In this episode we discuss: the art and science of 1 to 1 meetings. We are joined by Dr. Steven Rogelberg, CEO, Board Member, Editor, Author, Chief Talent Officer, Director.

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We chat about the following with Steven Rogelberg:

1. Are your one-on-ones actually driving engagement, or are they just another meeting on the calendar?
2. What message are you really sending when you cancel a one-on-one—and how does it impact employee trust?
3. Why is listening more than speaking the secret to making one-on-ones truly effective?
4. How can structured one-on-ones boost productivity, retention, and even inclusion within your team?
5. Are most managers failing at one-on-ones simply because they’ve never been trained to do them well?

• https://www.linkedin.com/in/rogelberg/
• stevenrogelberg.com

Dr. Steven G. Rogelberg is a Chancellor’s Professor at UNC Charlotte and a leading expert on meetings. An award-winning organizational psychologist, he has over 200 publications, 12,000+ citations, and received the prestigious Humboldt Award for his research. Adam Grant calls him the “world’s leading expert on how to fix meetings.”

His book The Surprising Science of Meetings appeared on 25+ “best of” lists, including The Washington Post’s #1 leadership book to watch. His latest book, Glad We Met: The Art and Science of 1:1 Meetings, has earned high praise, including recognition from SHRM and Forbes.

Rogelberg has been featured on CBS This Morning, CNN, BBC World, NPR’s Morning Edition, and major publications like The WSJ, NY Times, Bloomberg, and National Geographic. His keynotes have been delivered worldwide at top organizations including Google, Amazon, Pfizer, and the United Nations.

In 2022, he testified before the U.S. Congress and was the inaugural winner of SIOP’s Humanitarian Award.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

14:40 The Importance of One-on-Ones

17:48 Common Mistakes in One-on-Ones

23:40 Building Trust and Connection

26:51 Key Elements of Effective One-on-Ones

27:22 Surprising Insights from Research

30:34 Training and Supporting Line Managers

33:28 Creating a Culture of Effective Meetings

In this episode we discuss: Unlocking AI for Non-Technical Leaders. We are joined by Charlie Cowan, Founder of Kowalah and author of "How To Sell Tech" and “The Revenue Operations Playbook”.

Love The Operations Room? Please support us by rating and reviewing it here.

We chat about the following with Charlie Cowan:

• Is AI more accessible than we think?
• What’s the difference between AI agents and workflows—and why does it matter for businesses looking to scale?
• How can organizations build their own AI-powered tools instead of relying solely on SaaS solutions?
• What role does leadership play in AI adoption, and why is AI literacy now a must-have skill for future executives?
• Can a simple “power hour” or habit shift really transform your productivity—and what does AI have to do with it?

• https://www.linkedin.com/in/charliecowan/
• www.charliecowan.ai
• www.kowalah.com

Charlie works with CEOs and senior leaders looking to embed AI behaviours across their organisation.

With a 25 year career in SaaS, consulting and enterprise sales, Charlie bridges the gap between AI technology and practical applied use cases that help teams work smarter and faster.

Charlie is the author of two books - How To Sell Tech and The Revenue Operations Playbook.

Charlie is the founder of Kowalah, an AI-powered platform that helps buying teams to run a great buying processes, pick the right vendors and reduce the fear of messing up.

Charlie built Kowalah as a solo-founder using AI development tools.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

26:36 Introduction to AI Adoption for Non-Technical Executives

027:16 Understanding AI Optimism vs. Pessimism

28:08 Defining AI Policies for Effective Implementation

29:52 The Concept of Agentic AI

31:23 Distinguishing Between Agents and Workflows

33:01 Building Effective AI Agents

37:49 Evaluating Future Tech Stacks for AI Integration

43:05 Empowering Leadership in the Age of AI

46:06 Navigating AI Tools for Policy Management

46:23 Crafting Effective Prompts for AI Tools

49:54 Building a Data Repository for Enhanced Insights

51:44 The Power Hour: Maximizing Productivity

In this episode we discuss: Is the COO the single source of truth? We are joined by Eric Collins, Investor, Serial Entrepreneur, CEO & Founding Member at Impact X Capital investing in underrepresented entrepreneurs; Author of We Don’t Need Permission (amzn.to/3Qp6G9d); & Host of Channel 4's The Money Maker.

Love The Operations Room? Please support us by rating and reviewing it here.

We chat about the following with Eric Collins:

1. What makes the COO the true "source of truth" in scaling a venture-backed company?
2. How can COOs balance growth while CFOs maintain financial discipline—and why does this partnership make or break success?
3. Why is succession planning not just a CEO concern, but a critical step for every COO aiming to lead?
4. Can a COO ever match a founder's passion, or is their power found in something entirely different?
5. What does it really take for a COO to transition into the CEO seat—and what role does backfilling play in that journey?

• https://www.linkedin.com/in/ericdcollinsba/?originalSubdomain=uk
• www.impactxcapital.com

Eric Collins is a serial entrepreneur, investor, and host of Channel 4's The Money Maker. He’s held leadership roles at AOL, TimeWarner, SwiftKey/Microsoft, and Touch Surgery/Medtronic.

Appointed by President Obama to the Small Business Administration’s Council on Underserved Communities, Eric now serves on the boards of Cirata, UnLtd, Crux, and Autograph ABP. A sought-after speaker and Audi brand ambassador, he’s consistently featured on The Powerlist of influential Black Britons.

His award-winning book, We Don’t Need Permission (Penguin), advocates for investing in Black and underrepresented entrepreneurs as a powerful driver of social change.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

23:55 The unique role that the CEO plays in a scaling organisation

28:05 The value of the COO next to the CFO

30:58 Progressing as a COO

33:11 CEO and COO Succession Planning

33:51 The Passion of Founders vs. COOs

39:56 Planning for Success as a COO

43:16 Setting the Agenda in Board Meetings

In this episode we discuss: How to tackle mental health in an organization. We are joined by Chris Hatfield, Mindset & Well-being Coach.

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We chat about the following with Chris Hatfield:

1. What if naming your anxiety was the first step to taking back control?
2. How can leaders foster vulnerability without losing authority?
3. Is your ‘stress container’ full, and how do you know when it’s overflowing?
4. Are we truly addressing the root of anxiety, or just applying quick fixes?
5. What if managing mental health was less about avoidance and more about sitting with discomfort?

• https://www.linkedin.com/in/chrishatfieldsalespsyche/
• www.salespsyche.co.uk

A sales mindset and well-being Coach and Author of Sales Psyche. With over 15+ years of experience working with the likes of Meta, Google, Salesforce, Experian and O2. Focused on supporting salespeople and leaders in developing a healthy and high performing mind. Also founded a run community, Run Your Mind, that is focused on mental well-being.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

16:31 Understanding Anxiety

16:52 The Nature of Anxiety in Men

19:14 Coping Mechanisms for Anxiety

20:36 Proactive vs Reactive Approaches to Anxiety

22:46 Identifying When Anxiety Becomes a Problem

25:10 The Importance of Vulnerability in Leadership

29:01 Understanding the Stress Container Exercise

36:05 The Importance of Reflection and Action

37:59 Tools for Managers to Address Anxiety

34:14 Creating a Mental Health Culture in Organizations

39:18 Training Managers for Mental Health Awareness

42:49 Sales-Specific Strategies for Managing Stress

In this episode we discuss: Jumpstarting your workplace culture. We are joined by Eric Stone, International Keynote Speaker | Award Winning Author | Expert in Building High-Performance Cultures | Empowering Leaders to Drive Engagement & Transform Workplaces

Love The Operations Room? Please support us by rating and reviewing it here.

We chat about the following with Eric Stone:

• Is your workplace culture truly driving success, or just a ‘flavor of the week’ experiment?
• How can leaders balance structure and empowerment without losing control?
• What does a simple story like ‘Johnny the Bagger’ reveal about ownership and impact at work?
• Are we equipping employees with the right tools and trust, or just expecting results without support?
• What makes relationships the hidden engine behind high-performance workplace cultures?

• https://www.linkedin.com/in/eric-stone-clear-path/
• ericdstone.com and clearpathventures.com
• https://www.instagram.com/clearpathventures_/ c. https://www.facebook.com/profile.php?id=100040382190383 d. https://www.youtube.com/@ericdstone1/about

ERIC D. STONE’S passion for business led him to an influential twenty-six-year career at the iconic rental car company Enterprise Holdings, where he quickly became one of the most decorated Regional Vice Presidents in the company’s history. His ability to connect and motivate employees from all different generations and demographics allowed his teams to sustain top-level results and a culture of pride. Eric attributes much of this success to his ability to create, ignite, and sustain a high-performance culture—one that enabled him to lead his teams through challenges like 9/11, the Great Recession, the COVID-19 pandemic, and the Great Resignation—along with an extraordinary ability to adapt to the unexpected and help others do the same.

Eric is the author of the award-winning book Jumpstart Your Workplace Culture and an international speaker on leadership, employee engagement, and creating high-performance organizations. He retired from Enterprise in 2018 and founded Clear Path Ventures, which specializes in guiding young professionals and businesses as they navigate their path to success.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

17:17 Core Thesis of 'Jumpstart Your Workplace Culture'

18:25 Understanding Employee Engagement

19:04 Building Strong Relationships in the Workplace

20:17 Leadership's Role in Workplace Culture

23:57 Effective Communication Strategies

26:54 The Johnny the Bagger Story: A Lesson in Ownership

30:05 Empowerment vs. Accountability in Leadership

31:04 Balancing Standardization and Empowerment

32:33 Ego and Leadership: Letting Go of Control

34:18 Identifying and Nurturing Culture Carriers

36:12 The Importance of Clear Communication and Culture

In this episode we discuss: Making AI happen in 2025 for your organization. We are joined by Charlie Cowan, Author of "How To Sell Tech" and “The Revenue Operations Playbook”.

Love The Operations Room? Please support us by rating and reviewing it here.

We chat about the following with Charlie Cowan:

• How can professionals stay updated in an era where AI is rapidly disrupting industries like sales and marketing?
• With AI advancing faster than its everyday adoption, how can businesses bridge the gap between innovation and practical implementation?
• How can non-developers leverage AI tools to accelerate product development while overcoming emotional and technical challenges?
• In a world where restrictive AI policies hinder adoption, how can organisations balance data privacy concerns with fostering innovation?
• Rather than replacing jobs, how can AI be used to supercharge teams, enhance leadership effectiveness, and drive productivity?

• https://www.linkedin.com/in/charliecowan/
• charliecowan.ai
• https://v0.dev/
• https://replit.com/ai
• https://lovable.dev/
• Bolt.new
• https://www.cursor.com/
• https://codeium.com/windsurf
• https://notebooklm.google.com/

Charlie Cowan helps organisations accelerate AI adoption, guiding CxOs in embedding AI-driven processes to unlock new opportunities. As the founder of Kowalah, an AI-powered buying platform, he built the business from scratch—without prior coding experience—using AI tools. Now, he shares his journey to inspire others to embrace AI innovation.

An author of four books on sales, revenue operations, and go-to-market strategy, Charlie provides practical insights for scaling startups and sales teams. Passionate about AI and business transformation, he continues to drive conversations on the future of AI adoption and leadership.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

20:13 Introduction to Charlie Cowan and His Journey

23:14 The Impact of AI on Business and Personal Reinvention

25:35 Building Koala: The Journey of a Non-Developer

28:00 Navigating Challenges in AI Development

30:48 Balancing Consulting and Product Development

31:27 Leveraging LinkedIn for AI Insights

32:40 The AI Bubble and Company Policies

34:55 Embracing AI: Opportunities and Risks

41:28 Transforming Organisations with AI

44:02 Innovative Tools for Information Management

46:38 Practical AI Applications in Leadership

49:23 Final Thoughts on AI and Automation

In this episode we discuss: how to implement the first team concept. We are joined by Cassie Young, General Partner at Primary Venture Partners, and seasoned SaaS CRO/CCO.

Love The Operations Room? Please support us by rating and reviewing it here.

We chat about the following with Cassie Young:

• How can leaders ensure that their "first team" prioritises organisational success over individual functions?
• What steps can teams take to align incentives and build trust to resolve conflicts more effectively?
• How does empathy in communication and transparency enhance team dynamics, especially in structured yet flexible meeting cadences?
• Why is developing P&L fluency and understanding market dynamics essential for senior executives, and how can organisations address these gaps?
• How can leaders strategically network and cascade critical insights to maintain clarity and alignment within teams?

• https://www.linkedin.com/in/cassyoung/
• https://www.primary.vc/

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage venture capital firm in New York, backing companies like Chief, Alma, and K Health. She leads B2B software investments and oversees the firm's portfolio impact team, the largest of its kind among seed funds globally.

Previously, Cassie was Chief Customer and Commercial Officer at Marigold (formerly CM Group), where she led global operations and strategy across a portfolio of marketing tech brands, following Marigold’s acquisition of Sailthru in 2018. At Sailthru, she held multiple executive roles, ultimately serving as Chief Revenue Officer. Earlier, she led marketing and analytics teams at GLG, Savored (acquired by Groupon), and TheLadders, starting her career as an analyst at Citigroup.

A Duke graduate with an MBA from Tuck School of Business at Dartmouth, where she earned the Dero Saunders Award, Cassie is passionate about advancing women in leadership. In 2023, she launched On the Business, a program helping hundreds of senior women in software enhance their P&L fluency and boardroom skills.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

08:12 Introduction and Context Setting

19:17 Understanding the Concept of First Team

21:00 The Importance of Team Dynamics

21:35 Creating a First Team Mindset

23:00 Fostering Cross-Functional Collaboration

24:13 Aligning Incentives for Team Success

28:25 Overcoming Pushback on Team Engagement

31:12 Communicating with Empathy

34:04 Effective Meeting Cadences

41:03 Navigating Conflict and Accountability

42:23 Essential Skills for Executives

46:06 The Role of Founders and Leadership Styles

48:43 The Importance of Alignment and Communication

In this episode we discuss: What is a COO's strengths and gaps? We are joined by Divinia Knowles, The COO Coach.

Love The Operations Room? Please support us by rating and reviewing it here.

We chat about the following:

• How do COOs turn their knowledge gaps into strengths through experience?
• What can personality tests like the Enneagram teach us about effective COOs?
• How do COOs balance servant leadership with the challenges it brings?
• What’s the secret to building a powerhouse CEO-COO relationship?
• How can COOs use self-awareness to grow as leaders and advisors?

• https://www.linkedin.com/in/diviniaknowles
• www.daijo.io
• www.cooroundtable.com

Divinia Knowles is an accomplished operator and coach with extensive experience supporting startup and scale-up COOs, CEOs, and leadership teams through growth, exit, and beyond. With a career spanning roles as COO, CFO, CEO, and Board Advisor, Divinia has worked with companies like Pact Coffee and Mind Candy, helping scale global brands and drive success.

As the founder of the London COO Roundtable, Divinia has built a thriving network for operational leaders. Since 2017, she’s coached over 150 executives, combining advanced coaching accreditation with expertise in organizational psychology, resilience, and team dynamics.

To learn more about Beth and Brandon or to find out about sponsorship opportunities click here.

16:42 Exploring COO Strengths and Weaknesses

26:36 Personality Types and Archetypes in Leadership

28:09 The Shadow Side of COOs

29:06 Servant Leadership

30:21 The Relationship Between COOs and CEOs

35:24 Ruminating vs. Acting: Different Leadership Styles

37:24 Embracing Public Speaking and Thinking on Your Feet

39:28 The Ruminator: Processing Information Over Time

41:04 The Caregiver Archetype in Leadership

45:39 Balancing Empathy and Performance Management

47:54 The Nature of Relationships in Leadership

48:44 Directness and Good Intent in Communication

49:33 Embracing Self-Awareness and Personal Growth

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