Dynamic Reteaming: Mastering Team Change for Excellence Using Your Listening Muscle with Heidi Helfand

We live in a world of ever-changing team dynamics. How do we use listening and communication as a tool to help individuals and teams adapt well to change, manage conflicts and challenges, learn and grow?  How do team structures influence finding solutions to big challenges while creating meaningful people experiences? And what are the various ways we foster listening to help us in decision-making?

Heidi Helfand is the author of the book Dynamic Reteaming. She coaches software development teams using practical, people-focused techniques, with the goal of building resilient organizations as they double and triple in size.

Heidi is currently VP of Engineering at Kin Insurance, which offers affordable coverage to homeowners in catastrophe-prone regions. Her 20+ year career in SAAS launched Procore Technologies and AppFolio to IPO and Expertcity to acquisition by Citrix. She was on the original development team that built GoToMeeting and GoToWebinar. Heidi is based in Southern California.

In this episode, Heidi shares how she nerds out with listening because it is hard and a life-long practice. She highlights that to have effective communication, it pays to give someone the space for them to articulate what they want to convey. Often, solutions can be found which help craft decisions, whether their or yours.

She also talks about her book ‘Dynamic Reteaming’ which focuses on building effective teams amidst continuous team change. 

“People are going to come; people are going to go; your teams are going to change. Focus there. Don’t go for the quest for stability, because it’s unrealistic.” – Heidi Helfand   

Listen IN Notes:

03:22 – On discovering the power of listening: You rediscover the power of listening all the time, if you take the time to stop talking and try to focus on another person or what’s going on around you, you get clues that might surprise you.

03:46 – A moment she was surprised by the clues when she stopped talking: When you’re talking to another person, and you leave space, they most likely say things or offer solutions to their challenges that you wouldn’t have thought of. 

05:44 – Leveling the playing field and getting all voices heard: suggesting self-management strategies

08:26 – Facilitation techniques for small and bigger groups so that all voices are heard and everyone’s participation is encouraged.

13:02 – What makes listening important: be generous with your attention, it might really be life-changing for the other person because they feel like its a gift, especially when they have experienced otherwise.

15:03 – What it feels like for Heidi to experience that gift of listening

16:50 – Talking about her book on dealing with team change: Dynamic Reteaming by Heidi Helfand 

21:07 What she thinks about team change: When you find that team chemistry, which I think is almost magical, in some cases, you want to keep it . But just like other things, nothing stays the same; enjoy it while you have it.

22:24 Sharing how writing her book was a process of discovery and how she used grounded theory.

26:32 – Building a communication strategy around a structure: You have a picture of the current state and the future state. And then you write an FAQ document as one structure. Then you talk to different groups of people and iterate this document that tries to bring everybody to the same point of understanding about this change that we’re going to have.

38:42 – Heidi’s advice to a new manager: You might not feel like you’re always prepared from the start when you’re doing something new. But you don’t have to be perfect. You’re going to learn along the way.

41:51 – Inspiring words to hear from Heidi: It’s a busy world right now. It can feel quite chaotic and overwhelming, with everything we’re dealing with, with COVID, with working differently. Take care of yourself, prioritize your health and your family’s health, and just do the best you can. There are a lot of new challenges that we’re facing, globally. Give people a little grace and space and allow for messiness. We’re all in this together.

Key Takeaways:

 “I think you can reteam for learning and fulfillment to get into a better place. We want people to feel like they’re excited to come to work each day, they’re working and they’re learning, and they’re challenged. And it’s an enjoyable experience.” –  Heidi Helfand

“You might not get it right the first time when they join a team. But in talking with people, listening to what they want to do, where they want to go. Really cultivate a kind of career conversation and you can figure out how you can best support them.” – Heidi Helfand

“I try to listen as the default. Sometimes it’s hard if you’re particularly excited about a topic. You might want to get your words in. But I find that if you leave the space, it just allows other things to happen, and that’s probably a good thing because it’s more collaborative.” – Heidi Helfand

“You want to engage people in problem-solving, so they come up with their solutions. They figure out how they want to roll them out, and then they reflect on them and try to apply this as learning going forward.” – Heidi Helfand  

“I do always think you need a persistent visual of all of your people in teams. This is not an org chart. I’m talking about the software development companies that work in cross-functional teams; how you’re organized is important. And I just like doing that in an open, accessible way, like a Google sheet where anybody can make changes to it. Because as the teams change and own their change, people are going to move around. And so everybody keeps this shared thing updated.” – Heidi Helfand 

“It’s always this continual need to…refocus out and pay attention to other people. (When you focus and listen), it helps make decisions that help you figure out what to do.” – Heidi Helfand


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