Jessica Fain: Executives face extreme time constraints, influence is the key skill for product leaders, and empathy enhances executive engagement | Lenny’s Podcast

Understanding executive decision-making dynamics is key for product leaders to drive successful collaborations and innovations.

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Add us on Google by Editorial Team Mar. 23, 2026

Key takeaways

• Executives face significant time constraints, impacting their ability to focus on new initiatives.
• Influence is a critical skill for product leaders, essential for building momentum behind ideas.
• Misunderstandings often arise due to executives’ decision-making based on personal incentives.
• Product leaders should adapt communication styles to align with executive preferences.
• Meetings with executives should be viewed as learning opportunities, not just approval sessions.
• Empathy and curiosity are vital for product managers when interacting with executives.
• Influence should be seen as a tool for idea recognition, not manipulative politics.
• Stakeholder conversations can be leveraged as discovery interviews to refine ideas.
• Executives frequently operate under extreme context-switching pressures.
• Product leaders must be strategic in their communication to ensure effective collaboration.
• Understanding executive decision-making dynamics is crucial for product success.
• Applying user-centric skills to executive interactions can enhance product development.
• Influence increases the chances of good ideas being recognized and implemented.
• Engaging stakeholders constructively can lead to better project outcomes.
• Executives’ packed schedules require tailored communication from product leaders.

Guest intro

Jessica Fain is Sr. Director of Product for Collaboration and Scale at Webflow, where she oversees the product area focused on enhancing service for larger, collaborative web and marketing teams globally. Previously, she served as Chief of Staff to the Chief Product Officer at Slack, where she worked closely with leadership including Stewart Butterfield and learned how executives actually make decisions. Her career also includes product leadership roles at Box and brightwheel, giving her deep experience across enterprise, core product, and early-stage product development.

Understanding executive challenges

• Executives have limited time to focus on new ideas due to their packed schedules.

• I describe an executive’s calendar as a strobe light going off… they have not had the time, the energy, the wherewithal to center your problems.

  — Jessica Fain

• The constant context-switching faced by executives affects their focus in meetings.

• Executives are running around context switching in the most insane ways I’ve ever seen and everything that comes across their plate is an emergency.

  — Jessica Fain

• Executives often prioritize based on their own incentives, leading to misunderstandings.

• What I learned through that process is that people completely misunderstand how executives make decisions… they center their own desires, their own motivations, their own slice of the world.

  — Jessica Fain

• Product leaders must tailor their communication to executives’ unique challenges.
• Understanding these challenges is crucial for effective collaboration and influence.

The power of influence in product leadership

• Influence is arguably the most important skill for product builders.

• Influence might be the single highest leverage skill for product leaders outside of AI.

  — Jessica Fain

• Building momentum behind great ideas is essential for successful product development.

• I think as product builders there’s almost not a skill that’s more important influence and building momentum behind great ideas is the way that great products actually get built.

  — Jessica Fain

• Influence should be viewed positively, not as manipulative politics.

• I think that when people frame this as politics they’re completely missing the point politics is manipulating outcomes and people for your own gain influence is about increasing the odds that your good ideas survive.

  — Jessica Fain

• Effective influence ensures that good ideas are recognized and implemented.
• Product leaders must harness influence to navigate organizational dynamics.

Adapting communication for executive engagement

• Product leaders should adapt their communication styles to connect with executives.

• We as product leaders have to be communication chameleons… you have to think about do they really turn a spark with a design with a customer.

  — Jessica Fain

• Tailoring communication is vital for aligning with executives’ preferences and priorities.
• Strategic communication enhances collaboration and leads to successful outcomes.
• Meetings with executives should be approached as opportunities for learning and growth.

• One of the most disastrous things you can do is going into a meeting just looking for approval for your plan instead if what you go in with is how can I learn how can I strengthen this plan…

  — Jessica Fain

• Empathy and curiosity are key skills for engaging effectively with executives.

Leveraging stakeholder conversations

• Stakeholder conversations should be treated as discovery interviews to refine ideas.

• If we treat our stakeholder conversations as discovery interviews as a way to strengthen our ideas then we end up in a much much better place.

  — Jessica Fain

• Engaging stakeholders constructively can lead to improved project outcomes.
• Product leaders must proactively engage stakeholders to enhance collaboration.
• Viewing stakeholder interactions as opportunities for discovery fosters innovation.
• Constructive engagement with stakeholders strengthens product development efforts.
• Treating stakeholders as key users can lead to better alignment and results.

Enhancing product management with empathy and curiosity

• Empathy and curiosity are essential for product managers, especially with executives.

• As product managers one of our best sets of skills is curiosity and empathy and trying to understand our users… if we can take some of those skills of building great products and think about our executive as our key user here…

  — Jessica Fain

• Applying user-centric skills to executive interactions can enhance product development.
• Understanding executives as key users helps align product strategies with organizational goals.
• Empathy allows product managers to better navigate executive priorities and challenges.
• Curiosity drives innovation and strengthens product management practices.
• Building strong relationships with executives through empathy leads to successful outcomes.

Disclosure: This article was edited by Editorial Team. For more information on how we create and review content, see our Editorial Policy.