Innovating Out Loud

We take a lot for granted in innovation. Chief among them: that questions are where it all starts. So this episode, Larry Robertson and I decided to poke at our own assumption and see if it held up.

Larry’s an innovation advisor and the author of Great Question, a book he built by talking to more than 140 people — neuroscientists, teachers, artists, CEOs. What he found is that we’re a questioning species. Our brains actually do their best work in uncertainty, not away from it. We got into why “best” isn’t a fixed answer but something you build together, why asking “why” too early kills the good stuff, and how I once flipped a data center project by asking “What if communities asked us to build one?” instead of “How do we get permission?” We closed on AI — useful, but only if you’ve already got the muscle it can’t teach you. An hour in, our assumption held. Questions really are where it starts.

Five things worth carrying with you

* Questions aren’t a technique. They’re how we’re built. Your brain does its sharpest thinking in change, complexity, and uncertainty — Larry’s neuroscientists call it “innovation mode.” So questioning isn’t something you bolt onto the work. It’s the work.

* Quit leading with “why.” Start with “why” and you’re down a rabbit hole you won’t climb out of. Try Deb Meyer’s five instead: How do we know what we know? Is there a pattern? What if? Is there another way? Who cares? As Larry put it, a question is just going there. You’re not committing to anything yet.

* Flip the question and watch the whole thing change. For years the industry asked, “How do we get permitted to build a data center?” We asked, “What if people were asking us to build one?” You can’t solve that the same way. What came out didn’t look, sound, or run like a data center at all. Because innovation is value creation — if it’s not changing someone’s life, it’s just a cool idea.

* It starts with trusting yourself. Every field Larry studied circled back to the same thing: faith in your own questioning, earned from the wins and the flops. You can’t build that trust across a team if it isn’t there in you first. When you’re stuck, lean on the three things you can always trust — curiosity, play, and search.

* AI can’t teach you to question. It can help. But AI averages toward an answer, and you can’t amplify a skill you don’t have. Build the muscle yourself, and how you use AI will change. Skip that, and you’re just handing over the thinking that would’ve made you better.

You can find Larry’s book, Great Question: The Art of the Ask and Getting More of What Your Really Want everywhere books are sold.

Next up on Innovating Out Loud: Angus Fletcher. Story Scientist and author of books that have come up in many previous episodes. Wonderworks and Primal Intelligence live on my desk. This is a not to miss session. NOTE the change of time: 10:30 AM PT / 1:30 PM ET. July 23, 2026. Register here and see you then!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

Northern Wisconsin, 1905. A windstorm flattened whole stands of sugar maple across the Menominee reservation — millions of board feet on the ground, already starting to rot. The Menominee wanted to salvage the fallen timber and mill it themselves. The federal authority refused. Downed Indian timber, sold at volume, would depress the price of white-owned timber. Better the trees rot, he decided, than the price of white-owned timber fall.

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America turns 250 this weekend, and innovation retrospectives will hand the credit to technologies like the assembly line and the transistor. I wanted to sort 250 years differently — into what was encoded and endured, regardless of intent. A generous billionaire doesn’t pass the test; bylaws do. A bigoted clerk doesn’t fail it; maps do.

I discovered a wide range of examples.And what I believe is the opportunity to encode now what will endure for decades or even centuries.

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Menominee history: https://www.americanforests.org/article/menominee-forest-keepers/

Written with a team of cus tom AI assistants as part of my Innovating Out Loud practice. The ideas, mistakes, and final words are mine. Say it Ugly, Build it Better. Onward!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

Something you believe in is stuck. You can probably picture it without trying. Six, twelve, eighteen months in and still “almost there.” The room nods and nothing moves after. The champion’s gone quiet. You ask what went wrong and you get a shrug and four theories, none of which tell you what to do differently.

This week on IOL, we're releasing the latest version of Innovation Coach to help you get unstuck. But you have to dig deep for it to work.

Try it here: Innovation Coach 2.0

If you want to know when V3 arrives, comment “Let me know” and I’ll add you to the list!

From the book

* B2Me Journey — behavior change as a journey, steps not leaps; emotion before cognition. The updated tool respects the journey instead of skipping it.

* Do The Work — the knowing–doing gap. The deeper read is where knowing turns into doing.

* Minimize Uncertainty (a Trust Lever) — concrete next steps cut ambiguity and move you along the journey, instead of leaving you with a verdict and no path.

* Developing in the Open — the VS Code posture. We show you the tool and what we changed about it, not just describe it.

Developed in the open, with AI as a thinking and drafting partner. The thoughts and final words are mine. Say it ugly, Build it better. Onward!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

Three days short of 33 years at 3M, Jayshree Seth now leads the effort to put generative AI use-cases to work in R&D — which puts her between the hype and the people who have to live with it. Her message is bracing and oddly reassuring at once: AI can accelerate every step of the climb from data to wisdom, but it can't make the climb for you. Skip the human work and you don't reach the answer faster — you arrive at a confident-sounding one you can't defend. What she handed us was a working toolkit for doing it right, folded into four frameworks and one phrase we won't forget: Trace, Fast, Arcs, Flow.

JoAnn and Taryn spoke with Jayshree on the May 28th episode of IOL. Here are a few key takeaways.

Five takeaways

1. AI can accelerate the climb from data to wisdom. It can’t make the climb for you.

2. AI flips the pyramid — and DIKW becomes WIKD.

3. It’s not artificial intelligence. It’s "artificial diligence."

4. AI narrows the access gap and widens the judgment gap.

5. AI doesn’t just change jobs — it changes the jobs to be done.

Closing

The technology is ready. The organization usually isn’t — and that gap is human. Jayshree’s whole toolkit points at the same quiet truth: AI is most useful to the people who’d still know what to do without it. Watch the full conversation for all four frameworks, the books behind them, and why she thinks the unlikely candidates are the ones true innovation needs.

Check out Jayshree’s books, The Heart of Science Series: Engineering Blueprint (2024); Engineering Fine Print (2022); Engineering Footprints, Fingerprints, & Imprints (2020). All sales proceeds go towards a scholarship for women in STEM administered by Society of Women Engineers (SWE).

Our next session of Innovating Out Loud is on June 25th at 9 AM PT / 12 PM ET with special guest, Larry Robertson. He’s an author, advisor, innovator, speaker, columnists and collaborative partner of the Lab! He and JoAnn will be talking about his new book, Great Question: The Art of the Ask and Getting More of What You Really Want.

Never miss a live episode. Register for the series at: www.regenerouslabs.com/innovatingoutloud

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

It’s a warm evening in Mount Pleasant, Wisconsin, and you’ve brought a glass of wine out to the back deck the way you have for years. The grass, the fence, the slow blue dark coming down. And underneath all of it, something new. A hum. The kind you feel in your chest. A low, constant drone, loud enough to carry over a television and conversations around the fire pit. Some nights you give up on the backyard altogether. You’re considering moving. Three miles away, a 315-acre campus is running 24/7. The hum is the sound of it exhaling.

Your backyard is where this story really starts, but not how it was told this week at Microsoft Build.

Read or listen to the full piece here and on innovatingoutloud.substack.com

Connections to The Insider's Guide to Innovation at Microsoft:

Pattern #4: Innovating More Than Technology — The piece's spine: "not a technology challenge, a business model challenge." Every component already exists — heat exchangers since the early 1900s, quieter-fan designs sitting on the shelf. The book makes the same move, that the decisive innovation is rarely the device but the business model and value chain around it.

Pattern #3: Innovating With Everyone — "Build with the place, not around it." Bring community and nature to the table before the design sets. The DOTF team's own precedent in the book — 200 conversations inside and outside before a single concept was drawn — is the proof that the early, optional conversation is the one that changes the outcome.

Aim for Positive (#15) / Regenerative Design (#51) — Closing the loop to send a stream of value back into the place instead of throwing waste heat over the fence: surplus by design, not harm reduction. The book quotes Satya asking whether, at the core of the business model, "are you creating a surplus around you?" This piece asks him to finish the question.

Top-down, Bottom-up, Outside-in (#16) — All three are in the room and none are wired together: top-down names what to protect (electricity, jobs, tax base); bottom-up is the engineers who already want to build the heat loop; outside-in is the backyard no one invited. The book's argument is that durable change needs the three connected — which is exactly what "external pressure creates internal permission" names: the outside-in voice unlocking what the bottom-up already wants to build.

This piece was developed in the open, with AI as a thinking and drafting partner. The argument, the judgment, and the final words are mine. Say it Ugly, Build it Better! Onward!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

Between two stories sits one idea: technology is never neutral. It takes on the character of whoever designs it, builds it, and runs it. The tower and the city are built with the same stone. What changes is who decided and who participated.

Connections to The Insider’s Guide to Innovation at Microsoft

This piece connects directly to four frameworks from the book:

* Innovating With Everyone — Nehemiah didn’t hold a stakeholder meeting — he called his neighbors together and gave each family a section to own. The seven-company coalition that designed the Regenerative Data Center operated on Pattern #3’s central premise: engage early, engage widely, engage with empathy. Meet people where they’re at and move forward together.

* Top-Down, Bottom-Up, Outside-In — The windowless hall is a pure top-down artifact — decisions made in rooms far from the plain, ignoring the ground-level feedback and community signals coming in. The Regenerative Data Center inverted this deliberately: designed from the bottom up, with hundreds of outside-in voices, human and otherwise.

* Aim for Positive — A data center that takes from the county’s water, pulls from the county’s grid, and returns a number on a tax form is aiming for less bad. The Regenerative Data Center aimed for abundance — heat returned to homes, power that steadies the grid, ecology restored, economy supported — mutual benefit by design, not compliance.

* Language as Strategic Tool — Leo XIV’s encyclical is a masterclass in strategic language: naming “Babel” and “Nehemiah” rewrites what builders optimize for before they pick up a stone. “Mutual benefit by design” and “each neighbor builds a section” work the same way — deliberate terminology that reframes what a coalition believes is possible, and then makes possible.

Sources

1. Leo XIII. “Rerum Novarum: Encyclical of Pope Leo XIII on Capital and Labor.” Vatican, May 15, 1891. https://www.vatican.va/content/leo-xiii/en/encyclicals/documents/hf_l-xiii_enc_15051891_rerum-novarum.html

2. Leo XIV. “Magnifica Humanitas.” Vatican, May 15, 2026. https://www.vatican.va/content/leo-xiv/en/encyclicals/documents/20260515-magnifica-humanitas.html

Written with AI assistance. The thinking — and the stretch of wall — are mine.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

In December 2020, I was one year into my time at Microsoft and four months into intentional discovery for my mission, creating the Data Center of the Future.

Listen to the full episode to hear behind the scenes stories of what is possibly THE most important practice of innovation as a discipline. How AI, as it's packaged today, erodes it. And why you should make the space for it no matter how hard it may be.

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Don’t miss this week’s live Innovating Out Loud webcast with special guest Jayshree Seth — Corporate Scientist and Chief Science Advocate of 3M. She’ll be sharing her experience and frameworks bridging the gaps between research and practice, business and technology, and data and wisdom.

Thursday, May 28th at 9 AM PT / 12 PM ET.

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Connections to The Insider's Guide to Innovation at Microsoft

Intentional Discovery: purposefully exploring with the goal of ultimately having an impact on the world, residing in Pasteur’s quadrant (of the Stokes framework by the same name). The 200 interviews, the catalog of parts, the journey map from dirt to data — that is intentional discovery in practice. Because intentional discovery is a foundational practice of repeat innovation, it connects to many other frameworks in the book. Here’s a short list: (see the full piece on Substack)

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

Last week I signed up for an expedition to Antarctica.

I get terrible seasickness. I hate small planes. Antarctica has never appeared on any version of my bucket list.

I signed up anyway.

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Innovation culture talks constantly about the courage to change. It almost never talks about the voice that tells you not to.

Over nineteen weeks, this series has mapped a lot of terrain: systems, tools, collaboration architecture, AI as thinking partner, expert perception, incentive structures, the ecology of innovation at scale.

I’ve spent most of that time one level above the person doing the work.

This week I’m inside. Not to get philosophical — to get practical. The gap between knowing what good innovation practice looks like and being able to sustain it under real conditions lives right here. In the space where either one or both voices show up.

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Connections to The Insider’s Guide to Innovation at Microsoft

* Behavior is the Barrier: The barrier isn’t always in the organization — sometimes it’s in the practitioner. The first voice is Behavior is the Barrier operating internally. The innovator who can’t quiet it becomes the bottleneck in their own work.

* Cognitive Inertia: The first voice is cognitive inertia in first person. It doesn’t resist change in others — it resists change in you. The second voice is the compelling force that doesn’t come from policy, incentive, or peer pressure. It comes from accumulated internal evidence.

* The B2Me Journey — Applied Inward: B2Me, applied outward, is the journey a stakeholder takes from unawareness to advocacy, guided by the innovator. The second voice runs that journey internally. When the first voice fires the fear response — are we even doing anything worth doing? — the second voice doesn’t lead with logic. It leads with emotional reset: not every day is a breakthrough. We worked. We learned. Recovery before rationale. The internal B2Me journey is the same architecture as the external one.

IOL is produced with the help of AI, specifically Perplexity, Gemini, Claude, and a team of custom personas developed by Regenerous Labs. All insights, editorial choices, and final content are mine. Mistakes too.

Say It Ugly, Build It Better. Onward!

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

We’ve all given the presentation that flopped. The content was right. We knew the material. We rehearsed. And we walked out of the room knowing — somehow — that it didn’t land.

The post-mortem is honest. Nothing was wrong with the vision. The argument was sound. The slides were clean. The case was the right one to make.

And still...

Listen to the full piece on Substack or Apple Podcasts. And then try the next experiment: CORTX Reframer.

www.regenerouslabs.com/reframer

Take a deck or script you’ve been working on, run it through, and tell me what you find.

Say it ugly, build it better. Onward!

Connections to The Insider's Guide to Innovation at Microsoft

Behavior is the Barrier — Seventy percent of transformations fail for human reasons, not strategic ones. This piece is the pattern made personal: every presentation that flopped, every pitch that didn't land, every meeting where the right argument got the wrong response — the gap between knowing your audience and writing for your audience is where most of it lives.

The Knowing-Doing Gap — Knowing what to do and doing it are not the same. Holding three or four audience models in your head while you decide what goes on a slide is expensive cognitive work, so we shortcut and write for ourselves. The reframer pays the cost so you can act on what you already know.

Language as a Strategic Tool — Same vision, different register, different decision. The reframer doesn't change the case. It changes which version of the case the listener's brain can actually run. The lenses moving is what this pattern looks like in practice.

Start With Who — The reframer's first move is to ask who is in the room before it touches the content. The pattern most often applied to assembling the team applies just as much to addressing the audience. Different listeners need different stories — Start With Who, then build the case.

Innovate Upstream to Succeed Downstream — The decision happens in the room. The conditions for it are made before. The reframer is upstream work — done before the pitch, the renewal call, the board meeting — that determines what's possible downstream.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com

Last week on Innovating Out Loud, we sat down with Leo Chan — keynote speaker, corporate trainer, and LEGO® SERIOUS PLAY® facilitator — to take play seriously as a tool for innovation. Leo treats creativity as a muscle that atrophies without use, and play as the discipline that keeps it strong. We worked through what LEGO Serious Play actually does (it lets people think with their hands instead of their mouths), why teams that jump straight to solving pain points collapse divergence before it can do its work, and why showing up as yourself is the precondition for the joy that makes better thinking possible. Taryn drew the through-line: courage to be yourself unlocks play, play unlocks creativity, creativity unlocks innovation.

The conversation didn’t argue that work should feel less serious — it argued that taking play seriously is how the work gets sharper.

Key Takeaways

* Creativity is a muscle. Without practice it atrophies. Play is the workout that keeps idea-generation strong.

* Think with your hands, not your mouth. LEGO Serious Play turns the model into the basis of knowledge — visual, auditory, kinesthetic — and uses metaphor to carry meaning words can’t.

* “What Might Be All the Ways” (WMBATW) — Leo’s stretch on “How Might We.” It treats divergence as a discipline, not a phase to rush through.

* Stress shuts down the prefrontal cortex. Conformity is a stressor. Being yourself isn’t indulgence — it’s a precondition for the cognitive state innovation requires.

* To bring play into risk-averse rooms: build relational equity first, acknowledge the elephant, and promise the outcome. You won’t win everyone — focus on the ones willing to come along, and let the result speak.

Watch the replay for the exercises you can run Monday morning — and the moments where the polished answer gets set aside.

Say it Ugly, Build it Better. Onward!

Never miss the live session - register at www.regenerouslabs.com/innovatingoutloud

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit innovatingoutloud.substack.com