Jessica Fain: The Art of Influencing Executives

In a recent podcast discussion, product leader Jessica Fain, who has held influential roles at Box, Slack, and now Webflow, shared her insights on the art and science of influencing executives. Fain, recognized for her unique ability to drive product success, emphasized the critical skills product managers need to effectively communicate their vision and gain buy-in from leadership.

Understanding the Executive Mindset

Fain highlighted that a common pitfall for product managers is failing to grasp the executive's perspective. Executives are often inundated with information and are driven by high-level business objectives. Therefore, product managers must frame their ideas and requests in a way that directly addresses these objectives.

Fain stated, "You have to act like a CPO, to be a domain expert. Your executive is looking for you to be the deepest person in the room." She stressed that simply presenting a product idea isn't enough; it needs to be contextualized within the broader business strategy and demonstrate how it contributes to the company's overall success.

The Power of Curiosity and Empathy

Central to Fain's philosophy is the cultivation of curiosity and empathy. She believes these are the most potent tools in a product manager's arsenal, enabling them to truly understand the needs and motivations of both users and executives. "Product managers are one of our best sets of skills is curiosity and empathy to understand our users," Fain remarked.

However, she cautioned against a narrow focus. The empathy must extend to the executive level as well. "The moment that we're talking to an executive, we forget those skills and those talents," she observed, pointing out that executives, like anyone else, have their own goals and pressures. Understanding these can be the key to successful influence.

Bridging the Gap: From Idea to Execution

Fain addressed the common challenge of getting buy-in for new product ideas. She noted that executives are often busy and may not have the time or energy to fully engage with every proposal. This is where the product manager's ability to influence becomes paramount.

She explained, "You get paid to be a domain expert. Your executive is looking for you to be the deepest person in the room. Bringing your expertise to bear is crucial." This means not only understanding the product but also understanding the business context and how the product aligns with strategic goals.

The Art of Asking the Right Questions

Fain emphasized the importance of asking insightful questions to guide conversations with executives. Instead of just presenting a solution, product managers should aim to understand the underlying problems and objectives. "Tell me what are their goals, how are they measured, connect the thing you're pitching them with that success," she advised.

She also highlighted the need for product managers to be decisive, even when faced with uncertainty. "Sometimes you have the best idea and they just don't buy," she acknowledged, but stressed that the ability to kill or deprioritize things is also a sign of strong leadership and trust-building.

Key Strategies for Influencing Executives

Fain outlined several key strategies for product managers aiming to influence executives:

• Understand their goals and how they are measured.
• Connect your pitch directly to their success metrics.
• Bring deep domain expertise to the table.
• Ask questions that uncover their priorities and concerns.
• Be willing to show your work and the rationale behind your decisions.
• Build trust by demonstrating your understanding of the business.

She concluded by emphasizing that influence is not about manipulation but about building relationships and demonstrating a clear understanding of how your product contributes to the executive's and the company's success. "You have to act like a CPO," she reiterated, "You have to be able to communicate the value of what you're building."