Slack Frontiers, Almost Getting PIP’d, and Accepting Less Ambition

James Sherrett continues A Slack Story with 3 stories he hadn't told yet. First, how Slack launched its customer conference, Frontiers, starting in 2017 after customers began asking for it. He explains how the conference brought together customers, partners, product, and the Slack team, and how it created business urgency by serving as a deadline, including an on-site executive briefing program by 2019. He shares vivid details from Frontiers and the event’s “Frontiers” name inspiration from a Carl Sagan quote about humanity needing a frontier, noting omitted lines about knowing how to reach “a new world next door.” Second, he recounts a January 2020 warning from his boss, Marnie, that he was trending toward a performance improvement plan. Third, Sherrett reflects on accepting less ambition as he played smaller roles as Slack hired world-class experts to replace functions he initially led. He reframing his trajectory as a generalist pioneer who starts new initiatives until others can do them better. He emphasizes humility, change (“burn the metaphorical boats”), and the value of never underestimating sheer gall. He closes with some thoughts about self-awareness, challenge and selling out to do be the best you possible.

00:00 Intro and Feedback

00:40 Why companies host conferences

01:44 Building Slack Frontiers

03:09 Frontiers moments and meaning

05:11 Almost on a PIP

06:38 Resetting from complacency

07:37 Learning to accept less ambition

10:20 A generalist mindset

12:26 Never underestimate sheer gall

14:06 Finding some self awareness

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