Lesson Sixteen: You can't go home again

Working with the old team at a new place is still working at a new place

As my time at Square was winding down I started looking around for a gig that might make sense. I prioritized three things. First, I wanted to go to a company that was building a large infrastructure footprint again, at Square we didn’t build as much as we had at Facebook and I missed that pace. Second, I wanted to go to a company where I could work for more than the customary 4 years of vesting that had colored my decisions to go to Facebook and Square. Last, I wanted a place where part of working there for a long time meant that I would have a path into senior leadership roles, eventually.

In a serendipitous turn of events, one of my partners from my days on the Production Network Sourcing Team at Facebook reached out to me to see what my plans were as he knew my time at Square was most likely winding down. He had moved to Dropbox with several of our former teammates and they were looking for someone to come and help with a new direction.

Dropbox had made an interesting decision to pull some of their workload out of a Public Cloud. They planned to put that load into their own infrastructure. This meant they would need new colocation agreements with a focus on interconnection, they would grow their network footprint and they needed help managing all of the vendors required to spin up this new approach.

The approach was actually twofold and I thought it had the potential to be game changing in the way the things we had done at Facebook and Square were. In very large scale data centers, the team had developed a system called Magic Pocket. To put it in layman’s terms, they had achieved much better economics on the hardware required to host their own storage by developing a unique approach utilizing a commodity, spinning disk drives. 

Essentially, they had a little compute and a whole bunch of old school hard drives stuffed into a rack. Those hard drives were commodities, meaning a few vendors sold identical products so they were cheap and getting cheaper. If one broke, the cost to repair it was immaterial because you wouldn’t repair it, they were so cheap you could just buy a replacement and dispose of the malfunctioning drive. With the data on the drive replicated in other Dropbox data centers, it was no big deal.

The second part of the plan was to improve the performance of the Dropbox application for paying subscribers. Dropbox had started as a consumer play, but the real money is in selling cloud based software to Enterprise level customers. Where an individual would buy storage for $100 a year, the market was flooded with options which meant that in the long run Dropbox would be selling larger amounts of storage to generate the same revenue. Shifting to an Enterprise focus would move beyond simple storage and varied feature sets meant higher license fees and new revenue streams.

In order to improve that performance, Dropbox was looking to build a network of Points of Presence around the globe to get the latency sensitive portions of the application closer to the customers who used it. This was nearly identical to what I had helped to build at Facebook and I was excited to get back to that. My interviews were a virtual reunion with folks I had worked with in the past and I was excited to get started.

There was my friend from Finance at Facebook who would be approving all the money we would be spending. There was the Infrastructure leader I knew and loved, Dan the Plumber. One of the best bosses I had ever had interviewed me for a return to working for her. It felt like going home again. I learned pretty quickly that it wasn’t.

In the interview process I was pretty up front about why I wanted to come to Dropbox. It was fine that I would be doing a job I knew how to do well and had done before at Facebook, but my goal in the long run was to lead the team that managed the sourcing. I was looking to get back into being a manager of people.

I had read a book about how you never get what you don’t ask for and I took that idea and ran with it. I told anyone who asked and anyone who didn’t what my goal was. I made sure it was clear that I saw my current role as a temporary thing, even if that wasn’t what I meant to be conveying.

I had experienced a lot of new things in the 4 years since I had worked with any of the folks at Dropbox. I had grown and changed and learned. I wanted to use those newfound skills to push myself further and I didn’t see that stepping back into a role that was based on experiences from before all that was also like stepping into a time warp a little. I had some things to prove to them and I didn’t realize it because of my familiarity with them and strong personal relationships.

Additionally, there were folks I was just starting to work with that had designs on being promoted to leadership roles. Some of them considered me competition for the role they sought to grow into. I learned much later that one of the folks was even telling people I was saying things that I wasn’t. They had taken the view that they could only get ahead if no one else did and, honestly, Dropbox was a company that really valued social engineering to a fault. 

I still remember my first call with a colleague that should have driven this message home from the start but that I missed because I was bewildered. A senior leader in the organization asked me to reach out to a teammate I did not know and get some information from him. I set up the call and started by introducing myself. I explained what I was reaching out for, that I needed to get some data from him so I could take care of a request from his manager. 

“I don’t agree that you should have this information and I don’t care who asked you to get it.”

That was his response just before hanging up on me within five minutes of our first ever professional conversation. I sat in the conference room I was in and stared at the wall for a minute before reaching out to that senior leader, whom I knew well from our time at Facebook together, and explained what had just happened. He laughed a little and said, “Okay, I will chat with him.”

Promotion by friendship was commonplace. So, in a way… being a better friend to those above yourself in the Org Chart bred this sort of behavior. It was not much different than a clique in High School from that angle. If you wanted to be in the cool kids club you had to have a better relationship with the head cheerleader than the next guy. I was a friend with an existing relationship with the senior leader that some folks really wanted to impress and ingratiate themselves too. I was an obstacle and a threat.

My initial response to this was to simply ignore it. Eventually I took it head on and pointed out the fallacious nature of some of my teammates naked and disingenuous obsequiousness. I called it like I saw it and pointed out what were unethical lies and I didn’t pull any punches in doing so. When the entire structure of the organization was based on friendships, rather than actual knowledge and performance, this was not the best move.

Later, I read a book by Marshall Goldsmith called What Got You Here Won’t Get You There. I wish I had read it before I started at Dropbox, I would have saved myself a lot of heartburn. I was a textbook case of a person displaying an “excessive need to be me.” This is one of the 20 habits discussed in the book and a real barrier to building one's career.

What I mean by this is that I identified being straightforward, tackling issues bluntly and addressing folks head on as a characteristic that made me who I was. In a situation where I was seena s a threat, this would be perceived by some folks as threatening. They didn’t know what I knew about these people I had worked with before, that they didn’t really operate in the way where our friendship bled into our professional relationship. They weren’t going to promote me to a job I wasn’t qualified to hold because I was their friend. If the guy who hung up on me was more qualified for a job that was coming available, they would promote him into that role rather than me.

These two mistakes were related, the feeling that I was home again and failing to soften my message when I saw things that were not healthy. When I worked with most of these folks before at Facebook, I made a lot of good things happen by practicing full transparency. I was honest to a fault and calling it like I saw it didn’t hurt my work relationships because it was a part of the culture. Sure, there were missteps and I pissed some people off, but we were almost exclusively focused on getting things done and a short “hug it out” session after a rough interaction was all that was needed to get back to that.

Dropbox was not Facebook. While there were plenty of people I worked with at Facebook around me, there were a whole lot more who were not. These people had grown up in a different professional environment than I had and when I went full transparent with them it came off as an attack. Here I was this new guy who was part of a different clique in their eyes, and I am just telling everyone what needs to be done and how it should look. How could they take this as anything but an attack?

After 18 months, most of the folks I worked with at Facebook were gone. So what I had expected to be a long stay and coming back home type gig was completely different. That is not to say that there weren’t a lot of good people at Dropbox and that I didn’t learn from them. Quite the opposite is true.

The folks I was unimpressed with and found to be ethically shady were gone about 24 months into my stay, but because of the way I had approached things when I first entered the company I had missed a window of sorts. The folks who had made mistakes by promoting by friendship were left holding the bag by those individuals who had caused problems for me but didn’t seem capable of introspection on a level that was required to learn from the experience. All in all, Dropbox felt like Yahoo! part two for me. 

What I learned at Dropbox is really quite simple. You can try to go home again, but there will never be a situation that recreates the magic of the past. Even if you are surrounded by many of the same awesome people who made the past so magical.

You can also cling to who you were years ago. You can approach everything the same way. You can be the same authentic you that made a lot of great things happen as part of a great team before, but it most likely won’t work. We aren’t meant to repeat the same things over and over, we are meant to take the good lessons and build upon them to make something even better than what came before. 

We aren’t meant to go home again.