Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny)
Kevin Yen, Product Lead at Stripe, shares unique insights on becoming a successful PM, including starting in engineering/design/sales, the importance of writing, keeping a decision log, and automating user research. He also discusses hiring with 'unsell emails' and lessons from failure.
Deep Dive Analysis
13 Topic Outline
The Role of a Product Manager and Career Entry
Why Great PMs Need to Be Great Writers
Improving Writing Skills and Cadence
PM's Role with Engineering and Design: Drawing the Perimeter
Effective Feedback Strategies: The Silent Read
Developing Product Sense with a Decision Log
Unorthodox Hiring: The Unsell Email Strategy
Automating User Research for Direct Customer Exposure
AI's Transformative Impact on Future Generations
Lessons from Failure: Separating Identity from Job Performance
Recommended Books and Media
Life Mottos and Personal Philosophy
Competitive Eating Experiences
6 Key Concepts
Product Management (Kevin's Definition)
The practice of converting the potential of a team (engineers, designers, etc.) into as much realized value for someone as possible, with minimum loss. It's about unlocking the team's potential energy to solve customer problems and drive business impact efficiently.
Writing as Clarity at Scale
Writing is crucial for Product Managers because it enables clarity both internally (e.g., for PRDs, stakeholder alignment) and externally (e.g., compelling messaging for customers). PMs need to be able to write compelling messages in the voice of the person they are trying to serve to effectively sell and support their product.
Drawing the Perimeter
A PM's main job, especially with engineers and designers, is to define the problem space by adding reasonable constraints. This allows the team to be as creative as possible within defined boundaries, leading to more productive conversations and focused solutions by removing unnecessary decisions.
Product Sense
A mystical quality often described as the ability to make good decisions with insufficient data. It can be developed by gaining many repetitions in making decisions, documenting their rationale, and critically, observing their outcomes over time.
Unsell Email Strategy
A hiring tactic where, at the offer stage, a manager sends an email detailing the potential negative aspects or challenges of the role or company. This helps reinforce candidates' fears and ensures that only truly committed and well-aligned individuals accept the offer, leading to better long-term hires.
Separating Identity from Job Performance
The crucial understanding that personal worth and skill should be distinguished from a company's specific needs or an environment's compatibility. A career setback like a layoff might reflect a business's changing needs or a poor fit, rather than an individual's lack of competence, allowing for personal growth and finding a better-suited environment.
10 Questions Answered
Starting in roles like engineering, design, or sales provides foundational exposure to building good products and a unique perspective, allowing PMs to delegate responsibilities effectively when they are not the customer.
Aspiring product managers should consider starting as an engineer, designer, or salesperson, as these roles provide direct exposure to building, understanding customer problems, and translating needs.
Writing is crucial for product managers because it enables clarity at scale, helping them articulate thoughts, align stakeholders, and create compelling messaging that drives customer action and sales.
A PM should 'draw the perimeter' by adding reasonable constraints to the problem space, such as defining the target customer, jobs to be done, desired platforms, and core principles (e.g., speed over data consistency), allowing the team to innovate within clear boundaries.
Schedule a dedicated 'silent read' meeting where participants read and comment on the document in real-time, allowing the author to respond immediately and accelerate the feedback and iteration cycle.
The 'unsell email' strategy involves sending candidates an email at the offer stage that details the challenging or negative aspects of the role or company. It's effective because it filters out candidates who aren't truly committed or aligned with the realities of the job, leading to more successful and long-term hires.
Direct customer exposure is crucial because it provides PMs with raw, unfiltered insights into customer problems and experiences, which cannot be fully captured through reports or intermediaries, enabling them to build truly valuable products.
PMs can automate user research by using tools like Gong to monitor sales calls for specific keywords, integrating these alerts with Slack, and then using Zapier and Customer.io to automatically send personalized email invitations with Calendly links to relevant customers for interviews.
Kevin observes that his daughter perceives AI image generation (Midjourney) as simply another tool for 'drawing,' like a crayon, indicating that future generations will integrate AI seamlessly into creative processes, making its full transformative impact currently incomprehensible.
It's crucial to separate personal identity and skill from a company's specific needs or an environment's compatibility, recognizing that a layoff might reflect a business need or a poor fit rather than a personal failing, allowing for reflection on controllable factors and finding a better-suited environment.
19 Actionable Insights
1. Separate Identity from Job Outcomes
When facing setbacks like layoffs, distinguish between the business not needing your skills or a poor fit, and your actual competence. This helps re-evaluate what’s in your control and find a better environment.
2. Start Elsewhere Before PM
If aspiring to be a great Product Manager, start in roles like engineering, design, or sales. This provides foundational exposure to building, understanding customer problems, and brings a unique, insightful perspective to product development.
3. Cultivate Great Writing Skills
Product Managers must be great writers because writing creates clarity at scale, both internally and externally. The ability to write compelling messages in the customer’s voice is crucial, as you can’t build a product effectively if you can’t sell or support it.
4. Maintain a Decision Log
Keep a log of decisions you make, their rationale, and their outcomes. Practice by analyzing decisions made by other teams or companies, predicting outcomes, and reviewing them later to improve your ‘product sense’ (making good decisions with insufficient data).
5. Automate B2B User Research
PMs need direct exposure to raw customer material. Use platforms like userinterviews.com to source specific customer profiles, and integrate tools like Gong (for sales call alerts) with Zapier and Customer.io to automatically schedule interviews with relevant customers.
6. Draw the Problem Perimeter
As a PM, define clear constraints for your team, such as target customer segments, jobs-to-be-done, availability (e.g., web/mobile), and core product principles (e.g., speed over data consistency). This allows engineers and designers to innovate creatively within well-defined boundaries.
7. Implement an “Unsell Email” for Hiring
At the offer stage, send an email (3-8 bullet points) detailing potential downsides or fears candidates might have about the role or company (e.g., work-life balance at a startup). This helps identify truly committed A+ hires and prevents early departures due to misaligned expectations.
8. Talk to Customers Constantly
Never stop engaging directly with customers, even if you feel you ‘know’ them. The world and customer needs are constantly evolving, and continuous exposure to these micro-changes is essential for building relevant and successful products.
9. Always Seek the “Additional 3%”
Don’t just meet the minimum requirements of your job or product. Continuously challenge yourself to find and do the ‘additional 3%’ beyond what’s expected, fostering personal growth and creating more delightful products.
10. Conduct Silent Document Reads
To gather effective feedback, schedule dedicated meeting time (e.g., 20 minutes) where team members silently read and comment on documents in real-time. This focused approach speeds up the feedback cycle and ensures deeper engagement than asynchronous reviews.
11. Obsess Over Final Deliverable Details
As a PM, don’t delegate all granular details of the user experience. Be deeply involved in fine-tuning aspects like animation timing, as these small details can significantly impact product adoption and overall quality.
12. Read Compelling Writing to Improve
To become a better writer, consume as much good, compelling writing as possible from diverse sources (e.g., Paul Graham essays, sci-fi/fantasy). Focus on writing that pushes you to action, and practice varying sentence cadence (short, long) to maintain reader engagement.
13. Calibrate and Prioritize Deep Work
Regularly review and ‘spring clean’ your tasks to ensure you’re focusing on activities that truly deliver value to customers, rather than getting bogged down in internal processes. Be willing to push back on artificial deadlines to create space for high-quality work.
14. Invest Deeply in Candidates
As a hiring manager, be highly responsive and accommodating to candidates’ concerns during the offer stage, even if it means unconventional meeting times. This personal investment demonstrates commitment and helps secure strong hires.
15. Embrace “Everything Happens for a Reason”
Adopt the mindset that events, good or bad, are opportunities to learn and move forward. Instead of dwelling on the past, focus on your next actions, trusting that you’ll be able to connect the dots and understand the purpose retrospectively.
16. Recognize AI as a New “Crayon”
Understand that for future generations, AI tools like image generators are fundamentally new creative instruments, akin to a crayon. This perspective highlights the profound and unpredictable shifts in product expectations and user interaction that are yet to come.
17. Decision Log is Complementary, Not a Replacement
While a decision log is valuable for improving product sense, it is not a substitute for hands-on experience in building products. Continuous engagement in product development is crucial for genuine growth.
18. Build Your Own Website
Consider creating and maintaining your own website using raw HTML and CSS. This personal corner of the internet offers joy in hands-on creation and fosters a sense of ownership, even if it’s not frequently updated or shared.
19. Practice Everyday Kindness
Make a conscious effort to be kinder in daily interactions, such as saying thank you more often, holding doors, or waving in traffic. This simple practice contributes to a more positive and less conflict-driven world.
9 Key Quotes
PMs need as many reps as possible in making decisions, documenting the rationale behind those decisions, and then crucially, seeing the outcome of them.
Kevin Yien
If you can tell them that upfront and they can read that whole email and still be equally excited to join, you find yourself an A plus hire.
Kevin Yien
If you can't sell or support your own product, I don't trust you to build the product.
Kevin Yien
PM should be doing everything in their power to draw the perimeter of the space, of the problem space.
Kevin Yien
To me, it's just a fancy way of saying you can make good decisions with insufficient data.
Kevin Yien
I would rather hire an incremental designer than PM almost any day of the week.
Kevin Yien
We are not even beneath the dust on the surface when it comes to what's going to change.
Kevin Yien
There is a difference between you not being good at something and a business or company not needing that thing at a particular moment in time, or you being very good at something, but not in the way that a company needs.
Kevin Yien
Focus on what you control. Like, that's the one line. Don't worry about everything else. Don't worry about what other people think. Don't worry about what other people do. You cannot control those. You focus on yourself.
Kevin Yien
4 Protocols
Becoming a Better Writer
Kevin Yien- Consume as much good writing as possible to develop your own taste for what you think is good.
- Shift into producing your own writing and compare it to others, riffing off their style.
- Intentionally interrupt monotonous cadence in internal writing by varying sentence length (short, long, etc.) to maintain reader engagement.
- Read writing that compels you to action, not just informs, to understand how to drive desired outcomes.
Effective Document Feedback
Kevin Yien- Schedule a dedicated 20-minute focused meeting for document review, even if it feels like 'another meeting'.
- During the meeting, participants silently read the document and comment on it in real-time.
- The author responds to comments and questions in real-time to reduce latency and speed up the feedback cycle.
- Carve out a few minutes at the end for one or two really immediate discussion topics, if necessary.
Personal Decision Log for Product Sense
Kevin Yien- Maintain a daily log (e.g., Google Doc, Notion page) where you bullet-point daily events and decisions.
- As you encounter decisions (e.g., from other teams, companies, or your own work), use a hashtag (#decision) and write down what you would do in that position and your rationale.
- Set a calendar reminder for X weeks or months later to review the outcome of those decisions and compare them to your initial thoughts.
- Start small, perhaps 10 minutes once a week, and gradually increase the frequency as it becomes a habit.
Automating User Research
Kevin Yien (inspired by Beth Hills)- Use a call recording tool like Gong to monitor sales calls and set up alerts for specific keywords (e.g., product terms, competitor mentions, customer issues).
- Integrate Gong alerts with Slack to automatically post excerpts of transcripts where keywords are mentioned, along with the customer's name and email.
- Set up a Zapier workflow to take every new Slack post from these alerts.
- Use a tool like Customer.io to send an automated, personalized email to the customer mentioned in the alert, including a Calendly link specifically for user research, inviting them to a conversation.