Hosted by Elizabeth Freedman
Listed under Business › Management, Business › Careers, Business
★5.0on Apple Podcasts · 3 recent reviews
The Unwritten Playbook of the C-Suite Executiveland is the podcast for senior leaders, aspiring executives, and anyone who wants to understand what it really takes to lead and succeed at the top.
41 episodes · publishes weekly · latest 2026-09-03 · ~33 min/episode
Rank
#4559
Substance
53.8
/ 100
Breakdown
Scored 2026-09
Updated monthly
Across the index
#4559 of 6203
Substance
Top 73%
outscores 27% of the index
Executiveland ranks #4559 on The B2B Podcast Index with a substance score of 53.8 out of 100, scored across 5 recent episodes. It scores highest on insight density and originality. The episode delivers a handful of actionable frameworks (75% reconnection rule, event stakes checklist, best-question technique, 90-day kill cycles) that a senior leader could implement. However, large stretches are consumed by extended personal anecdotes, repetitive affirmations, and recycled platitudes - 'know, like, and trust' surfaces multiple times and Simon Sinek is cited twice - dragging down the per-minute idea yield substantially.
Averaged across 5 recently scored episodes, with cited evidence.
The episode delivers a handful of actionable frameworks (75% reconnection rule, event stakes checklist, best-question technique, 90-day kill cycles) that a senior leader could implement. However, large stretches are consumed by extended personal anecdotes, repetitive affirmations, and recycled platitudes - 'know, like, and trust' surfaces multiple times and Simon Sinek is cited twice - dragging down the per-minute idea yield substantially.
“there's the 75% reconnection rule. And what that means is that if you're going to intentionally spend four hours a month networking, three of those hours should be spent connecting with the network you already have, as opposed to going out and finding new people.”
“we end up categorizing the different types of events that you go to into a low, medium, and high stakes. And as a leader, you should only be going to high-stakes events.”
The episode coins some memorable terminology ('dopamine handshake,' 'unintentional audience abuse,' 'conversational concierge') and the 75% reconnection heuristic is a crisp reframe of common advice. However, the conceptual scaffolding leans heavily on widely circulated frameworks - the Go-Giver, Simon Sinek's why, and standard CRM drip logic - offering little that is genuinely contrarian or first-principles.
“And it's just this dopamine handshake where we're both feeling great and we're starting a conversation off on a very positive note.”
“unintentional audience abuse is we've we've all sat in an audience where the speaker is speaking to just facts, figures, and platitudes”
Keith Bailey brings credible practitioner grounding - Marine Corps background, global sales roles in apparel - and now runs a coaching firm with genuine client work in AEC, legal, and industrial real estate. From a strict B2B operator lens, however, he is primarily a communications coach and facilitator rather than a scaling founder or C-suite executive who has built or run a significant business, capping the depth of battlefield-tested insight.
“I had eight fun-filled years in the Marine Corps”
“I did uh global sales for for two prominent brands in the apparel industry”
A few named anchors - Tom Mitchell at DLR Group with his birthday-song ritual, Scott Tibbets and the Mars rover actuator company - add texture, and specific heuristics (75% rule, 90-day cycles, top-five list) are usable. The episode lacks hard outcome data, ROI figures, or before/after case studies that would move it into high-specificity territory.
“the gentleman by the name of Tom Mitchell, he's the senior principal for the DLR group”
“he built a company that ended up uh building the actuator motors that uh activated the Mars rover when it landed”
The host surfaces useful topic transitions (tools/systems, career transition scenarios, remote-work context) and occasionally shares her own experience to prompt candid responses. However, she is uniformly affirming, never challenges a framework or asks for disconfirming evidence, and several questions are explicitly leading - telegraphing the desired answer before the guest speaks.
“I love that. Best question. That's so helpful, Keith.”
“is what I'm describing accurate from your view?”
2026-07-02
4 periods tracked.
12 scored on substance · 40 tracked in total.
"Everything becomes easier when it's not about you." with networking expert Keith Bailey
2026-08-06 · 49 min
Encore: The Hidden Trap of Overgiving
2026-07-02 · 21 min
Every Leadership Team Has a Thinking Problem
2026-06-18 · 25 min
Why “Why Should Anyone Care?” Is The Most Important Question, with Chief Marketing Officer Roanne Neuwirth
2026-06-11 · 49 min
Encore: When Bad Teams Happen to Great Leaders: Why Smart Executive Teams Underperform
2026-06-04 · 23 min
Thinking About Leaving Corporate for Consulting? What Senior Leaders Need to Know First, with Coach Melisa Liberman
2026-05-28 · 49 min
"Our job is to do great things" - Maia Josebachvili, Chief Revenue Officer of AI at Stripe
2026-05-21 · 38 min
Why Executives Lose Confidence in Leaders
2026-05-14 · 23 min
From ‘You’ll Never Make It’ to the C-Suite: Dr. DeRetta Rhodes, EVP & Chief People & Culture Officer, The Atlanta Braves
2026-05-07 · 48 min
“Every Time You Walk in the Room, You’re Being Evaluated” - Ricky Hopson, Catalent Group President and Chief of Staff
2026-04-30 · 38 min
Why Ego Is the New Enterprise Risk with Deborah Borg, EVP, Chief People & Culture Officer, IFF.
2026-04-23 · 51 min
Plot Twist: Your Executive Role Just Changed
2026-04-16 · 14 min
This is great for anyone interested in insightful and helpful perspectives about success in the workplace - this is NOT just for people in the C-suite. I think Elizabeth shares stories and examples that are fascinating and educational - for anyone who works with and influences others. I like her compassion, humor, and energy.
- afreedman
Executiveland is EXACTLY the podcast C-suite professionals have been waiting for! Elizabeth has a fresh, no-nonsense take on common issues facing executive leadership. Her insider perspective and decades of experience in a variety of settings give her a unique perspective and insight into the challenges faced in what is often a (paradoxically) lonely space. Can’t wait for the next episode!
- Ceiling Unlimited
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