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Heidi Helfand

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76
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2024-01-18
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2024-01-18
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  1. “Mockups done in Photoshop, like here you go. I don't think we would have been fast enough. That was not good for the innovation that we needed. So it's like also like innovation by isolation. It's good for emergencies. You know, I was at another startup. We had performance issues with our first product. People went into”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “So it was a privilege, and I was like delighted to be part of this other team. And yeah, I was really, really exciting. So then looking back over the years, I was like, yeah, you know, isolated teams, beneficial silos. You know, again, it's going against green of what some of these books say. You want to de-silo everything. No. Sometimes there's a reason why you have a problem, you want to solve the problem. This was like, were we going to have, I mean, was this company going to go into? Like, 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. And, you know, ever since. So yeah, that's the story of Expert City. And from my perspective, ask different people. I have different vantage points. But, you know, that if we would have stayed within our teams and we would have had to develop with pixel perfect.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “Create a forgotten password flow because, like, none of these patterns existed back then. And like, we got to do this stuff. We got to deploy. Like, you know, more frequently. And the product was called Go to MyPC, where you could see and operate someone's computer from a distance. And that, you know, 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 go to meeting and go to webinar as a technical project manager at that time. And yeah, so taking a team off to decide, giving that team process freedom, they didn't want us distracted from the drag, from the, you know, when you're working on an existing product line, you get this cadence and it can become a mature cadence. You know, 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 maybe.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “And so it was like do or die. I mean, we had to shift. This was like before Lean Startup. So four subsidy epithy was the book. It was the manual. It was like 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, right? 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 like liberated from that. We got to work in other ways. And I remember, you know, working with an engineer and like we were figuring out how to like”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “And I get it. I just didn't get it. I cried. I was like, I acted out. I sent this email. Like, how can we kill the marketplace that must live? You know, I was like, like, 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. 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.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “On the marketplace, we're not going to do that product anymore. We're killing it because nobody's buying it. And like made six bucks or something last month. And he said go to the beach. You know, 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, so I remember that day and I'm looking around my office at all these flows on the walls, like really like, you know, these were domains, like kind of like domain-driven design was like all these like web domains and which interactions were going to happen and all these hopes and dreams. And it was the first time in my career where something was, you know, we were told not to work on something. And it wasn't paused. You know, some people say, oh, we're going to pause this and they never get back to it. This thing was like gone.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Place this like eBay of services is what we talked about in the early days. And I was like really into this. This is 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. I was like my title was like navigation designer. We made this up. So I was very into like it was before the words like UX and other things people were talking about information architecture and other subgenres 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 like in there and you 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, we are stop working.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “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 is called Expert City. 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, you know, the vision was global worldwide experts. We were going to be like this market.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Our retaming 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, you know, again, reorganization is a traditional word. It implies on the large. It implies top-down changes that you have no san. It's just, it's something different than what I consider re-teaming, which is these five patterns that happen at different levels.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “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. Teems grow bigger and then they split into two or more teams. Opposite of grown 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 differences.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “Make a schedule, bias 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.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “Product market fit. Hey, have we delighted them or not? If only it could be that easy. No, we have the people here. So let's focus there too.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “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 they're part of the org evolves and changes, 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, reaming is hard, reorg are hard. You can't lump them all into one thing with, you know, 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, you know, retaining 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”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “Write about it, and I credit her to that pat waters she's awesome. And, you know, so a lot of the times it's kind of like, you know, 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, right? You're getting acquired. Like you're probably not going to have a stand-up meeting and talk about, should we get acquired or not? No, you're not part of that decision, right? How is the change going to? Going to get rolled out, or how are we going to do it? You know, 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.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “Changes in any part of your life. I mean, his book is not written about software development or product development. You know, 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. It's called Ride. And we had a chief people officer at ProCore, and she's now at UKG Pat Waters. 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. I Googled this for a while. I couldn't find anything on it and encouraged her.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “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, you know, 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, you know, and leaders can, you know, paint the vision and picture about the benefits of the new reality and the purpose and why we're here and anchored at 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”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “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.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “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 retaming activities when they're changing their strategic priorities. He talks about this globally. Very, very interesting space. And it's even more open than putting the names on the whiteboards. They have teens 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. And 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, you know,”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “For this, and then they could have their discussion. So I really like that the opportunities were shared and presented. So it wasn't some sort of thing that happened. Know in some kind of back room for the whole time, like we like unearthed the beginning of a plan. I think sometimes you. When you convene people for a meeting to talk about anything, it's good to have like a starting point. So we had this starting point. We had a variety of different things. And I call it whiteboard retaming in my book. And I write about that.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “It's like when somebody is suggesting that maybe you do something different or that something different happens, you know, sometimes it can be kind of triggering. Like 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 teen structure with everyone's names on it. It had like 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?”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “I really like it when there's transparency in reorgs. There's a story in my book from Christian Linwall at Spotify about how they reorged a large infrastructure team. And they visualized it on whiteboards and brought people over to the whiteboards to see the future teen 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 like 80 people involved in this platform organization that was splitting from two large kind of 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.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “That 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. I guess that's where I live and breathe.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “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. You know, there's this, there's a reason we're there as a business, but there's also a lot of company building that happens and building the people structures and just kind of 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 in my career helping make teams and organizations successful So there is this people layer however you know 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 and getting product market fit talking to customers”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “If you end up fast growing company or a shrinking company, look there, don't look at trying to fight the natural evolution. So I was just trying to prove a point and to illustrate that teens 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.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “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, like 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 know, 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 teams kind of morphed and changed. So I feel like”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “Retaming is hard, reorgs are hard. You can't lump them all into one thing with, you know, 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 all late, it could be that easy. No, we have the people layer. So let's focus there too.”

    2024-01-18 · Lenny's Podcast · The art and wisdom of changing teams | Heidi Helfand (author of Dynamic Reteaming) · IDENTIFIED FROM THE TRANSCRIPT · source