Diane Sadowski-Joseph, co-founder of Clarinet, joins me to talk about what it actually means for a company - and its leaders - to become AI-enabled.

We start with the increasingly common mandate to “do the AI thing.” Diane explains why that instruction is almost meaningless until leaders connect AI back to the business outcomes they already care about: growth, profitability, market share, efficiency, and better decision-making. AI isn’t the strategy. It’s another lever available to help execute the strategy.

We also get into the very human side of AI adoption: fear, identity, judgment, resilience, and why leaders don’t need to become AI experts. They need what Diane calls decision-grade fluency - enough hands-on understanding to know when AI is useful, when it isn’t, and how to make better strategic decisions around it. We unpack A, B, and C loops for redesigning workflows, how to move from fear to curiosity, what causes “AI slop,” and why managers need to get much clearer about what good work actually looks like.

Links Mentioned
Clarinet
Diane Sadowski-Joseph on LinkedIn

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Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

Time Stamps:
01:00 – Why “Do the AI Thing” Is a Blurry Mandate
03:30 – The Fear and Identity Crisis Behind AI Adoption
05:40 – Why Judgment and Discernment Matter More Now
08:20 – AI Is Redesigning Work, Not Just Adding Another Tool
12:20 – Strong Convictions, Loosely Held
15:50 – The “Aggressive Resilience” AI Requires
18:20 – Why You Don’t Need to Become an AI Expert
22:10 – Decision-Grade AI Fluency
26:10 – The Superuser Flywheel: Start With Friction
28:30 – How Do You Prove AI Is Creating Business Value?
29:20 – A Loops, B Loops, and C Loops
33:00 – Connect AI Efficiency to Outcomes That Matter
36:50 – What Good Leadership Looks Like in the AI Era
38:10 – Why Teams Produce “AI Slop”
40:40 – Be Clear About Where the Saved Time Goes
42:50 – How Clarinet Helps Companies Become AI-Enabled

Terry Young, author of Possibility Sciences: A Discipline for Turning Bold Ideas Into Reality, joins me to talk about why bold ideas so often die before they ever make it into the real world.

We get into what Terry calls the “Possibility Gap” - the distance between what humans can imagine and what our existing systems can actually bring to life - and why closing that gap requires more than better brainstorming or better technology. It requires changing the incentives, structures, and habits that quietly push organizations back toward incrementalism.

Terry also explains concepts like Return on Future, patient capital, moonshots, zero-waste innovation, and why innovation may be shaped less by individual bravery than by the systems surrounding people. We also talk about human-AI collaboration, where AI can help us navigate the known at scale while humans bring judgment, curiosity, and the ability to explore the unknown.

Links Mentioned:
Possibility Sciences
Possibility Sciences: A Discipline for Turning Bold Ideas Into Reality
Become a Possibilian

Get in touch with Emily:
Want to chat with Emily? Book a quick clarity call here.

Free Leadership Resources

LinkedIn
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Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

Time Stamps:
01:20 – The Possibility Gap: Why Great Ideas Never Become Reality
03:20 – What Is a Possibilian?
04:50 – Return on Future vs. Short-Term ROI
06:10 – Stick, Stack, Fund: Why Bold Ideas Need Patient Capital
08:00 – Commercial Realism, Ethics, and the Possibilian Ethos
10:20 – Why Big Missions and Moonshots Matter
13:10 – Tackling Human Trafficking as a Systems Problem
16:00 – Rebuilding the Innovation Operating System
18:20 – Why Incentives Shape Innovation More Than Bravery
22:20 – Building a New Discipline and Seeding It Into Old Systems
25:50 – Zero-Waste Innovation and Why Every Idea Matters
27:50 – Stop Hoarding Ideas and Start Building on Them
31:30 – AI + Humans: Hybrid Intelligence
34:30 – Making Money and Doing Good at the Same Time
35:50 – The Book, Possibility Sciences, and Becoming a Possibilian

Private equity firms invest with a value creation plan. But the strategy on the slide deck only matters if the company can actually execute it.

Brea Page, founder of Keep75 and a former Google Chief of Staff and strategy leader, joins me to talk about what happens after the investment: turning strategy into operating rhythms, getting founders and PE firms aligned on expectations, building reporting that creates an early-warning system, and helping leadership teams shift from doing everything themselves to actually scaling through the organization.

We also dig into Brea’s “champion and challenge” model for the Chief of Staff, why PE-backed companies often need someone dedicated to keeping execution from slipping, and how a strong Chief of Staff can turn a strategy from an idea on paper into measurable business results.

Along the way, we talk about founder transitions, PE/portfolio-company communication, internal Chief of Staff promotions, the danger of giving someone the Chief of Staff role without taking away their old job, and why the operating partner + embedded Chief of Staff model may be one of the strongest ways to support portfolio companies as they scale.

Links Mentioned:
Keep75
Brea Page

Get in touch with Emily:
Want to chat with Emily? Book a quick clarity call here.

Free Leadership Resources

LinkedIn
Website
Newsletter

Who Am I?
If we haven’t met before - Hi👋 I’m Emily, Chief of Staff turned Executive Leadership Coach. After a thrilling ride up the corporate ladder, I’m focusing on what I love - working with people to realize their professional and personal goals. Through my videos here on this channel, books, podcast guest spots, and newsletter, I share new ideas and practical and tactical tools to help you be more productive and build the career and life you want.

Time Stamps:
04:10 – From Google to Private Equity
06:00 – How Operations Create Value
10:50 – The Founder Shift: Accountable vs. Responsible
13:50 – Translating Between PE and Portfolio Companies
18:40 – What “Founder-Led” Means After PE Investment
20:20 – Why PE-Backed Companies Need Chiefs of Staff
24:30 – What a Chief of Staff Actually Does
26:20 – Operating Partners + Embedded Chiefs of Staff
30:20 – Hiring and Matching the Right Chief of Staff
36:30 – The Ideal PE Operating Model + Keep75

#chiefofstaffpodcast #ChiefOfStaff #COSpod