Diana Stepner's Profile
Diana Stepner
Recent Messages
#12_hype-house - September 29, 2025 at 04:00 PM
Humanities majors might be the secret to impactful AI product development. I attended the Reforge AI Summit, alongside 70 product leaders from @OpenAI, @Shopify, @LinkedIn and @Netflix. I explore why the AI revolution isn't just about tech. it's about TASTE.
#08_advice-questions - September 27, 2025 at 11:46 PM
Hi! I'm advising , which is an AI sales coach that joins sales calls alongside sales reps, helping them close their deals faster. WingRep also preps Sales folks for calls and debriefs with them afterwards, goal being to help with next steps and advice on how to advance every deal. Sales managers also receive weekly coaching insights and rep scorecards. Here is a link to a short .
Would you like to learn more? If so, ping me and I can connect you to the founders.
Thank you!
#productcohort-diana - September 14, 2025 at 05:35 PM
Building products with AI, I recommend this snippet from . The rest of the article is paywalled, yet the intro is valuable.
Points being:
• "The biggest mistake I see AI founders make is treating PMF like a checkbox," I recently shared in our last cohort AI Product Management Certification. "In the AI world, PMF is a moving target. Your users' definition of 'intelligent enough' changes every month as they interact with better AI systems elsewhere."
• This creates what I call the AI PMF Paradox: you need to achieve a fit with a market that's constantly evolving its expectations of what AI should do.
#productcohort-diana - September 08, 2025 at 05:21 PM
During the last product session, we discussed moats (in relation to a castle, drawbridge and moats). Anyone considering AI from a Product perspective will appreciate .
Quotes which stood out to me
• If SaaS moats were about “switching costs,” AI moats are about compounding returns. Every new user, every new interaction, every new distribution channel must make your product stronger and harder to copy.
• The second moat is distribution and in many cases, it’s even more decisive than data.
• The third, and often most underrated, moat is trust. AI is probabilistic. It hallucinates. It fails silently. It produces outputs that can be biased, unsafe, or downright wrong. Which means the biggest bottleneck to adoption isn’t accuracy, it’s trust.
#productcohort-diana - September 02, 2025 at 04:22 PM
Helps to break us a bit out of the hype mode too 😉
#productcohort-diana - September 02, 2025 at 04:14 PM
Nice slightly contrarian viewpoint re: AI being a platform shift
#productcohort-diana - August 28, 2025 at 03:12 AM
Hi! Thank you for the opportunity to share Product insights with you all. Attached are the slides from today's session. Key points we covered were:
• Deliver ≠ Launch – it’s about ensuring ongoing value and growth. MVPs (or MLP), controlled launches, and feedback loops keep products evolving.
• Business Models – from traditional models to new “human in the loop” offerings, AI shifts how we differentiate beyond just features and is impacting pricing, business models, branding.
• Keep Evolving – products are never finished. Success comes from iterating, adapting, and refining strategy as markets and customers change.
Any questions along your product journey, please DM. Thanks!
#productcohort-diana - August 25, 2025 at 04:24 PM
Hi! Ahead of our session on Weds, Aug 27th, I wanted to share a product-related article called as it resonated with my product 🧠.
Why did I like the article?
• Despite all the tech changes, context continues to rule. Companies are seeking to capture as much context as possible to make their AI offerings relevant and sticky. Context is defined as data, interaction history, and preferences.
• I'm a fan of Anthropic’s Model Context Protocol (MCP), especially the fact they made it open / interoperable. I am a fan of growth and believe companies which 'open' offerings enable increased innovation.
• Cory Doctorow coined the term “Enshittification” to signify the gradual decline in quality of online platforms or services, often driven by profit-seeking behavior at the expense of both users and business partners
• Protocols enabled the web, such as http and smtp, and continue to prove critical. Companies often go from initial product focus to a platform which supports multiple products to APIs which invite broader interaction.
In summary keeping the web and AI open enables products and companies to thrive in the AI-centric world through benefiting and providing increased context. When you build your products / company, consider how you can use & contribute to openness.
#12_hype-house - August 19, 2025 at 03:00 PM
Your company's biggest competitive advantage isn't AI. It's humans who can navigate the dragons of organizational complexity.
When products become "organizational archaeology" - layers of decisions made by people who no longer exist - AI hits its limits. It can analyze code but can't navigate the "dragons" of unwritten context.
I wrote an article on how to navigate the AI era by turning uncertainty into an advantage.
#12_hype-house - August 01, 2025 at 03:18 AM
Shared the 5 essential insights I've discovered while mentoring product leaders. All of these can be found in .
#productcohort-diana - July 30, 2025 at 05:23 PM
Hi! Thank you for joining the session today. If you missed it, the Session 3: Develop – From Problem to Prototype slides are included here. <@U085ZL0JS0Y> will be sharing the recording shortly as well.
This session was all about reducing risk by turning our assumptions into experiments and validating ideas before we go too far down the develop path. We explored how to ideate, prioritize, prototype, and test quickly without over committing to an idea too early.
Any feedback, thoughts or suggestions? Share them in the comments or DM me.
#12_hype-house - July 23, 2025 at 04:43 PM
@Diana Stepner has joined the channel
#productcohort-diana - July 22, 2025 at 06:02 PM
Ahead of our session next week, here is a lens into my own product thinking...
By flattening our voices to fit someone else’s template (or worse, an algorithm’s), we don’t just lose clarity.
• We lose connection.
• We lose creativity.
• We lose valuable ideas.
Language matters, and losing that human nuance could mean losing the best people. We need to foster an environment where employees feel valued, not just efficient.
#productcohort-diana - July 14, 2025 at 05:03 PM
I'm a fan of Peter Yang. He's a product manager at Roblox and focuses on building. His recent article on reminded me of the product series here at Gildre. The approach is...
1. Discover: Find the boring, high-friction workflows
2. Design: Make AI invisible and trustworthy
3. Develop: Build systematically and plan for failure
4. Deploy: Treat every first-use like a launch
Sound familiar 😉 Excellent to see the direct application to AI-specific product development. If the link proves tricky to access, just let me know. Enjoy!
#productcohort-diana - June 25, 2025 at 09:55 PM
Hi! Great speaking with all of you today. The slides from today's session are attached. We'll share a link to the recording shortly. Any questions, feedback, etc. please DM me. Thanks again!
#00_announcements - June 24, 2025 at 01:58 AM
@Carol Palombini What site / tool / platform did you use to create the landing page? It looks great!!!
#productcohort-diana - June 23, 2025 at 03:27 PM
If you're interested in tech and/or are using AI in your work, I recommend listening to this from Andrej Karpathy (Stanford, OpenAI, and Tesla) on how Software Is Changing (Again)
• Evolution of software development paradigms: Software 1.0 (traditional programming), Software 2.0 (neural networks), and Software 3.0 (Large Language Models), emphasizing the fundamental shift in how we interact with and program computers.
• Large Language Models (LLMs) are comparable to operating systems, a new kind of computer with both superhuman capabilities and significant limitations, such as hallucinations and lack of self-knowledge.
• Best practices for working with AI systems, including keeping AI "on a leash" through human oversight, the importance of GUIs for easier interaction, and the concept of an "autonomy slider" to adjust AI involvement based on task complexity.
Enjoy!
#productcohort-diana - June 03, 2025 at 01:24 AM
Not a traditional product article, yet this with Dan Shipper from Every (which is amazing) resonated on so many product + tech leadership levels.
Quotes which resonated:
• ...to be at risk of AI disruption. The leverage has shifted from what you can do to how you show up while doing it. Competence is now table stakes.
• that ... emotional intelligence is already the number-one criteria for managers when considering a team member for a promotion or salary increase. Some of the most brilliant founders, executives, and creative professionals I’ve worked with weren’t stuck because they lacked intelligence or strategy. They were stuck because they didn’t know how to deal with their emotions.
• No matter how powerful AI becomes, ... you’ll still need to be deeply connected with other humans... If you want to be a part of a high-performing team, you’ll need to be deeply connected with other humans.
• Nadella’s focus on rebuilding Microsoft around an empathy mindset, emphasizing and self-reflection, has led to a .
#productcohort-diana - May 19, 2025 at 04:00 PM
This week's product article is --> ? . Great questions to consider as you explore your product idea.
- Transform Existing Workflows, Don't Just Add Features The most successful AI startups fundamentally reimagine how work gets done rather than just adding AI capabilities to existing processes.
- Focus on Customer Pain Points, Not Technology Great AI products emerge from acute, specific moments of customer frustration - not theoretical problems. Find the deepest pain point first, then apply AI as the solution. "Trust the problem more than the solution."
- Identify Your Unique Data Advantage In AI development, data isn't just fuel - it's the entire engine. The most promising startups transform specialized data in ways that were previously impossible or prohibitively expensive. Bonus insight: Execution matters more than the idea itself. Even great-sounding ideas can fail with poor execution, while seemingly "bad" ideas can succeed when executed well.
#productcohort-diana - May 15, 2025 at 04:17 PM
Thank you <@U08QMCRN1QX>. Greatly appreciate all your additions and insights!
#productcohort-diana - May 14, 2025 at 09:44 PM
I'd love your thoughts too. Please complete this short, (2 minutes). You can also DM me. I'll use the insight to improve the next call. Thanks again!
#productcohort-diana - May 14, 2025 at 09:38 PM
Articles
• (oldie, but a goodie)
• (incl. Sean Ellis test, 40% of users respond “very disappointed" when asked "how would you feel if you could no longer use the product?"
• (search the transcript for Lovable) and/or listen to the podcast
#productcohort-diana - May 14, 2025 at 09:35 PM
Hi! Great to see everyone today. Here are a few items.
•
• Slides - attached.
#productcohort-diana - May 12, 2025 at 04:00 PM
As you can tell, I read a lot 😉 If you're wondering about pricing your product / service / offering, this article explains a number of pricing models. More importantly it also gives a glimpse into what your pricing infers about your product / service / offering.
Most founders admit their early pricing is essentially a guess. Focus on learning rather than maximizing revenue before finding product-market fit. Freemium converts only 2-5% of users but can drive massive adoption, while paid pilots convert an impressive 60-90% of customers. Your pricing sends strong signals about your positioning - Superhuman launched at $30/month to appear premium, while Atlassian used rock-bottom pricing to spread virally through organizations. Treat early pricing as an experiment, run small tests, and be ready to adjust as you learn what your market actually values.
#productcohort-diana - May 05, 2025 at 03:56 PM
Ahead of our call next week, here is a related topic...
Why do customers praise your product but never purchase? This frustrating gap between enthusiasm and action signals "product purgatory"—your solution may be valuable but lacks urgency. The insightful "Magic-Wand Test" reveals whether your product fails due to perceived value or activation hurdles. If prospects would take it fully implemented for free yet still won't buy, your challenge isn't the product but its priority level (usually #7 on their list). The solution isn't to add features, but to narrow your focus to customers facing immediate catalysts like regulatory deadlines or leadership mandates where urgency drives decisions.
#productcohort-diana - April 29, 2025 at 04:51 PM
Ahead of the tomorrow, attached is a nice product-market fit example from First Round Capital on . Main points being...
- Stay Close to Customers (Really Close) • Direct access to users even via Slack, text, etc. provides constant real-time feedback • Starting with founder-led sales can build deep trust (even more than features) • Manual onboarding is an excellent way to start, especially as you learn the pain points firsthand
- Solve a Real, Painful Problem (Not Just a Cool Idea) • Early pivot moved from "interesting" (LLM memory) → to urgent need (PDF parsing bottleneck) • PMF showed up when customers pulled the product, not when founders pushed it.
- Execute Simply and Quickly • Ugly MVP launched fast - and that's a good thing • Focused on being better at one core thing (reading documents like humans)
- Be Methodical About Growth, Not Flashy • Tiny, high-leverage team (hit $1M ARR with 4 people) • Priced for serious users, filtered out tire-kickers • Said no to one-off feature and asks that didn’t fit the core vision
- Founder Energy and Learning Loops Matter • Obsession with customer success was contagious • Failure at the micro level (bad demos, awkward sales calls) was embraced as part of the learning curve. • Big growth came from iterating fast, caring hard, and staying scrappy.
#productcohort-diana - April 21, 2025 at 04:01 PM
Hi! If you are building a product with AI, here are a few interesting quotes from a with the CPO of OpenAI re: how to build for the future...
• When you're talking about databases, I bet the database you used this year is probably 5% better than the database you used two years ago, but that's not true at all with AI. It's like every two months computers can do something they've never been able to do before and you need to completely think differently about what you're doing.
• Everything we're used to with computers is about giving a computer very defined inputs. You're confident that if you do the same thing three times, you're going to get the same output three times. LLMs are completely different from that. You probably get spiritually the same answer for the same question, but you don't get the same answer every time.
• We point ourselves in a direction so that we have some rough sense of alignment. I don't for a second believe that what we write down in the roadmap documents is what we're going to actually ship three months from now, let alone six or nine. But that's okay. It's like the Eisenhower quote, "Plans are useless. Planning is helpful,". We're going to throw out the roadmap halfway because we will have learned new things. The moment of planning is helpful even if it's only partially.
• We use ensembles of models much more internally than people might think. If we have 10 different problems, we might solve them using 20 different model calls, some of which are using specialized fine-tuned models, using custom prompts for each one. You want to break the problem down into more specific tasks versus some broader set of high level tasks. And then you can use models very specifically to get very good at each individual thing. And then you have an ensemble that tackles the whole thing.
#10_brandmarketingcohort-lysle - April 17, 2025 at 12:00 AM
#10_brandmarketingcohort-lysle - April 16, 2025 at 07:18 PM
doesn't work for me. I already have the Zoom app downloaded as well. no luck
#10_brandmarketingcohort-lysle - April 16, 2025 at 07:02 PM
Zoom is being funky ... hope to be in the call soon...
#productcohort-diana - April 09, 2025 at 03:56 PM
There is so much happening in the product space today. A great from Andrew Chen from A16Z highlights how important your product is today. Quotes [especially Product is (unfortunately) King] that stood out to me were:
• So I have bad news: Your product actually has to be very good. I wish I lived in a world where you could have amazing marketing and growth strategies, have a shitty product, and you would win. Then marketers would run tech, and they do not. It’s the people visionaries that create the products that run tech, and that’s a good thing!
• The reason is that even if you do a ton of work to acquire a bunch of users, it won’t matter if they leak out of the DAU (daily active user) number. I’ve come to think of great marketing strategy as a multiplier effect on your inherent product quality. If you have a great product, you will multiply that into greatness. If you have a shitty product, you will multiply that into… well, you get it.
#03_events - April 07, 2025 at 05:52 PM
Thank you for sharing the slides. Sorry I missed the session. Great points!
#productcohort-diana - March 31, 2025 at 04:48 PM
After a great call with <@U08CN7ATAD8>, I wanted to share an article on product sense. It's a mysterious skill every product leader needs but few can define. I wrote an article on what it actually is, how you develop it (spoiler: it's not overnight!), and why it needs constant refreshing to stay relevant.
At its core, product sense combines two critical abilities:
1. Customer empathy – deeply understanding what makes a high-quality product for your specific users
2. Creative judgment – having strong, validated opinions about what solutions will succeed
It's the skill that helps you:
- Identify important customer problems worth solving
- Build compelling strategies to address those problems
- Know which features to prioritize in new products
- Enhance existing products to better meet user needs
- Interpret data to achieve product-market fit
To learn more visit
#10_brandmarketingcohort-lysle - March 24, 2025 at 06:18 PM
A friend shared an article which includes the power of Brand. Sharing as it aligns with the impactful sessions we've experienced with @Lysle Wickersham -->
#08_advice-questions - March 14, 2025 at 07:04 PM
Well connected group. 🙂 I'm a leadership coach and tend to focus on people in & around product. Happy to chat with your client. I'm and
#productcohort-diana - March 11, 2025 at 01:49 AM
Have you heard of Vibe Coding? Here is an intro and what It means for Product
• What is it?
◦ Vibe coding is a new way of building software using AI, where people give simple instructions (like "make the button bigger" or "add a login page"), and the AI generates the code automatically. This means that building software is becoming faster, easier, and more accessible—even for people who don’t know how to code.
• Why It Matters?
1. More People Can Build Software
◦ AI will handle most of the coding, meaning more non-technical people will be able to create software.
◦ Just as social media made everyone a content creator, AI-powered coding will allow more people to build apps and tools.
2. From Coding to Visual Building
◦ Today, vibe coding mostly happens with text-based commands, like chatting with ChatGPT.
◦ In the future, it will shift to visual tools, where PMs and designers can simply describe the experience they want, and AI will build it with no engineering required.
3. Software Becomes Disposable & Customizable
◦ Instead of relying on standard tools and libraries, AI will generate custom code for every project, making software more adaptable.
◦ Imagine tweaking an app like you edit a Google Doc, making changes in real-time without needing an engineer.
4. The Role of PMs Will Evolve
◦ Less focus on “how” things are built (since AI handles the code).
◦ More focus on defining the right problem and desired outcomes (e.g., “make signup easier” instead of “add a progress bar”).
◦ Software will adapt itself based on user behavior rather than following fixed rules set by engineers.
5. Changes in Team Structures
◦ If AI makes coding cheaper and faster, engineering-heavy teams may shrink, while roles like PMs and designers could become even more critical.
◦ However, demand for software could explode, leading to even more engineers building at a much faster pace.
6. AI in Marketing & Sales
◦ Just as AI can generate code, it can also automate marketing and sales.
◦ Imagine giving AI a simple goal like “market our app to Gen Z,” and it automatically creates social content, buys ads, and runs influencer campaigns.
7. Challenges & Risks
◦ AI-generated software is still messy—handling complex business rules, security, and edge cases is difficult.
◦ Many early AI-built products feel low quality, but just like AI images/videos improved quickly, software will get better fast.
• What This Means for the Future
◦ Less time managing engineers, more time guiding AI tools to build products.
◦ Faster prototyping and iteration, making user feedback even more important.
◦ A shift from shipping features to defining goals and letting AI optimize them.
AI-driven development won’t replace PMs, but it will change how we work. Instead of asking engineers to build things, we may soon describe what we want, let AI create it, and refine it based on user feedback. 🚀
#08_advice-questions - February 13, 2025 at 08:26 PM
Building on the respecting their time comment --> start and end meetings on time.
Capture notes + actions. Send the actions the same day in which the meeting occurred.
Provide the client with visibility into the running action list -- review during each call.
Identify what tools the client uses already. When possible use the client's tools to make sharing and communication as seamless as possible. e.g. if they do not use WhatsApp, find out what they use instead.
#productcohort-diana - February 13, 2025 at 12:23 AM
If you feel stuck when building or maintaining a product, have you considered your team may not be aligned? They hear the same words, but the interpretation might differ from what you expected.
Prompt --> How can you ensure your team members are aligned?
Teams often lack a shared goal, context, and language when being formed. This can be devastating later on, if not resolved.
The Team Alignment Map, created by Stefano Mastrogiacomo, is a visual tool that allows participants to prepare for action: hold more productive meetings and structure the content of their conversations. It can help teams have more productive kickoffs, with better engagement and increased business success.
Each building block illustrates essential information to be discussed with your team. Identifying perception gaps early on can prevent you from being misaligned without even knowing it.
A copy is attached. Enjoy!
#10_brandmarketingcohort-lysle - February 13, 2025 at 12:12 AM
Excited as well!!!
#productcohort-diana - January 28, 2025 at 03:01 AM
Insight to wrap up January and begin February. It's a preview of our discussion for May - Innovation Roundtable Session 5 - Foundation for Product Development.
Successful product development hinges on three core elements: observation, action, and feedback.
1. Observation
a. Start by studying successful products and leaders in your category (there are always competitors) to understand their approaches
b. Gather diverse perspectives from customers and stakeholders.
2. Action
a. Embrace rapid prototyping and iteration rather than seeking perfection - quality emerges from quantity of attempts.
b. Break complex features into smaller, testable steps and focus on critical (most risky) needs first.
3. Feedback
a. Create tight feedback loops by sharing examples and getting real user feedback.
b. Both products and product skills develop in phases - from initial understanding, through experimentation, to optimization
c. Be prepared to unlearn and adapt strategies as customer + market needs evolve.
#00_announcements - January 17, 2025 at 04:56 PM
Not sure how to respond to this as I'm a product leader 😉
#10_brandmarketingcohort-lysle - January 16, 2025 at 10:50 PM
Loved the session @Lysle Wickersham. Looking forward to the next one in February! It's saved in my calendar 🙂
#08_advice-questions - January 08, 2025 at 09:09 PM
Hi! I am using Notion to document / capture everything. I'm also a fan of Jasper and Granola for note capturing w/o a bot.
Other folks really like
For me, I'm a fan of starting each day by identifying what is the ONE work thing I must do today.
#local-bayarea - January 08, 2025 at 05:00 PM
Hi! If you're in town next Wednesday (Feb 15th), you're invited to a book launch. We're celebrating the launch of my book - . Looking forward to seeing you there!
#productcohort-diana - January 08, 2025 at 04:00 PM
My first BIG NEWS to kick off 2025! I'm thrilled to announce the launch of my new book, , written in collaboration with two incredible co-authors, is now live on !
Sharing this news with you all as I'm a start-up founder too. The product is "me". Get excited to apply the upcoming branding expertise from @Lysle Wickersham to the product your startup is delivering - whether it be a service, software, or something else.
Looking forward to learning together!
#productcohort-diana - January 06, 2025 at 04:28 PM
Welcome to 2025! As we look ahead to the year, keep in mind building a business is like building yourself - both are products of your experiences. Instead of waiting for a year end of a new year to reflect, get started today. Why? The most successful products - whether businesses or personal growth - are built through deliberate, incremental improvements (aka consistent small steps).
I was reading recently (I built my business on Saturdays while working full-time), and he posed a powerful question:
"What's the most obvious thing I could do today to make my business better?"
This reminded me of product development. We often overlook small improvements because they seem too minor. But these tiny changes compound over time. The same applies to personal growth. You are a product - constantly evolving, learning, and improving through experiences.
Here's what I've learned:
• Your business is your product - it reflects your learnings, experiences, and passions.
• Your goal is to solve problems and improve lives - whether through your business or personal growth.
• Both paths have ups and downs. Both require consistent small improvements.
So choose a question to ask yourself today:
• What's one small experiment you could run to improve your customer experience?
• What minor enhancement have you been postponing because it seemed too small?
• What tiny step could you take to improve yourself?
#08_advice-questions - December 23, 2024 at 06:56 PM
@Austin Lortie - thank you so much for the recommend. Charles sounds perfect. 🌟 Greatly appreciated!!!!
#08_advice-questions - December 20, 2024 at 09:43 PM
Hi! Does anyone have a lawyer they recommend who is familiar with the healthcare space? A startup friend is hoping to speak with a lawyer who is familiar with home health, health insurance and regulatory requirements. Thank you!!!
#productcohort-diana - December 19, 2024 at 08:58 PM
Hi! As we get ready to wrap up 2024, I wanted to wish everyone a Happy Holidays! 🎉 I'm excited to kick off our product community journey together in the New Year! This channel is all about learning how to discover, define, develop, and deliver you product. We'll focus on on the sweet spot where customer needs meet business value.
My background spans 20+ years of product management across various industries, from emerging media to education technology. I've led teams through digital transformation, built products from 0 to 1, and navigated enterprise organizations. Currently, I write a , coach product people + leaders, and advise startups on building customer-centric, scalable products.
Until our product sessions kick off later in 2025 🌟, I'll be sharing product info in this channel to kick off the learning and discussions, covering topics like:
- Creating effective company + product strategy stacks
- Navigating the balance between empowerment and execution
- Incorporating AI thoughtfully into your product development
What excites me most about this channel is the opportunity to learn from each other. Product is a team sport - we go farther together. Whether you're just starting your journey or looking to level up your knowledge, this channel will provide a place to grow together. Reach out with any product questions that come to mind. Thanks!
Have specific product challenges you'd like to tackle? Topics you want to explore? Drop them in the comments below or reach out directly at [email]. Let's shape this learning journey together!
Looking forward to exploring the art and science of product management with you all!
ProductLeadership #ProductManagement #CommunityLearning
#03_events - November 05, 2024 at 07:39 PM
Hi! A reminder about an event next week, I'm running an Innovation Roundtable on "Time Management and Mental Health". Definitely well timed! To register . We'll start with a bit of a share out and then dive into questions such as...
• What specific time management techniques have you found most effective in balancing your work and personal life as a founder? Can you share a particular method or tool that has significantly improved your productivity?
• What has been the most difficult part of your professional journey the past 12 months?
• Do you incorporate any mindfulness or mental health practices, such as meditation, exercise, or therapy, into your daily routine? How do these practices influence your overall productivity and well-being?
Looking forward to seeing you on Tuesday, November 12 from 10:00 AM - 11:00 AM PST!