The Wow! List How Risky Are You?

Roshini Rajkumar

By Roshini Rajkumar

1. Preparation

2. Confidence

3. Rewards

The Prouty Project interviewed three CEOs from three diverse organizations about each of their true norths. I was struck by what each had to say about teams and future visioning and especially impressed by their thoughts regarding risk. For this month’s WOW! List, I mesh their pithy lines with my executive coaching advice. Partly to give them much deserved shout-outs, but also to showcase how I learn terrific lessons from CEOs around me that fundamentally improve the advice I give to the C-Suite clients I work with and their teams. You, too, can learn so much when you keep your eyes and ears open to the pearls of wisdom already floating around you.


Without great risk, there is no great reward, as the saying goes. But before the risk, solid preparation is needed – both to help your employees and to benefit your customers. Michael Happe of Winnegabo Industries Inc., shares how building the right team “will pay off exponentially in the future.” I like to say make sure you find A-people, even if it takes longer. These are people who are the best at what they do for the compensation your organization can provide. Preparing for your A-Team requires contemplation, strategy, and communication with key members of your board and current senior leaders. Much of this preparation is really on you because it involves your gut and understanding of the market and your vision for the brand. I also respect how Happe suggests you not only “recognize and mitigate risk, but you also embrace it.” Remember, you will learn from anything that doesn’t go as planned, and you might even come out quite ahead of where you envisioned.


CommonBond Communities CEO Deidre Schmidt says, “Taking risk is how we learn and develop confidence.” Confidence is your best asset and your best accessory. It doesn’t land overnight, and it’s worth growing with some calculated risks as well as some heavily researched but intuitive gut feelings. When employees and colleagues see you opening yourself up to risk, experiencing wins, and trying for bigger wins, you empower them to have confidence to take risks themselves. Certainly, you protect against flagrant wastes of time and money, but you get the point.


Now, time for the rewards. They may appear gradually or land like a lottery. The strategic leader can’t rest even when rewards happen. The question becomes just how much risk can we keep taking? Mortenson CEO Dan Johnson reminds us how, “The other job of the CEO is to constantly be looking ahead.” My suggestion is to break this long-game time into three parts: research, thinking, meeting. Keep abreast of latest trends and breakthroughs in your industry as well as any other industries of interest to your key clients and your own technology. Schedule time to think about how new and improved techniques could really work in your organization. Get out and meet people so they know you and your brand are engaged with the outer world. When you do these three things, you are naturally preparing for future wins and gaining confidence at the same time. You can then intelligently discern future risks worth taking. Dare to WOW!

Roshini is a presence engineer, personal brand strategist, licensed attorney and author of “Communicate That!” She hosts News & Views with Roshini Rajkumar on WCCO Radio and is an analyst for media outlets around the country. When she’s not on the air, Roshini is an executive coach, keynote speaker and event emcee. For more powerful presence content, go to