When hypergrowth causes you to fail internal stakeholders (like Operations), apologies are insufficient. Rebuild trust by going to the CEO and board *together* with the slighted team to advocate for a drastic roadmap pivot that prioritizes their needs, demonstrating true commitment to their success.
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For a controversial strategic shift, a co-founder's "moral authority" is invaluable. They can absorb the risk of looking foolish and give up their responsibilities ("Legos") to spearhead a new initiative. This allows them to champion a new direction with a level of credibility that can overcome internal skepticism.
The Browser Company's pivot required spending the "trust points" they'd built with their team and community. Leaders must be prepared for this painful drawdown and the internal/external backlash, even when they have high conviction in the new direction. It's a necessary but difficult part of a major strategic shift.
During major internal changes (e.g., tech refactoring, price hikes), users can feel neglected. Bending Spoons found that monthly video updates for Evernote were crucial for reassuring the community, demonstrating progress, and putting a human face on the company to directly address concerns.
Before a major business pivot, first identify what can be let go or scaled back. This creates the necessary space and resources for the new direction, preventing overwhelm and ensuring the pivot is an extension of identity, not just another added task on your plate.
As companies grow from 30 to 200 people, they naturally become slower. A CEO's critical role is to rebuild the company's operating model, deliberately balancing bottom-up culture with top-down strategic planning to regain speed and ensure everyone is aligned.
Go beyond visual roadmaps. Create a monthly written document for executives that explains *why* the roadmap changed, details priorities, and includes data from recent launches. This forces intentionality, builds trust, and fosters deeper, more accountable conversations with leadership.
When rebuilding ZICO, the founder realized his first mistake was a relentless focus on speed. His new approach prioritizes building to last, embracing his own leadership limitations by delegating, and fostering a culture of emotional transparency to create a more resilient business.
The pivot from Arc to Dia was also a cultural and technical reset. The Browser Company gave their team a "blank page," allowing engineers to build a new, faster architecture and designers to rethink the experience. This chance to fix old problems and pursue new ideas was key to getting team buy-in.
When pitching a long-term strategic fix, regional leaders prioritized immediate revenue goals. The product team gained traction not by dismissing these concerns, but by acknowledging their validity. This respect builds the trust necessary to balance short-term needs with long-term investment.
Robinhood is shifting its planning process to focus on what will be announced at its next public product keynote. Instead of setting abstract internal goals, this aligns the entire company around concrete, customer-facing deliverables and creates a powerful, immovable deadline for shipping.
