Lessons from Lilith Fair on Innovation and Leadership
- Pam Stoik
- 5 days ago
- 3 min read
As a Gen Xer, as a woman and as a Canadian you could say I am the EXACT target market for the documentary, Lilith Fair: Building a Mystery. But as someone keenly interested in building transformational cultures, this film hit on a much deeper level.
The Origins of an All-Female Concert
Back in 1997 when Sarah McLachlan launched Lilith Fair, she did it almost out of spite: promoters told her an all-female music festival would never work because no one would want to see two women back-to-back on a lineup, let alone a day’s worth of female artists.
But as with many female founders who are doubted by a male-dominated industry, she did more than build a case: she built proof.
McLachlan started small by doing the “unthinkable:” having Paula Cole (another woman!) open for her while on tour in 1996. Not surprisingly, the tour was a success and paved the way for a full-blown all-female music extravaganza—Lilith Fair which became the top-grossing touring festival of 1997 earning about $16 million. Over three years, it also raised more than $10 million for women’s charities and redefined what a successful festival could look like.
Timeless Lessons in Innovation:
Why did Lilith Fair work? Because it followed the timeless principles of good innovation...
Challenge assumptions. Everyone said it couldn’t be done. But McLachlan felt this was simply untrue, and her micro test with Paula Cole suggested she was heading in the right direction. Innovation starts when you start challenging the status quo and look for the cracks in the “we’ve always done it this way” mantra.
Create new value. It wasn’t just concerts — it was community, representation, and belonging. That’s what people showed up for. Many attendees described it as a safe space in a concert world of violence and misogyny (a Woodstock revival in 1999 was a disaster in this regard).
Align purpose with profit. Lilith Fair was a business success because it stood for something bigger: supporting women's music and women-centred charities.
Take feedback and adjust. In its first year, Lilith Fair was criticized for being “lily white” and “mom music.” Organizers took the complaints to heart and responded by including more diverse artists including Erykah Badu, Missy Elliott and Queen Latifah and “edgier” bands like L7. Being open to feedback isn't a sign of weakness, but one of openness. And that approach is paramount to building trust and a rock-solid relationship with your client base.
Stay true to the vision. In a moment of self-doubt, Sarah McLachlan openly considers including male headliners in the mix until Emmylou Harris reminds her of the original vision. Ambiguity and doubt are ALWAYS a component of innovation. But as with any creative endeavor, knowing when to stop and what NOT to do are as important as the adjustments along the way.
Turn critics into advocates. Initial party poopers like Sandra Bernhard and Chrissie Hynde were invited to experience the magic of Lilith Fair for themselves. In my own experience, this is paramount to innovation success. Instead of avoiding naysayers, invite them into the fold and allow them to see behind the curtain.
Disruption isn’t always loud or tech-driven — sometimes it’s about designing a new space that no one has had the guts to create. If the system doesn’t make room, build a new one.
In our current environment—where female founders in Canada make up just 4% of all venture capital funding1 and south of the border, women’s rights continue to be eroded—it seems like the world is in desperate need a Lilith Fair-type Renaissance.
After all, Lilith Fair didn’t just prove the doubters wrong: it showed that doing what’s different can also be what’s right for an industry, for society and even for investors...
Source: Women Entrepreneurship Knowledge Hub. (2024). The state of women’s entrepreneurship in Canada 2024. https://wekh.ca/wp-content/uploads/2024/04/WEKH_The-State-of-Womens-Entrepreneurship-in-Canada-2024.pdf
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