Lenny Rachitsky Explains How Product Managers Can Effectively Influence Executives

In a recent LinkedIn post, Lenny Rachitsky shares insights from Jessica Fain on how product managers can overcome common challenges when presenting ideas to executives. Rachitsky highlights Fain’s journey to understand the internal decision-making processes at executive levels, particularly after her own product ideas struggled to gain traction.

Rachitsky relays Fain’s initial realization that executive attention is highly fragmented and unpredictable. As Rachitsky puts it, quoting Fain’s experience:

“People don’t realize that an executive’s calendar is like a strobe light going off. Budget meeting, a people problem, a legal issue—then your product review. You’ve been prepping for three weeks. They haven’t thought about you since the last meeting. They may not have gone to the bathroom today.”

This observation, according to Rachitsky, underscores a fundamental disconnect many product managers face when trying to influence senior leadership. The post emphasizes that Fain learned to shift her approach from a transactional request to a more empathetic and curious engagement, mirroring how she interacted with end-users.

The Power of Executive Empathy and Curiosity

Lenny Rachitsky details how Jessica Fain’s experience at Slack, where she served as Chief of Staff to the CPO, fundamentally altered her perspective on executive influence. Rachitsky explains that Fain discovered the importance of aligning product pitches with an executive’s immediate concerns and anxieties. This involves understanding what is actively worrying the executive, rather than simply presenting a well-researched product proposal in isolation.

Rachitsky highlights a specific tactic Fain advocates for, which involves disarming executives through thoughtful questioning. As Rachitsky notes:

“Why ‘that’s so interesting, what led you to believe that?’ can help you disarm an exec”

This approach, Rachitsky explains, moves away from a defensive posture and encourages a more collaborative dialogue, fostering trust and understanding. The goal is to make the executive feel heard and understood, creating a more receptive environment for the product manager’s ideas.

Strategic Communication and Trust Building

The article further elaborates on Fain’s strategies for effective executive communication, as presented by Rachitsky. One key takeaway is the importance of a concise and impactful meeting opener. Rachitsky points out Fain’s emphasis on a specific technique:

The 60-Second Opener

According to Rachitsky, Fain suggests that product managers often skip a crucial initial step in executive meetings. This brief opening is designed to quickly orient the executive and set the stage for the discussion, respecting their limited time and attention span. While the exact content of this opener isn’t detailed in the post snippet, Rachitsky frames it as a vital, yet often overlooked, element of successful executive engagement.

Responding to Feedback and Building Trust

Lenny Rachitsky also touches upon Fain’s playbook for handling executive feedback, a strategy she calls “Stewart plus two more.” While the specifics of this method are not fully elaborated in the post, Rachitsky frames it as a structured approach to incorporating CEO feedback. Furthermore, Rachitsky highlights a counterintuitive yet powerful trust-building mechanism that Fain advocates for:

“Why killing your own project is the ultimate trust-building move”

This concept, as relayed by Rachitsky, suggests that demonstrating a willingness to make difficult decisions, even if it means sacrificing one’s own initiatives, can significantly enhance an executive’s confidence in a product manager’s judgment and commitment to the broader organizational goals.