How I evaluate a project management platform (and why it matters less than you think)

Back in May I wrote that there are two kinds of operations people: ones who love their project management tool, and liars. A few people asked the obvious follow-up. If it almost doesn't matter which one you pick, how do you pick?

Here's how I run an evaluation. And at the bottom, the scorecard I'd use today, free to download.

The steps

Start with the work, not the feature list. Ask the people doing the work what they'd hand off first if they could. Find the person running the real schedule out of a spreadsheet and ask what it does that the official tool doesn't. That list is your requirements document.
Weight before you watch. Decide what matters most before the first demo. Otherwise the slickest presentation quietly rewrites your priorities.
Make vendors demo your workflow. Send two or three real scenarios ahead of time and ask to see those, not the highlight reel. You learn more from watching a vendor struggle with your actual process than from an hour of features you'll never use.
Score right after each demo, separately. Everyone scores on their own before you compare notes. It keeps the loudest voice in the room from becoming the evaluation.
Read the unglamorous rows. Security review, admin hours, data export, what happens when you leave. Nobody demos these, and they're where regret lives.
Find out what's oversold. Talk to a reference customer who looks like you and ask what they wish they'd known. Every platform I've evaluated was easier in the demo than in real life.
Negotiate before you fall in love. Price locks, renewal caps and seat flexibility are easiest to get before you've told your team which tool is coming.
Roll it out around people. The person who kept the spreadsheet is your best champion, or your biggest risk. Bring them in early.

Why it matters less than you think

You can do all of this right and still end up with a tool that becomes the place truth goes to die. That's not a failure of the evaluation. The tool was never the source of truth. The people who refuse to let the work fall apart are.

A good evaluation won't find you a perfect tool. It finds you the least painful fit, with your eyes open about the gaps, and a plan for the humans who will fill them.

Free download: the scorecard

Preview of the Project Management Platform Scorecard: categories and criteria with a weight column, scores for five platforms, and an automatic weighted score and rank. — Shown with sample scores.

Download the PM Platform Scorecard (Excel). No email required.

It's more than you need, on purpose: 71 criteria across 14 categories, from resourcing and time tracking to security, integrations and the AI roadmap. Delete what doesn't apply to you, weight the rest, and score each platform after its demo. It totals and ranks everything for you, with a summary by category. It opens in Excel, Google Sheets or Numbers.

What a spreadsheet can't do for you: write requirements with the people who actually do the work, get vendors to demo your reality, spot what's being oversold, or roll the tool out so it sticks. That's the part I help with. If you're in the middle of a platform decision, let's talk.