Don't rebrand for the sake of it. A successful rebrand should be a deliberate move to signal a fundamental shift in your business, such as an expansion, a new mission, or a deeper commitment to core values like sustainability. It's an external reflection of an internal change.

Clients often say they want an agency to “push” them but then resist progressive recommendations. Vaynerchuk coaches his team not to “fold like cheap chairs” when challenged. The ideal client has a genuine appetite for change, not just one who pays lip service to it.

Enduring 'stay-up' brands don't need to fundamentally reinvent their core product. Instead, they should focus on creating opportunities for consumers to 'reappraise' the brand in a current context. The goal is to make the familiar feel fresh and relevant again, connecting it to modern culture.

When stretching an iconic brand like Tim Hortons with celebrity partnerships, the leadership team proceeds "eyes wide open," accepting that not every customer will approve. This prevents analysis paralysis and allows the brand to evolve without being held captive by the need for universal consensus.

Ford's CMO credits their rebrand's success to a two-year process of embedding the new strategy across all departments, from HR to product development. This ensured it was more than a marketing campaign by influencing core business operations and decision-making.

After the P&G team bought an initial campaign idea, the agency returned the next day to argue against it, believing a different, riskier concept was stronger. This demonstrates the profound conviction required from creative partners to achieve breakthrough work.

A founder's reluctance to rebrand often stems from sentimental value (e.g., a family member designed it), not business logic. Overcoming this emotional barrier is a critical first step, recognizing the difference between a simple logo and a comprehensive brand identity that can scale.

Brands must identify their non-negotiable "soul"—the central promise to customers. Cracker Barrel's logo change failed because it altered its core promise of "southern hospitality," breaking customer trust. Evolving is crucial, but changing the core is a mistake. Reversing such a change is smart brand stewardship, not capitulation.

To rally senior leaders around a brand reinvention, AT&T's CMO had them share stories about brands they personally admired. This exercise revealed that brand love stems from product and service—not just ads. It successfully reframed brand building as a collective, company-wide responsibility.