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

Reteaming 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. (laughs) If we could just build the software, deliver to the customer, get the product market fit. "Hey, are... Have we delighted them or not?" If only it could be that easy. No, we have the people there, so let's focus there too.

(instrumental music) 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. This episode is brought to you by productroadmap.ai and Ignition. Productroadmap.ai is the first AI roadmapping suite. It helps ensure roadmaps drive revenue by instantly aligning product with your sales and marketing teams to capture upsell opportunities. Built by early leaders from Rippling and Craft, it automatically identifies feature gaps from your CRM data and your customer conversations, adds them to shareable roadmaps easily prioritized by revenue impact, and then seamlessly closes the loop with sales reps via targeted notifications when feature gaps are closed. As part of Ignition's broader go-to-market operating system, productroadmap.ai can also help create better handoffs and collaboration with product marketing teams by giving both teams the tools to research, plan, orchestrate, and measure the process of building products and going to market. Packed with integrations, AI automation, and communication tools, it's truly a one-stop shop for product and marketing to bring things from concept to launch. To sign up, go to productroadmap.ai and use promo code Lenny to get 75% off your first year. This episode is brought to you by Hex. If you're a data person, you probably have to jump between different tools to run queries, build visualizations, write Python, and send around a lot of screenshots and CSV files. Hex brings everything together. Its powerful notebook UI lets you analyze data in SQL, Python, or no code, in any combination, and work together with live multiplayer and version control. And now, Hex's AI tools can generate queries and code, create visualizations, and even kickstart a whole analysis for you all from natural language prompts. It's like having an analytics co-pilot built right into where you're already doing your work. Then, when you're ready to share, you can use Hex's drag and drop app builder to configure beautiful reports or dashboards that anyone can use. Join the hundreds of data teams like Notion, AllTrails, Loom, Mixpanel, and Algolia using Hex every day to make their work more impactful. Sign up today at hex.tech/lenny to get a 60-day free trial of the Hex team plan. That's hex.tech/lenny. Heidi, thank you so much for being here, and welcome to the podcast.