Lesson Twelve: 1:1's are required at fast paced companies to maintain sanity

Building relationships in the quiet moments will carry you through the tense moments

Early in my career I realized that a leader should focus their schedule around being available for every individual member of the team they are charged with leading as often as they possibly could. I made sure that no matter how many people called me boss, I put 30 minutes on each of their calendars once a week. It was rough when I had a team with 20 people and that meant at least two 30 minute discussions on average per day.

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I remember that it became so all consuming to try and make this work with all the other meetings and work I had to tackle that one review period when I wrote my self assessment I just listed out every member of my team and a paragraph about where we were in their personal development plan. That was what we discussed in these 1:1’s, their personal development. Professional training, tasks the team had to do and that they wanted to learn about and specific project updates.

I was nervous to turn this self assessment in, but to my surprise our VP held it up as something all of us should be doing. I didn’t really think about the deeper message there, I was just relieved that he didn’t see it as a copout and avoiding bigger, more important projects. 

At the time I was not new to frontline management and thought I had really figured out a formula for success. 1:1’s were a big part of it and I would tell my team that it was their time. No one ever called me on it, but the truth is that I set the agenda in these 1:1’s that were “their time.” I am the one who decided they would be about professional development and I needed them to give me project updates so I could tell my boss what was going on with all the things floating through our sphere.

When I moved from Covad Communications, and leading a large team of people, to Yahoo!, where the only people I ever really led didn't actually report to me, I started to see this differently. I loved having 1:1’s with my boss at Yahoo! He was easily the best boss I had ever had up to that point, and we laughed about how crazy some of the things that went on at Yahoo! were. He was great at redirecting my focus away from being pissed off about something that really wasn’t worth my energy.

But the 1:1 was pretty much about me keeping him in the loop on the projects I was working on. The agenda was set by him, though I never really thought of it as a bad thing. He was a great mentor and walking through the projects really helped me learn and develop as a professional when I had just transitioned from leading people to being an Individual Contributor.

When I moved to Facebook, I once again had a great opportunity to learn from my boss. She had been a pre IPO employee at Cisco, Google and now Facebook. She was tough as nails and the 1:1’s were “no bullshit” territory. I was the domain expert, she hadn’t really managed the specific area of the business I was accountable for on a full time basis so there was definitely some knowledge transfer of me to her, but we spent most of the time talking about the projects on my plate and reviewing the email I sent out with weekly updates.

She was also a great mentor. She helped me figure out how to survive, what language to use in the weekly updates to not raise an unwarranted alarm about lack of forward progress and when to ask for help. She helped me focus on what was important and gave me a roadmap to navigate the different kinds of office politics that existed at a crazy fast growing company like Facebook.

While Yahoo! was mired in Corporate Feudalism, Facebook was the exact opposite. It was more like Uncorporate Sparta. We all reported to one another in a sense and we fought like siblings as we pushed each other to make big things happen. If there was even a question about your effort it was a really bad thing, we were mostly just focused on delivering and a high level of effort was assumed.

All of this is to say that while these bosses and mentors are people I still hold in high esteem, the 1:1’s that I did with my team at Pac-West were really not that much different than how my leaders at Yahoo! and Facebook conducted their 1:1’s. They were about navigating a professional maze and giving project updates.

The best 1:1’s I ever had, and probably will ever have, were at Square. I don’t want to give the impression that we didn’t talk about projects or that they weren’t about business and getting things done, but they had a different flavor. My first boss at Square was a guy who worked at Yahoo! when I worked at Yahoo! He and I never really crossed paths there, but we were in the same large sub organization and he was familiar with the HRC.

He was the first leader, me included, that I ever saw really live the idea that 1:1’s were not about what he needed to get out of me. When he said “This is your time” he absolutely meant it. I spent hours walking around the neighborhood at 5th and Mission in San Francisco. Sometimes we were so engrossed in conversation about our families, his time at a small telephone company in Maine, my time at Pac-West that we didn’t even notice we were walking through broken crack pipes on the corner of 6th and Mission, at the time a pretty notorious neighborhood for drug related crime. Not that anyone on that corner ever gave us any grief.

At this time my marriage was falling apart, mainly because I had fallen back into a pattern of leaving my house before the sun rose and sitting at my desk until well after most people had left the office. To cope with that I would drink a lot, my boss also drank but he wasn’t enabling my behavior. After a few months he actually started a 1:1 saying, “I am worried about you.”

I thought for sure he was referencing the drinking but he followed up by saying, “There is all kinds of stuff to get done but there is no reason you need to be at your desk after 5 pm.”

Another 1:1 we talked a lot about professional philosophy and time at Yahoo! While I had yet to put the name “Corporate Feudalism” as a way to describe Yahoo! he made a different observation. He told me that he thought of everyone he worked with at Yahoo! as a bunch of good people who had been set adrift in a raging ocean. They had all found debris to latch onto and they came together to turn it into a flotilla.

What he was really saying, or what I took what he was saying to mean, was that the single most important thing about building a team that could survive those raging waters together was relationships. That a team of people pulling together to construct a flotilla in order to survive the waves needed to be interconnected like a spiderweb.

Each member of the team needed to have a bond in order to have each other’s best interest at heart. Having 1:1’s focused on relationships rather than projects was a key part of that strategy and it worked very well.

Square was not like Facebook. At Facebook we had a multibillion dollar revenue stream for the taking and all we had to do was move fast. We thought of the world as a board game, something like Risk. If a competitor owned a specific market, we would surround that market and overwhelm them from multiple adjacent markets and eventually take it over. An easy illustration of this was how we dominated Brazil after first playing second fiddle to Orkut, a company Google acquired to hold off our growth. We had such a juggernaut with big display advertising sized margins that we were able to put infrastructure just about anywhere and turn on the growth machine. Even when Google tried to stand in our way.

Square was a much different bird. We had a little device to plug into the headphone jack that made credit card processing easy and seamless for small businesses that hadn’t really been able to justify taking credit cards before. The reason they couldn’t take credit cards was because the margins were not as sweet and thus the banks that controlled the market charged a lot of money for hardware that was deployed on site as a way to increase their take. We were upending that model and those banks were not our friends as a result.

We were being attacked by banks, card issuers and other players in the internet payments market. The Google equivalent in our space was PayPal, and even though we had some of the early executives from PayPal working for us, they had a big head start in the internet based payments space.

This meant that our entire product strategy would shift on what felt like a six week rotating basis. We always had the Square Reader as the base of the strategy, the game changer if you will. But finding other revenue streams to grow in conjunction with that was a bit of a rambling wander through an unexplored wilderness. 

We were going to become the “Social Payments” company at one point. We got beat to the punch by Venmo and they attracted the attention of PayPal, who we were trying to get a leg up on. They did a good job of deflecting our attempt to beat them by buying Venmo and arming them with an existing ecosystem. PayPal pulled the “surround our territory” move that we so often pulled against other social networks at Facebook against my new team at Square.

We, at one point, thought our future might be in providing streamlined processing for large, established brands. The first big one we landed was Starbucks and our Infrastructure team, me included, was focused on putting together a plan that worked for that. Eventually, we saw that this was not the path for us long term. But this was after working really hard to make it work and putting that much effort into a potential path only to decide to go another way is demoralizing.

There are other examples of this kind of experimentation that lead to the realization that we needed to find another path. All of this whipping around was stressful. The only way we made it through that as a team was because we all had relationships with one another, fostered by the environment our leader set up by focusing 1:1’s not on projects, but on humanity. 

Before long our entire team was working together in 1:1’s that were not about the work as much as they were about knowing each other and caring about our mutual success. It makes me laugh to look back and think I was overwhelmed trying to maintain an average of two a day with my direct reports and leaving the personal understanding of each other to random interactions in the break room, or at the metaphorical water cooler.

This type of environment is hard to maintain as the company grows. Eventually, you aren’t locked in a battle with the unknown and 1:1’s become just about projects. I think that is a shame but I understand it. If there is one lesson I learned at Square that was unique it was this, we are on a flotilla together and we are only as strong as the bonds between us. Use your 1:1’s to focus on people and not projects.