Brian Wong

I'll let you in on a little secret ... My #1 interview question when hiring new team members is “Tell me about a [….] you love and why” For a product position that could be “Tell me about a product you love and why” For an engineering position: “Tell me about a project you love and why?” For a marketing position: “Tell me about a marketing campaign you love and why? For an infodev position: “Tell me about documentation or product help you have used that you love and why?” This is a powerful question that allows interviewees to express their personal motivations/passions, critical thinking skills, and how they approach their work as a genuine conversation instead of a standard list of interview questions. 1. Reveals Passion and Communication skills By asking candidates to discuss something they "love," you give them an opportunity to express genuine enthusiasm, which can be an indicator of passion for their field. This is valuable in any role because passion often correlates with motivation and resilience. It also puts them in a place where they can show their best communication and persuasion skills. 2. Uncovers Depth of Knowledge The question invites candidates to dive deeper into what makes a product, strategy, or approach effective, giving insight into how well they understand their field. For example: Product role: It shows if they have thought critically about user experience, design, and functionality. Support role: It may reveal an understanding of customer psychology and empathy. Sales role: It highlights whether they grasp the nuances of successful sales tactics and customer engagement. 3. Shows Alignment with Company Values Candidates’ responses can reflect whether they value similar qualities as the company does, such as innovation, customer-centric design, or transparency. 4. Demonstrates Analytical Skills and Reasoning Asking “why” requires candidates to articulate the reasoning behind their choice. This sheds light on their analytical and critical thinking skills—qualities that are essential in any role but especially important in roles that require strategic decision-making. 5. Encourages Authenticity and Personal Expression This question is more open-ended and personal, allowing candidates to feel comfortable sharing their unique perspectives. This can lead to more genuine responses, which helps the interviewer get to know the candidate beyond rehearsed answers. 6. Assesses Creativity and Problem-Solving Approach Their answer can demonstrate creative thinking or innovative approaches they appreciate and potentially would bring to the role. In product management, for example, it can indicate a candidate’s capacity to think outside the box. This question is so versatile and strives to create a genuine conversation that explores a person's passions and experience over standard rapid-fire questions. Genuine conversation will always be better for both the interviewer and the interviewee.

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Product is fun, complex, messy, and there are no shortcuts. Once you accept that—and embrace it—amazing things happen to your career. Cat Hicks, PhD puts this better than anyone: "Doing research with developer teams, something that really strikes me is how much people look for ways to make complex problems easy rather than make it easy to work on complex problems What I mean is, sometimes it's really useful to admit we just are trying to accomplish tough things. Asking how we can support our teams who NEED the time and space to work through that, it's often a much more tractable lever than trying to change the inherent nature of the work I think it behooves me to say as a psychologist here that I think people are actually really excellent at working on complex problems! It's one of the reasons research with developers is so great. Overall devs love to learn, love to be curious, love to innovate. It is core stuff. What would it look like if we could ask, "how do I make this the absolute best environment for complex problem-solving" instead of "how do I take away all these annoying hard problems." The stuff we want to accomplish in the world is hard. But can be joyful to accomplish."

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While some folks hire entire Figma design teams for their personal websites, I'm here at 6:30 AM explaining to my partner why I need a third coffee to "write stuff." 2022: "I'll share monthly insights about building companies!" 2024: checking it -> Writing consistency matches crypto winter performance 📉 But look - AI got better at English faster than I got better at writing. That's what we call product-market fit. New strategy for 2025 - Actually write 12 articles - Convince partner these dawn coffee raids are essential business ops Track my progress (or lack thereof) here: https://lnkd.in/e6bkkxvH P.S. If my partner reads this - yes, this is exactly what I'm doing at 6:00 AM either wiring or reading the book. Note: Will open source my coffee consumption metrics in Q3 2025. Full transparency, like web3 promised.

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Question for engineering leaders (managers, directors, VP's, etc): I'm curious about the current landscape of developer productivity analysis + management tools - things like LinearB and Jellyfish. Which tool, if any, are you using? Any opinions/pros/cons on the tool you're using (or the entire domain overall)?

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UPDATE: It's here! For anyone who missed my talk at this year's Product Collective (Acquired by Pendo) INDUSTRY, you can watch it right now (link in comments below). I'm already working on iterating with some great feedback from the conference, but you tell me - what else would you like to see? What's missing? What could be better? Hit me with that feedback 😎 #product #productmanagement #productstrategy #productleadership

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In my experience of interviewing and working with many product leaders, a common trait among the great ones is treating their craft more as a science than an art. Delighting users, creating magical experiences, and ultimately developing software that users love to use is a science. An immediate red flag during interviews is when product leaders can't express details beyond "talking to customers" on how they build lovable products. While talking to customers is paramount, I listen for the structure and tools they use to become customer-centric and experts in the users they serve. Here’s what I look for: Methods to Listen For When Evaluating How Product Leaders Create Lovable Products: 🗺️ Journey Mapping: Understand what users do before and after they interact with your product or attempt to accomplish their job. 🔑 Key Moments Identification: Reveal the key moments that matter in the user journey. 😌 Emotional State Awareness: Understand the emotional states of users and how they change as they progress through the journey. 📊 Data Collection and Analysis: Collect and analyze data to understand funnels, drop-off rates, attrition, etc. I’m also on the lookout for specific techniques on how the product leader builds high-performing product teams. Here are some of the practices to listen for: 🏆 Recognition and Rewards: Establish clear KPIs that define success, create accountability, and drive alignment. Implement a system for recognizing and rewarding team achievements and individual contributions. 🤝 Consistent 1-on-1s: Conduct regular one-on-one meetings to mentor and guide the career and development of the product management team. 👥 Team Collaboration: Allow teams to craft their process and evolve it over time. My favorite team performance ceremony is the retrospective, where the team can gather in a safe place and collectively define how they will improve. 🔄 Cross-Functional Alignment: Create alignment between product, engineering, sales, marketing, and leadership. This involves regular cross-functional meetings, transparent communication of goals and progress, and a unified vision that ties the efforts of all departments together. Ensuring that all teams are moving in the same direction is crucial for driving consistent and sustainable growth. Overall, there are many important items across both themes that define effective product leadership. By listening for a product leader who employs these structured methods, companies can make a better hire to turn insights into actionable strategies, ensuring that the user experience is not left to chance but meticulously crafted and continuously improved, while building and managing high-performing teams that drive success.

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For a long time, I had very naive ideas about prioritization. Here's what I've learned over the years. 1. Unless you are a tiny startup, your company is designed to do multiple high-priority things at once. The argument, "Well, if everything is high priority, nothing is high priority," almost never works (while rational). The 🐘 in the room is that the mix of high-priority things has changed, and the org design is no longer fit for purpose. What seems rational to you—oh, obviously that team is overwhelmed and we need to set priorities—is, behind the scenes, "Crap, we got the budget wrong for that group. Anyone want to contribute? No? Hmmm. Surely they are inefficient and can juggle more than one thing, right?" See below. 2. Most senior execs know that the plans will change. They know that by March, there will be a new set of priorities. So they focus on budgets, not priorities. So when you see lackluster strategies and vague priorities, remember that there is a whole other prioritization activity that centers around the allocation of money, how people get bonuses, very back-of-the-napkin revenue attribution models, etc. 3. Humans, in general, are not great at building a mental model for capacity. Capacity in software is hard. People aren't fungible. The architecture is what it is. You can't have huge teams. You are building the factory (to meet the needs of a strategy) AND the factory is building "the product." Oh, it isn't a factory: it is more like gardening. This is important because our mental models for what we are prioritizing (e.g., focus, capacity, typing, bandwidth, etc.) are often all over the place. 4. Most companies are not progressive when it comes to thoughtful re-orgs, org redesign, reallocating capacity, etc. The simple thinking is: "If we stop doing X, then we should let those people go because they fit in this cell on the spreadsheet." People too heavily couple the finance spreadsheets with one-row-per-person, and the (most often useless and made-up) % allocations to things. This means that basic things like having priorities and reducing work in progress are fraught with very justified fears around layoffs. To some, a pristine list of force-ranked priorities looks like heaven. FINALLY, we can make decisions. To others, it is NOT GOOD. This is why efforts to visualize WIP often turn into Game of Thrones. There's a silver lining with all this! If you are aware of these tendencies, you can figure out approaches to prioritization that can nudge the org in the right direction. Knowing that the theoretically pristine force-ranked list of efforts is likely not possible, you can devise other strategies like building more realistic models with finance and being more open to "everything in high priority" yet focusing on the actual conflicts/trade-off decisions, etc. And embrace products like Runway and DoubleLoop that engage people in tangible discussions about how $s flow into outcomes and then back into your core models.

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We've had an EM role open on our team for several months. This is a post about everything we learned from why we haven't filled it yet. I'd love to get your help in filling it! 🤝 The role: - EM for our 0-to-1 team within Postman, with the goal of defining and winning our category for a new kind of API-level monitoring/observability tool. Our team came into Postman through an acquisition and we're now building the Postman version of our product, using the same tech. - Help scale our product and team from alpha into beta. We are a department with six engineers and approved headcount to grow a lot more in the next year. - The role is 60% prioritization/roadmap management, 40% building the team. The current team members are high-ownership, independent, founding engineer types. 🤔 Misconceptions, miscalibrations, and lessons: - Initially, the role was called "Senior Engineering Manager, Observability." Instead of getting the product engineering managers we were looking for, we primarily got interest from platform/infra EMs. We got thousands of inbound applications and spent months zeroing that out. 🙀 - Previously, our recruiters were sourcing a lot of folks with observability backgrounds. We've learned that since we're actually building a new kind of observability product, much more focused on UX, the profile we're looking for is product-focused rather than tech-focused. No observability experience required. - When people think Postman, they often think of our core product: the API client. So we were getting more interest from folks looking to scale a product, rather than 0-to-1 "I want to build a team and product" types. Postman actually has several other products, for instance testing and Flows, our no-code tool. There is a lot of interesting 0-to-1 work on our way to growing as a multi-product platform! - Some people have the perception that Postman isn't one of the high-growth companies because they're not seeing lots of their friends joining Postman. Postman has quadrupled since 2020, BUT a lot of the engineering growth has been in India. (Postman is the biggest SaaS company to come out of India!) Our team is part of a recent change to grow our US engineering presence. Many of us leaders across the company are looking for folks to join early cohorts of US-based product engineering and platform teams. 💡 What we've changed on our end: - We've deemphasized the "observability" part of the job and emphasized the "new product" and "product engineering" parts of the job. - We've also switched our own reachouts to look for people with product engineering experience at SaaS companies with product-led growth. 👩‍🚀 Help us find our EM! We now have a solid pipeline, but haven't yet made a hire. We'd love to hear from you if: - You have thoughts about how to improve our EM search. - You know someone we should meet. - You're a scrappy EM looking for an opportunity to build a new product while growing a team. Look forward to hearing from you!

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Last Tuesday, Malsgufa, our legacy CMS backend, was shut down. This milestone for BI's Tech and Product team culminated years of planning, effort, and execution. Malsgufa's first commit was on July 25, 2014, leading to 5,186 commits across nearly 30 repositories. Built and maintained by scores of engineers, its deprecation represents significant cost savings (20 production replicas, 3 instances of Solr, and an insane number of Zookeeper instances!), reduced security risk, and the elimination of an often-blamed boogeyman. The journey began in January 2020. Our challenge: moving traffic off Malsgufa without rebuilding everything in Muse. Initially, we tried GraphQL as an intermediary between Viking and our services, but progress was limited by Viking's complex Angular/Vue architecture. In January 2023, we pivoted to the strangler fig pattern with a shim. This approach proved far more effective – all Malsgufa traffic went through the shim first, with verbose logging to track unhandled requests. Meanwhile, we built Story Versioning API (SVAPI), incorporating lessons learned from Malsgufa's limitations around history and publishing states. We ran four major migrations (stories, custom pages, slideshows, and videos), building support in Muse and shimmed compatibility for Viking. Traffic gradually decreased from a torrent to a trickle, leading to the gloriously uneventful shutdown. Next, we will deprecate Viking by Q2 2025, unifying our users in the Muse ecosystem to create the industry's most innovative CMS. Special thanks to the entire Story Creation team: Chase Gruber, Chris Speziale, Daniel Arita, Danny Feliz, Dasha Lary, Dawin Camillo, Eric Saam, Frederica Chen, John Laslo, Kelly Filush, Morgan Cohn, Sarah Pai, Tyler Greenfield! Thanks also to DaD, Engagement, Helpfulness, Cloud Engineering, Test Engineering, and Operational Excellence! Finally, we recognize Malsgufa itself. Developed as a unified CMS backend to support Business Insider's expansion into new markets, it served our global newsroom reliably for a decade, publishing millions of stories despite no major changes in recent years. While it became less sustainable as our business evolved, it deserves our respect. Thank you, Malsgufa. May you rust in peace.

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After an absolutely amazing 3 years (to the day quite literally), I am leaving Retool for my next adventure. It’s been a wild (and fun) ride of growing and scaling engineering from a group of 13 to an org of 100+, building 4 net-new product lines, and expanding the business. The thing I’ve always held strongly is that the team here *just ships*, and reflecting on my time, it’s heartwarming to think about how much landed: not just our new products in Workflows, External, Mobile, and RetoolDB, but everything ranging from runtime rewrites, to new component libraries, multiplayer, debug tools, our AI suite, new source control systems, a new IDE — the list just goes on and on. Retool is an incredibly special product, company, and organization to me — not just because of my time and experience there, but because of what we are trying to do: bring more good software into the world, especially when most internal tools don’t get the TLC they would otherwise need to be good. It spoke to me from first principles as a builder (both software and orgs) when I first joined, and continues to do so today all the same. It’s an incredible group, and one that I’ll miss so dearly. David Hsu and Anthony, thanks for bringing me in several years back and leading this charge. And for those reading who aren’t familiar with Retool, you should absolutely check it out; it’ll accelerate your eng team, but more importantly, your business overall. As for me, in terms of what’s next: I’m excited to build again. More to come there, but after a 10 year hiatus, I'm back to the startup-founding days!

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For smaller orgs scaling-up and becoming bigger orgs - it's HARD to keep your once smooth UX from become disjointed. First, you started as a tiny team of folks wearing multiple hats and cranking out your core features. Now years later, you're financially able to scale. You're becoming a "real company" with lots of new team members who don't share the same memory and history as the core team. There's a REAL and qualitative difference between a small and large design effort on a digital SaaS product. However, here are just a few things I keep in mind when prepping large organizations to maintain their polish as they begin their growing pains: 1️⃣ Accountability 2️⃣ Cross-Collaboration 3️⃣ Automation 4️⃣ Thoroughness In this short clip I touch on each... #SaaS #ProductLeadership #ScalingSuccess #UX #PLG

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A lot of companies are going to learn quickly that having principal/staff PMs aren’t a silver bullet. If senior PMs can’t make reasonably good progress in a company, you have problems elsewhere. Principal/staff PMs are more experienced, obviously, but a lot of work doesn’t require principal / staff level experience (or shouldn’t require if, at least).

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I advice 1-2 CEOs each week on how to select their CTO or founding engineer The average tenure of a startup CTO is < 2 years But the impact on the company - positive or negative lasts a long time after they are gone -> Early-stage companies lose momentum by choosing the wrong CTO So it is mission-critical to look for the right attributes in your first/next CTO: 1/ Hands-on capabilities Should rollup their sleeves and get into the dirty details from day#1 2/ Experience working with offshore teams Such CTO can handle cultural & language barriers much better 3/ Obsessed about creating value every week Huge red-flag if they focus on fancy tech And complex architectures or expensive tools 4/ Clearly connects with your mission Startups are a slog A clear connection with your mission goes a long way 5/ BONUS: Has some entrepreneurial experience Can empathize with the tradeoffs a CEO has to make every day If you need more help selecting your CTO DM me with the message “world-class CTO”

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Companies ghosting you is not new. I hear from product managers that in this market, companies are becoming less applicant-friendly, to the extent that they regularly ghost candidates after interviews. I agree with that. But it's not a new behavior. It has increased temporarily because there is a supply-demand gap favoring a large supply of product managers and not enough jobs. But let's break it down: why does this behavior exist? It's not because companies are bad or recruiters are inherently evil. It's because 1) Their incentives are all towards getting the right person in fast and 2) People generally avoid unpleasant activities - like paying a bill or telling a candidate that they were rejected Here's what you can do as a candidate: 1. If you don't hear back, don't just assume you did not get the role. Recently, one of our clients did not hear back for two weeks and assuming he did not get the role at a significant Fintech company, only to get later informed that he was indeed moving to the final stage 2. Follow up many times over with the correct language 3. Always position yourself as the prize. Never appear desperate in your reachouts 4. Move past ghosting or rejections fast. In our program, we emphasize radical acceptance, which means that candidates should get out of this loop quickly. Remember, ghosting is not new; it's just become more common. But at the end of the day, you own the impact it has on your mental state. --- P.S., If this resonates with you, and you: - Are a product manager - You love to take action - You are committed to career growth But if you need help landing that ideal next role, DM me "dream role" and I will send you details. We only work with selected folks and have started to limit how many people we accept every month.

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If you really need multiple backend repos before you have multiple teams question whether you should be multiple companies. If not you’re probably better off as a monorepo if so you’ve got bigger concerns. At UpContent we’re actively retreating from the architectural complexity of micro-repos, as a smaller team it’s just unnecessary and most tech these days support multiple separately deployable components/services in a mono repo. Exceptions might be tiny services that don’t hit your main db and for whatever reason are in another language. People always forget that part of microservice architecture principles were separate databases and no shared code. People also forget they were a way for large companies to segregate duties with fully autonomous teams each owning a service not a strategy for startups with one team. Multi-repo is a very valuable tool in the tool box but it is one for after your first team split and when you process in place to handle cross team coordination.

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I’ve been doing a lot more recruiting and one trend I’ve noticed is a tendency to talk about using a framework when really describing a process. There are two key differences: Frameworks are structured but open ended and are not prescriptive. Processes are prescriptive sequential steps. It’s important to identify when you want to use one or the other: - Coaching an engineer: Framework - Planning: Probably framework with a tiny bit of process for scheduling - Recovery of a data center: Process A more engineering centric / systems view would be to look at frameworks as the interfaces in engineering and process as the implementation behind the interface. Too often we’re focused on the implementation of the process before we’ve established what the framework is we want to use.

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What's the biggest blunder a candidate can make in the first few minutes of a Product Sense or Analytical Thinking interview? The quickest way to torpedo a structured interview off the bat: diving right in without outlining the game plan for the interview in a structure way. Don't do that. ⚡️ Want to go just a little deeper? Check out the free recording of my Maven lightning lesson. 👨‍🏫 Want to go a lot deeper? Check out my upcoming course on Maven (second cohort kicks off next week). Links in the comments👇

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