Overwhelmed by Onboarding? Me too.

What’s Your Onboarding Process Like?

I recently spent some time researching different project management software options. We’ve been using Basecamp for our cre8d design projects since forever, but I wondered if there might be a more modern tool better suited to running my new food blog, Friday’s Pizza, behind the scenes.

So I signed up for a new tool, quickly hit some limitations, upgraded to a paid plan, and spent a good chunk of time setting up some basic tasks. I consider myself pretty tech-savvy and love trying new things, but I found the experience overwhelming and slow. It made me wonder—if I’m feeling this way, how might clients feel the first time they use Basecamp?

Meanwhile, my inbox was flooded with emails from the software provider:

• A welcome email.
• A sales rep suggested I upgrade again (because they noticed I’d clicked on a restricted feature—creepy).
• An invitation to a webinar.
• A one-on-one setup call offer.

AI popped up in every corner of the software, asking if I needed help writing or summarizing things. It felt like too much. Inauthentic. (Do you remember the joy of receiving a newsy email from a friend? This was the opposite.)

After a while, despite all the shiny features, I started wondering if Basecamp might work just fine for my needs after all. So I gave it a try and flew through my project setup with a sigh of relief. Maybe I didn’t need something new and fancy, just something familiar and calm.

That’s one of the things I appreciate about Basecamp. It’s polite. No bombardment of sales emails, no relentless pop-ups. Just a clean, calm interface with help available if I need it. I recently asked on X if anyone had a website that made them feel calm when they used it—and the only responses were about sites that did the opposite.

Jason Fried and David Heinemeier Hansson, the makers of Basecamp, have been outspoken about AI. They’re excited about its possibilities but aren’t interested in using it for customer support—not for the high-touch, human kind. Because sometimes, people don’t just need answers. They need to be heard.

“Great customer service is not just about answers. It’s about receiving, hearing, listening, empathizing, recognizing, and knowing what it’s like to actually be frustrated when something isn’t quite right. Great customer service is about being there for someone. Not just telling them something.” – Jason Fried

This whole experience got me thinking about onboarding—how we introduce people to something new. When setting things up for Friday’s Pizza, here’s what I’ve done so far:

• Created a welcome page for new subscribers with a personal message about what to expect. I’m planning to add a short video of me in the kitchen to make it even more personal.
• Updated the confirmation email so it feels like it came from me, not a robot.
• Added a thank-you page that actually welcomes people instead of something generic.

I also decided to stick with just one email a week (on Fridays!). No multi-step onboarding sequences, no special offers—just a single, simple, valuable email. Because honestly, when was the last time you read all five emails in an onboarding sequence?

So, what’s your onboarding process like? Try testing it yourself—sign up as if you were a new subscriber and walk through each step. Is it clear? Personal? Overwhelming?

Maybe it’s time to make it a little more human. What do you think?