Live From INTERACT: Engineering Leadership Screwups

**Conor Bronsdon** (0:00)
So, the engineering team is mainly doing it, or who's mainly doing this?

**Luca Rossi** (0:04)
At the beginning, it was the three founders, and we ended up managing like 50,000 bookings manually this way. And so we had to make shifts to manage them, and literally wherever we went, we had to work with backpacks.

**Conor Bronsdon** (0:18)
This episode is sponsored by LinearB. Accelerate your development pipeline with data-driven engineering metrics, continuous improvement automation, and project visibility while cutting your software development cycle time in half. Sign up for your free demo at linearb.io and mention the Dev Interrupted Podcast discount for a one-month free when you sign up for an annual Pro membership. Hey, everybody. Welcome to another special edition of the Dev Interrupted Podcast. This is Conor Bronsdon, Dev Interrupted Community Leader. We're releasing the final set of interviews from our Interact Engineering Leadership Conference, which happened virtually back in September and featured more than 700 engineering leaders from 75 different countries across the world.
Our final Interact episode is a combination of three separate conversations that are tied together by a single, crucial theme, engineering leadership screw-ups and what we learned from them. No one is immune to making mistakes, and the following speakers, head of engineering at Translated Luca Rossi, senior director of engineering at Equinix, Shweta Saraf, and Chris Downard, VP of engineering at GigSmart, were gracious and humble enough to share with our audience the very real and sometimes humorous consequences of the decisions they made as leaders.
Our first screw up story comes to us from Luca Rossi. Luca, can you introduce yourself to those of us in the audience who may not be familiar with you?

**Luca Rossi** (1:34)
Hi Conor, thank you so much for having me. Absolutely. I write an engineering leadership newsletter called Refactoring.club. It goes out weekly to more than 10,000 subscribers. I'm one of them.
I know, thank you. I'm head of engineering at translator.com and I've been co-founder and CTO of wanderio.com, which was a VC-backed startup in the travel space.

**Conor Bronsdon** (2:01)
Fantastic. Well, we're really excited to have you here with us today and I'm stoked to have you share with the Interact audience this engineering leadership screw up story that I have. Can you tell us a bit about that?

**Luca Rossi** (2:13)
Yeah, I mean, it was hard to choose one because we have had so many. So I had to choose the one that feels more like humorous to me and also that has maybe the best lessons learned that I could think of. So this story is about doing something that, I mean, didn't really scale and that was not a bad thing by itself, but it turned out to be kind of a nightmare for some aspects. My startup worked in a travel space and allowed people to compare and book transportation, flights, trains, buses. And for some time we worked with a meta-search approach. So if you search how to go from A to B, you would get how to go with flights, with trains, and then you went to the transport company's website to book and to pay for the tickets, like Skyscanner does, right?
But at some point we saw the opportunity to close the funnel within our website and within our app, so to make people make the payment and book the tickets on our own platforms. But we weren't really sure that that would be the right call, from the business point of view, from the user experience point of view. And it would also be a very intensive engineering activity because we would have to connect the booking systems of all of our partners, and there were maybe tens of them. And we estimated that it would take several months, like four to five months to do this.
So we decided to try to do something, just try it out if this would work in a lean way, do things that don't scale way. And we just integrated the payment gateway, that are like Stripe, to make people make the payment on the website. But then when a booking come, we would get a notification and we would go manually to the transport company website and book the tickets. So the engineering team is mainly doing it?

**Conor Bronsdon** (4:12)
Or who's mainly doing this?

**Luca Rossi** (4:15)
At the beginning, it was the three founders. Last time? Yeah, I mean, it's all founders. When in doubt, it's on founders. And so we released it and it was actually a great success. We were really happy because people were happy about the feature. We actually released this in a very little time to market, let's say. And we started receiving these bookings that there weren't even so many bookings because our volumes were small.