7 Advanced Coaching Questions That Reveal Blind Spots and Break Dysfunctional Patterns
Release Date: 11/04/2025
The Art & Skill of Coaching
Coaches are consuming more content than ever—books, podcasts, trainings—and yet many still freeze on calls, overthink what to say next, or default to advice-giving when clients get emotional or stuck. In this episode of The Art and Skill of Coaching, I name the skill gap most coaches feel but can’t articulate: the gap between knowing coaching concepts and being able to execute them cleanly in real time. I’m joined by Cat—ASC graduate, peer coach, and collaborator inside The Art & Skill of Coaching—who helps break down why content consumption doesn’t create mastery, and what...
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What actually changes when you invest in a high-level coaching certification? In this episode of The Art and Skill of Coaching, I’m joined by one of my current Art and Skill of Coaching (ASC)students—just one month away from graduation—who shares an honest, behind-the-scenes look at her experience inside the program. Jess is a holistic wellness coach with 15 years of experience bridging nutrition, fitness, and mindset. Despite her background, she noticed clear gaps in her coaching skills, confidence, and session effectiveness—gaps that ultimately led her to ASC. We talk about: The...
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Why do some clients change—and others stay stuck? In this episode, I break down the difference between surface-level coaching and deep, identity-based coaching, and why working at the level of being creates more sustainable results than focusing on behavior alone. You’ll learn: Why deep coaching is nonlinear and messy The skills coaches need beyond basic techniques How identity shifts naturally change behavior Questions that immediately deepen your coaching This is the work we teach inside The Art & Skill of Coaching—psychologically grounded, science-based, and...
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Feeling exhausted, overwhelmed, and frustrated—even though you’re working hard? You’re not broken. You’re not on the wrong path. You’re likely stuck in movement instead of momentum. In this episode, I explain: Why thinking, processing, and preparing can actually keep you stuck How movement feels productive but doesn’t create results The coaching mistake that leads to burnout and stagnation How to shift into momentum through aligned, imperfect action Whether you’re a coach or a high-performing professional, this episode will change how you approach growth, change, and...
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In this special Ask Me Anything episode, Jess DeMarchis—therapist-turned life coach—kicks off the new year by answering your most asked questions about coaching, business, money, and personal growth. Pulled directly from Instagram DMs, Jess is interviewed by her friend Megan in an honest, fun, and wide-ranging conversation that blends personal stories with professional insight. Together, they cover everything from Jess’s early leadership influences and favorite coaches, to why she transitioned from therapy to coaching, how she runs her coaching business, and how she thinks about money,...
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Description: In this episode of The Art & Skill of Coaching, Jess breaks down the fastest and most evidence-based way to develop coaching mastery. If you’ve ever wondered why you’re not improving as quickly as you want — or why practice alone isn’t enough — this episode explains the exact path professional coaches use to grow. You’ll learn: why information and inspiration don’t lead to real skill the Learn → Witness → Practice framework for building mastery how supervised coaching accelerates your growth the difference between repetition and correct repetition ...
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Description: What separates a good coach from a master-level coach? In this episode of The Art & Skill of Coaching, Jess breaks down the psychology-based tools, trauma-informed frameworks, and advanced questioning techniques that Master Coaches use to create deep, identity-level change with their clients. You’ll learn: The 3 things Master Coaches do differently in every session How interventions like Thought Clearing (CBT) and Motivation Mapping (MI) actually work What trauma-informed coaching looks like—and why it matters How great coaches ask questions that shift perspectives...
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Description: Most coaches genuinely want to help—but good intentions don’t override impact. In this Master Coach Series episode celebrating 200+ podcast episodes, Jess breaks down the seven coaching mistakes even well-trained coaches are unintentionally making that keep clients stuck. These mistakes show up across every niche—from life coaching to business coaching. Inside this episode, you’ll learn how to coach at a higher, more effective, more ethical level by avoiding the patterns that derail client progress. You’ll learn: Why cheerleading actually prevents transformation How...
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Description: Welcome to Episode 1 of the 4-part Master Coach Series, celebrating 200 episodes of The Art and Skill of Coaching— a top 2% global podcast dedicated to psychology-based coaching. Today, we’re kicking off the series with a foundational episode: The 4 core skills most coaches think they have… but don’t. Because while empathy, intuition, and “holding space” matter, they are not what create consistent, repeatable change. Coaching is a skill set rooted in psychology, neuroscience, and evidence-based methods — and in this episode, you’ll learn the exact skills that...
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Description: Yes — I’ve been fired by clients. And after 10+ years as a therapist-turned-coach, I’m telling you why this isn’t a failure… and what great coaches do differently. In this episode, we break down the psychology behind client ruptures, refund requests, mismatches, and conflict inside the coaching relationship. You’ll learn how to prevent and navigate difficult client dynamics with clarity, leadership, and actual coaching skill. Learn more about The Art & Skill of Coaching certification: ASC Waitlist: Stay in Touch: IG...
info_outlineDescription: If your clients keep hitting the same wall—emotionally, behaviorally, or relationally—it’s not because they’re broken. It’s because the pattern is serving a function they don’t yet see. In this episode, Jess DeMarchis, therapist turned life coach and founder of the Art & Skill of Coaching, shares seven advanced coaching questions that uncover hidden functions in dysfunction, bring awareness to emotional patterns, and help clients build self-trust and regulation.
Learn more about The Art & Skill of Coaching certification:
https://www.jessicademarchis.com/the-art-skill-of-coaching
ASC Waitlist:
https://purple-lion-72607.myflodesk.com/ascwaitlist
Stay in Touch:
IG @jess_demarchis_coaching
The Coach Skill Audit:
https://purple-lion-72607.myflodesk.com/coachskillaudit
Coach Question of the Week:
https://purple-lion-72607.myflodesk.com/agcj1mr1y3