Feature Interview: Jennifer Hollett on Leadership + Technology

Making a case for new technology and voices starts at the top.

Groundforce Digital
5 min readAug 17, 2015

This interview series is presented by Groundforce Digital.

Jennifer Hollett is an award winning broadcast journalist (CBC, CTV, MuchMusic) and a leader in Canada’s new generation of political activists (digital director on Olivia Chow’s Toronto mayoral campaign). She is also the co-founder of Super PAC App, a “Shazam” for political ads. Jennifer is the NDP candidate in the new Toronto riding of University-Rosedale.

What do you see as the most important digital tools for community organizing? Why are they important?

The top five most important digital tools right now are Twitter, Facebook, Email, Data and Search. When news breaks, it breaks on Twitter first. As an organizer, you want to insert yourself and your campaign into the flow of information. That’s Twitter. If you’re not on Twitter, you’re missing valuable conversations (local, national and international) and the opportunity to build relationships with key journalists, community leaders and influencers.

I like to describe Twitter as a big city, and Facebook as a small town. Twitter is where you follow people you’d like to know, Facebook is who you know.

Facebook is where you see your friends and family, and what they’re up to, where you’ll bump into someone from your hometown or university. Its personal nature is what makes it so effective for social influence. Then there’s Email. On Olivia Chow’s mayoral campaign we raised half of the $1.9 million dollars through our email campaigns and Olivia’s website. Email is the original social media, still very effective for reaching people. However, a phone call always goes a long way, and can sometimes be the most effective ask.

Speaking of data, in Canada, we’re still so far behind the gains made with data in Barack Obama’s campaigns. Be it a simple A/B subject line test on MailChimp, or more sophisticated data analysis offered with other technology providers, we should be making decisions based on evidence not gut feelings, or how it’s always been done.

And lastly, a few thoughts on the importance of search. People need to be able to find you. Most of us start with Google. Can people find your email, phone number or office easily enough? Make sure anyone who wants to connect, can do so easily. An easy to navigate, mobile friendly website, with search engine optimization is not to be overlooked.

What are the biggest barriers you see for campaigns or organizations looking to adopt these tools? Do you have suggestions for overcoming these barriers?

New technology is overwhelming, even to those who work in the space. As soon as you “get it,” the “it” changes. Right now with organizing and communications it’s Twitter and Facebook and NationBuilder, but more and more people are asking about opportunities with Instagram, Snapchat and Periscope.

Sometimes your best digital strategy is about saying no.

Strategy is key. My mentor, the legendary organizer and Harvard professor Marshall Ganz defines strategy as “how we turn what we have into what we need to get what we want.” It’s really important to map out what success looks like, and to move beyond vanity metrics. For example, if your goal is to recruit 50 volunteers, success looks like 50 new volunteers who came to the campaign through digital, not 2,000 followers on Twitter who live outside of where the campaign needs people on the ground. No, we won’t be using Ello, since the people we are looking to reach aren’t on the platform.

In your opinion, what is the single most important thing a senior manager can do to foster young leaders within their campaign or organization?

As a candidate, after I ran (and lost) the federal Toronto Centre NDP nomination, I created a Google survey to get anonymous feedback from our core team of volunteers. Feedback, debriefs, and post-mortems are vital, win or lose, and throughout campaigns. One comment stood out: “give volunteers responsibilities, not tasks.”

Give volunteers responsibilities, not tasks.

I used this feedback in my second nomination (which I won) and current campaign, and have witnessed incredible results and leadership development. Ask for feedback, and then act on it.

What advice would you give to a young people who care deeply about an organization and want to help it keep up with the times? How can they help it evolve?

I’m a fan of reverse mentoring, as it empowers emerging and established leaders. Position learning and growth as a skills and experience exchange. It’s an adaptive way of allowing older employees to learn social media or new technology from younger employees, and giving younger employees the chance to learn more about the organization, sector, or case studies from older employees. But don’t assume all young people understand digital, and that all older people don’t. I have found late adopters some of the biggest champions for digital, as both allies and power users themselves.

When you think of organizations or campaigns that are getting it right in terms of leveraging new technology for community organizing, who do you think of? Why?

I’ve been attending protests actively for the last 25 years, and I was incredibly moved on the first day of action for Bill C-51 in Toronto back on March 14.

Bill C-51 is an election issue for many, and digital tools will continue to drive this issue throughout the federal campaign. It’s incredible to think this started out as an online petition and series of Facebook events.

The week following the national day of action, public support for the bill dropped to 45 per cent and the media shifted from calling the bill the “anti-terrorism act” to Bill C-51. Both were due to on-the-ground organizing and digitally driven movement, building off of Idle No More and Occupy, in partnership with civil liberties activists and online tools and communities at Leadnow.ca. Digital tools will continue to drive this issue throughout the federal campaign.

About Groundforce Digital: We work at the intersection of politics, technology, business and community. We help organizations grapple with complex community organizing challenges by laying down digital infrastructure designed to allow a new generation of civic leaders to experiment and chart new paths forward. Get in touch! http://www.groundforcedigital.com



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