Photo Credit: Todd Quackenbush,
Photo Credit: Todd Quackenbush,

When was the last time that you truly, spectacularly failed? A big, loud splashing belly flop that left you breathless, with stinging skin and resounding laughter poolside?

“Success is the ability to go from one failure to another with no loss of enthusiasm.”

Winston Churchill

As leaders, we practice mindful celebration of successes — large and small. We know that catching people doing something well and celebrating the win helps to energize and motivate teams. But what about those that try something bold and new that doesn’t work? Are they relegated to the “lessons learned” section of the agenda? Encouraged to go back to coloring within the lines?

Try these three things to blast your organization into a new stratosphere.

Model Strategic Risk Taking

Think out loud, be playful with ideas with your team, and then go for it. Weigh the strategic benefits and risks. Envision success in a spectacular manner. That new service? People will LOVE it and never knew that they needed it. You’ve dreamed about it for years, believe that you’ve got the resources in place, and the timing in the market’s right. You make an investment, put a high performing team on it and… regulations change. Or the price point’s too high and your marketing splash resembles that belly flop.

Be honest and clear about the results. Don’t be afraid to admit that something just wasn’t right and this didn’t work. Be proud for trying and be public about it to your organization, your Board. Don’t apologize for making the best decisions you could and then taking a strategic risk. Pick yourselves up and move on to the next.

Reward Leaders and Teams Who Try and Fail

Encourage audacious ideas. Have serious discussions about their merits. Together poke holes in each one and send them back for more work until you all are satisfied that this could be fabulous from all perspectives. Include creative, bold thinking in your ideal leadership candidate position descriptions. On performance reviews, put these efforts at the top of the agenda along with the efforts that are “successful.” How could you redefine “success” in your organization?

Embrace the value that failures enhance your organization’s power with customers, in the market, and with investors.


Celebrate the risk taking, the thought process, and best decision-making at the time. Celebrate the belly flop, the product that was off the mark despite best efforts. Differentiate calculated, strategic risk taking from poorly thought out planning and implementation. The outcome isn’t the key here, it’s the thinking outside the box with solid planning and implementation. Highlight these efforts at meetings, in person, with the teams who took the risk. Never desert them. Show the organization that creative, bold thinking’s valued and you’ll find instances of innovation everywhere.

Choose to take the risk of a spectacular belly flop. The sweet sounds of success will be your reward.


An Executive Leadership Coach emboldens you to dream big and take risks for remarkable breakthrough results.  For more ideas contact BreakAway Leadership Coaching founder, Karyn Grant at [email protected] or visit