Thoughts on team collaboration, productivity, and why most project management tools get it wrong
We pretend sprints create urgency. We pretend story points predict timelines. We pretend standups keep us aligned. What if we dropped the theater and just did the work?
Fancy PM tools promise automation, insights, and seamless collaboration. But most teams use 10% of the features. Could a simple spreadsheet work just as well?
You make a plan. Budget time, scope features, estimate timelines. Then reality hits. Why do projects always deviate from the plan, no matter how carefully you plan?
What if project management wasn't a role, but a shared responsibility? Can teams self organize without a dedicated PM? Or is that just chaos waiting to happen?
Your company went remote. Embraced async. Hired across time zones. But somehow, your calendar is still packed with meetings. What happened?
Alignment is hard. It requires shared context, quick decisions, and constant communication. But does it require everyone online simultaneously?
Traditional project management was built for colocated teams with sync communication. Remote work changed everything. Do the old methods still apply?
Daily standups were designed for colocated teams. But when your team spans six time zones and works asynchronously, do standups still make sense?
AI generates summaries, drafts updates, creates reports. Everything moves faster. But are we actually getting clearer, or just producing more content to sift through?
AI promises to automate project management. Update tickets, generate reports, forecast timelines. But is the role itself going away, or just the busywork?
We estimate stories, track velocity, and forecast sprints. But does all that math actually help us ship better products, or are we just generating metrics?
Bad process slows you down, creates friction, and demoralizes teams. But can you really just have no process at all? Where's the line?
You're deep in code. Making progress. Then you remember: better update the ticket. And just like that, the flow state is gone. Is the overhead worth it?
Kanban boards work great for predictable tasks. But creative work is messy, nonlinear, and hard to define. Does it even belong on a board?
You build a roadmap. A week later, priorities shift. Customer needs change. A competitor launches something new. How do you plan when nothing stays stable?
Planning feels productive. You're thinking ahead, reducing risk, being strategic. But when does planning cross the line into procrastination?
Daily standups. Story point tracking. Sprint commitments. Velocity reports. Agile promises autonomy, but sometimes it feels like surveillance. What's the difference?
Agile was supposed to free us from rigid waterfall timelines. But somehow we still have sprints, release dates, and deadline pressure. What happened?
We didn't start with features. We started with beliefs about how work actually happens, and those beliefs became the foundation of everything we built.
Estimation takes time, it's usually wrong, and it doesn't make the work go faster. So what happens if you just... stop?
Every team estimates their work. Story points, t-shirt sizes, hours, days. And every team knows the estimates are wrong. So why do we keep doing it?
Standups, sprint planning, retrospectives, backlog grooming. Agile comes with a lot of ceremony. But does a tiny team actually need all that structure?
Solo developers and freelancers are sold the same enterprise PM tools as 50 person teams. But do you actually need project management when you're a team of one?
Evaluating new tools feels productive. You're improving the system, optimizing the workflow. But are you actually just avoiding the real work?
Teams jump from Asana to Monday to Notion to Linear, always convinced the next tool will finally solve their problems. Why do we keep switching?
The tool was supposed to help us stay organized. Now we spend more time feeding it than actually shipping. When did we flip the script?
Mention Jira in a room full of developers and watch the collective groan. What is it about enterprise PM tools that developers find so unbearable?
We've handed over decision making to algorithms that rank, prioritize, and sort our work. But should we trust a tool to know what matters most?
Sometimes the act of tracking and organizing work feels like it takes more energy than the work itself. Why does managing projects feel so exhausting?
Get notified when we publish new posts about team collaboration, productivity, and building better software.
No spam. Unsubscribe anytime.
Exploring the intersection of people, process, and tools
How small teams coordinate without meetings and overhead
Remote-first practices that respect everyone's time
Why most PM tools fail and how to build better ones