The Modern CEO's Guide to the Chief of Staff Role

In this episode of The Modern CEO, we covered the rising significance of the Chief of Staff role, joined by experienced Chief of Staff Catherine Shepherd and Nick from the Chief of Staff Association.

Catherine provides an insightful look into her day-to-day responsibilities, the importance of building trust and authority, and how she amplifies the effectiveness of a Principal or CEO.

Nick offers a broader perspective on the evolving nature of the role globally and identifies key indicators for organizations to know when they're ready to hire a Chief of Staff.

Tune in to understand the vital role a Chief of Staff plays in enhancing leadership and operational efficiency.

00:00 Introduction to the Chief of Staff Role
00:17 Meet the Guests: Catherine and Nick
01:21 A Day in the Life of a Chief of Staff
03:11 Stakeholder Engagement and Project Management
05:25 The Fixer Role and Ad Hoc Responsibilities
08:50 Different Models of Chief of Staff
11:36 Delivering Value to the CEO
16:13 Building Trust and Authority
17:56 When to Hire a Chief of Staff
24:11 Pathways to Becoming a Chief of Staff
30:08 Finding the Right Chief of Staff
33:22 Authority and Decision-Making
37:21 Conclusion and Contact Information 
#TheModernCEO #MrJoeLeech #ceocoach

Thanks for watching! If you enjoy my content and you want to get in touch to find out how I could work with you, or someone you know, you can reach me on LinkedIn at linkedin.com/in/joeleech, or via email at: joe@mrjoe.uk Subscribe to the YT channel at  @mrjoe-coach ​

The Modern CEO Podcast, Episode 3: The CEO’s Guide to Success (Execution-First Leadership)


What separates good CEOs from great ones? In this episode of The Modern CEO, Joe is joined by Professor Steven Kaplan of the University of Chicago Booth School of Business,  one of the world’s leading voices on CEO performance, hiring, and boards.

About the guest:

• Steve Kaplan is a top private equity scholar and Chicago Booth professor.
• Co-created the Kaplan-Schoar PME and co-founded Booth’s New Venture Challenge.
• His students launched companies like GrubHub, Venmo, and Simple Mills.
• Named one of the top 12 business school teachers in the U.S.
• Serves on Morningstar’s board and has taught at Booth since 1988.

Together they covered:
👉 Why execution (not likability) is the top trait of high-performing CEOs
👉 How to avoid “analysis paralysis” at the top
👉 What boards often get wrong when choosing a CEO
👉 Practical advice for founders preparing to hand over the reins
👉 The biggest blind spots leaders face in times of uncertainty

Whether you're a CEO, board member, or aspiring leader.. this episode will challenge how you think about leadership and decision-making.

👉 Full episode available now.

Subscribe for more conversations on modern leadership. ‪@mrjoe-coach‬

🔗 Learn more about Professor Steven Kaplan: Chicago Booth Faculty Profile
🔗 Learn more about The Modern CEO Podcast: mrjoe.uk 

Thanks for listening! If you enjoy my content and you want to get in touch to find out how I could work with you, or someone you know, you can reach me on LinkedIn at linkedin.com/in/joeleech, or via email at: joe@mrjoe.uk

Sally is Head of Engineering at Farewill, a company who helps people deal with death, think wills and funerals. Before that Sally was acting Engineering Director / web discipline lead at UK challenger bank Monzo.
Sally's website https://sallylait.com
Sally on Twitter https://twitter.com/sallylait
Farewill (They are hiring!) https://farewill.com/careers

Mr Joe Leech talks to Christian Gonzalez from YouTube.

Christian on LinkedIn: https://www.linkedin.com/in/christian-gonzalez-yt/

Christian lead’s a team of quantitative and qualitative User Experience Researchers at YouTube and has worked with various product teams at Google. He has a PHD in Human Factors and Applied Cognition and together we talk about how research drives product decision making at YouTube.

Mr Joe Leech talks to Martin Eriksson. Martin has helped shape the product management industry as we know it. As the co-Founder of both ProductTank and Mind the Product – together, the world’s largest product community that brings together people in more than 200 cities across the world. He’s also co-author of the best-selling book, Product Leadership: How Top Product Managers Launch Awesome Products and Build Successful Teams.

Mind the Product virtual conference, November 2020 https://www.mindtheproduct.com/mtpcon/digital/

Martin's Product Leadership book
https://amzn.to/31CKtgr

Mr Joe Leech talks to Curtis from Delivery Hero; the largest global food network outside of China, with more than 4 million food orders a day operating in 600 cities across the world. With brands like Food Panda they are a food global powerhouse you probably haven’t heard of as they don’t have a US or UK presence.
Curtis talks about planning product for many languages, countries and brands. How to be an expert at not being an expert and the importance of being upfront with the senior team.

Mr Joe Leech talks to Harpal Singh. Harpal has taken three AI / ML products from zero to $20M+ in revenue and scaled two products to $100M and $300M+ He’s also winner of the 2019 Product visionary award.
- Harpal Singh’s Website https://www.harpalsingh.com/
- Harpal on LinkedIn https://www.linkedin.com/in/harpalcpo/

Mr Joe Leech talks to Booking.com / Rentalcars.com Global Head of Product Sarvesh Govindappa Sarvesh talks high level decision making, roadmap planning and large scale re-platforming.

Mr Joe Leech talks to Erin Casali from Wordpress / Automattic. Erin is Head of Design for Jetpack at Automattic, the creators of WordPress·com. WordPress powers one third of website on the internet today.

Episode 2 — The CEO’s Guide to Being Punched in the Face (Metaphorically, Mostly)

What does it really feel like to lead when the stakes are high, the spotlight’s on you, and everything’s breaking at once?

In this episode of The Modern CEO, Joe sits down with Roan Lavery, CEO and co-founder of FreeAgent — a UK-based accounting software platform for small businesses.

They talk about the real punches leaders take: the transition from co-founder to CEO, the weight of responsibility, and the difference between having opinions and actually leading the change.

From building FreeAgent over 18 years to managing through chaos and calm, Roan shares raw, behind-the-scenes lessons every leader needs to hear..

Listen now and hit subscribe for unfiltered conversations on power, pressure, and presence of the Modern CEO.

What really happens when the CEO–investor relationship breaks down?

In this bold first episode of The Modern CEO, Joe Leech and guest Paul Traynor (veteran VC and author) unpack the unspoken dynamics between CEOs and private equity investors.

Expect sharp insight, real stories, and the kind of candor that never makes it into investor decks.

From brutal clarity to boardroom blowups, we talk about:

• When to say “Back me or sack me”
• Why soft skills matter more than spreadsheets
• The hidden fears driving investor behavior
• And what happens when trust breaks down at the top

No fluff nor filter but straight talk on what it actually takes to lead.

mrjoe.uk

Note: This episode contains strong language.

The Rules Have Changed. Welcome to The Modern CEO.

This new season of the podcast is for leaders who aren’t following the old rules, they’re rewriting them.

In this short kickoff, Joe Leech shares what to expect this season: unfiltered conversations, bold insights, and real talk about power, pressure, presence, and the hard calls every CEO has to make.

No fluff. No safe takes.

Let’s redefine leadership, starting now.

Today I’m joined by Carole Egerton. Carole is founder and Chief Product Officer for Clear Eye Test and formerly of Glasses Direct. Clear is bringing the eye test into the home and building an ecosystem for virtual global eyecare.

We talk culture, unshipping and of course making better decisions.

Clear Eye Test. https://www.cleareyetest.com
Carole on LinkedIn https://www.linkedin.com/in/caroleegerton/

This time I’m joined by Tin Kadoic from Instagram. Tin leads the design management team for Reels at Instagram and was previously at Airbnb.
We talk culture, unshipping and of course making better decisions.

* [Tin’s website](https://blackduke.com/)
* [Tin on Instagram](https://www.instagram.com/blackduke/)
* [Tin on Twitter](https://twitter.com/tinkadoic)
* [Tin on Linkedin](https://www.linkedin.com/in/blackduke/)

Transcript: https://mrjoe.uk/s1-e11-culture-process-unshipping-with-tin-from-instagram

I’m joined by Selena Hadzibabic. Selena is VP of product for the global wedding company the Knot Worldwide. You might know them as Hitched in the UK, Wedingwire in North America and India. We talk optimising decision making, decisions now or later and how to asses the competitions' decisions.

- Selena on Twitter https://twitter.com/dzishn
- Selena on LinkedIn https://www.linkedin.com/in/selena/

For the full transcript and more episodes please visit https://mrjoe.uk/category/podcast/

Joe Leech talks to Meri Williams. CTO of AI healthcare startup Healx, former CTO of Monzo, Print on demand Moo and Marks and Spencer. Chair of the fantastic lead developer conference. We talk collaboration with Product & Tech, overlap of disciplines, inputs to decision making and more.

Jeff is the co-author of Lean UX as well as the Harvard Business Review Published Sense and Respond. He coaches organisations to create a better culture that creates better products. We talk retraining execs to trust the team and what do when your competitor offers a product for free.

- Jeff's website https://jeffgothelf.com
- Jeff on Linkedin https://www.linkedin.com/in/gothelf/