated for someone on your team;
• Asked for a raise;
• Chaired a visible committee in your company or within a professional organization.

I bet if I was sitting down with you over a cup of coffee you could identify more than one of those items on the list as decisions you have made.  See, you ARE a risk-taker.  Frame your next decisions and opportunities that feel too risky in terms of decisions you have executed successfully in the past.

Reframe risk-taking to give you this positive perspective: “Making a courageous move is also the highest form of service,” said James Strock, author of Serve to Lead.  “Courage, always, when you strip it down, is about love for someone or something.  And that’s what leads people to do extraordinary things and to put themselves at risk.”  What if, in taking the risk, seizing the opportunity, we realized we were doing it for the greater good?  That courageous, best-for-all, decision makes us successful, and sought-after, leaders.