Heidi Helfand (author of Dynamic Reteaming)18 January 2024

The art and wisdom of changing teams

8Frameworks

12Insights

Episode overview

Heidi Helfand explains why team change is inevitable and why organizations should give the people layer as much attention as products and delivery. She presents five reteaming patterns—one by one, grow and split, merging, isolation, and switching—and describes practical ways to manage each. The conversation also explores transparent reorganization, innovation through isolated teams, knowledge redundancy, common anti-patterns, and the listening skills Heidi learned through co-active coaching.

Key ideas

Reteaming occurs through five patterns: one by one, grow and split, merging, isolation, and switching.
Transparent reorganizations can expose opportunities, surface design mistakes, and give employees meaningful input while retaining a clear decision-maker.
Isolated innovation teams work best with process freedom, protection from distractions, an empowered executive sponsor, and direct decision-making lines.
Growing and splitting teams can improve communication and focus, but may create new dependencies and shortages of shared specialist roles.
Switching people or pairs can improve learning and fulfillment while creating knowledge redundancy and reducing single-owner risk.
Common anti-patterns include allocating people fractionally across many projects, making unexplained personnel changes, and scattering high performers in hopes of reproducing team chemistry.
There is no permanent perfect organization structure; teams continually trade problems as company conditions, priorities, and life-cycle stages change.
Good listening requires deliberately moving attention from internal thoughts to the speaker, while also noticing body language and the wider environment.

Transcript available · source text is retained privately and is not published

Frameworks in this episode

Innovation6 steps

Innovation by Isolation

The beneficial silo: how to actually make a startup-within-a-company work.

Read →

Leadership4 steps

Knowledge Redundancy Through Pairing and Pair Switching

No single owner of any system — pair, rotate pairs, and your org becomes fault-tolerant.

Read →

Leadership4 steps

RIDE — Decision-Making Clarity for Change

For any change, name who Requests, who Inputs, who Decides, and who Executes.

Read →

Communication5 steps

Story of Our Team

A merge ritual: two timelines on a wall become one shared history.

Read →

Leadership6 steps

The Five Patterns of Dynamic Reteaming

Every team change is one of five patterns — name it, then manage it deliberately.

Read →

Leadership4 steps

The Reteaming Anti-Patterns

The three ways leaders reliably wreck a reorg: percentages, poof, and spreading stars.

Read →

Communication4 steps

The Three Levels of Listening

Internal, focused, global — know which level you're on and deliberately move up.

Read →

Leadership5 steps

Whiteboard Reteaming

Roll the draft org chart out in public and let the people in it fix it.

Read →

People & resources mentioned

Attributed to the moment in the episode. Timestamps are approximate.

People · 14

Heidi HelfandMentionsafter two decades in the tech industry Heidi became fascinated with how teams are organized
“today my guest is Heidi helland”
▶ Watch at ~0:00approx.
Heidi HelfandCoinedafter two decades in the tech industry Heidi became fascinated with how teams are organized
“in her book Dynamic reteaming Heidi delves deep into why change is actually good for your teams”
▶ Watch at ~0:30approx.
John CutlerMentionsI talked to John Cuddler actually and he gave me this framework that is like completely stuck in my mind
“huge thank you to John Cutler for introducing me to Heidi”
▶ Watch at ~1:00approx.
Lenny RachitskyMentionstoday we've got another very special compilation episode something I've been pulling on more and more with the podcast and the newsletter
“thanks Lonnie great to be here”
▶ Watch at ~3:30approx.
Christian LyallMentionsmentioned
“there's a story in my book from Christian Lyall at Spotify about how they reorg a large infrastructure team”
▶ Watch at ~8:00approx.
Chris SmithMentionsmentioned
“Redgate software in Cambridge UK Chris Smith is a colleague of mine”
▶ Watch at ~10:30approx.
Daniel CoyleCoinedmentioned
“there's some research in the book the culture code by Daniel Coyle”
▶ Watch at ~36:00approx.
Bruce TuckmanCoinedmentioned
“forming storming norming performing tuckman's model”
▶ Watch at ~42:00approx.
Richard SheridanMentionsChief storyteller and co-founder of Menlo Innovations
“Richard Sheridan who is the chief Storyteller and co-founder of a wonderful company called meno Innovations”
▶ Watch at ~43:30approx.
Dan PinkCoinedmentioned
“it's like autonomy Mastery purpose it's like Dan Pink's book drive”
▶ Watch at ~46:30approx.
Damon ValenzonaMentionsmentioned
“there's stories in the book Damon valenzona told was telling me one about how it's like it's a band”
▶ Watch at ~52:00approx.
Ichak AdizesCoinedmentioned
“there's a book by sakadas called managing corporate life cycles”
▶ Watch at ~55:00approx.
Sheryl SandbergMentionsI was at a fireside chat with Cheryl Sandberg once at Airbnb
“advice Cheryl Sandberg shared when she came to the Airbnb offices”
▶ Watch at ~56:30approx.
Henry Kimsey-HouseCoinedmentioned
“co-active training institute coactive domcom is my coactive coaching training so I learned it from them Henry kimsey house”
▶ Watch at ~1:00:30approx.

Resources · 29

Dynamic ReteamingCoinedbook · Heidi Helfand
“in her book Dynamic reteaming Heidi delves deep into why change is actually good for your teams”
▶ Watch at ~0:30approx.
IgnitionMentionssoftware · Ignition
“as part of ignition's broader goto Market operating system”
▶ Watch at ~2:00approx.
HexRecommendssoftware · Hex Technologies
“heex brings everything together its powerful python or no code in any combination”
▶ Watch at ~2:30approx.
Dynamic ReteamingMentionsbook · Heidi Helfand
“it's called Dynamic ret teaming the art and wisdom of changing teams”
▶ Watch at ~4:00approx.
SpotifyMentionssoftware · Spotify
“Christian Lyall at Spotify”
▶ Watch at ~8:00approx.
ProcoreUsescompany
“we did this at procore as well inspired by Christian and his story”
▶ Watch at ~8:30approx.
Redgate SoftwareMentionscompany
“Redgate software in Cambridge UK Chris Smith is a colleague of mine”
▶ Watch at ~10:30approx.
UKGMentionscompany
“she's now at ukg Pat Waters”
▶ Watch at ~14:00approx.
ExpertcityMentionscompany
“your time at a company called expert city”
▶ Watch at ~20:00approx.
The Four Steps to the EpiphanyUsesbook · Steve Blank
“four steps The Epiphany so we had built this thing we spent all this time on this Marketplace but nobody would buy it”
▶ Watch at ~23:00approx.
GoToMyPCCoinedsoftware · Expertcity
“the product was called go to my PC where you could see and operate someone's computer from a distance”
▶ Watch at ~24:00approx.
GoToMeetingCoinedsoftware · Expertcity
“we built go to meeting and go to webinar”
▶ Watch at ~24:30approx.
GoToWebinarCoinedsoftware · Expertcity
“we built go to meeting and go to webinar”
▶ Watch at ~24:30approx.
Chicken McNuggetsMentionsproduct · McDonald's
“the Chicken McNugget was saved by an isolated team SWAT team”
▶ Watch at ~26:30approx.
TeamworkMentionsbook
“there's a book called teamwork it's an old book from I think the 70s”
▶ Watch at ~26:30approx.
McDonald'sMentionscompany
“they reported straight up to one of the executives at McDonald's”
▶ Watch at ~27:00approx.
Ahrefs Webmaster ToolsRecommendstool · Ahrefs
“it's called hre's webmaster tools it's free and it can help you bring more traffic to your website”
▶ Watch at ~32:30approx.
The Culture CodeMentionsbook · Daniel Coyle
“there's some research in the book the culture code by Daniel Coyle”
▶ Watch at ~36:00approx.
Menlo InnovationsMentionscompany · Richard Sheridan
“a wonderful company called meno Innovations in anber Michigan”
▶ Watch at ~43:30approx.
DriveMentionsbook · Dan Pink
“it's like autonomy Mastery purpose it's like Dan Pink's book drive”
▶ Watch at ~46:30approx.
AirbnbMentionscompany · Brian Chesky, Joe Gebbia, and Nathan Blecharczyk
“Cheryl Sandberg shared when she came to the Airbnb offices”
▶ Watch at ~56:30approx.
Co-Active Training InstituteUsescourse
“co-active training institute coactive domcom is my coactive coaching training”
▶ Watch at ~1:00:30approx.
The Facilitator's Guide to Participatory Decision-MakingRecommendsbook
“I also like the leader guide to participatory decision making”
▶ Watch at ~1:01:30approx.
The Surprising Power of Liberating StructuresRecommendsbook
“liberating structures is another one”
▶ Watch at ~1:01:30approx.
Leading Intelligent TeamsRecommendsbook
“leading intelligent teams is one”
▶ Watch at ~1:01:30approx.
TransitionsRecommendsbook · William Bridges
“and of course transitions by William Bridges”
▶ Watch at ~1:01:30approx.
ShipIt DayUsesevent · Atlassian
“how did they do their shipet day or they originally called it FedEx day changed it to shipet day”
▶ Watch at ~1:07:00approx.
AtlassianUsescompany
“we copied and learned from atlassian”
▶ Watch at ~1:07:00approx.
Lenny's PodcastMentionspodcast · Lenny Rachitsky
“you can find all past episodes or learn more about the show at Lenny podcast.com”
▶ Watch at ~1:10:00approx.

Spot an error or want something removed? Request a correction or removal.

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 2

Myth Buster05:00

Stop Trying to Keep Teams Perfectly Stable

Heidi pushes back on the standard advice that you should keep teams intact and ride the forming-storming-norming-performing curve. In a fast-growing (or shrinking) company, teams inevitably morph and change, so fighting that natural evolution is a losing battle. Her own experience going from the 10th employee to a company of thousands proved stable teams weren't even possible.

Popular team advice says keep teams the same to reach 'performing' — but that assumes stability many companies never have
In fast-growing or shrinking companies, team structure morphs whether you plan for it or not
Better to work with the natural evolution than fight it

“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…”
Heidi Helfand · 05:00

#reteaming#team-stability#org-design#startups

Myth Buster51:30

Why Spreading Your High Performers Backfires

A common instinct is to take a magical, high-energy team and scatter its members across other teams so their excellence rubs off. AppFolio's John Walker actually ran that experiment — and it didn't work. The chemistry didn't transfer; instead he felt he destroyed the very team that had it. High performance is a property of the team, not portable individuals.

The idea: spread members of a high-performing team so other teams catch the energy
John Walker tried it at AppFolio — 'it didn't happen'
Splitting the team destroyed the chemistry rather than multiplying it
This became one of Heidi's reteaming anti-patterns

“let's just spread the people from that team across the other ones and then we'll have that and it didn't work like you didn't have…”
Heidi Helfand · 52:00

“John felt like he essentially destroyed that when he split up split up that team”
Heidi Helfand · 52:30

#anti-patterns#high-performing-teams#team-chemistry

Hot Take· 1

Hot Take54:30

Your Great Team Is a Melting Ice Cream Cone

For people who dread change because their team is amazing right now, Heidi offers a reframe: nothing lasts. She pictures herself holding a melting ice cream cone. Companies move through life-cycle stages, people turn over, and the company today isn't the company of a year ago. The move is gratitude — appreciate the great team while you have it, because change is inevitable.

Great teams don't last — the company of today isn't the company of a year ago
She visualizes it as holding a melting ice cream cone
Companies move through life-cycle stages (referencing Adizes' corporate life cycles)
The response to inevitable change is gratitude, not fear

“so nothing lasts and I sometimes I have like a picture of myself with an or like holding an ice cream cone that's melting you…”
Heidi Helfand · 54:30

“these are our lives and you know we we have to have gratitude and appreciate what we have because naturally things evolve and change”
Heidi Helfand · 55:00

#change#team-culture#impermanence#mindset

Explainer· 2

Explainer37:00

The Signals That a Team Has Grown Too Big

As teams grow, facilitation and communication break down, and there are concrete signals it's time to split. Meetings get longer, decisions get harder than when there were five of you, and the work diverges so much that people stop paying attention in standups. If you normalize teams having input into their own structure, someone on the team usually raises the split first.

Meetings taking longer and decisions getting harder are early warning signs
'It was easier when there were five of us but now there are 13'
Divergent work means people tune out in standups
Splitting can create new dependencies — one PM, one designer, one QA now stretched across teams

“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…”
Heidi Helfand · 37:00

“it was easier when there were like five of us but now they are 13 the work becomes Divergent they're working on this one thing”
Heidi Helfand · 37:00

#grow-and-split#team-size#scaling#org-design

Explainer59:00

The Three Levels of Listening From Co-Active Coaching

Asked her secret to being a great listener, Heidi credits co-active coaching training and lays out three levels. Level one is internal listening — you're distracted, thinking about lunch. Level two is putting your full attention on the other person. Level three is global or environmental listening — reading the room, body language, a sudden pain in someone's neck, a face turning red — all of which is information.

Level one: internal listening — distracted by your own thoughts ('what am I going to have for lunch')
Level two: anchoring your full attention on the other person
Level three: global/environmental listening — the room's vibe, body language, physical cues
Learned via Co-Active Training Institute (Henry Kimsey-House)

“so you have level one which is internal listening like if you and I are talking but I'm thinking about like what am I going…”
Heidi Helfand · 59:00

“and then level three is like Global listening Environmental Listening if a marching band suddenly walked behind you I'm going to point that out because…”
Heidi Helfand · 59:30

#listening#coaching#communication#leadership

Story· 4

Story08:00

Whiteboard Reteaming: Doing Reorgs in the Open

Inspired by Christian Lyall at Spotify, Heidi describes running a Procore reorg transparently — rolling out whiteboards showing every team's name, mission, open headcount, and people's positions, then inviting the ~80 affected people to give feedback. Employees caught design mistakes and surfaced roles they wanted. It's scary to expose plans early, but it turns a back-room decision into a shared one and gives people choice.

Whiteboards showed team names, missions, open hiring slots, and everyone's current position
~80 people in a platform org splitting from two clusters into three were invited to give feedback
People identified design mistakes and raised their hand for roles they wanted
Redgate Software goes further with open self-selection where teams pitch and people choose

“and they visualized it on whiteboards and brought people over to the whiteboards to see the future team structure that that the leaders wanted and…”
Heidi Helfand · 08:30

“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…”
Heidi Helfand · 11:00

#reorgs#transparency#self-selection#reteaming

Story22:00

How an Isolated Team Saved Expert City (and Became GoToMyPC)

At Expert City, Heidi's first tech job, the CEO walked into her office and killed the marketplace product she'd poured herself into — it had made about six dollars the prior month. She cried and even emailed to protest. Then she was pulled onto a small team off to the side, freed from waterfall, that built GoToMyPC — the pivot that saved the company and led to GoToMeeting and GoToWebinar.

The original marketplace ('the eBay of services') made ~$6 in a month and was killed outright
The CEO told her to 'go to the beach' rather than start work that would need maintaining
A small isolated team, freed from waterfall, could deploy frequently and iterate fast
That team built GoToMyPC — the pivot that saved the company

“stop working 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…”
Heidi Helfand · 22:00

“the product was called go to my PC where you could see and operate someone's computer from a distance and that you know was essentially…”
Heidi Helfand · 24:30

#isolation#pivot#startups#innovation

Story26:30

The Chicken McNugget Was Saved by an Isolated SWAT Team

Isolation isn't a new idea. Heidi points to a story from a 1970s book called Teamwork: the Chicken McNugget was struggling in test markets, so McDonald's pulled in a consultant and a tiny team that worked in a different plant, reported straight up to an executive, and fixed it. The pattern of a small, protected, senior-sponsored team recurs across decades.

A small team worked in a separate plant, not where the product was normally developed
They reported straight up to a McDonald's executive
The McNugget had been struggling in the Indianapolis test market
The story appears in an old book called Teamwork

“the Chicken McNugget was saved by an isolated team SWAT team”
Heidi Helfand · 26:30

“they reported straight up to one of the executives at McDonald's and yeah the Chicken McNugget uh lived on because it was like having challenges…”
Heidi Helfand · 27:00

#isolation#swat-team#case-study#innovation

Story56:30

Sheryl Sandberg: Constant Reorgs Are the Best-Case Scenario

When someone at Airbnb asked Sheryl Sandberg how to cope with constant change and reorgs, her answer flipped it: that's good. Having to change because you're growing so fast is the best-case scenario, because the alternative — not growing — is far more painful, with layoffs and businesses going away. Heidi ties it to keeping a wide vantage point: remembering the company is doing well.

Sandberg's reframe: constant change from fast growth is the best-case scenario
The alternative — no growth — is harder and more painful, with layoffs
Growth, especially hypergrowth, necessarily leads to change
Heidi's CTO echoed it: 'it's great to be at a successful company'

“the fact that you're growing so fast and having to change is the best case scenario because the alternative is you not growing”
Lenny · 56:30

#change#hypergrowth#leadership#mindset

Takeaway· 3

Takeaway28:00

Making an Isolated Team Actually Succeed

For an innovation-by-isolation team to work, Heidi gives concrete conditions: put the team in its own physical region, have a leader explicitly tell everyone else not to disturb them, build shared ownership through pairing so people can peel off without becoming a knowledge silo, and make sure they report to someone with real decision-making authority. She's candid that any of these patterns can be screwed up — 'balconies and basements.'

Give the team its own separate location or claimed area
A leader must publicly tell other teams not to pull these people into other work
Use pairing and shared ownership so someone can join without becoming the single owner of a system
They should report to someone with real decision authority so decisions don't get reversed
Every pattern can be done badly — 'balconies and basements'

“number two tell other people not to disturb this team that's key and hearing it from a leader is really really important”
Heidi Helfand · 28:30

“for all of these patterns there are it's like kind of like balconies and basements there's you know you can screw it up too”
Heidi Helfand · 34:00

#isolation#team-protection#shared-ownership#leadership

Takeaway43:30

Switching Teams Builds a Safety Net Against Layoffs

Beyond fulfillment, switching people between teams builds knowledge redundancy so no single person is the 'tower of knowledge' for a critical system. Heidi cites Menlo Innovations, which has all team members (not just engineers) work in pairs and rotate pairs regularly. When someone leaves, the knowledge doesn't leave with them — real fault tolerance, which mattered at AppFolio where systems processed large rent payments.

Aim for multiple owners of a system, not one 'tower of knowledge'
Menlo Innovations pairs all team members and switches pairs on a regular cadence
Redundancy means a departure doesn't take critical knowledge with it
Especially vital for critical systems like AppFolio's rent-payment processing

“well have multiple owners of a system so not only one person is that Tower of knowledge that owns that one system”
Heidi Helfand · 43:30

“but switching also helps build that knowledge redundancy in your company a little more fault tolerance so if someone leaves they don't leave with that…”
Heidi Helfand · 44:00

#switching#knowledge-redundancy#pairing#resilience

Takeaway47:00

There's No Perfect Org Structure — Only Problem Trading

Lenny shares a manager's line: there's no perfect org structure, only the best idea you have at the time, plus the issues you then design processes to catch. Heidi agrees and reframes reorgs as continuous problem trading — conditions change, COVID happens, you grasp the current state and pick the least-bad of several options, knowing each has pros and cons.

Any org is just the best idea at the time, with known downsides to manage
Reorg decisions are 'problem trading' — every option has pros and cons
Conditions constantly change, so structures must keep evolving
Heidi ties it to Toyota Kata: grasp the current condition, aim for the next target condition

“there's no perfect org structure there's only the best idea you have at the time for what the org could be”
Lenny · 47:00

#org-design#decision-making#problem-trading

Key ideas

Frameworks in this episode

Innovation by Isolation

Knowledge Redundancy Through Pairing and Pair Switching

RIDE — Decision-Making Clarity for Change

Story of Our Team

The Five Patterns of Dynamic Reteaming

The Reteaming Anti-Patterns

The Three Levels of Listening

Whiteboard Reteaming

People & resources mentioned

People · 14

Resources · 29

Insights & moments

⚡Myth Buster· 2

Stop Trying to Keep Teams Perfectly Stable

Why Spreading Your High Performers Backfires

◆Hot Take· 1

Your Great Team Is a Melting Ice Cream Cone

✶Explainer· 2

The Signals That a Team Has Grown Too Big

The Three Levels of Listening From Co-Active Coaching

❝Story· 4

Whiteboard Reteaming: Doing Reorgs in the Open

How an Isolated Team Saved Expert City (and Became GoToMyPC)

The Chicken McNugget Was Saved by an Isolated SWAT Team

Sheryl Sandberg: Constant Reorgs Are the Best-Case Scenario

▲Takeaway· 3

Making an Isolated Team Actually Succeed

Switching Teams Builds a Safety Net Against Layoffs

There's No Perfect Org Structure — Only Problem Trading

Myth Buster· 2

Hot Take· 1

Explainer· 2

Story· 4

Takeaway· 3