Real Experiences With Project Management Tools

Your project management system isn't broken—it's dead I watched a Fortune 500 company spend millions on new software. Same broken processes, prettier dashboard. Blunt reality check: Everyone defaulted back to Excel. Status updates lived in email threads. Real decisions happened in chat. Why? Because that's what people trust. Excel never crashes. Email proves you sent it. Chat gets instant answers. Blunt reality check Part 2: Your teams don't trust the data. PMs update status because they have to, not because it helps. The real work happens in Slack DMs and hallway conversations. I've watched companies chase the perfect PM tool for 20 years. Microsoft Project. Asana. Monday. Jira. ClickUp. Same story, different name. Guess what's still running most projects? 📊 Excel sheets everyone downloads and edits 📧 Endless email threads no one can find 💬 Chat messages that disappear in 3 days Why these tools fail: 1. They track status, not progress. ↳ Project statuses get logged in spreadsheets not where the work actually happens. ↳ Manual updates instead of real-time data. ↳ Reports that are outdated before they're read. 2. They're built for reports, not results. ↳ Fancy dashboards that look great in meetings. ↳ Features nobody uses. ↳ Complexity that kills adoption. 3. They ignore where work actually happens. ↳ Email threads that never make it to the system. ↳ Slack decisions that change everything. ↳ Side conversations that actually move projects forward. Here's what actually works: ✅ Build around execution. ↳ Live where the work happens. ↳ Automate the boring stuff. ↳ Make it easier to do work than track work. ✅ Connect everything. ↳ Your CRM knows things your PM system needs. ↳ Your financial tools have critical project data. ↳ Stop making people copy/paste between systems. ✅ Invest in integration. ↳ The best PM system isn't a new tool—it's someone who can make your existing tools work together. ↳ Yes, even with Excel and email. ↳ Because those aren't going anywhere. The truth is: A junior developer who can connect your systems will do more for project success than any software package. Been there. Built that. Watched it fail. Rebuilding it right. What's the biggest PM tool failure you've seen? Drop it in the comments. 👇 #ProjectManagement #Leadership #Technology #Integration #DigitalTransformation

After 13 years in product Here's what I expected my PM toolkit to look like in 2025: • AI writing all my PRDs • AI running my standups • ML predicting every user need • Automated roadmaps that update themselves Reality check: I still use sticky notes. But here's what else happened. My toolkit did evolve. Just not how I imagined. AI tools? They're here. I use Anthropic's Claude for stakeholder prep, ChatGPT for user interview synthesis, and Cursor for quick prototypes. But you know what's still in my toolkit from day 1? Excel. Whiteboard markers that work (rare). The ability to say "I don't know" without panicking. And my secret weapon: asking "why" until people get mildly annoyed. I thought technology would replace the messy human parts of product work. Instead, it amplified them. Now I can be wrong faster. Test assumptions quickly. Pivot before the entire quarter is shot. The tools that survived 13 years aren't the shiniest ones. They're the ones that help me understand people better. Because at the end of the day, we're not building for robots. We're building for humans who still can't figure out how to unmute on Zoom. What's the oldest tool in your PM toolkit that you still swear by? P.s. If anyone says JIRA, we need to talk about your life choices. :-)

When I was at 37signals, I interviewed customers using Jobs-to-be-Done to understand why people switched. Here’s a typical story. Jim owns a digital agency. He uses Google Sheets, Google Docs, whiteboards, chat, and email to manage projects. One day, something changed. Jim adds two more remote employees. They’re juggling eight projects at the same time instead of three. There are lots of balls in the air. There are messy email threads. Projects start slipping through the cracks. Jim can no longer make progress. He looks into project management software. He tries Asana, but it doesn’t stick. Adoption is low. He tries Basecamp for 30 days. It sticks. So he buys it. Jim can make progress again. This is what Jobs-to-be-Done looks like. Events and circumstances generate demand. Why am I talking about this? If you know the events or circumstances that cause people to struggle, you can write a cold email like this: “Hey Bob - You’re probably using Excel, Google Drive, meetings, and chat to manage projects. When you’re juggling 7+ projects, it’s hard to see where projects stand without asking people or digging through emails. Agencies use Basecamp to get everyone on the same page - see exactly what needs to be done, by who and when. Used by 3k+ agencies. Think this might help?” What changed that caused your prospect to struggle?