A Culture of Risk Taking – Walking the Walk

By Jaime Walman

It was a very hot day in June 2018. I was sitting around my kitchen table with my Strategy Team during one of our “porch days” (a thing I came up with to get us out of the office one day a week during the summer months).

Sometimes, they involve sangria.

Three years ago, Hillel Ontario created and built a very successful peer-to-peer fundraising campaign called On One Foot. The feedback we had received from our student leaders and campus staff was that they didn’t want to re-do On One Foot for a fourth year – the brand was tired, the idea had become old, and we reject complacency. We needed something new, a fundraising idea that would bring together all nine of our schools in a creative, innovative, and unique way.

At the same time, we had been given a $1 million gift to be invested in “talent,” the largest single gift ever given to a Hillel in Canada. We wanted to tie this in somehow, and the idea of a “talent show” was brought forward as obvious, but a simple talent show wasn’t enough.

Here is the conversation that ensued.

Social Media Springboard Fellow: “We should bring Netta!”

Me: “Who is Netta?”

Social Media Springboard Fellow, with eyes wide open, while frantically searching online to bring up the Eurovision video of “Toy.” “You don’t know who Netta is?? How is that possible?”

Non-Jewish Marketing Pro: “Jaime, if we brought Netta, we would break the Jewish world.”

Cue very strange video of an Israeli making chicken noises.

I had just spent time with Marc Newburgh, Hillel Ontario’s CEO, crafting our organizational goals for 2018-2019. He continued to stress the importance of risk taking in our organization and the desire for us to model that from the top. What better way, I thought, than to believe we could bring Netta to Toronto for her inaugural Canadian performance?

“Ok. Let’s do it”

And Out of Sync was born.

On January 24th, over 100 Jewish students from across the province competed in an epic lip sync battle, headlined by Netta Barzilai. The audience voted for the winning school in real time. Their prize? A private meet and greet with Netta after the show. Contributing over $100k, our donors walked away telling us that Out of Sync was the most fun they had ever had at a fundraising event, and our students can’t wait to do it again.

But how did we actually get here?

By learning a lot about risk-taking.

1. Believe Everything Is Possible

Everyone told me there was “no way” we would really be able to afford Netta or convince her to come to a Hillel event. We “got” Netta with a very simple email I wrote to her manager from my cottage during the summer. I didn’t say anything special …  I didn’t have a connection …  I just asked. Just like in fundraising, if you don’t ask you won’t receive. What do you have to lose?

2. Surround Yourself with People Who Trust You

I have the best team. They work so hard, they support each other and they care deeply and passionately about our work together. And when they think I’m totally wrong, are super skeptical, and think it can be done better, they trust that I will listen and course correct. Their optimism and faith in us as a team is unparalleled. Surrounding yourself with people who trust you enough to believe that going off a cliff isn’t even an option is key. And if you do fall, at least you fall together.

3. Be Willing To Be Wrong

During most of the planning of Out of Sync, I felt like I had no idea what I was doing. Building something from scratch means questioning yourself [and others?] at every turn- there’s no blueprint, no data from which to make decisions, and no path to follow. You will make many, many mistakes. And you will fail in little ways and may fail overall. Accepting that and living with it for a period of time is scary. But so worth it.

4. Make Sure The Boss Is Behind You

Change is hard. Pushing people in an unproven direction is scary and you will likely encounter resistance at every turn.

Moving away from our successful On One Foot campaign was not a popular decision with our stakeholders. Spending significantly more money building a brand-new event wasn’t either. Thankfully, Marc and I had talked through all of the risks and he was behind me 100%. If the boat sank, having someone else sailing nearby to bail you out of the water, if possible, is a good thing.

5. Ask for Help. A lot.

In the weeks leading up to Out of Sync, our morning routine in the office would be my telling everyone about the nightmare I had the night before about this event. The absurdity of my dreams ranged from me curled up in a ball in the corner of the DJ booth to my missing my son’s hockey game because I couldn’t get off the phone with El Al. No one can do this alone. Ask for help, take help when it’s offered, and/or hire really good help to support you (I did all three!) You are not an island.

“Out of Sync” was aptly named not solely for its nod to the fine art of lip sync. It is meant to symbolize the way in which it is not business as usual at Hillel Ontario … that we are striving to do things differently, deviate from the “norm” and illuminate the hidden (and not so hidden) talent that lies within each of us.

Pass the sangria.

Jaime Walman is Chief Strategy Officer, Hillel Ontario.