The Consequences Of Ownership

Problem

There was a joint project for rolling out a VPN technology at Datadog, which involved various parts of the organization, including Security. It was a really big project and we had an estimated timeline of around six months, but because of various other factors we only got the Proof of Concept done and we did a soft roll-out to a few teams before the decision around who was going to own the project and run fell to the ground.

Actions taken

Everybody thought someone else was running the project, so my boss came to me and asked me who should own it. I was one of the main people involved with the project's design and nobody else really wanted it, so I needed to decide whether I was going to own it or pushback. I had to weigh up the fact that the work didn't fall exactly into the skillset of my team, with the fact that by owning the project, we'd have a lot of impact and say on secure access. As the head of security, this was really important. I didn't have anybody with time available to run it, so I knew that if I took it on I would have to run it by myself for a period of time. I decided to own it and the day after I took it they cut the timeline from six months down to just three. A week after, they brought it down to just two months. I suddenly owned a project that was much more intensive. We managed to get it rolled out in two months and it was fine, but because we didn't do all the proper testing we had planned to do in the six months we had allocated, there were a whole bunch of unforeseen stability issues that my team was then expected to fix. I got feedback from my team that over the two month period they felt they weren't properly lead because I was so busy. For a period of time, my team suffered a little bit, but it provided long-term benefits.

Lessons learned

I opted to own the project because I saw it as important and I didn't want someone who didn't care about it to be in charge of it. However, this lead to a number of unforeseen circumstances that really complicated my primary job duties and it was a really painful process. I was blamed for stability issues that weren't my fault and that I was trying to fix, I had to spend a bunch of late nights troubleshooting, dealing with vendors and training people about the technology. If you're going to own something you have to know that it won't work out the way you plan. I had no way to pushback against the shortened timeframes. However, there will always be unforeseen things you'll have to deal with, so you should have contingent agreements and SLAs pre-agreed before you agree to take on a project.