Coachful Coaching Leadership Podcast

What if the authenticity we keep demanding from leaders isn't actually a real, measurable thing?

In this episode, I sit down with Maya Rupert, who managed Julián Castro's 2020 presidential campaign, becoming only the third Black woman in U.S. history to run a presidential campaign, and later served as a senior advisor to Elizabeth Warren. Today she's Executive Vice President at Blue State and the author of The Real Ones: How to Disrupt the Hidden Ways Racism Makes Us Less Authentic.

Maya challenged something I hear constantly in the corporate world: that we can just "sense" when someone is or isn't authentic. She argues that judgment is mostly vibes, shaped by how many versions of "someone like them" we've seen before. Which means the narrower our reference points, the harder it is for women and people of color to ever be read as authentic, no matter how genuine they are.

We get into how she defines real, self-reflective authenticity, what it was like running a campaign with no budget for message testing, why she asks every candidate to define winning beyond winning, and the one lesson from politics and movement work that business still hasn't learned about getting people to truly own their work.

If you've ever been told to "just be yourself" and wondered whose self they meant, this one's for you.

🎧 Chapters
00:00 Welcome and Maya's introduction (plus a guest appearance from Crispin the cat)
01:45 Maya's path and why she wrote The Real Ones
04:01 How do you actually define authenticity?
05:54 The vibes-based test we use to judge leaders
09:49 What the 2020 campaign cycle revealed
11:48 Inside a presidential campaign: likability is "squishy"
14:46 The irony of measuring your own authenticity
18:21 When there's only one winner: redefining what winning means
20:25 The values Maya looks for in the leaders she backs
22:39 What business still needs to learn from movement work
26:38 What worries Maya most right now
30:43 The one thing she'd fix overnight
31:56 Bring joy to your hustle
35:17 Where to find Maya and The Real Ones

📕 Maya's book, The Real Ones, is out now wherever you get your books.
Find Maya online: @MayaRupert on X, maya.rupert on Instagram and Bluesky

Your brain is wired to protect you from your own breakthroughs. That's why you can't think your way out of the things that matter most.

Dr. Marcia Reynolds calls coaches "external thought disruptors." She's one of the most credentialed voices in the field: 5th global president of the ICF, ranked top 5 coach in the world by Global Gurus, ICF Circle of Distinction honoree, and author of the international bestseller Coach the Person Not the Problem.

In this conversation, Marcia and I dig into why self-awareness alone isn't enough, what AI genuinely cannot replicate in a coaching session, and how the identity you're quietly holding onto is usually what's keeping you stuck.

Find Marcia at covisioning.com

Chapters:

0:00 Welcome and introducing Dr. Marcia Reynolds

1:13 Where "coach the person, not the problem" actually came from

3:24 The self-awareness gap: why high performers don't know themselves

7:05 What AI can and cannot do in coaching

9:16 Co-regulation and the energetic connection between coach and client

14:42 How coaches override the protective brain to create real transformation

16:38 When people start questioning purpose: the midlife inflection point

18:38 David's story: leaving 23 years in corporate to build something meaningful

20:49 Why defining yourself by your job title is a trap

23:42 How to coach at the identity level, not just behaviors and goals

27:45 Marcia at 70: skydiving, purpose over profit, and a life well lived

30:53 The honest truth about building a coaching business

33:17 Coaching is just one modality. Purpose is the product.

37:49 Where to find Dr. Marcia Reynolds

What if belonging isn't a soft, feel-good idea but the actual infrastructure that decides whether your team performs?

In this episode of the Coachful Coaching Leadership Podcast, I chat with Andrea Carter, organizational scientist, founder of Belonging First, and adjunct professor at Adler University. Fresh off presenting at Google HQ in London for the launch of the Global Workplace Happiness Report, Andrea breaks down what her research across 150,000 employees reveals about why people stay, perform, and actually feel happy at work.

A few things we get into:

- The finding that people are least happy at work when they're with their boss, and what that says about how we train managers

- Why organizations keep investing the most in what matters the least

- The five measurable indicators of belonging: comfort, connection, contribution, psychological safety, and well-being

- The difference between engagement (who's busy) and contribution (who's creating real impact)

- Why employees experience work as a relationship while organizations treat it as a transaction

Andrea also shares a free diagnostic, the Belonging Breakdown, so you can see where belonging is breaking down on your own team.

Learn more about Andrea's work: https://belongingfirst.com

Connect with Andrea on LinkedIn: https://www.linkedin.com/in/andreadcarter/If you enjoyed this episode, please like, subscribe, and share it with someone who leads a team.

Chapters:

00:00 Welcome and introductions

01:30 Andrea's detour to Google HQ in London

03:31 Happy workers perform measurably better

04:33 Why people are least happy with their boss

06:38 Why companies invest the most in what matters least

07:54 Belonging as performance science: the five indicators

10:00 Engagement vs contribution

12:00 Why psychological safety is only one fifth of belonging

14:00 The problem with most resilience training

15:49 What good infrastructure looks like

19:00 When AI does more harm than good in HR

23:24 Fitting in vs belonging: the 50-50 equation

26:45 What do we actually do about it

29:14 The Belonging Breakdown diagnostic

30:20 What drives Andrea's passion for this work

33:14 Bringing joy to your work today

You Haven't Delegated. You've Just Handed Off the Task. — with Brooke Dukes

Most founders think they've delegated. They haven't. They've handed off the task and kept the ownership, and that's why their growth has stalled.

Brooke Dukes has built four businesses, consulted Fortune 500s for over two decades, and now runs Success by Design — a leadership operating system for founders who've become the bottleneck in their own company. She's also the author of Burn On Not Out and host of the podcast by the same name.

In this conversation, Brooke and I get into why "my bandwidth is my company's ceiling" is the most uncomfortable sentence a founder can say out loud, the five-day exercise she gives every client to prove the bottleneck isn't their people, and the moment at 33 — on a corporate jet, in preterm labour, walking away from a six-figure bonus — that ended her Fortune 100 career.

If you've ever told yourself "if I don't do it, it won't get done," this one's for you.

Chapters00:00 Intro01:29 Four businesses in, here's what Brooke learned04:34 Why growing companies actually stall06:36 Early warning signs you've become the bottleneck08:06 The five-day exercise that reveals where the real problem is11:45 The pushback every founder gives (and why it doesn't hold up)14:47 What being the bottleneck actually costs you19:40 Burn on, not out: the corporate jet moment that changed everything23:16 Leaving a Fortune 500 on your own terms27:06 Why you can't have a Plan B as a founder31:01 The 90-second rule for handling doubt34:52 Brooke's advice for bringing more joy into your day

Connect with Brooke DukesPodcast: Burn On, Not OutBook: Burn On Not OutCompany: BMD / Success by Design

How do you disagree with someone without the conversation falling apart?

Ron Harvey spent 21 years in the U.S. Army and now leads as VP of GCS Consulting. In this episode, he and David Fung unpack what most leaders get wrong about disagreement, respect, and leading people in a world that's changing fast.

A few moments that stood out:

→ Why most disagreements aren't really about the issue→ The difference between appreciating people and tolerating them→ How to spot toxic positivity on a team→ Why your worldview needs an annual upgrade, like your iPhone→ Why coaching isn't about making your team better, it's about making you better

Chapters

00:00 Intro: Meet Ron Harvey

01:11 21 years in the U.S. Army

02:00 "People always matter" — where it comes from

04:57 How to disagree without losing respect

07:57 What respect actually looks like as a behavior

12:57 Why "just make a difference" is Ron's north star

15:12 How to measure the intangible

18:04 Why coaching is about making YOU better, not your team

20:11 The most common leadership mistake Ron still sees

21:04 The vulnerability exercise Ron runs with executive teams

23:41 Toxic positivity vs. toxic negativity

26:39 Finding the sweet spot between the two extremes

28:23 Why your worldview needs an annual upgrade (the iPhone test)

32:14 What to carry from the past, and what to leave behind

35:55 Stop driving through life looking in the rearview mirror

37:19 Ron's advice for finding more joy

39:26 Where to find Ron

Norman Wolfe spent 40+ years inside organizations, including a long stretch at Hewlett-Packard, before noticing something nobody could explain: 70% of companies fail at strategy execution, despite shelves of books telling them how to succeed. His answer? We're stuck in a paradigm trap, treating organizations as machines and people as component parts.

In this conversation, Norman shares the framework behind his book The Living Organization, the three forces that actually create results (doing, relationships, and context), and the story of how he once crushed a goal at HP that he completely forgot about and never tracked. We also get into why mental models quietly run our lives, how improvisation is a more useful operating system than control, and why the leaders who push hardest often achieve the least.

A conversation for anyone who's tired of grinding and wondering if there's a better way to lead.

Find Norman at quantumleaders.com.

Chapters

00:00 Why organizations aren't machines

03:00 The 70% strategy execution problem

06:30 What 40 years of leadership taught Norman about ease

09:00 The three forces: doing, relationships, and context

13:00 The HP goal he hit without trying

17:00 Why who you're being is what you attract

20:00 The non-time based reality of results

24:00 Leading through uncertainty in 2026

26:00 What improvisation teaches us about control

33:00 Mental models and why they break

36:30 Norman's one piece of advice for living your best life

Full show notes: coachfulcoaching.com/coachful-coaching-leadership-podcast/living-organization

In this episode of the Coachful Coaching Leadership Podcast, I sit down with Will Steel, a high performance and executive coach, author of Free to Lead, and a former RAF fast jet pilot turned commercial pilot turned coach to founders and business leaders.

Will shares the moment in officer training when he almost got kicked out for "keeping his head down," and how being told to actually be himself led to him graduating 18 weeks later with the leadership trophy. From there we get into the real stuff: the limiting beliefs that quietly run people's lives, why business owners hit a ceiling around the $1M mark, and how one of his clients went from working 60 to 70 hours a week down to 12, while growing the business from barely keeping the lights on to $7M.

We also talk about:

• The "I'm not enough" story almost every leader is secretly carrying
• Why you can't logic someone into giving up control (and what actually works)
• How a scientist doubled his income and cut his hours in half after one single insight
• The simple practice Will uses to stay grounded and grateful

If you're a founder, business owner, or leader who feels like the lid on your growth is you, this one is worth your time.

Find Will at willsteel.com and grab his book Free to Lead at willsteel.com/freetolead.php

Listen to the Coachful Coaching Leadership Podcast on YouTube, Spotify, and Apple Podcasts.

Why Great Salespeople Don’t Feel Like Salespeople (With Darren Mitchell)

What if the best salespeople… don’t actually feel like they’re selling?

In this episode, we sit down with Darren Mitchell, Sales Leadership Coach and founder of Exceptional Sales Leader, to break down the biggest misconceptions about sales and why most people are getting it completely wrong.

With 800+ podcast episodes and decades of experience, Darren shares why sales isn’t about pushing products… it’s about service, curiosity, and guiding people to better decisions.

If you’ve ever felt uncomfortable “selling” or struggled with how to build trust with clients, this conversation will challenge how you think about sales—and leadership.

In this episode, we cover:
00:00 – Introduction to Darren Mitchell
02:10 – Why sales has such a bad reputation
05:30 – The biggest misconception about sales
09:15 – Why “selling the pen” is outdated
12:00 – Car dealerships, Tesla, and the shift to buyer-driven sales
17:45 – Why most sales training fails
21:00 – Talking yourself out of a sale (and how to avoid it)
25:30 – What top 1% salespeople actually do differently
29:30 – Bringing more joy into a high-pressure sales role
34:00 – Where to find Darren

Connect with Darren Mitchell:
🌐 Website: https://exceptionalsalesleader.com/
🎙 Podcast: https://exceptionalsalesleader.com/podcast
💼 LinkedIn: https://www.linkedin.com/in/darren-j-mitchell/

Coachful Coaching Leadership Podcast:
🌐 Website: https://coachfulcoaching.com/
🎥 YouTube: https://www.youtube.com/@coachfulcoaching
🎧 Spotify: https://spotify.link/NTBgVJIL3yb
🍎 Apple Podcasts: https://apple.co/41Cz5gI

About Coachful Coaching:
Coachful Coaching helps leaders build high-performing, human-centered teams through practical coaching, communication, and leadership frameworks. If you’re a technical leader looking to grow your influence and impact, you’re in the right place.

If you enjoyed this episode, make sure to like, subscribe, and share it with someone who still thinks sales is about “convincing people.”

Lead the Person, Not the Drivers with Matt Martocci

What does real leadership look like when the pressure is high, the market is noisy, and results still matter?

Matt Martocci, Chief Commercial Officer at hc1, shares lessons from a career across healthcare, pharma, SaaS, and commercial leadership, including roles at Salesforce, Definitive Healthcare, GHX, Millennium Health, and Novartis.

In this conversation, he breaks down why great leaders focus on people before metrics, why motivation is often misunderstood, and how presence, feedback, and recognition shape high-performing teams.

The episode also explores the future of healthcare technology, the growing role of diagnostic data, and how better leadership decisions can lead to better business and patient outcomes. Matt shares practical insights on standing out with customers, keeping teams engaged during tough stretches, celebrating wins, and leading in a way people actually remember.

Chapters
00:00 Intro
02:29 What Matt does at hc1
03:47 Why the hospital lab matters more than people think
05:19 How hc1 uses data to identify anemia risk before surgery
06:19 Prevention, healthcare, and the role of diagnostic tools
08:22 Why Matt joined a smaller, entrepreneurial company
09:17 From pharma rep to people-first leader
12:06 Why leadership is often more about motivation than coaching
13:38 How to keep teams motivated when results are not going your way
15:16 How to stand out with customers in a world full of meetings
16:24 Why it is okay to ask customers for feedback
17:01 Practical ways to get real-time feedback in the room
18:53 “Never miss an opportunity to tell somebody they did a good job”
20:51 Why great leaders start debriefs with the positive
23:28 Where face-to-face business still matters in an AI world
26:48 Why attention spans are changing how we communicate
27:38 The importance of celebrating wins
28:42 Matt’s mantra: be present
29:37 “Lead the person, not the drivers”
30:48 Where to find Matt

Connect with Matt Martocci
LinkedIn: https://www.linkedin.com/in/mattmartocci

Coachful Coaching
Website: https://coachfulcoaching.com/
YouTube: https://www.youtube.com/@coachfulcoaching
Spotify: https://spotify.link/NTBgVJIL3yb
Apple Podcasts: https://apple.co/41Cz5gI

For more conversations on leadership, growth, and bringing more joy to your hustle, subscribe on YouTube and follow on Spotify or Apple Podcasts.

In this episode of the Coachful Coaching Leadership Podcast, we sit down with Ian Watts — author, speaker, and go-to expert on workforce transformation.

Ian has scaled HR systems, recruited and retained hundreds of team members, and helped transform leaders across 30+ industries, from middle America to the Middle East. As the founder of SB Dream Coach and Employee Success Group, he’s shared stages with speakers like ET, the Hip Hop Preacher, and has been featured on Fox News (Detroit) and PBS (Detroit). After two decades as a servant-leader, Ian’s mission is simple: **build businesses that bless the world.**

In this conversation, we get practical about:

- Why “money doesn’t hug you back” (and what actually drives loyalty)

- The ACTS Method: Aspirations, Calling, Transformation, Support

- How to lead when deadlines are brutal without losing your culture

- Why small acts of appreciation create outsized loyalty over time

- How to create more joy through focus, gratitude, and daily “priming”

Find Ian:

Website: employeesuccesscompany.com

CHAPTERS

00:00 Intro: Ian Watts + the “money doesn’t hug you back” idea

00:43 “Build businesses that bless the world”

00:56 Detroit, poverty, and the money chase

03:48 When chasing money feels empty

05:43 Sales pressure, performance culture, and the BMW chase

07:40 Why Ian started Employee Success Group

10:04 The ACTS Method (Aspirations + Calling)

12:10 Transformation + Support (showing people they matter)

13:47 The IKEA story: why small gestures stick for decades

15:54 Short-term targets vs culture (leading under pressure)

17:02 “Little hinges swing big doors” (small appreciation, big impact)

20:10 Ian’s “big door” right now (perspective, meaning, emotion)

23:24 Who shaped Ian: Uncle Kelvin + Pastor Christopher Brooks

26:11 Finding purpose: faith + the SHAPE framework

28:31 “Life is a team sport” (you need others to see yourself clearly)

32:36 More joy: focus, gratitude, enjoying the journey

35:26 Priming + the RAS (your brain finds what you focus on)

37:34 Where to find Ian + closing