In this segment of To Be Continuous, Edith Harbaugh and Paul Biggar talk with Kris Gale about effective team structure for continuous delivery. This podcast is brought to you by Heavybit, a 9-month program for developer startups.

Kris is co-founder and CTO of Clover Health, a unique health insurance plan focused on driving down costs and producing improved health outcomes. Formerly, Kris was VP of Engineering at Yammer.

Edith is CEO and co-founder of LaunchDarkly, a continuous delivery tool of “feature flags as a service.” LaunchDarkly powers software teams to quickly launch, measure and control their features.

Paul is founder of CircleCI, a continuous integration and deployment platform that automates development workflows and IT operations, allowing developers to ship quality software significantly faster.

[soundcloud url=”https://api.soundcloud.com/tracks/232834454?secret_token=s-3aRuL” params=”auto_play=false&hide_related=false&show_comments=true&show_user=true&show_reposts=false&visual=false” width=”100%” height=”166″ iframe=”true” /]

Edith: So, Kris, what do you like best about continuous delivery?

Kris: So, I like continuous delivery, because I think it’s sort of the first step of building a learning organization. It’s sort of a fundamental capability that a team needs to be able to learn collectively about what it’s doing in the world. The first step is being able to sort of ship increments of value continuously.

The second, I think, is to be able to measure the result of any incremental change you’ve made, so you can back out of a bad path that you’re on, or sort of refine what you’re doing and know that quantitatively.

The next step then, is to move from a sort of historical corporate planning, so this is a our six-month milestone, our two-year roadmap, our marketing commitments for Q3 of next year, into sort of an assumption that if we are shipping continuously and learning continuously because we’re measuring what we’re doing, whether it’s quantitative or qualitative measurements.

The next step is really being able to assume that in your planning, and know you’re going to have more information in the future than you had in the past. So your plans that you made six months ago are necessarily lacking information than plans you would make today would have, so sort of institutionalize that.

And then kind of the last part, and this is all kind of enabled by continuous delivery, the last part is building organizational fluidity.

So as an organization, whether it’s your project planning structure, or your accountability to your work flows, are fluid, so if you learn something new, you’re not locked into, oh we have a sixth person, I don’t know, sign-up flow team, and we just discovered that we have no levers for moving engagement right now in the sign-up flows, so we’re committed to that and we’ve got this implicit prioritization that’s built into our org chart. So, to have organizational fluidity where you’re adapting the organization to what you’re learning continuously.

Edith: Oh. You know that’s fascinating. Paul and I have talked a lot about, I think, more the mechanics of continuous delivery. We put it as kind of the last step to software org, when you’re really talking about how that changes entire organization beyond software. So, this would be a great time for you to introduce yourself, and tell us more about you.

Kris: Yeah, so I’m Kris Gale. Most recently, I was the VP of Engineering at Yammer. I heard you talking about Yammer in a previous episode. I’d love to dig into any of that, if you’ve got questions. Currently, though, I’m the co-founder of a company called Clover Health. So, what we’re actually doing is offering health insurance for seniors, with the idea that we can fill gaps in care, and actually prevent hospitalizations.

We’re not trying to be people’s doctors, but we’re trying to look across their consumption of health care and say, “Oh, here’s an opportunity ‘to inflect the probability with which ‘this population of people will be admitted to the hospital.” So, for example, making sure they get treatments regularly, get follow-up visits with specialists, that particular bio-markers don’t deviate outside of a specific range. And all this stuff is really interesting to me, because the health care industry as a whole doesn’t change what it does continuously.

We’re sort of locked into what people learned in medical school, or what people learned on their first day on the job at, say a big health insurance company, or something like that. But, to be able to power workflow with software, you’re able to continuously iterate and continuously refine and optimize the intervention protocols that are leading to these prevented diseases.

Edith: Yeah, I mean, I heard that you were pretty good at data loops, and that this is just basically using data loops for good, I think is how you say it.

Kris: See, the way we were talking about data loops, we were actually talking a little bit before we walked up here, is this idea that there’s something you intend to do. There’s data that you collect in doing it. There’s your objective assessment of that data to determine whether you’ve added or removed value or improved something.

And then closing the feedback loop, to get back now to actually modifying what you’re doing, and form find out new data. So, that’s sort of the data feedback loop, is from doing something to measuring it and deciding to do something differently the next time.

The tighter you can close that feedback loop, the more opportunities you have to optimize in a short amount of time.

Paul: So, it’s kind of what you might call the shipping loop, if you implicitly believe that data is a key part of shipping.

Kris: Yeah, yeah, and I would say that I think I do.

Edith: No arguments here.

Paul: Well, I think it is interesting, because I think that a lot of people don’t actually have measurements as part of their feedback loop, and especially, I think this especially happens in a small organization, where you have a start-up that sort of comes out of a founder’s vision, or something like that.

And so, one of the questions that I’m very interested about is, you were doing a big thing, with lots and lots of people. And now you’re doing a very small thing with, I presume, a small handful of people. How much of what you’ve learned still applies at that very small scale?

Kris: 

So, yeah, a lot of the project workflow strategy that we came up at Yammer was really about how do you maintain that agility, that velocity of value delivery, and ability to react to new information, and not be locked into, “Well, this is just the way we do it,” in the face of new information. At scale.

So, Yammer’s whole process was really about, how do you take these advantages we had, when there were like four or five of us in the really early days, and not have that big bureaucratic company, “Oh, we know we should be doing something better, “but we’re not,” because of momentum, inertia, bureaucracy, all these things. Like, how to break that. So, what’s cool about starting over with a much smaller team is, we’re just there again. We’re back at that five person size.

Edith: You’re a lot bigger than five people.

Kris: We are now, yeah. So, like nine months ago, we were. We’re like 65 people now, already. It keeps growing really, really fast. It’s been really helpful to me to have been through the process of scaling a software engineering team and seeing what that looks like. So, it’s like, “Oh, I’ve seen this problem before, “not worried about this.”

Paul: So, when you started, did you immediately set out organizational goals, and mission, and values, and that sort of thing that would help the company scale it?

Kris: Yeah, no, that’s a great question. I’m obviously a really big believer in the way we approached this problem space at Yammer, but I didn’t want anything to be dogmatic. I didn’t want anything to be–

Paul: You wanted it to grow organically.

Kris: Yeah, I wanted it to grow organically, to a certain point, but there have definitely been times where I stepped in and I said, “Nope, I’m buying a physical board “to track our projects, “because, just the way we’ve been doing this “with sticky notes, “I know that it needs this other dimension “of information capture. “I know that we’re suffering because it’s not there.

“So, I’m gonna actually pull the boss card and do this.” There have only been like three or four times I’ve done that in the last year, but it’s things where, like– Okay, I’ve seen where this goes off the rails, if we don’t address this right now.

Paul: And is that a result of knowing, sort of directionally, how the company should be doing things, or setting things up in some way that you didn’t get, that you didn’t end up in these bad places?

Or was it all sort of retroactive, and you know, a couple places where you pulled the boss card?

Kris: Yeah, it was mostly, like, observing patterns, saying, “Okay, we made this mistake three or four times, “and I’m noticing that our process or our approach here “is divergent from a known good approach “that I’m aware of.

“So, let’s at least–” I still wanna give the team full empowerment to iterate and own the process themselves, but let’s at least just pull the boss card, get it back on the rails, and then say, “Okay, let’s see how this works.” Just give everybody a chance to work in a way that I know to be okay for a few iterations, and then give them the keys again, and say, “Okay, take this where you want.”

Edith: Also, Kris, what I’m dying to know now is, what are those three or four key things where you gotta play that card?

Kris: Yeah, so, one is single project focus. Really, really important to me for software engineering teams. So, what I mean by that is, if you are on a project, that is your only accountability. You are not being split between three deliverables.

The other is that everybody work in cross-functional teams. So, that means not giving, for example, I might tell you, “Build out the back end for this feature, and I’ll do the front end.” So, in order for us to do that, we would have to agree to the abstractions ahead of time.

And again, I’m pretty opposed to planning, and locking in planning, because the information that we have now, when we’re trying to lock in those abstractions, is going to necessarily be incomplete.

Edith: I love that quote, because it’s so true. I think you put it more, it’s like you always know more in the future. It seems so obvious.

Kris: Yeah, I was actually– So, we had Parker from Pivotal Labs over at the office yesterday, and he said that there was this saying they had a Pivotal, that I really, really liked. He said somebody there would always say, and I wish I could remember who it was, would always say,

“You will always make better decisions with more information, and you will always have more information in the future.”

This is so much more concise than any way I’ve ever said that. But I think it exactly captures it.

Edith:

But, on the other hand, my old boss, Gregg Brockway the founder of TripIt, he always said, “A good enough plan today is far superior to a perfect plan tomorrow.”

Kris: Absolutely.

Edith: He’s like, “You just gotta start moving.”

Kris: Yeah, but I think the key is not locking yourself into that “good enough” plan. To allow yourself the mutability of changing that plan over time, so you’re not constrained by that.

Edith: Yeah, but that was TripIt. I mean, I think he’d seen so many, because he came out of the travel industry, where people just got paralyzed. Like completely paralyzed. “Oh, we need to plan for five years, “and what business travel will be like then.” It’s like, well, nobody knows.

Paul: I think the kind of key point to that is that in order to get that information, you have to get moving today with whatever information you have available. Otherwise, you’re just not gonna have that future information. You’re gonna be in the same place.

Edith: Well, look, sometimes, though, it’s painful. Sometimes you move backwards, then. Like, you don’t always move forward. Sometimes you start moving, and when you’re looking back, you’re like, “Actually we took, like, three steps back “before we started moving forward.”

Kris: It can definitely happen.

So to complete that thought, when we assign teams, we would always assign a cross-functional team with a business objective. So, it would never be I give you a back-end task, and I take the front-end task. It would be collectively, let’s accomplish this business goal.

So hopefully, we’re iterating day by day on the abstractions. So, we are collectively accountable to one another, and to this business goal we’re trying to deliver. Not onto some specific set of tasks that we broke off when we first decided to assign out the work.

So, that’s one of the other ones, is always cross-functional teams. Always single project focus within those.

Paul: So, there’s an interesting thing that you’re talking about there. It’s not just cross-functional teams, but it’s also that those cross-functional teams get put together for a specific project, is that right?

Kris: That’s absolutely right.

Paul: So, are those teams teams that will have worked together in the past? Is there explicitly trying to make sure that the people know how to work together?

Kris: Yeah, so this is one of my other core principles that I am pretty, pretty set on, which is rotation, is this idea that cross-functional teams are rotational and ephemeral. So, that would mean that maybe the three of us come together to ship a feature.

We’re all within the same organization, but when we’re done shipping that feature, we’re gonna break up.

You might be the back-end person that goes onto another iteration of this feature area, or maybe, you know, the two of us work on some other feature. Maybe it’s three completely different people. But constantly rotating people around, I think is really important in an organization.

I have totally heard the arguments about, you know, you can build high trust teams if they’re stable and stay together. But I’m trying to optimize for trust across the entire organization. So, across Yammer, we had 220 people in engineering. They would all rotate through these two to 10-person cross-functional teams together.

Which meant that you, basically within three to six months, would work with a pretty significant portion of those 220 people, and would start to build trust across the larger organization. Whereas had we just torn off four people and said, “You’re a team,” they would– And I’ve seen this throughout my career in engineering, where it’s like, “We do everything right, and that team has no idea what they’re doing.”

Edith: It’s their API’s are bad.

Kris: Yeah, yeah they use this weird language, or this approach, or we use this style guide, or whatever. So, it sort of forced that rotation, so that we’re all sharing best practices among one another and building, maybe lower trust, maybe not getting to that very, very, very highest level of trust among a group of four people, but across the entire organization, getting to like 40% or 60% of what’s possible versus 0% if you don’t ever work with those people.

Paul: So, interested in structurally how that ends up, because one of the things you got when you split people up by team is you end up with a sort of microservices architecture.

And this team works on this repo, or this project, or whatever works on this service or this API. And when you have those teams that are forming and splitting up and they’re ephemeral, and it’s only a small period of time, architecturally, what does that do to your application or your architecture, you know, across your entire product?

Kris: Yeah, no, totally. It was actually very intentional that we ended up with that kind of architecture for working this way. For two years, we had a big monolithic Ruby on Rails code base, and for two years we said, “This is a big problem. We should break this up.”

And everyone agreed, and everybody was on board with breaking it up, and two years later, we had never done it, because we continued to work in such a way that supported that sort of architecture.

So, the key for us was to say, well one of, the– So, something to dig into here a little bit, is these cross-functional teams are made up of representatives of what we call functional teams. So, front-end engineering might be one.

Paul: Right, right.

Kris: We had one called Core Services, which I actually owned the service-oriented architecture that you’re describing. Or there’s little micro-services that collectively made up our service-oriented architecture.

Paul: And this is sort of a matrix style, where you’re a member of the team, but you’re also a member of the back-end team, or you’re a member of the front-end, or the core services, or whatever.

Kris: Yeah, so I might be a member of core services. My manager is one of the core services managers. But all the work I do is going to be within the context of the cross-functional team, with the front-end engineer, maybe a client’s engineer, whoever’s necessary to get end-to-end with a value proposition.

And then, I’m always going to be a core services member, when I go into these cross-functional things, but it’s the fact that all the members belong to functional teams that makes that team cross-functional.

For more on Continuous Delivery and to find out about new episodes you can follow the show on Twitter at @continuouscast.