Prioritizing a candidate's skills ('capacity') over their fit with the team ('chemistry') is a mistake. To scale culture successfully, focus on hiring people who will get along with their colleagues. The ability to collaborate and integrate is more critical for long-term success than a perfect resume.

Canva avoids a delegated M&A team. The COO personally sponsors acquisitions, focusing on the acquired founder's motivations and cultural fit—often assessed over a drink. This deeply personal approach ensures the founder's vision aligns with Canva's distribution power, leading to successful integrations and high founder retention.

Chipotle CBO Chris Brandt filters candidates based on a simple, visceral question: 'Would you be willing to walk into a conference room with them at 5 PM on a Friday?' This test prioritizes collaborative spirit and cultural fit over pure skill, ensuring new hires won't disrupt team dynamics, even if they look good on paper.

Move beyond surface-level discovery questions. Asking 'What do you value most in a partner?' forces prospects to articulate their core needs for a relationship (e.g., responsiveness, consultation). Their answer quickly reveals if there is a fundamental values alignment, a better predictor of success than technical fit.

Technical competence is the easiest part of a technical co-founder to evaluate. The real risks lie in misaligned goals (lifestyle vs. unicorn), personality clashes, and incompatible work styles. Prioritize assessing these crucial "human" factors first.

Before an LOI, share your high-level vision, then have the target's founders pitch back their own 6- and 12-month post-acquisition roadmap. This pre-commitment exercise reveals true alignment and integration potential far more effectively than traditional diligence, creating a joint vision early on.

During a merger, prioritize people over process. Technical integration is secondary to building trust between teams. Use simple, cultural activities like joint happy hours and "show-and-tells" about the tech stack to humanize the engineering effort and foster empathetic collaboration early on.

When a CEO consistently emails on nights and weekends, it's a clear signal of a high-intensity work culture with low work-life balance. For candidates, this isn't just about the CEO's schedule; it's a cultural red flag or green flag depending on their own work preferences and expectations.

Assessing cultural fit can't be done in a formal, time-crunched diligence process. Snowflake approaches M&A like dating, building relationships with companies over time. This long-term engagement allows for genuine discovery of values and operational style, de-risking the 'cultural diligence' aspect of a potential acquisition.