In this episode, strategist and author Jonathan Bennett—advisor to CEOs, boards, and founders—breaks down exactly how and when to stand up an advisory board, why founders should hire a chair first, and how structure and accountability pull leaders out of isolation. The conversation covers paid vs. unpaid advisors, what to do when disagreements arise, and how quarterly decks become an early-warning system for both risk and opportunity.

You will hear a live case study on a $5M trades business planning a future exit, learn the baseline systems and KPIs required before a board can help, and understand how a skilled chair’s network can fill functional gaps, recruit leaders, and prep a company for sale. Jonathan also opens the curtain on his “portfolio life,” the realities of CEO coaching, and a behind-the-scenes advisory series where listeners can eavesdrop on real-world boardroom conversations.

Don’t miss this conversation between Ken Eslick and Jonathan Bennett!

Looking for your next leader? Contact us: ken@theleaderslab.co or take the Free ScaleUp Leadership Survey at theleaderslab.co

00:00 – Welcome & Why Boards Belong in Your Playbook (guest intro + pillars: Hire, Scale, Sell) 01:02 – Jonathan’s First Board Seat: governance by immersion and what stuck 03:12 – Feeling Alone as a Founder? Build “Scaffolding”: mentors vs. coaches vs. advisory boards 05:04 – Making It Real: 4 handpicked advisors, quarterly packs, brutal questions, accountability 07:28 – How to Get on (and Build) Boards: why young leaders should join one 10:01 – When to Form an Advisory Board—and What to Pay: from bootstrap to $20M+ examples 12:10 – The Better Model: Hire the Chair First and let the chair recruit for blind spots 14:15 – Recruiting Your Board Like a Pro: use a formal search (yes, a recruiter) and interviews 16:22 – Cadence & Consequences: quarterly rhythm, ad-hoc in crises, and what if you ignore advice? 18:45 – Virtual vs. In-Person: Zoom practicality vs. the magic of dinner + a full-day board 21:02 – Case Study: $5M HVAC/Plumbing Owner Eyeing an Exit—the chair’s profile and board mix 24:55 – Before the Board Helps, Fix the Foundation: KPIs, finance hygiene, and leveraging the board’s network 28:42 – Inside Jonathan’s Portfolio Week: four boards, executive advising, and selective consulting 30:58 – Coaching vs. Advising: decision-making, tough HR calls, and “sometimes just give the answer” 33:10 – Deep Listening & ‘Clearly Then’: why presence matters and where to hear real sessions

#ThePlaybookPodcast #AdvisoryBoard #FounderToCEO #ScaleToSell #LeadershipPlaybook

Stop trying to be indispensable—the business grows the moment you aren’t.

You don’t scale by doing more—you scale by replacing yourself in the right seats. In this episode, Onika and I unpack the uncomfortable shift from “I do everything” to “I build the team that does everything,” including the identity and ego traps that keep smart leaders stuck.

We walk through the practical side: how to decide who should take the wheel (sales, ops, GM), how to define the bullseye profile beyond a generic job description, and how to run a fast—but not sloppy—process that candidates actually enjoy. We also get tactical on onboarding cadence, 30/60/90s, and the difference between owning the process vs. trying to be in every interview. If you want to move up a level, your job is to multiply leadership—starting now.

Segments:

00:00 — Why you can’t grow until you replace yourself

02:05 — My early lesson: doing it all vs. building a team

03:45 — Identity & ego: the hidden throttle on scale

05:10 — Trusting others and becoming a “master delegator”

05:55 — Delegating budgets: why section leads beat heroics

06:55 — Succession planning as important as the financial plan

08:15 — Beyond generic JDs: aim for the bullseye avatar

10:55 — Pitch your company to candidates like a product

13:30 — Hiring ≠ delegation; hiring = leadership multiplier

15:20 — Proactive vs. reactive hiring (and the “beer goggles” trap)

19:05 — Speed with respect: candidate communication that wins

25:10 — Onboarding cadence and 30/60/90s that set people up to win

29:10 — The personnel-file wake-up call: feedback must match decisions

34:05 — Hard truth: no one is indispensable—build leaders or plateau

36:05 — The promotion unlock: develop leaders at every level

Looking for your next leader? Contact us: ken@theleaderslab.co or take the Free ScaleUp Leadership Survey at theleaderslab.co

#Leadership #SuccessionPlanning #Hiring #ScalingUp #TalentAcquisition

In this episode of The Playbook, presented by The Leaders Lab, Ken Eslick and co-host Onika Kwatsha go deep into the question every great leader must ask: Who am I, and why do I lead?

They break down how your inner drivers define your company’s culture, growth, and eventual legacy — and why leadership isn’t about control or charisma, but contribution, clarity, and connection.

Topics covered:

• Leadership as a mirror: what your team sees in you reflects what’s inside you.

• Management vs. leadership: the hidden cost of leaning too far into admin.

• Burning your calendar: when structure stops serving you, start over.

• The six human needs framework (certainty, variety, significance, love/connection, growth, contribution).

• Blind spots, DISC, and radical self-awareness.

• Hiring for difference, not comfort — why “cloning yourself” kills innovation.

• Ken’s 3-step leadership lens (inspired by Tony Robbins)

Timestamps

• 00:02 – Why leadership starts with you

• 02:04 – The six human needs explained

• 07:29 – Manager vs. leader

• 13:35 – Time-blocking and burning your calendar

• 26:29 – Turnover, ownership, and tough calls

• 31:04 – Blind spots and self-awareness

• 36:34 – Hiring beyond your mirror

• 43:42 – Vision, why, and cultural ripple effects

• 45:30 – Ken’s leadership philosophy in three lines

“Leadership isn’t a title—it’s a mirror.”

“If you don’t plan your week, your week will plan you.”

“Great leaders see things as they are—then better than they are—and ultimately guide people to the better.” If you are looking for your next great hire or want to connect with us, we would love to hear from you. Please go to the leaderslab.co or email: ken@theleaderslab.co