The art of influence: The single most important skill that AI can’t replace | Jessica Fain (Webflow, ex-Slack)
Jessica Fain, a product leader at Webflow and former Chief of Staff at Slack, shares expert strategies for influencing executives. She reveals common misunderstandings about executive decision-making, offering tactical advice on communication, empathy, and aligning ideas to gain buy-in and build trust.
Deep Dive Analysis
24 Topic Outline
Introduction to Jessica Fain and influence as a skill
Why great ideas fail without executive buy-in
Understanding executive calendars and decision-making
The role of curiosity and empathy in influencing leaders
Influence vs. politics and genuine learning
How to disagree with executives respectfully
Leveraging AI to understand executive perspectives
Presenting ideas and options effectively
Tailoring communication to executive styles
Understanding and aligning with executive incentives
The Customer Love Sprint example at Slack
Disarming executives and responding to subtle feedback
Importance of speed in follow-up and building momentum
Running high-impact meetings with clear context
Why influencing executives is part of your job
Asking for more resources and thinking in 10x bets
What to do when your idea gets rejected
Building trust and shrinking big ideas into experiments
Common mistakes when influencing leaders
Growing into your next role by broadening context
How AI is changing influence and product work
Using AI to simulate executive feedback and improve pitches
Protecting our brains from overwhelm in the AI era
Lightning Round and final thoughts
6 Key Concepts
Executive Calendar as a Strobe Light
Executives' calendars are fragmented, with constant context-switching between urgent, diverse topics, meaning they often lack prior focus or deep context on specific issues presented to them.
Global vs. Local Optimization
Executives typically optimize for the overall company's success (global maximum), while individual contributors often focus on their specific area (local optimization), which can lead to misalignment if not addressed.
Influence vs. Politics
Influence is about increasing the odds that good ideas survive by genuinely understanding and engaging others, whereas politics is defined as manipulating outcomes and people for personal gain.
Shrinking the Change
A change management concept where a large, scary, or overwhelming initiative is broken down into much smaller, low-risk experiments or proof-of-concepts to build momentum and trust.
Product Citizenship
A trait of senior product roles that involves embedding back into the organization, sharing best practices, mentoring, and broadening others' horizons on tooling, technology, storytelling, and strategy.
Strategy Clarity
The critical importance of clearly defining what a company believes, its most important problems, and where to invest resources, especially in the age of AI, to empower teams to build the right products quickly.
8 Questions Answered
Influence and building momentum behind good ideas are essential because without buy-in and backing from key stakeholders and executives, great products cannot be built and careers can stagnate.
Executives often make rapid decisions with limited information, constantly context-switching between urgent issues, and are optimizing for the global maximum of the company, not local team priorities.
You can disagree by bringing your domain expertise to bear, asking curious questions like "What led you to believe that?", and helping them unpack their reasoning, then responding with your insights.
AI tools can be trained on past meeting transcripts or executive communications to predict potential pushbacks, identify weaknesses in ideas, and understand an executive's current priorities before pitching.
A common mistake is presenting only one option, which limits discussion and doesn't demonstrate the full range of considerations, making it harder for executives to buy into the proposed solution.
Building trust involves consistently delivering impact, actioning on past feedback, shrinking large initiatives into smaller experiments to reduce risk, and being willing to deprioritize or kill projects that aren't working.
AI is shifting the leverage from execution (like data analysis or note-taking) to deciding what work survives and influencing others to buy into ideas, making core skills like user empathy, curiosity, and strategic alignment 10x more important.
With AI accelerating building and decision-making, clear strategy is crucial to anchor empowered teams, ensuring they build the right products and avoid compounding mistakes at a faster pace.
17 Actionable Insights
1. Understand Executive Context & Goals
Executives operate in a “strobe light” calendar, constantly context-switching. Understand their goals, how they’re measured, and connect your pitch to their success to gain buy-in.
2. Set Meeting Context Effectively
Start meetings with 30-60 seconds of context: state the purpose, recap the last discussion, outline today’s goals, and ask if there’s anything else they hoped to cover to help executives quickly orient themselves.
3. Approach Meetings to Learn, Not Convince
Go into meetings with a mindset of learning and strengthening your plan, leveraging the executive’s expertise, rather than just seeking approval for your own ideas.
4. Ask “What Led You to Believe That?”
When an executive says something you disagree with, ask “That’s so interesting. What led you to believe that?” to understand their perspective and co-create a better solution, rather than directly refuting them.
5. Anticipate Executive Concerns Using AI
Use AI tools (like a GPT trained on past meeting transcripts or Slackbot queries) to understand an executive’s priorities, potential pushbacks, and weaknesses in your ideas before pitching.
6. Present Multiple Options
Avoid presenting only one solution. Instead, offer at least three options (including your preferred one) to demonstrate thorough consideration and facilitate a more productive discussion with executives.
7. Tailor Communication to Executive Style
Understand and adapt to each executive’s preferred communication style (e.g., docs, data, design, customer stories, dashboards) to engage their “best brain” and expertise most effectively.
8. Align Your Work with Company Strategy
Deeply understand company OKRs, positioning, and leadership’s beliefs, embedding this strategic insight into your team’s culture and product proposals to ensure alignment and relevance.
9. Follow Up Quickly on Executive Feedback
Respond to executive feedback and follow-up items in a timely manner (e.g., within an hour or two, not a week) to maintain momentum and enthusiasm for your initiatives.
10. Ask About Urgency and Priorities
When an executive suggests an idea, ask “How strongly do you feel about this?” or “Do you think that trumps these other priorities?” to contextualize its urgency and importance within their broader workload.
11. Proactively Address Discussion Themes
In meeting documents, create a “themes for discussion” section at the top to highlight major controversial points for live discussion, while addressing smaller, clarifying questions offline.
12. Think 10x and Ask for Resources
When presenting ideas, consider the 10x or accelerated case. If an executive’s ask seems unreasonable, articulate the additional resources (e.g., more people, closer alignment) needed to achieve it.
13. Shrink Big Ideas into Experiments
To build momentum and trust for a big or scary idea, shrink it into a small, low-risk experiment or proof of concept (e.g., a one-week project) to test its viability and reduce perceived risk.
14. Be Willing to Kill Projects
Demonstrate a senior mindset by identifying and advocating for the deprioritization or killing of projects that are not working or not aligned with company goals, even if you’ve invested time in them.
15. Broaden Your Context and Perspective
To grow into a leadership role, expand your viewpoint beyond your immediate domain to understand the entire business ecosystem, industry, and e-staff conversations, showing up as a strategic thinker.
16. Codify Product Philosophy for AI Agents
Define your product philosophy, beliefs about product-market fit, success metrics, and guardrails to effectively train AI agents as teammates, ensuring they align with your team’s values and prevent missteps.
17. Be Authentic in Influence
Recognize that influence and trust-building can be achieved through various personality types (shy, introverted, data-oriented). Focus on being authentic to your own strengths rather than mimicking others.
9 Key Quotes
It's your fault if the leaders didn't buy into your idea.
Jessica Fain
I describe an executive's calendar as like a strobe light going off.
Jessica Fain
It's not my fault, but it is my problem.
Annie Pearl
Politics is manipulating outcomes and people for your own gain. Influence is about increasing the odds that your good ideas survive.
Jessica Fain
That's so interesting. What led you to believe that?
Jessica Fain
You get paid to have an opinion. You get paid to be a domain expert.
Jessica Fain
I will tell you, I am not a big fan of the what's top of mind for you question.
Jessica Fain
I think one of the biggest things you can do to build trust is kill things, deprioritize things.
Jessica Fain
I think that we are entering a golden age of product management, not of product managers, but of product management.
Jessica Fain
2 Protocols
Stuart Plus Two More Design Review Protocol
Jessica Fain- Go through the design review with Stuart.
- Implement exactly what Stuart asked for.
- Create two other versions that the team felt good about.
- Use these versions as a forum for conversation to debate the merits of each approach.
Customer Love Sprint Protocol
Jessica Fain- Engineers stop current work for two weeks to focus on craft.
- Engineers get to pick what specific improvements they work on.
- PM, design, and customer support provide support and tons of ideas.
- The only rule is that engineers must ship something good for users.
- Hold a fun judging competition with executives to celebrate the work.