Thread by @epatt6

This Friday's #prodmgmt story is about the extremely fraught process of "doing a rebuild" 💀 and then moving customers over to your new app.

If you work in tech long enough, you'll find a CTO or VP of Eng who really would like to rebuild the app. New backend, new UI, whatever...

This is usually because the existing app is full of issues and hardcoded logic and built on an outdated stack. For this story, we had all of those things. The app wasn't resilient and it needed a facelift asap.

The engineering team carved out 18 months to rewrite the app.

Carving out 18 months to rewrite it was by itself a problem - customer success teams and other stakeholders were told to "just wait" many times with no real idea of when "later" would be 😓

(as an aside, this itself caused the CTO to get fired about 12 months into the project)

So we did our best and redesigned a lot of functionality while we were rewriting it.

I did a lot of work to make sure workflows were covered, and I learned a lot in the process.

Some features I had to copy/paste from old to new, which wasn't my idea, but 🤷🏽‍♀️

At a certain point, everyone ran out of patience. Customers were getting increasingly frustrated that bugs weren't getting fixed, leadership had already fired the CTO and wanted us to "just ship it".

Me and the rest of the product dev team started to just throw it together ASAP

Ironically, I actually missed this release because I was in the hospital (which everyone hated!), but I know it went very badly.

Change management was forgotten in our rush, so we just sent out a "New app, check it out!" email and hoped CS would cover.

As you can imagine, it was a shitshow. CS was overwhelmed with complaints and upset customers. There were a TON of bugs.

We actually rolled it back and then rolled it out again twice if memory serves. (this is why I require my PMs to create rollback plans now 🙃)

Customers eventually forgave us because we still had a great niche product that was really sticky.

But those 3 months after the initial launch were very messy. Lots of hotfixes and lots of hard conversations.

After the launch, we realized a lot of the "copy/paste" features we did weren't actually done well - they didn't quite work the same and customers hated them.

It took persistence, but the product team got some affordance to break these features down more and rebuild them.

This was something I had wanted to do from the start, but given the new understanding about our customer's needs, it was really great fun.

Customers were hard to reach at first, but our internal teams helped fill in the gaps.

And we eventually turned it around, because people have short memories, and the new rebuild was faster, less flaky, and the new workflows were better optimized ✨

So key takeaways:
1. Rebuilds are awful time sinks, but sometimes can't be avoided. If you have to do them be absolutely sure to keep "maintenance" capacity so people don't hate you.
2. NEVER RUSH A RELEASE - especially a big one! Slow & steady. Make release and comms plans

3. Customers hate change but will get through it with enough time. Make sure you tell them early and often about big changes.

And NEVER get frustrated with repetitive questions! Take a deep breath &answer them again. Don't tell people to RTFM. 😊