How do executives typically make decisions, and how does this affect product managers?

Executives operate with extremely busy, fragmented schedules, constantly context-switching between urgent issues. They often come into meetings without deep prior context for specific problems. Product managers need to help executives get into the right mindset by providing clear context and understanding their global optimization goals, rather than focusing solely on their own localized problems.

Is influencing executives a form of 'politics' or manipulation?

No, influence is distinct from politics. Politics is about manipulating outcomes for personal gain, while influence is about increasing the odds that good ideas succeed. It's reframed as a learning process, treating stakeholder conversations as discovery interviews to strengthen ideas with genuine curiosity and empathy.

How can product managers balance presenting their point of view with an open, learning mindset?

Product managers should come in with a clear recommendation but also be prepared with multiple options, showing they've considered permutations. The default is to summarize the conclusion, but have the detailed process in an appendix if asked. This approach shows both conviction and a willingness to learn and strengthen the plan.

What is the 'Minto Pyramid Principle' and how can it be used for executive communication?

The Minto Pyramid Principle suggests presenting information backward compared to the typical linear process. Start with the recommendation, then outline the conclusions that led to it, and finally, present the supporting evidence. This caters to executives' need for quick, high-level information first.

Instead of asking 'What's top of mind?', what are more effective questions to ask executives?

Instead of the generic 'what's top of mind,' ask 'spicier' questions that uncover emotional drivers or external pressures. Examples include: 'Tell me how you spent your day,' 'What's the most urgent priority you're scared about messing up?', 'What pressures are you facing?', or 'Tell me what the board is pushing you on?'

How can product managers use executive incentives to their advantage?

Product managers should deeply understand an executive's goals, metrics, OKRs, and even board pressures. Then, they must explicitly connect their product proposals to how they will help the executive achieve those specific successes, aligning incentives and demonstrating the broader company impact.

How do product managers build trust with leaders, especially when pitching new ideas?

Building trust involves consistently delivering impact, showing results, and acting on past feedback. For new ideas, 'shrink the change' by proposing small experiments or proof-of-concepts to reduce perceived risk. Additionally, be willing to 'kill' projects that aren't working, demonstrating a commitment to company outcomes over personal investment.

How is AI changing the skill of influence in product management?

AI is lowering the barrier to execution, making it easier for anyone to build initial versions of products. This shifts the PM's leverage from being master executors to being adept at deciding what to build, aligning teams, and securing funding for subsequent, more complex versions. The core skills of user empathy, novel insights, and influence become even more critical.

What role do AI agents play in the future of influence and product leadership?

AI agents act as intelligent colleagues that can expedite work. Product leaders must 'onboard' these agents with their product philosophy, success criteria, and historical context. This means codifying personal beliefs and leveraging agents to amplify work, while simultaneously setting guardrails to catch hallucinations and apply unique human judgment and taste.

Key Moments

The art of influence: The single most important skill left that AI can’t replace | Jessica Fain

Lenny's Podcast

People & Blogs6 min read94 min video

Mar 22, 2026|366 views|16|1

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TL;DR

Influence is AI-proof, requiring empathy and understanding execs' goals to build better products.

Key Insights

Influence is a critical skill, especially important as AI automates execution but not human connection.

Understanding executive decision-making involves recognizing their time constraints and aligning with their goals and incentives.

Empathy and curiosity, skills used for understanding users, should also be applied to understanding executives.

Influence is about increasing the odds of good ideas surviving, not manipulation; it requires genuine learning and collaboration.

To influence effectively, tailor communication to the executive's style, be prepared with options, and offer solutions aligned with company goals.

Building trust with leaders is paramount, achieved through consistent results, actionable feedback, and demonstrating a broad understanding of the business.

THE POWER OF INFLUENCE IN PRODUCT DEVELOPMENT

Influence is presented as perhaps the single most important skill for product leaders today, especially as artificial intelligence increasingly handles execution. Building momentum behind great ideas and securing buy-in from stakeholders and executives are crucial for building successful products. The ability to influence is not about manipulation but about ensuring good ideas gain traction and are implemented effectively, making it a skill that AI cannot easily replicate. This skill involves a deep understanding of how to connect with leaders and advocate for product vision.

UNDERSTANDING EXECUTIVE DECISION-MAKING

A common mistake is underestimating the intense pressure and time constraints executives face. Their calendars are described as 'strobe lights,' filled with urgent, context-switching demands. Product managers must recognize that executives don't have the same dedicated time to focus on a single problem. Therefore, it's essential to help them contextualize your needs by understanding their goals, how they are measured, and connecting your pitch directly to their success metrics. This requires empathy and a strategic approach to communication.

THE EXECUTIVE AS A KEY USER

Product managers are skilled in empathy and curiosity when understanding users, but often forget to apply these skills when interacting with executives. Instead of solely focusing on getting approval for their own ideas, a more effective approach is to treat executives as a key user. This means going into discussions with a desire to learn, gather feedback, and strengthen the product plan by incorporating the executive's domain expertise and context. This collaborative approach fosters better products and builds stronger working relationships.

THE ART OF CONVERSATION AND BUILDING TRUST

Effective communication with executives requires tailoring the message to their preferred style and understanding their priorities. Tactics include asking insightful questions like 'That's so interesting. What led you to believe that?' to uncover underlying reasons for their opinions. Building trust is fundamental and is achieved through consistent results, demonstrating domain expertise, and showing a broader understanding of the company's strategic goals. Crucially, influencing and building trust involve being genuine and collaborative, not manipulative.

STRATEGIC PRESENTATION AND DELIVERING OPTIONS

When presenting ideas, it's often beneficial to start with a clear recommendation and then provide supporting evidence and explored options, rather than overwhelming executives with detailed processes. Having a recommendation ready is key, but so is being prepared to discuss alternative approaches. Presenting multiple options allows executives to see that various possibilities were considered, strengthening the final proposed solution. Offering well-reasoned alternatives demonstrates thoroughness and expertise, leading to better decision-making.

ALIGNING WITH EXECUTIVE INCENTIVES AND GOALS

A powerful lever for influence is aligning your pitch with the executive's incentives and goals. This involves understanding what success looks like for them, how they are measured, and demonstrating how your proposal will help them achieve those objectives. This extends beyond individual pitches to informing regular roadmap planning and team culture. By deeply understanding and embedding company goals, OKRs, and strategic positioning, teams can ensure their work directly contributes to leadership priorities.

TAKING THE REINS AND EMBRACING LEADERSHIP

To be seen as senior and demonstrate leadership, it's important to proactively address executive cues and requests. When an executive expresses interest in a topic, taking initiative to explore it further, present findings, and offer solutions is crucial. This proactive approach, often involving quick follow-up and demonstration of insights, builds momentum and shows commitment. It's about not just reacting to directives but anticipating needs and driving towards desired outcomes, thereby becoming a strategic partner.

THE ROLE OF TRUST AND KILLING BAD IDEAS

Building trust with leaders is a continuous process that involves delivering results and acting on feedback. A significant way to build trust and demonstrate senior thinking is by being willing to kill or deprioritize initiatives that are not working, even if significant effort has been invested. This shows alignment with company goals and a focus on outcomes rather than personal investment in an idea. Reducing the perceived risk of new ventures through phased approaches and clear milestones also builds confidence.

THE BROADER CONTEXT OF EXECUTIVE KNOWLEDGE

Executives possess a broad context from inter-departmental discussions, industry trends, and peer insights that is often inaccessible to individual product teams. A key aspect of influence is extracting this information through curiosity and empathy, and then applying it to strengthen your own thinking and proposals. This involves asking executives about their pressures, concerns, and the information they are acting upon, then integrating that perspective into your work. This broadens your own viewpoint and positions you as a strategic thinker.

AI'S IMPACT ON THE SKILL OF INFLUENCE

AI is poised to automate many execution-focused tasks, elevating the importance of human-centric skills like influence, empathy, and strategic thinking. As AI becomes more capable of data analysis and coding, the differentiator for product managers will lie in deciding 'what' to build and 'why,' and then effectively getting organizational buy-in. Influence becomes paramount in navigating the proliferation of ideas and ensuring resources are directed towards impactful initiatives, especially in distribution and building trust.

NAVIGATING THE FLOOD OF INFORMATION WITH AI

The rapid advancement of AI and agentic tools means that execution will become faster, but mistakes can also compound more quickly. This increases the need for strategic clarity—a clear articulation of what problems are most important to solve and where to invest resources. AI and agents can serve as powerful collaborators, assisting in research and idea generation, but humans remain critical for setting direction, exercising judgment, and ensuring strategic alignment. Understanding and training these agents on core principles is key.

HUMAN STRATEGY AND JUDGMENT IN THE AGE OF AI

In an era of AI-driven content creation and execution, humans remain vital for defining strategy, exercising judgment and taste, and mastering distribution. While AI can generate code and ideas, humans must decide what initiatives are truly strategic and will resonate with users and the market. The ability to discern what software actually works, matters, and can be successfully brought to market, coupled with building trust with users and internal teams, will be the enduring differentiators. This requires deep user empathy and business acumen.

CULTIVATING AUTHENTICITY AND LEADERSHIP MOMENTUM

Developing influence should be an authentic process, allowing individuals to leverage their unique personality traits rather than conform to perceived expectations. Whether introverted or extroverted, data-driven or people-oriented, one can build trust and influence by staying true to oneself. Demonstrating proactive leadership, expanding one's perspective to encompass the entire business, and connecting individual work to broader company goals are essential for growth. This not only helps achieve personal career goals but also strengthens the organization.

Mentioned in This Episode

●Products

●Software & Apps

●Companies

●Organizations

●Books

●Concepts

●People Referenced

Mastering Executive Influence: A Cheat Sheet

Practical takeaways from this episode

Do This

Approach executive interactions with curiosity and empathy, viewing them as discovery interviews to strengthen your ideas.

Understand and align your pitch with the executive's goals, incentives, and success criteria, demonstrating how your proposal amplifies their success.

Set context at the beginning of meetings (30-60 seconds): state the topic, link to previous discussions, outline current goals, and confirm if they have other topics.

Be prepared to present multiple options for solutions, even if you have a preferred one, and be ready to elaborate on considered alternatives.

Cater your communication and presentation style to the executive's preferences (e.g., doc, data, quiet reading time, PowerPoint).

Ask 'spicier' questions beyond 'what's top of mind' to uncover underlying emotions, pressures, and beliefs (e.g., 'What led you to believe that?', 'What is the board pushing you on?').

Take initiative and quickly act on subtle hints or feedback from executives, showing responsiveness and leadership mindset.

Build long-term trust by demonstrating consistent impact, delivering results, and effectively addressing past feedback.

Reduce the perceived risk or investment of big ideas by proposing smaller experiments or proof-of-concepts ('shrinking the change').

Be willing to 'kill things' and deprioritize projects that aren't aligning with business goals, demonstrating a senior, company-first mindset.

Clarify urgency and scope when executives suggest ideas: ask 'How strongly do you feel about this?' or 'Does this trump existing priorities?'

Expand your worldview beyond your immediate team or feature; think about the entire business, ecosystem, and industry to be seen as a strategic thinker.

Maintain strategy clarity in the age of AI, codifying shared beliefs and important problems to anchor empowered teams.

Avoid This

Forget curiosity and empathy when interacting with executives; don't just focus on your own ideas and incentives.

Go into a meeting solely seeking approval for your plan; instead, aim to learn and strengthen your ideas with executive input.

Disrespect or devalue an executive's experience or insights; if you don't believe they know something you don't, consider working elsewhere.

Overwhelm executives with too much upfront detailed process or proof points (e.g., 16 participants from 15 geos); put excessive detail in an appendix.

Present only one option for a solution, as it can make you appear to have not considered alternatives.

Wait too long to engage with executive feedback or follow-up items, as they move quickly and you may miss your chance.

Jump on every executive request without contextualizing its urgency or importance relative to other priorities.

Become so obsessed with a prototype or idea that you are unwilling to accept its potential failure.

Miss opportunities to broaden your context and understand the broader organizational and industry dynamics that executives are privy to.

Common Questions

Influence is crucial because it's how great product ideas gain momentum and secure the necessary buy-in and backing from key stakeholders and executives. Without it, even the best ideas can 'die on the vine,' limiting career progression and product success.

Topics

Mindset & Self-Improvement AI & Machine Learning Leadership & Management Product Strategy Team Alignment Product Leadership Trust-building Career Growth Stakeholder Management Executive Communication Influence Skills AI In Product Management

Mentioned in this video

Companies

dbt Labs

A company that uses Omni for shipping analytics.

Brightwheel

An all-in-one platform for early education, another company where Jessica Fain was a product leader.

Microsoft

Current workplace of Annie Pearl.

Figma

A design tool mentioned as a place to keep draft files of multiple product options.

McKinsey & Company

A management consulting firm where Barbara Minto was the first female consultant.

Twitter

Mentioned as a platform where Jeff Weinstein constantly tweets and shares about Stripe and also as a place for exhausting debates in the PM community.

Salesforce

Cited as an example of a dominant software tool, used when discussing the proliferation of new tools due to AI.

Casa

A household assistant service that tracks home details, provides assistance for repairs, product replacements, package pickup, and handyman credits.

Amazon

Mentioned as the source for purchasing a towel warmer and for Casa to send light bulbs.

Atlassian

Where Tamar Yehoshua is currently CPO and Head of AI.

Glassdoor

Previous workplace of Annie Pearl where she was CPO.

Vanta

A sponsor of the podcast offering a trust management platform to help companies with SOC 2 or ISO 27001 compliance, AI automation, and continuous monitoring.

Stripe

A financial services and software company where Jeff Weinstein is a product manager.

Google

Mentioned in the context of Gemini and its tools for distribution.

Airbnb

Mentioned in relation to its core value 'Be a Host', aligning with Jessica Fain's life motto of 'First the guests'.

Organizations

BuzzFeed

A company that uses Omni for shipping analytics.

Box

A cloud content management company where Jessica Fain was a product leader.

IDC

A global provider of market intelligence, advisory services, and events for the information technology, telecommunications, and consumer technology markets. Cited for a study on Vanta customers.

UC Berkeley

The university campus where The Greek Theatre is located.

People

Jessica Fain

Guest and product leader at Box, Slack, Brightwheel, and Webflow, known for her expertise in the art and science of influence, especially with executives.

Annie Pearl

Jessica Fain's first PM manager at Box, and later CPO at Calendly and Glassdoor, now at Microsoft. She coined the phrase, 'It's not my fault, but it is my problem.'

Noah Weiss

Succeeded Tamar Yehoshua as CPO of Slack and is also a former podcast guest. He codified early Slack product principles with Ethan Eisman.

Ethan Eisman

Head of Design at Slack who led the initiative to write product principles with Noah Weiss.

Ali Rayl

An early Slack employee who implemented the 'Hey Stewart, what do you think?' practice to get early feedback from Stewart Butterfield on designs.

April Underwood

Former CPO of Slack, who inspired Jessica Fain to understand executive decision-making better by offering her a Chief of Staff role. She also taught Jessica a tool for product strategy meetings.

Tamar Yehoshua

Succeeded April Underwood as CPO of Slack and is now CPO and Head of AI at Atlassian. Jessica Fain also served as her Chief of Staff.

Stewart Butterfield

Co-founder of Slack, known for his incredible product sense and craft. Jessica Fain learned from approaches to engage with Stewart for product strategy.

Rachel Woolley

Jessica Fain's manager at Webflow and CPO, who was a guest on the 'How I AI' podcast. Her feedback led to a more comprehensive presentation of product options.

Ilan Frank

Jessica Fain's boss at Slack, now CPO of Checker. Known for always having a customer anecdote ready to bring his enterprise expertise to discussions.

Barbara Minto

Author and former McKinsey consultant, known for her 'Minto Pyramid Principle' for presenting information to executives.

Jeff Weinstein

A PM at Stripe described as the epitome of thinking on behalf of the entire business, constantly tweeting and sharing about Stripe as a company.

Jimi Hendrix

An incredible musician whose poster of him playing at The Greek is Jessica Fain's favorite.

Software & Apps

Slack

A popular business communication platform where Jessica Fain held product leadership roles, including Chief of Staff.

Webflow

A no-code web development platform where Jessica Fain is currently a product leader.

Omni

A sponsor of the podcast that helps product teams ship AI analytics using a semantic layer, preventing LLMs from directly generating SQL in production.

Perplexity AI

A company that uses Omni for shipping analytics.

Lovable

A tool that allows users to build working apps and websites by chatting with AI, useful for marketers, PMs, and founders.

Checker

Where Ilan Frank is currently CPO.

GPT

Referenced as a tool that can be trained on past product review transcripts to predict executive pushback.

Gemini

Google's AI model, mentioned as an example of continued dominance in the market due to its distribution tools.

Calendly

Previous workplace of Annie Pearl where she was CPO.

Google Calendar

Used as an example to illustrate how executive calendars are often blocked and busy.

Cloud

Mentioned as an AI tool that is amazing for getting feedback on ideas, including identifying weaknesses.

Loom

A video messaging tool used by Kev to quickly present a design review framework.

Codex

An AI coding tool mentioned as being good at generating ideas for product improvements.

Concepts

Office Hours

A practice at Webflow for early strategic alignment conversations, even before a one-pager is ready.

SOC 2

A compliance standard that Vanta helps companies achieve.

ISO 27001

An international standard for information security management, which Vanta helps companies comply with.

Red Teaming

A military tactic, now applied to businesses, which involves taking an outsider's perspective to an idea to identify potential failure points.

Books

A History of Burning

A book telling the story of Indian indentured servants brought to Uganda to build the British railroad.

The Overstory

A book mentioned by the host, believed to be a multigenerational story centered around a tree, similar to Jessica Fain's recommended genre.

Homegoing

A historical fiction novel about the West Coast of Africa and the impact of the slave trade, following two split parts of a family through generations.

Pachinko

A historical fiction novel telling the multigenerational story of a Korean family moving to Japan, loved by Jessica Fain for its 'window into a different world.'

Media

The Bear

A TV show mentioned as trending on the podcast, which Jessica Fain admires for its depiction of emergency healthcare workers' difficult work and care.

Locations

The Greek Theatre

An iconic outdoor amphitheater on the UC Berkeley campus, where Jimi Hendrix performed, and a place Jessica Fain loves for its culture and music.

Products

Towel Warmer

A product Jessica Fain bought for her husband, described as a cheap and easy way to brighten the day, providing warmth after a shower.