Leveraging Leadership

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

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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

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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:
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

Executive presence isn't a checklist of confident behaviors, and it isn't a persona you put on when you reach the C-suite.

Jacque McCormack, co-founder of JetStream Advisors and an executive coach with more than 15 years of experience working with leaders and executive teams, joins me to unpack what executive presence actually looks like in practice: how people experience you, how you flex between authority and approachability, and how you stay grounded enough to respond intentionally when the pressure rises.

We talk about the difference between performative confidence and quiet confidence, the leadership models we unconsciously copy, and why a new executive role can be a chance to deliberately evolve your leadership brand. Jacque also shares specific considerations for women navigating the authority-approachability double bind, along with practical communication tools like bottom-line-up-front messaging and emotional granularity.

A big theme throughout the conversation: executive presence is less about looking the part and more about knowing the wake you create - especially when things get difficult.

Links Mentioned:
JetStream Advisors
Previous Leveraging Leadership conversation with Noel Sobelman

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Want to chat with Emily? Book a quick clarity call here.

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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:
00:50 - What executive presence actually feels like
03:20 - Performative confidence vs. quiet confidence
05:30 - The authority-approachability spectrum
08:40 - Audit the leadership model you're mimicking
12:40 - Starting fresh in your first C-suite role
15:10 - Define your leadership brand and the wake you create
20:40 - Executive presence and the double bind for women
24:40 - Bottom-line-up-front communication and emotional granularity
27:20 - Leadership halos, shadows, and stress responses
29:20 - The pause: responding instead of reacting
34:20 - Emotional sovereignty is a muscle, not fake it till you make it
36:10 - Matching leadership horsepower to the organization
38:20 - Why leadership development became a calling

#chiefofstaffpodcast #ChiefOfStaff #COSpod

Noel Sobelman explains innovation portfolio management and how companies can bridge the gap between strategy and execution. He shares a medical device company example where shifting from safe, incremental projects to a more balanced mix led to higher growth. The conversation also covers using tools like metered funding, managing risk, and how roles like Chief of Staff help leaders focus on what's best for the whole company instead of just one business unit.

Links Mentioned:
Noel Sobelman’s Book: Innovation Portfolio Management: Linking Strategy to Execution

Connect with Noel Sobelman 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:
01:14 What Portfolio Management Means

03:55 Medical Device Turnaround Story

07:33 De Risking with Metered Funding

12:41 Saying No and Staying Agile

14:05 Governance and People Dynamics

19:16 Assessing Your Current Portfolio

23:51 Finding the Right Mix

26:33 Decision Focused Portfolio Reviews

28:32 AI and Maturity Benchmarking

33:36 Success Metrics and Gold Standard Example

Stan Lewis, a former OSHA investigator and mediator, explains how most workplace whistleblower cases come down to communication issues and how managers can prevent problems by listening early. He shares practical mediation tips, like letting people vent, asking what success looks like, and using company policy consistently. Stan also talks about the importance of addressing conflict when it’s still small and relates his “Freedom from Mental Captivity” framework from his new book.

Links Mentioned:
Pre-order Evict The Doubts Squatting Rent-Free In Your Mind Book

Stan Lewis’ Website

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

Free Leadership Resources

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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:
01:01 What OSHA Really Does

02:50 Preventing Issues Through Communication

05:20 Early Resolution and ADR

07:00 Mediator Questions That Work

12:41 Setting Expectations and Offers

15:59 Prework and Breaking Stalemates

22:23 Handling Workplace Tension Early

30:08 Speaking Their Language DiSC

35:01 Evicting Doubts and Wrap Up

JonRobert Tartaglione shares how to lead through influence without direct authority, drawing on his background in psychology and examples like political polarization and message framing. He explains why Chiefs of Staff need to use persuasive, not just expressive, communication and offers practical tips, such as using diagnostic questions, hedging language, and leveraging social norms in organizations. The conversation covers what actually works to change minds, why logic alone is rarely enough, and how to avoid manipulation or coercion.

Links Mentioned:
Influence51 Website

Connect with JohnRobert on LInkedIn

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Want to chat with Emily? Book a quick clarity call here.

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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:
01:14 Academic Journey and Psychology

03:26 Political Psychology and Polarization

06:55 Strategic Communication Modes

14:50 Persuasion vs Manipulation

20:55 Illusion of Explanatory Depth

23:52 The Art of Listening

27:59 Expressive vs Persuasive Communication

32:20 Loss Aversion in Business

38:31 Social Norms and Behavior

Emily Sander shares three simple exercises to help anyone sound more confident in meetings, interviews, and presentations. She walks through the "expert game," explaining how to act like the world’s leading authority on random topics like Flashdance or koala bear feeding habits. The episode includes practical tips like recording yourself, using variety in your voice, and practicing for just 30 seconds a day.

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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:
01:18 Exercise One Expert Game

03:07 Expert Game Examples

09:02 Exercise Two Three Things

13:37 Range and Emotion Variations

17:03 Exercise Three Five Things

20:02 Daily Practice Habit

22:57 Record and Refine Voice

26:44 Pick the Right Moment

27:46 Results and Final Wrap

Bobby Shelton shares his journey from chasing external accomplishments to finding real satisfaction through self-leadership, including losing 180 pounds and shifting his focus after reaching personal low points. The conversation covers the difference between "easy-hard" (doing things for others' approval) and "hard-hard" (pursuing what matters to you), and offers advice on setting simple, personal standards, like refusing to eat M&M's, to build discipline. The discussion also touches on faith, burnout, and how to align your inner life with your work as a founder, CEO, or Chief of Staff.

Links Mentioned:
Bobby Shelton’s Website

Bobby Shelton’s Book

The Self-Leadership Lab Podcast

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

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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:
01:06 Easy Hard vs Hard Hard

02:34 Losing Yourself to Find Yourself

05:08 Burnout and External Validation

07:58 Finding Alignment and Purpose

11:59 Mirror Moment and Commitment

14:30 Purpose and Daily Standards

17:18 Build Standards One Step

20:31 Faith Philosophy and Selfless Leadership

34:56 Redefining Success and Closing

Emily Sander answers a listener question from Megan, who just got promoted and is transitioning between teams. She gives advice on setting up the old team for success, like handing off tasks to a "go-to" person and clearly communicating that change to everyone. Emily also suggests doing a listening tour with the new team to learn from their experience and explains the importance of being confident, having a plan, and not expecting everything to go perfectly.

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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:
01:47 Reset After Limbo

03:09 Hand Off to Jim

04:52 Set Clear Boundaries

07:09 Align with Both Bosses

09:58 Lead the New Team

12:55 30 Day Listening Tour

16:25 Set Expectations and Culture

19:04 Reinvent Your Leadership

21:35 Bumps Are Normal

22:46 Congrats and Wrap Up