Wyatt Fleming

𝗜𝘁'𝘀 𝗙𝗿𝗶𝗱𝗮𝘆. 𝗟𝗲𝘁'𝘀 𝗽𝗹𝗮𝘆 𝗮 𝗴𝗮𝗺𝗲. I'll give you the scenario. You tell me what you'd do. --- You are a Staff TPM. Launch is in 5 days. Engineering lead pulls you aside and says: "The feature works but I'm not comfortable with the scale testing we've done. I'd want 2 more weeks. But I also know the business pressure — so I'll go with whatever you decide." Your CPO is presenting this to the board next Thursday. Your CEO announced it at a conference last month. Your on-call team is already booked out. What do you do? A) Launch on schedule, document the risk, put monitoring in place B) Push back to leadership immediately and own the delay C) Launch a limited rollout — 5% traffic — and call it a phased launch D) Ask engineering to define exactly what "not comfortable" means before deciding Drop your answer and your reasoning. 👇 No wrong answers. Only honest ones. (I'll share what I did when this happened to me — after 20 comments.) #TPM #StaffTPM #ProgramManagement #TechLeadership #ScenarioFriday #RiskManagement #ProductLaunch #DecisionMaking #Friday #BigTech

6

3 Comments

Your engineering team says they need to move away from Client Side Rendering (CSR). Before you approve that migration, ask why. I've seen companies spend six months rebuilding a working product. The old CSR app was fine. Users weren't complaining. But someone convinced leadership that SSR was "the modern approach." The result? Higher infrastructure costs. A longer release cycle. And the same user experience they had before. CSR isn't outdated. It's a tradeoff. For internal tools and dashboards, CSR keeps things simple. No server rendering costs. Fewer moving parts. Your team ships faster because there's less complexity to manage. For B2B products behind authentication, SEO doesn't matter. Your users found you through sales, not Google. CSR handles that just fine. The leadership question isn't "Is CSR still valid?" It's "What does our product actually need?" When your team proposes a rendering strategy, ask: - What user problem does this solve? - What's the cost of migration versus staying put? - Are we chasing trends or solving real pain? Sometimes the answer is yes, move to SSR. But sometimes the answer is that your current setup works, and a migration is an expensive distraction. Not every product needs the latest architecture. Some just need to ship and serve users well. I'm curious how others navigate this. When your team pushes for a major frontend shift, how do you decide if it's worth it?

90

14 Comments

Hiring a tech co-founder isn’t the same as hiring a developer.  It’s getting married. Okay, let me explain it to you. Early on, it feels electric. You find a brilliant engineer, they’re excited, and features ship fast.  The market responds, and momentum feels unstoppable. Then real life shows up. They want to refactor the database, but you want to ship.  They feel burned out by the pace, you call it commitment, and small disagreements turn into tension. By month twelve, you’re not building together anymore. You’re negotiating. Your co-founder questions direction, resents decisions, and disengages while still owning core systems. Here’s the trap.  Firing a co-founder feels like blowing up the company, while keeping them feels like slow-motion failure. Most founders treat this like a skills hire.  Basically, it’s not; it’s a partnership decision. The difference between a great technical co-founder and a bad one isn’t talent. It’s alignment with what winning looks like under pressure. That’s why soft skills matter more than speed. How they disagree, how they trade off, and how they handle growth. Whether they want to scale or just want to code. The conversations most founders skip are the ones that matter most. How do we decide when we disagree? What’s non-negotiable? What would make you want to leave? A tech co-founder is 70% culture fit, 30% skills. Get that ratio wrong, and you’ll spend more time managing the relationship than building the product. PS: Before you commit, ask yourself this. Do you agree on how you want to win?

18

9 Comments

“Developers are a resource. They don’t talk to product people.” I overheard that on Seattle’s light rail, and it stuck with me. I make it a point to talk directly with the people who use the software — delivery drivers, paralegals, and others doing the real work. Every conversation saves me hours of coding the wrong thing. When developers are treated as “resources,” they’re cut off from the feedback that makes their work valuable. Talking to users isn’t a luxury — it’s how you build the right thing faster. You don’t need a big product team or AI tools for that. Just curiosity and a conversation.

246

42 Comments

For software engineers navigating today’s market 👇 A quick reminder that doesn’t get said enough: Your value isn’t defined by how fast you land your next role. I’ve spoken with strong engineers lately—people who’ve shipped real systems, scaled platforms, and solved hard problems—who are questioning themselves because the market feels slower and noisier than it used to. A few things worth keeping in mind: 👉 Hiring cycles are longer, not worse 👉 Great teams are being more selective, not less interested 👉 Interviews today favor depth, clarity, and judgment—not buzzwords 👉 The engineers who stand out can explain why they built something, not just what they built If you’re in between roles or quietly exploring: 🔹 Invest time in articulating your impact 🔹 Clean up how you tell your technical story 🔹 Be intentional about the companies you engage with (signal > volume) 🔥 Strong engineers are still being hired 🔥 The bar just looks different right now.

2

I see so many startups claiming they want to hire elite Software Engineers, but then demanding a coding task before even having an intro call. That’s not how you attract top talent.

27

18 Comments