The art and wisdom of changing teams | Heidi Helfand (Author of Dynamic Reteaming)

Heidi Helfand: Reteaming is hard. Reorgs are hard. You can’t lump them all into one thing with oh, it’s all great all the time. No, it’s not. If we could just build the software, deliver to the customer, get the product market fit, hey, have we delighted them or not? If only it could be that easy. No, we have the people layer, so let’s focus there too.

Why I Studied Reteaming

Lenny: Today my guest is Heidi Helfand. After two decades in the tech industry, Heidi became fascinated with how teams are organized, how org structures change and how to set teams up for success through that change. She now teaches workshops and runs courses and consults on how to effectively reorganize your teams. And in her book Dynamic Reteaming, Heidi delves deep into why change is actually good for your teams, why you’re better off not having super stable teams, how to effectively execute reorgs, and through that, how to reduce attrition, stagnation, and knowledge silos. In our conversation, Heidi shares the five types of reteaming, anti-patterns to avoid when making org changes, what sort of team structure is most conducive to creating totally new products, why being transparent about your reorg plans is definitely worth considering. Also, how Heidi became such a great listener with a lot of really interesting insights and advice there and so much more. Huge thank you to John Cutler for introducing me to Heidi. With that, I bring you Heidi Helfand after a short word from our sponsors.

Heidi, thank you so much for being here and welcome to the podcast.

Heidi Helfand: Thanks, Lenny. Great to be here.

The Human Element

Lenny: It’s great to have you here. So I had this colleague at Airbnb, her name was Jana, and she always had this joke that she shared that if it’s been six months and she hasn’t switched teams or hasn’t moved desks, she knew there was this reorg coming, there’s something happening, something was coming to change everything. And you wrote a whole book about this general idea of teams changing, reorgs, you call reteaming. I have the book right here. It’s called Dynamic Reteaming: The Art and Wisdom of Changing Teams. I feel like just people underestimate the opportunities and benefits of change, and I think that we see it as a scary thing. So I’m really excited to spend time with you and chat about this topic. Before we get into the meat of it, I’m just curious why you decided to spend so much of your time researching this area of team change, reorgs, reteaming.

Heidi Helfand: Yeah, that’s a good question. It wasn’t necessarily planned. I had been working in a variety of different fast-growing startups for most of my career in 20 years in software-as-a-service companies in particular. And I read a lot of books to try to get better at my work and what we’re doing in our teams. I have a lot right over there as you can see, and a lot of the books I would read on teams and the advice that I would get from people would be, you really want to keep your teams the same. You want to go for that forming, storming, norming, performing kind of thing. And I had thought about that and I was like, wait, well it wasn’t really possible for us when I was at a startup and I was the 10th employee and we grew to 900 people and now thousands of people, our team’s kind of morphed and changed.

So I feel like if you’re in a fast-growing company or a shrinking company, look there, don’t look at trying to fight the natural evolution. I was just trying to prove a point and to illustrate that teams change. And I was also curious to see, well, was that just my experience and the experience of my colleagues in Southern California? What is it like for other people? So I was just curious.

Career Opportunities in Reteaming

Lenny: You have this code in your book where you say something like, sure, we deliver software on time, we make products people love and want to buy, but there’s this people layer that happens that people may not be thinking enough about. Is there anything more you can say to that?

Blank Slate and Open Self-Selection

Heidi Helfand: Yeah, I think a lot of the things that I would read about teams just are naturally focused on, well, you want to build things that customers love. You want it to be an enjoyable experience, you want to deliver on time. There’s a reason we’re there as a business, but there’s also a lot of company building that happens in building the people structures and just when you go from one to many to a multitude, there’s a lot of work that goes into it. This is enablement type work and it’s where I focused a lot of my time and my career helping make teams and organizations successful. So there is this people layer, however, I’ve thought about this a lot over the years and I think it would be highly convenient if we could just focus on building products that people love and getting product market fit, talking to customers.

It would be great if it could only be that, but the reality is we’re humans together and there’s a lot of opportunity to build companies that delight people where they’re excited to be included in decision-making about how the organization grows and changes or shrinks. So yeah, there’s this whole kind of other area of work that I think just doesn’t get enough attention and I guess that’s where I live and breathe.

Challenges of Transparent Reteaming

Lenny: Awesome. Okay, so I definitely want to get into the five types of reteaming as you described, but before we get there, what I find with reorgs and change is that it often leads to the biggest career opportunities because there’s new roles to be filled. If things aren’t changing, there’s not going to be all of a sudden, “Hey, we have this new role that we want for you.” I don’t know. A lot of the leaders that move up quickly are the ones that seem to take advantage of change and think ahead and get involved and position themselves in a way where like, “Okay, cool, there’s a new position. Oh, clearly it’s going to be Heidi.” Is there anything you can share there? Any advice for people that maybe see reorgs coming and what they can do to help themselves in that pending change?

A Transition Framework for Change

Heidi Helfand: I really like it when there’s transparency in reorgs. There’s a story in my book from Christian Lima at Spotify about how they reorged a large infrastructure team. They visualized it on whiteboards and brought people over to the whiteboards to see the future team structure that the leaders wanted and they got input into the design. We did this at Procore as well inspired by Christian and his story and we had… I think there were 80 people involved in this platform organization that was splitting from two large clusters of teams into three. And I remember when we rolled out the whiteboards from a back office where we were talking about this change for a few weeks and it was scary to roll these whiteboards out because it impacts people’s day to day. It’s like when somebody is suggesting that maybe you do something different or that something different happens, sometimes it can be kind of triggering. You want to know what’s going on. So anyway, but we had courage together.

So we rolled these whiteboards out and it had the team structure with everyone’s names on it. It had the name of the team, the mission of the team, how many open slots for hiring across all of these different teams, and then people’s names in their existing team positions. And people were invited to look, give feedback. They identified mistakes that we had in the design, “Oh, this team might be better over here and here’s why.” And people had the opportunity to see opportunities within their own company that they might say, “Hey, I’m interested in this, might I be considered for this?” And then they could have their discussion. So I really liked that the opportunities were shared and presented, so it wasn’t some sort of thing that happened in some kind of back room for the whole time. We unearthed the beginning of a plan.

I think sometimes when you convene people for a meeting to talk about anything, it’s good to have a starting point. So we had this starting point, we had a variety of different things and I call it whiteboard reteaming in my book and I write about that. And there’s even structures that are more open than that. Redgate Software in Cambridge UK. Chris Smith is a colleague of mine and they do regular open self-selection reteaming activities when they’re changing their strategic priorities. He talks about this globally very interesting space and it’s even more open than putting the names on the whiteboards. They have teams give pitches and this is what they’re looking for and they have a whole method for enabling people to say, “Hey, I’m interested in this.” I think that really helps because sometimes you might think, “Oh, no one’s going to want to work on this.” But people can be delighted by working on things that another person doesn’t think are particularly interesting.

So giving choice is important. And again, there are different grades of transparency. We weren’t up for doing this kind of open reteaming self-selection event, but we were open to the whiteboard variant.

Lenny: I imagine individual employees hearing this of just being involved in the reorg strategy sounds amazing. Executives and leaders hearing this are probably really afraid and feel like there’s no way this can work well. And so what I want to understand is how do you actually set this up for success? What I’m imagining when you do this is many people disagree. There’s teams people want to join, there’s teams people don’t want to join. It seems like there’s a consensus challenge where do you wait for everyone to agree? Does someone end up making a decision? Does it distract everyone from the work they’re doing when you’re kind of involving everyone in the reorg? Versus what typically happens, it secretly is planned amongst executives. No one knows it’s coming. And I think the reason they do that is because they don’t want to distract anyone and they don’t want anyone to start freaking out until it’s like, “Here’s the final plan. Here’s what we’re doing.” So what other advice do you have for people that want to practice this way of reteaming and reorging where they involve the actual team in the plan?

The RIDE Decision Clarity Framework

Heidi Helfand: There’s a book by William Bridges called Transitions: Managing Life’s Changes. I have it right here. Making Sense of Life’s Changes. He talks about endings, neutral zone, and new beginning. Ending: you’re going through a change, your team is changing. Neutral zone: the period of kind of liminality where you’re like, “Gosh, I don’t know how this is going to go.” You’re not quite comfortable. You’re not quite in that new reality yet. You’re still thinking about what it was like before. And once you’re in that new reality and leaders can paint the vision and picture about the benefits of the new reality and the purpose and why we’re here and anchor to that to try to raise positivity. But once I learned about that transition framework, going through any subsequent changes myself became a lot easier to grasp and it really kind of makes changes in any part of your life. I mean, his book is not written about software development or product development.

Sometimes we’re going to have a say, we’re going to be able to participate, sometimes we’re not. And being clear on who the decision maker is in a change is really important.

There’s another framework that I really like. I don’t think it’s in my book, but I’ve written about it in my new book, but it’s called RIDE. And we had a chief people officer at Procore and she’s now at UKG, Pat Wadors. She taught us the RIDE framework for decision making clarity and it’s who’s requesting the change, who can give input to the change, who’s the decider on the change, and who’s going to execute on the change? So it’s like R-I-D-E. And I googled this for a while; I couldn’t find anything on it. I encouraged her to write about it and I credit her to that, Pat Wadors. She’s awesome.

So a lot of the times it’s like, what’s the problem you’re going to solve? You have a current state and a future state and that future state might be up to discussion, but maybe it’s not depending on what it is. You’re getting acquired, you’re probably not going to have a standup meeting and talk about should we get acquired or not? No, you’re not part of that decision. And then how’s the change going to get rolled out or how are we going to do it?

In other cases at the team level, maybe you have a retrospective and you determine, “Hey, I think we’d be a bit more effective and we’d be able to deliver at a better cadence if we were two teams instead of one team.” And if teams have the ability to talk about that and impact and have some agency into how their part of the org evolves and change, I think that could be really cool. I think that could be really empowering. I think that could help us feel more ownership in that company that we’re in. It doesn’t always have to be like decision making equals hierarchy or the person at the top. It doesn’t have to be like that.

But again, reteaming is hard. Reorgs are hard. You can’t lump them all into one thing with, oh, it’s all great all the time. No, it’s not. It’s not. But anyway, we need to focus there. We got to focus on this people layer because reteaming is inevitable. We might as well get better at it because we’re going to have to deal with it. If we could just build the software, deliver to the customer, get the product market fit, hey, have we delighted them or not? If only it could be that easy. No, we have the people layer. So let’s focus there too.

Lenny: On this transparent collaborative reteaming, final question here is just would you recommend time boxing this so that it doesn’t suck up everyone’s brain power for weeks and weeks and weeks? Or is it very dependent?

The Five Reteaming Patterns

Heidi Helfand: Yeah, you got to time box it.

The Five Reteaming Patterns

Lenny: Okay. Is there advice you have on how long?

Isolation Pattern: The Expertcity Story

Heidi Helfand: Make a schedule biased towards shorter as opposed to longer. You don’t want to deliberate on this forever, because especially as you include more people, it can be distracting. So you want to proceed as expediently as you can.

Lenny: Okay, let’s talk about the types of reteaming. This is kind of the core of your book and we haven’t even gotten there yet. So you’ve identified there’s five ways teams change. Can you just walk through them, help people understand what they are. And then also, we use this term reorg a lot in this conversation. I think that’s the way most people think about change. After we go through this list, what does reorg refer to when it’s maybe from the perspective of these five ways of teams changing?

Isolated Teams and Innovation

Heidi Helfand: Sure. Okay, so the five patterns of reteaming. One by one, someone joins your company or someone leaves your company, grow and split. It’s a growth pattern. Teams grow bigger and then they split into two or more teams. Opposite of grow and split is merging. Sometimes two or more teams merge together. It’s more of a shrinking pattern. We might be seeing more of this these days as companies downsize. Things merge together and consolidate. Isolation is, or innovation by isolation. Start a new team off to the side, a beneficial silo, give that team process freedom, great for catalyzing new product lines within your existing company. Also great for emergencies and they just happen anyway if we have incidents and people have to come together, solve an incident and then go back to their teams. And switching. So switching is moving from one team to another team. You can do this at a variety of cadences, short term, long term.

And then difference between a reteaming and a reorg. I think reorg is a word that has very traditional baggage and connotations. And when I was writing Dynamic Reteaming, it just didn’t feel like an appropriate word to use for, well, Sue is looking to learn a little bit about how our web operations work, she’s going to move to that team. It didn’t feel appropriate to call that a reorg because Sue’s moving and switching from one team to the next. I think reorg again… Reorganization is a traditional word. It implies on the large, it implies top-down changes that you have say no. It’s something different than what I consider reteaming, which is these five patterns that happen at different levels.

Lenny: Awesome. So let me just repeat back these five. So one by one, basically people joining your team, leaving your team, something very natural. People do all the time.

Revisiting the Expertcity Story

Heidi Helfand: Your company.

The McNuggets Story

Lenny: Or your company, yeah. Growing, splitting a team gets really large and then it’s like, okay, let’s just split this into two, focus them on specific things instead of this one team trying to cover too much. Merging teams, the opposite of that. Isolation. I want to chat about that one a little more where you just have a team off to the side and they’re just dedicated to something that you find really important. So with isolation, you have this awesome story of your time at a company called Expertcity, which turned into something people know most likely and ended up being a great outcome because of this reteaming into an isolation team. Could you talk about that?

Heidi Helfand: Yeah, so I’ve been at different startups that have grown bigger and one of them, I was the 15th employee. I started as a web editor and became an interaction designer. And we were going to change the world and it was very exciting. We were in Santa Barbara, California. So the company’s called Expertcity. And we were working on our first product, which was a marketplace for tech support. So imagine you have a problem on your computer, you can go to our website and then you can select an expert to see and control your screen to help you solve your tech support challenge. And so we had the screen sharing technology that we were inventing in the company. We had the web-based software to manage the interaction between the customer and the expert. We had the experts. We had in-house experts and then the vision was global worldwide experts. You were going to be like this marketplace, this eBay of services is what we talked about in the early days. I was really into this.

This was my first job in tech and I became an interaction designer working on kind of front-end UI flows with engineers. It’s actually before the word interaction designer, my title was navigation designer. We made this up. So I was very into… It was before the words like UX and other things. People were talking about information architecture and other sub-genres of design. And we had individual offices. I had all the interaction flows on my walls. I was really into the words and one day I was in there and we were working on a new flow. We had all these hopes and dreams for this product and the CEO came into my office and he said, “Heidi, stop working on the marketplace. We’re not going to do that product anymore. We’re killing it because nobody’s buying it and made six bucks or something last month.” And he said, “Go to the beach.” We were by Santa Barbara. I’m like, “What do you mean go to the beach?” He’s like, “Well, I don’t want you to start any work that you’re going to have to maintain later as we figure out our next step.” And I was like, “Okay.”

I remember that day and I’m looking around my office and all these flows on the walls. So really these were domains like domain-driven design. It was all these web domains and which user interactions were going to happen and all these hopes and dreams and it was the first time in my career where we were told not to work on something. It wasn’t paused. Some people say, “Oh, we’re going to pause this,” and then they never get back to it. This thing was like [inaudible 00:22:59]. And I didn’t get it. I just didn’t get it. I cried, I acted out, I sent this email like, “How can we kill the marketplace? It must live.” It was quite an experience.

But then, and I don’t know what the timing was, I was invited to be on this team off to the side and there was market validation going on. Our founders and product and others became students of market validation, Four Steps to the Epiphany. So we had built this thing, we spent all this time on this marketplace, but nobody would buy it. And so it was like do or die. We had to shift. This was before lean startup. So Four Steps to the Epiphany was the book, it was the manual, it was guiding the way. And so there were people that had a ton of conversations with potential customers about this new thing that we were going to build.

And so I was invited to be at this team off to the side and there was a small team and we didn’t have to do waterfall software development. We were freed from that. We were liberated from that. We got to work in other ways. And I remember working with an engineer and we were figuring out how to create a forgot password flow because none of these patterns existed back then and we got to do this stuff. We got to deploy more frequently and the product was called GoToMyPC where you could see and operate someone’s computer from a distance. And that was essentially the pivot that I feel like saved the company. Later we went on, we got folded back into the teams and we built GoToMeeting and GoToWebinar as a technical project manager at that time. So taking a team off to the side, giving that team process freedom. They didn’t want us distracted from the drag.

When you’re working on an existing product line, you get this cadence and it can become a mature cadence. Maybe people work in two weeks or one week now, but when you’re working on something new, you need faster iteration loops. And our founders knew that need. So it was a privilege and I was delighted to be part of this other team and it was really, really exciting. So then looking back over the years, I was like, yeah, isolated teams, beneficial silos. Again, it’s going against green of what some of these books say, oh, you want to desilo everything? No, sometimes there’s a reason why you have a problem. You want to solve the problem. This was like, I mean, was this company going to go under? I didn’t think of those kind of things at the time because I was just super into the work and very passionate and motivated about what we were building. But yeah, isolation pattern came up and we used it at another startup as well ever since.

So yeah, that’s the story of Expertcity and from my perspective. Ask different people at different vantage points, but that… If we would’ve stayed within our teams and we would’ve had to develop with pixel-perfect mockups done in Photoshop like, “Here you go,” I don’t think we would’ve been fast enough. That was not good for the innovation that we needed. So it’s also like innovation by isolation. It’s good for emergencies. I was at another startup, we had performance issues with our first product. People left teams, brought a consultant in, went into a conference room for a couple of weeks, figured out some major changes that needed to happen, solve them, went back to the teams. This is not a new concept. The Chicken McNugget was saved by an isolated team, SWAT team.

There’s a book called Teamwork. It’s an old book from, I think the ’70s, I have in my bookshelf here, and there’s a story of the Chicken McNugget that you can read about where they brought in a consultant and had a very small team who worked in a different… They didn’t work in their same plant where they were developing the product. They worked in a different plant. They reported straight up to one of the executives at McDonald’s. And yeah, the Chicken McNugget lived on because it was like having challenges in the test marketplace in Indianapolis. So we didn’t make this up. It’s just like some of these things are kind of like, “Oh, it’s like a noticing,” and then you’re like, “Oh, that’s pattern.” So it’s collection.

Running Innovation Teams in Large Companies

Lenny: There’s this idea of a startup within a big company. Everyone’s like, “Oh, it’s just like the startup within a big company. We have all the resources that we need. There’s no less risk, but we can innovate and try new things.” Rarely does it feel like it work out. You’re sharing stories where it does. Is there anything you found or any advice for how to actually be successful in this idea of having a team off to the side doing something innovative and different?

The Growth of SecureDocs

Heidi Helfand: At AppFolio we did this. So there’s a company called SecureDocs; it branched off into its own company and it was just acquired, I believe in 2022. When SecureDocs was happening, I was not on that team. I was on the other teams and I was watching, and again, same pattern. A team was created off to the side and they were given process freedom. They worked in more of a daily sprint style as opposed to the two-week sprint style that our other teams were doing at the time at early AppFolio. And so, one, isolate the team or put them in a different area. We could still see them. We were in this big open room, but it was their team area. I mean we had these impermanent walls between some of the teams. It was their region and they claimed it and they named themselves.

And so, one, separate location. There’s another story in the book about a team that incubated a product idea within Citrix and they were in a garage of all places, so they were really isolated. But just put the team in a different region, make it that area. That’s number one.

Number two, tell other people not to disturb this team. That’s key. And hearing it from a leader is really, really important. No, you’re not going to pull them into something else. They’re working on this other thing. So people need to shed their skin of the other things that they’re working on. If you take a bigger picture, kind of forest through the trees picture, you want people pairing and switching pairs so they’re not single owners of the system. So when they have an opportunity to do something that could be really important to the company beyond one of these isolated teams, they can fade out and not be the only owner that has to transfer knowledge and then field questions for two years on how that system works. You want to build this redundancy in your teams. So that’s like if you really want to plan ahead, do that first. Have that as part of how you operate, building this team redundancy and switching, because then it frees people to not be the only owner of a system and chained to a system.

And so isolate them. Tell people not to bother them. Do pairing and have shared ownership so it’s easier for somebody to switch into something like this. Process freedom. Again, they can do things differently. Ideally they report up to someone that really has decision-making authority and decisions won’t get reversed. Or they have to go through some complex web of like, “Is it okay if we do this?” No, you need a clear decision-making structure. They saw that at the McDonald’s case study as well, which is not in my book, but it’s in [inaudible 00:30:52] book called Teamwork.

And then that group, having that senior leader that they report into, getting the clear lines of communication there is also really important. So not having this heavyweight bureaucracy of, I don’t know, quarterly business updates where everybody’s making a slide deck for two years before they go to that meeting, trying to relieve the team of things like that and make it lighter.

And some of these teams, like SecureDocs became another product at AppFolio that was very, very successful. At one point, I think it was before we went public, it branched off into its own separate entity. I think maybe they shared a board member or something. I don’t know how that worked, but it became its own entity. SecureDocs became separate and then it grew from there. And then it became this wonderful successful product that was recently acquired. People come and go at companies and companies grow and change and morph, and that was one case of departures that it’s like bitter, sweet. You’re happy for your friends and colleagues say, “Oh, he’s going to be a CTO. He’s going to be the CTO.”

There’s this entity. I remember visiting their office in Santa Barbara. It’s great to see your friends succeed and thrive. And we developed other companies in that way.

Success Factors for Internal Startups

Lenny: Awesome. I think it’s really nice to hear there’s many success stories of this idea of a mini little startup within a company, and these are really good tips.

I feel like to me one of the most important ones you’ve talked to. And this is having an executive essentially sponsoring this team and supporting and protecting it versus some managers just like, now we’re going to go do this off to the side, because otherwise no one’s going to really take that seriously.

Heidi Helfand: Yeah, I think that’s really, really important. I’ll also say that things don’t always succeed a hundred percent. I’ve seen isolated teams within companies where someone has the opportunity to sell something, they talk to their friends who are the engineers who build the feature for them, but then it leaves something for other people to maintain later and they weren’t involved in the decisions. And it can be a big mess for all of these patterns there. It’s like kind of like balconies and basements. You can screw it up too. It’s not all stuff is hard. That’s why I like to lean into it and I’ve written about it. Things take effort. The tree is going to drop the leaves and you got to sweep them up. Everything takes work and effort.

Overview of Other Reteaming Patterns

Lenny: We’ve talked about the isolation pattern. I thought it’d be good to talk through the rest of the patterns real quick and share maybe one or two tips for how to be successful or make it work well or better.

The One by One Pattern

Heidi Helfand: Sure.

Lenny: Before you start, actually, I think I missed a nuance and you corrected me, but I think I missed it, which is for the one-on-one pattern, it’s actually describing joining the company specifically not joining a team. Is that right?

The Growing and Splitting Pattern

Heidi Helfand: Yeah. And in the book it might be a little blurred because this is like some of the… Switching and one by one sound very similar, and they do have some Venn diagram overlaps, but I’ll distinguish them as I talk about them.

Lenny: Cool.

The Merging Pattern

Heidi Helfand: So one by one, someone joins your company or they leave your company. So the tip with one by one is when someone joins, help them feel a sense of belonging, and you can do that through not having their first day be them sitting over there alone. You could have someone have a first pair. There’s a chapter in my book about onboarding. This is in the space of onboarding. Also with one by one, when people join, you also need to pay attention to the people who are already there and it’s good for them to know when someone is joining the company; that it shouldn’t be a surprise. So visualizing the hiring and the opportunities is something that I think is a really good idea. It could be challenging for someone if somebody joins and they become their manager, but what if that person wanted to be the manager and then they brought in someone from the outside to become the manager?

So you need to pay attention to the new hires that are joining, help them feel a sense of belonging, get them to talk about themselves, which is said to increase their sense of connection and retention. There’s some research in the book The Culture Code by Daniel Coyle, which talks about that. But then it’s also important to coach the people through change that are already at the company, especially if they weren’t involved in the particular decision, bringing on this new leader that comes in and brings in all their people. So you got to pay attention to different people.

Grow and split is a natural thing that happens when you’re like startup scale up and growing bigger and bigger. The first team probably grows bigger and then splits into two or three. So when the team gets bigger, facilitation and communication tends to break down. So some signals that teams might bring up when they feel like a change might be helpful is the meetings are taking longer. You’re in that case where it’s harder to make decisions. It was easier when there were like five of us, but now they’re 13. The work becomes divergent. They’re working on this one thing, they’re working on something else. No one’s paying attention in the standup so much anymore because this work has diverged. And those are a few of the signals. And then someone typically brings it up. If you normalize the idea that it’s okay for teams to have input into their future structures, maybe they’ll bring it up and decide that, “Hey, it might be better if we split.”

Sometimes splitting though can create dependencies that weren’t there when you were together as one team. So you inherit other problems or you might inherit challenges like, all right, the team decides it’s far effective if they split into two or three, but we just have one product manager, we just have one designer. We just have one person who helps us anticipate quality challenges. So it’s a lot of problem trading when you do a lot of this stuff. Like anything, you have a challenge, how might we solve it? Well, there’s option A, option B and option C. So that’s grow and split and it’s very common I think when your company is growing and changing, kind of like that.

Merging is the opposite of grow and split. Two or more teams combine together. Or at a higher level, a company acquires another company and then there’s a merging that happens. So merging I think is related to when companies downsize or shrink, things consolidate, come together, or again, when at the company level companies combine, one acquires another, gets acquired. How that goes down varies, but there’s this concept called panarchy that I write about in my book that a lot of these changes is changes at the individual level, the team level, the team of teams level, department level, the company level. So yeah, merging. So there’s a business decision that the companies merge together and then changes might ensue.

So maybe the company wants to get ahead on building and having another vertical in their SaaS company. We acquired a company at AppFolio to bring us faster into workflow software for law firms. So we acquired a company based in San Diego, and that got us a couple of years ahead. I remember one of the leaders saying that. So again, we weren’t involved… I wasn’t involved in this decision as an IC at the time. So it could be a business decision for merging at that level. It could be that people leave, there are departures and teams and responsibilities consolidate together. That’s merging. So it could be that kind of shrinking that we’re seeing. It could be that the company is having one leader instead of three and there’s a consolidation and the teams kind of merge together. So it’s the opposite of grow and split.

One activity I do like to do with teams that merge is called story of our team. That’s in chapter 13 of the second edition. So with story of our team, each team makes a timeline of… They stand in order of when they joined their team and they make a timeline with milestones of when they joined their team, when people left, and significant events and things they created that they’re excited about and that they’re proud of. And that they branch together with their newly merged team, and then it’s good to get a shared sense of history. So you have these teams or companies that come together, they make shared timelines, they share their milestones and things that they built that they’re proud of. They tell each other about it and then they have a sense of like, “Wow, we didn’t know that. Oh, I didn’t know that you had built a system like that. We did too.” Or, “We’ve never built anything like that. That is so cool. What did you learn from that?” We get to learn about each other and then we’re together. We’re like, “All right, we’re this merged entity now. What’s next?” Looking out to the future so we have the same shared vision. So I love doing that. There’s different tactics you can do before, during, and after each of these patterns. Yeah, that’s merging.

Isolation we talked about before. Put the team up to the side, give them process freedom, have them report up to a decision maker, tell the other teams not to bother them. Let them work at the cadence that they want to work at. That makes it easier. If you are doing a short-term thing, you got to work it out with the larger entity so you don’t create something in isolation that other people have to maintain. There’s ways that this can be messed up.

And then switching. Switching pattern is really tied to learning and development and fulfillment. It could be that you want to work with other people. Like forming, storming, norming, performing, Tuckman’s model, he forgot the phase called stagnating. Sometimes it feels like we’re in a team for too long. We’re tired of working with these people. We want a little variety. We want to work with that person over there. Or maybe we want to work on a new system. We don’t have the opportunity to do that in our current team, but what if we could work on that system over there with those people? It could totally refresh us. It could be like having a new job within our same company. It could extend the lifespan of the amazing employee in your company. So switching is tied to that kind of fulfillment, which is one of the reasons why I made it separate from one by one and tied that to the company.

The other thing with switching is that you could create safety nets in your company through switching. I just wrote a newsletter post about this yesterday because maybe we’re going to have some more changes this year. Maybe companies are going to be hiring less. I don’t like the thought of companies downsizing or having layoffs or anything like that, but I think to myself, well, have multiple owners of a system. So not only one person is that tower of knowledge that owns that one system. There’s some stories in my book where I interviewed Richard Sheridan, who is the chief storyteller and co-founder of a wonderful company called Menlo Innovations in Ann Arbor, Michigan. They built their company Menlo to have people work in pairs. Not just the software engineers; team members work in pairs and they switch pairs at a regular cadence. And you know that when you’re joining the company because you’re involved in some kind of pairing. So there’s parity from when you’re interviewing to when you’re at the company.

But switching also helps build that knowledge redundancy in your company. A little more about tolerance. So if someone leaves, they don’t leave with all the information in their head. We had that. At that first startup Expertcity, we had some single owners of systems and when they left, it just becomes a challenge and a setback. And at AppFolio we shared a founder between the first startup and the second startup. Many of their early engineers from that first startup went to the second startup.

I was 10th at AppFolio. I was 15th at Expertcity. So we wanted to work together. So it was that global idea of switching one by one or similar. But anyway, at the second startup we had the chance to do things differently. So we had pairing and switching pairs and test-driven development. We had help to do that, but this kind of redundancy built safety into our systems, especially when AppFolio is processing a lot of rent payments. There’s a lot of money. There’s ACH going through. Those are critical systems and it’s very important that things are safe and secure. You don’t want to haphazardly switch people around. You can screw this up, again, that balconies and basements concept. You don’t want somebody over here, they will switch every two weeks and have no say in their team. There’s ways to screw all of this up, but there’s other ways to do it well.

I remember when we were at our first team at AppFolio and we did a grow and split. It grew and it split into two or three teams. I remember there was a loss for some of the engineers who wanted to pair program with some of the other engineers, and they started a regular rotation themselves from one team to the next, and that brought fulfillment. It brought joy. I mean they would see each other in the workspace every day, but they wanted to work together. It brought them learning joy and fulfillment, and I love that. For those who are like keep the team stable and the same forever, I’m like, “Well, what about that?” It brings me satisfaction and joy when I see my colleagues. It’s like autonomy, mastery, purpose, like Dan Pink’s book Drive, when people are really given some agency and the opportunity to work a little bit differently than maybe that traditional boxed version you might see on my bookshelf. You can really create not only products that people love, but companies that people love and want to be at.

Lenny: All these stories of team changes and reorg, it made me think about a quote that one of my managers always used to say about reorging and changing teams is that there’s no perfect org structure. There’s only the best idea you have at the time for what the org could be. And then there’s the issues with that org that you identify as you’re putting in place and then set up processes and systems around to try to catch that dependencies, as you said, or overlap of ownership. Is there anything along those lines that comes up of just things you found of just like, there’s never going to be the perfect way to do it. This is just our best idea at the time and here’s how we deal with the downsides of this approach?

Our Team’s Reteaming Story

Heidi Helfand: Yeah, I think there’s a lot of wisdom to what your manager said and your colleague there because yeah, I mean as time goes on, conditions change. We evolve and change. We’re subject to different influences. COVID happens. We weren’t dealing with that 10 years ago. We grow and adapt and morph. We try to get together and make the best decisions that we can when we’re faced with challenges, and a lot of it is problem trading. We have this challenge today. We decide, oh, there’s a few ways we could handle this. Pros and cons of each solution. It’s like the Toyota Kata, like grasp the current condition. You’ll experience you have challenges. What’s the next evolution or the next target condition? How might you get there? And then you’re there and you’re like, okay, grasp the current target condition. What’s it like? What are you experiencing? Oh, we might try this. We’re always transforming from the current state to the future state.

So to that, I would ask people, well, how do you want that to be? And how do you want to show up and be as a leader? You want to just be like, “All right, I’ve got to get this done. The reorg is done by an email and we’re just sending it out, or this small team change. And here it is; it’s done. Goodbye.” Or is it a little bit where you get people’s input? And that in itself, you got to weigh what you’re dealing with, again. But I like to think about that. What kind of leader do you want to be? Leaders need patience. It’s hard to be a leader. It’s challenging, but what kind of an environment or vibe do you want to cultivate in your teams and what do you want the people to be like?

I have a degree in teaching English and applied linguistics, and I remember studying Paulo Freire and other educational problem-posing methods of education. We have these teams that solve these complex problems and challenges and build these really cool things for customers. Let’s involve them in some of the org decisions that are going to be part of their daily life. Really, you like that idea. Again, it’s not perfect. You can’t involve people on everything, especially if they’re wide-scale changes that you just can’t.

Lenny: Along these lines of doing things badly sometimes, you have this whole section on anti-patterns of reteaming. I think there’s about five of them. I don’t know if you have these all top of mind, but if you do, I’d love to hear some anti-patterns.

The Isolation Pattern

Heidi Helfand: Yeah. Well, one of them is people always think that reteaming is, you have a pool of people and you’re assigning them to a bunch of different projects like, “Okay, you’ll work 10% on this one, 5% on this one, 20% on this one. We are going to allocate the resources from our component-based teams into these different projects.” We did that in Waterfall like many years ago, but that doesn’t really work. A lot of the times the percentages don’t add up. It’s very hard for people to multitask and be involved in multiple efforts at once. It’s hard for the brain with all the context switching that needs to happen in that case. So I call that the percentage anti-pattern.

There’s also, I probably wrote about it like, poof, they’re gone or suddenly they’re here. Reteaming or having people suddenly show up and you weren’t expecting them or suddenly they’re gone and there’s no communication around it whatsoever, that’s another anti-pattern.

Lenny: One of the ones I love is this idea of spreading high performers. This idea of we’re going to spread the high performers across other teams.

The Switching Pattern

Heidi Helfand: That’s an AppFolio story. Jon Walker was telling me back in the day that… I mean, he did this experiment. He had this thought that many of… There’s one team that was like, I guess they were delivering at this cadence that they loved and they were building this stuff and there’s this energy and you can almost feel it. Like let’s just spread the people from that team across the other ones and then we’ll have that. And it didn’t work. He didn’t have that. It didn’t happen. And that was a visceral learning for him that it doesn’t essentially work. And people are like, what does it take to be a high performing team? What does it take to have that magical team experience where there’s that chemistry and the people are together? And there’s stories in the book. Damon Valenzona was telling me one about how it’s like’s a band and we’re with off each other. We’re creating this music together. So John felt like he essentially destroyed that when he split up that team. So that’s the story that inspired that anti-pattern.

Lenny: The reason people are worried about reteams and reorgs is this… A lot of times it’s exact reason that you just shared, which is our team is amazing. I don’t want it to change. I don’t want to split. I don’t want to add anyone. I don’t want to remove anyone. I guess is there anything else along those lines to help people feel better about, no, this is actually going to be okay and/or it’s inevitable. It’s not going to last.

Safety Nets for Switching

Heidi Helfand: I think sometimes you have that awesome team situation. It’s an enjoyable experience. People are learning. You’re looking forward to it every day. You’re delivering the stuff that people love. You’re telling people what’s going on. You have that matched expectation where people aren’t breathing down your neck because it’s late or something. Sometimes you want to keep that team together. You don’t want to destroy that dynamic. But the thing is, maybe that’s a small startup that grows and you need to grow because you have a bigger vision and it needs to be more than these 10 people. And so there is sometimes this feeling of loss, like, “This is our company. This is my experience at this company of 10 people, but suddenly we’re 20 people. It doesn’t feel the same like it did anymore and it feels different.”

And people, they always ask the question, “How do we maintain our culture? It feels different than it was before.” The thing is, it is different, and our companies go through stages. The company of today is not the company it was a year ago. The people turn over and change, what we work on turns over and change. The whole world and industry and global events change and put different pressures on us, and we got to live in this global context. So nothing lasts. Sometimes I have a picture of myself holding an ice cream cone that’s melting. Not to be a total downer, but appreciate it when you’re on a team and you love it and it’s amazing because these are our lives and we have to have gratitude and appreciate what we have because naturally things evolve and change. It’s just inevitable. So we appreciate what we have.

A lot of us can look back on our careers and remember those times when we were, in my case, skipping through the halls because I was so happy. And I was like I couldn’t even tell you. Well, why was I skipping through the halls at that moment? What was it? Well, it was the people and the conditions and what we were doing and the time, the era almost because yeah, it does change.

There’s a book by Ichak Adizes called Managing Corporate Lifecycles. It’s one that many of us read for years at AppFolio, maybe the previous company as well. The Adizes Institute influenced some of our leaders and they influenced us with this. And it talks about the different stages of companies from birth. There’s go-go stage, maturity, death of companies. These are like lifecycles. The company grows and changes and morphs and changes. The people in the teams do that as well. I have an ecocycle in my book where I talk about that kind of aging and changing. Then there’s a disruption and you have a new beginning. We’re part of these stories that are in progress. This is not an unchanging, unmoving entity that we work in. So just be kind to each other, enjoy your experiences and learn as much as you can.

Lenny: It reminds me of advice Sheryl Sandberg shared when she came to the Airbnb offices. Someone asked her: “What advice do you have to deal with all this constant change?” Like the quote I shared at the top of the episode of every six months, there’s a massive reorg. Our culture’s changing. Teams keep changing. It’s constant flux. What is your advice to deal with that? And her advice was: That is good. The fact that you’re growing so fast and having to change is the best case scenario because the alternative is you are not growing and it’s much harder and much more painful because the changes are much harder. People get let go. Your business may go away. So her advice is just, this is good. Change means things are… And growth leads to change, especially hypergrowth, and that you should appreciate this time versus be afraid of it and think that it’s a negative.

Knowledge Redundancy and Safety

Heidi Helfand: And it seems like she had such a wide vantage point and could see the forest through the trees of the fact that, well, this company’s doing well and this is why we’re growing and changing. And I remember one of my leaders, CTO Jon Walker, AppFolio, he told me that once too. He was like… I’d be having a problem or something and I’d come to him and he’d always say to me, “It’s always great to be at a successful company, Heidi.” And it’s like, well, yeah, sometimes you don’t think about the finances when you’re in your day to day and you have a problem with another person or they come to you and they have a problem with this other person. But in the grand scheme of it, how is the company doing? It’s really a critical vantage point that we need to remind ourselves of. But yeah, I wouldn’t say all change is always good. Your mileage may vary there, but the general idea that the company is doing well, you’re growing and changing, you’re trying to make things happen, I think is definitely the space I’d rather be in than the opposite.

The Satisfaction of Switching

Lenny: And I think it’s especially true for people that haven’t worked at a company that didn’t work out where they think this sucks when really this is pretty good compared to all the things that could be happening.

Heidi Helfand: Yeah, yeah, definitely. So we coach and help each other as we go along.

No Perfect Organizational Structure

Lenny: Final question before we get to a very exciting lightning round. Used to work with John Cutler, who was a previous guest on this podcast, and he had a question that he wanted me to ask you. He said that, “Heidi is one of the best listeners I’ve ever worked with.” And so the question is, what’s your secret to being a good listener?

The Leader You Want to Be

Heidi Helfand: Well, listening is a muscle to build and to always work on. You got to put your attention out. Focus on the other person. Sometimes if I’m looking down, maybe I reconnect and look at them. You got to read body language and other things. I’m trained as a co-active coach, which involves different levels of listening. So you have level one, which is internal listening. Like if you and I are talking, but I’m thinking about what am I going to have for lunch? I’m in level one. I’ve got to redirect it out to you and focus on you. So when I focus on you is I’m in level two listening. I’m putting my attention out and I’m really anchoring towards you. It’s a coaching skill.

And then level three is global listening, environmental listening. If a marching band suddenly walked behind you, I’m going to point that out because it’s in my field. I’m not going to ignore that. I’m going to bring that up. So we pay attention to the vibe and the feel in the room and where we’re at. But then also if you’re talking about something and suddenly you go like this or you have this kind of sudden pain in your neck when you’re talking about this one thing, I might notice that you’re doing this and touching your neck because that’s information. That’s a kind of listening, and so I might ask you about that. Or if the face turns red or you look down or away, it’s another kind of listening. So Co-Active Training Institute, coactive.com is my co-active coaching training, so I learned it from them, Henry Kimsey-House and-

Common Reteaming Anti-Patterns

Lenny: Wow, that is an awesome answer. There’s a lot of depth there. So coactive.com, I’m going to check that out. So you actually got trained in this skill. Okay, that’s great. That’ll make people feel better. They’re like, okay, amazing. I’m going to check this out. I’m going to try to be a better listener through the rest of this podcast episode from these tips.

Heidi Helfand: I will say that sometimes I’m not a good listener though.

Team Transience and Cherishing the Moment

Lenny: Yeah, so it goes. Heidi, is there anything else you wanted to touch on or share before we get to our very exciting lightning round?

Heidi Helfand: I don’t think so. I really appreciate your questions and talking with you.

The Art of Listening

Lenny: Well, we’ve reached our very exciting lightning round. Are you ready?

Heidi Helfand: Yeah.

Rapid Fire Q&A

Lenny: All right. First question, what are two or three books that you’ve recommended most to other people?

Heidi Helfand: Leading Intelligent Teams is one, Liberating Structures is another one, and of course, Transitions by William Bridges. I also like the Leader’s Guide to Participatory Decision-Making.

Lenny: Is there a favorite recent movie or TV show that you really enjoyed?

Heidi Helfand: I did like The Bear, the cooking-related show, the restaurant-related show, and gets into the hospitality industry. I really like that. Movies, there isn’t really one that stands out. I always look forward to being on an airplane to see what movies are playing, but no movie for you.

Lenny: What is a favorite interview question that you like to ask people that you are interviewing?

Heidi Helfand: I always like to ask people, “Well, why do you want to join our company? What is it about working with us that would be exciting for you? Why our company as opposed to another one?”

Lenny: What do you look for in their answer that is a good sign?

Heidi Helfand: They have some knowledge about what we do, what we build. Maybe they bring up that they’ve noticed something on one of the websites or a product launch that we just announced, just that maybe it’s part of their story in their career. They’re going in this direction, and they heard about us and they thought, “Wow, I would love to work on that.”

Lenny: Is there a favorite product you’ve recently discovered that you really love?

Heidi Helfand: I’m very into vintage clothing and specifically real wool cashmere, not synthetic blends. I also like vintage blazers. A lot of the times where I’m giving a talk, I’m wearing a vintage blazer. I really like the clothing and design, and I kind of really, really love unusual vintage pieces that I could find, but they do need to… A lot of the fast fashion that’s out there today is a lot of these blends with these materials that you’ve never heard of, but there’s something special about vintage cashmere, for example.

Lenny: Do you have a source for some good stuff? Is it like eBay? Is it stores locally? Is there a site? Is there somewhere you’re finding some good stuff?

Heidi Helfand: I travel around the world and I give talks on reteaming. I do workshops. And usually I go to vintage and antique stores. I was just in Berlin. I was doing that. I was doing it in London. And yeah, I love thrifting, Salvation Army, Goodwill, any of these places that we have in many of the US cities, the Humana line of stores that I’ve been to in Europe and other places. I try to find the small, unusual antique places as well. My aunt’s an antique dealer in Michigan, and she doesn’t specialize in vintage clothing, but I just love that idea of discovering unique and unusual things that maybe they remind you of times in the past. Maybe you find that, “Oh my gosh, we had that mug back in the ’80s or whatever, or in the ’90s.” Things can kind of remind people of other times. So I like that. I think there’s information stored in unique items.

Lenny: Beautiful. I bet Berlin has some really cool vintage stuff, really wacky stuff.

Heidi Helfand: Yeah, there’s a lot of really interesting places to explore, and I think it’s just so much more interesting than some of the brand new kind of stuff.

Lenny: Agreed. Two more questions. Do you have a favorite life motto that you often find yourself coming back to or sharing with friends or family, either in work or in life?

Heidi Helfand: I like asking people how can you be kind to yourself?

Lenny: Say more.

Heidi Helfand: I ask myself that too. I used to run a lot in Santa Barbara at Ellwood, which is a beautiful trail that you can go down to the ocean, you come back up. It’s like More Mesa in Santa Barbara, and I would run and then I’d be like, “God, this is so hard.” And then I would walk for a little while and I’d think to myself, “Well, how can I be kind to myself? I mean, what am I doing here? Does it have to be fast? No. I am here to decompress and enjoy, so how can I be kind to myself?” I think sometimes I get hard on myself or have very high expectations kind of achiever mentality, and I’ve learned through the years that it’s okay to slow down. It’s okay to not go, go, go the whole time. So I would ask other people that as well, especially if they’re going through a challenge or burning midnight oil or whatever. It’s like, “What about self-care? How can you be kind to yourself?”

Lenny: Beautiful. Final question. I was scouring your LinkedIn and I saw a quote from the CTO of AppFolio in his endorsement of you. Said that you were the unofficial director of fun at AppFolio. Is there a story that comes to mind of something that you did at AppFolio that created a lot of joy and fun for the team?

Heidi Helfand: We had these hack days, and I think they do that to this day. So twice a year we’d bring people together and we copied and learned from Atlassian. I remember we had calls with some coaches from Atlassian for how did they do their ShipIt Day, or they originally called it FedEx Day, changed it to ShipIt Day. We followed their model and we’d had this two o’clock on Thursday at two o’clock on Friday where we’d build whatever we wanted and we’d have a theme, and then we’d have goofy prizes at the end that were like traveling trophies. One of them was like a clickety-clack keyboard that we spray-painted gold by the railroad tracks, but people could work on anything. There were teams that formed… We did it with a self-selection marketplace. People formed their topics and teams, and one team hid geocaches throughout Santa Barbara. They’re there to this day because we registered them with the Geocaching website. Another team built a vintage video game machine, and it was in the dev room. Another one they catapulted. They built this… Is it a trebuchet?

Lenny: Yeah.

Heidi Helfand: That catapult this fruit in the parking lot. I don’t know how we got away with that, but we were in the early days. We did a lot of fun stuff like that, and you could work with different people, build these larger relationships, which later makes it easier for reteaming, because then later if you reteam, you’re not strangers with people, so you want to cultivate the community. So we had this department of fun. We would plan the fun in a variety of other ways as well.

Lenny: So fun. Heidi, you’re awesome. I think we’ve helped a lot of people feel better about the endless change that they’re probably going through right now. Two final questions. Where can folks find your book, find you online if they want to reach out, and how can listeners be useful to you?

Heidi Helfand: You can go to heidihelfand.com or Google my name and I come up. Heidi@dynamicreteaming.com, heidi.helfand@gmail.com you can find me. I’m out there. And yeah, I love to work with companies and teams going through change, and I do that in a variety of ways. Teach workshops, do talks. So if any of this is interesting, reach out.

Lenny: And then do you also consult and work with individual companies or not?

Heidi Helfand: I do. Yeah. I do that now. I like to work on a retainer basis or I’ll even join a team, so looking for the-

Lenny: All right.

Heidi Helfand: … next one.

Lenny: Amazing. And we’ll link to all this stuff in the show notes. Heidi, thank you again so much for being here.

Heidi Helfand: Thanks so much, Lenny.

Lenny: Bye everyone.

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Glossary

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