Everyone knows it, but no one wants to say it out loud: DoD onboarding sucks.

You get through the hiring gauntlet—a process I’ve written about before—and once you make it through the interviews, paperwork, and security screenings, you show up… only to wait. You wait for access. You wait for a laptop. You wait for clarity on what you’re even supposed to be doing.

I’ve worked at the Department of Defense, Amazon, and Redfin. I’ve seen how different organizations treat the first few days, weeks, and months of a new hire’s experience. At DoD, we too often forget that onboarding isn’t just a logistical task—it’s a readiness issue. If we want people to move fast and deliver outcomes, we need to give them the tools and the trust to start doing that on Day 1.

We tried to do things differently at the Defense Digital Service (DDS). We used Macs. We used Gmail. We used Slack. The goal was to meet new hires where they were—using tools familiar to folks coming out of tech. It was a smart intent: minimize the learning curve, remove the unnecessary friction. But even with all that, I still found myself completely stuck trying to navigate militarycac.com/macnotes.htm. Anyone who’s ever tried to use a CAC with a Mac in DoD knows exactly what I’m talking about—the endless driver installs, the weird pop-ups, the arcane browser settings. It was maddening.