3 Ways to Encourage Your Team to Take Risks

“You miss 100% of the shots you don’t take.” – Wayne Gretzky, NHL Hall of Famer

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There are plenty of reasons to play it safe. Families of origin where failure was punished. Toxic perfectionistic bosses. Fear of letting others down. And on we go. No one wants to fail, but most of us agree (at least philosophically) that a certain amount of risk is necessary to success in anything worthwhile.

So, as a manager, how do you overcome the fear your team experiences and encourage them to “go for it”?

1. Ditch the rhetoric and celebrate failure

We all know the guy. The “failure is not an option” guy. He’s a poser, trying to look tough and spouting platitudes he himself cannot fulfill. (Have I ever been that guy? Umm….perhaps. 😉 )

But the truth is, failure IS an option, and if you want to advance, to a certain extent you need to embrace failure. Innovation won’t happen if all you ever do is reward success. Sure, outcome oriented thinking is important, but the process of trial and error is often where the most important and profitable ideas come from.

I have 4 kids, and when oldest was an infant someone gave us the stacking rings toy every little kid gets. One day, when my son was trying (and failing) to stack the rings, one of my friends said, “I love that toy. Process matters!”

His comment was a revelation to me! I never thought of it that way. In order for my son to learn how things work, he needed the process. He needed to learn how things work, how to persevere and how to solve problems. If he had done it perfectly the first time, what would he have learned?

So how can we celebrate failure?

First, change the way you talk about success and failure with your team. Years ago I heard a phrase from a friend that I have now repeated about a million times. (I confess I rarely give him credit!)

“I’d rather give speeding tickets than parking tickets.”

I let my team know that it’s okay to “go for it”, even if they break a few speed laws and fail along the way. Sure, they may end up in my office for a conversation where we try to learn from our experience, but I let them know they’ll also get a “high five” for trying something new! By normalizing innovation and risk, and by minimizing the consequences of failure in context, the team feels the freedom to dream and act. Another phrase I am fond of is “failure is the tuition for success“. Naturally we’d prefer to pay community college tuition to Ivy league tuition, but I’ve found that the cost of failure on the way to success is almost always worth it.

Then, we need to find a way to reward people for taking risks, learning new skills and innovating! Of course, it’s important that they’re taking appropriate risk – risk they can learn from – but most leaders I talk with have performance measures that focus on success metrics. By tying our rewards exclusively to success we fail to incentivize innovation and new “outside the box” thinking, leaving us with a status quo that is often defeating, uninspiring and ultimately counter-productive to actual long-term success. So, in your performance evaluations, try adding elements that motivate your team to step up and try something new, regardless of the outcome.

2. Model it yourself

Your team is watching…always watching. There’s a reason we get pounded with “actions speak louder than words” from the time we’re kids. Because it’s true!

So if you say you value innovation, creativity and new ideas but you never take action yourself, your words say one thing and your actions another. Your people are smart and will quickly see that safety and being careful is what you actually value, and the work they produce will reflect that.

Several years ago I was leading a large team that had been using the same formula of success since the 60’s. As we moved into the 21st century I started to realize (all too slowly, I’m afraid!) that we needed a seismic shift in our strategy. It was risky and a few of my leaders thought I had lost my mind, but after working together we decided to take the plunge and make significant changes.

Some of the changes worked really well, and others were…well…failures. But by being honest about both with our team members, our leadership team sent a strong message about what we valued. When the time came to engage others and ask them to take risks (see below!) we had already modeled how to handle both success and failure. That demystified the process and made them more confident about how we’d react as their leaders when they took risks.

3. Empower your team

Empower – the 21st century buzz-word. But what does it mean?

Webster states that “empowerment is the state of being empowered to do something the power, right, or authority to do something”. But what does it mean to empower your team members?

A simple google search of “empower your employees” will give you a myriad of “the 12 ways to…” and “5 strategies to empower…” posts. Many of them are very good. That said, I think the bedrock of empowerment is found in one word.


By learning to trust your team and by giving them decision making power appropriate to their level of skill and experience, you’ll feel the energy, happiness and fulfillment level of the team go up demonstrably. As a bonus you’ll get increased productivity as well – expanding the influence of your team. As I often say, “If I need to control every decision and process for the team, we’re going to have to have very small goals.”

Give away some of the decision making

For example, in the organizational of change I mentioned above, one of the strategies we employed was putting together task forces for the 8 main elements of our business. While each team had a member of the leadership team on it, the structure was intentionally flat. The team knew they were a decision making body for that area, and if they came up with any reasonable idea we would execute it. Needless to say it increased the engagement of our team members and made for a vibrant work environment.

But let me also give you a couple things to remember. Some people on your team will have difficulty with any ambiguity. They not only want to know what you want as the outcome, but they also want to know how you want it accomplished. The ultimate goal is to get them to embrace their own version of “how”, but they may need a little more hand-holding to get them there.

For other folks on your team, you simply need to point in a general direction and they’ll hit the ground running. For these folks, you share the outcome you desire and let them figure out the way to get there. Just remember that their path will likely be different than yours, which may lead to slightly different outcomes, as well. But by giving them the keys to the car, you demonstrate that you trust them and are willing to live with the risk accompanying their decisions – successes or “tuition”.

Wrapping it up

By encouraging you to normalize risk and accept failure I’m not saying we shouldn’t pay attention to results. We have to, or we won’t be in business for long. But playing it completely safe is unlikely to get you where you want to go. Don’t be afraid to encourage risk by celebrating failure, modeling risk and empowering your team. Your workplace may occasionally be a little more “exciting” than you’d like it to be, but the results may be more exciting, too!

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