Coffee House Coaching

 1️⃣ Best Coaching Advice Received“Your presence is a present.”Presence is active, not passive — it requires intention and effort.Yoga and meditation built her ability to refocus repeatedly.Being fully seen and heard is itself support. 2️⃣ What She’s Still ImprovingChoosing what thread to follow when clients offer many entry points.Prioritizing the question that creates the greatest impact.Staying deep without chasing every possible avenue.Discipline in focus inside complexity. 3️⃣ Most Courageous MomentStopped a recorded PCC session mid-way because it felt performative.Recognized she was coaching for assessment rather than authenticity.Restarted the session to return to intuitive presence.Refused to compromise integrity for performance. 4️⃣ What Makes Her UncomfortableVery little — discomfort energizes her.She thrives when clients go deep.Challenge excites her, especially when clients feel hopeless.Real change happens below the surface. 5️⃣ Advice for New CoachesLearn business skills — coaching skill alone isn’t enough.Be ready to wear marketing, logistics, and operations hats.You need very little to start — just begin.Start before you feel ready. 6️⃣ Something She Had to ConquerLetting go of performance mentality.Learning to trust intuitive coaching.Separating empathy from emotional absorption.Feeling with clients, not for them. 7️⃣ Using AI in CoachingDoes not use AI note-takers in sessions — protects presence.Uses AI for idea generation and blog structuring.Believes AI coaching increases accessibility.Human presence and intuition remain irreplaceable.Sees AI as enhancement, not replacement. 8️⃣ What She’s Learned About HerselfShe can put people at ease quickly.She holds space well, especially in emotional moments.Silence is powerful and intentional.Deep listening changes relationships beyond coaching. 🎉 Fun Stuff HighlightsFavorite Yoga Pose: Viparita Karani, held for up to 60 minutes.Working On: Bird of Paradise — almost there.Favorite Movie: Titanic. Full heart. No apologies.

1) Best coaching advice you’ve gotten“It doesn’t have to be anything.”Let go of outcomes to make room for discovery.Presence creates space clients rarely experience.Coaching works precisely because nothing is being driven. 2) What are you still trying to improve about your coaching?Communicating the value of coaching in the marketplace.Calling in the right people, not everyone.Refining the “howl” so the wolves answer.Balancing intention with non-attachment. 3) Most outrageous thing you’ve done, tried, or said in a session?Saying the thing politeness says not to say.Naming contradictions clients don’t realize they voiced.Choosing courage over being liked.Trusting that bravery serves the client, not the ego. 4) What still makes you squirm or feel uncomfortable?Realizing you misunderstood where the client was going.Moments of energetic or values mismatch.Knowing a client is thrilled while you’re quietly dreading sessions.Recognizing when it’s not a good fit. 5) Advice for someone new to coachingGet serious about the business side early.Don’t confuse caring with giving it away.Channel generosity intentionally (not randomly).Coaching is a profession, not a hobby with invoices. 6) Something you had to conquer to become a great coachThe need to rescue or make things better.Staying in your lane when therapy is needed.Knowing your edges and referring out.Letting clients have their stuff without taking it from them. 7) How are you using AI in your coaching practice?To get to people faster, not replace connection.For thinking partners, not final answers.Designing processes and exploring ideas.Speed to relationship, not content automation. 8) What have you learned about yourself through coaching?Messy you is still a gift.Perfection is optional, presence isn’t.Emotions carry wisdom when welcomed.Sharing beats performing every time. Fun Stuff Question: Favorite mealIt’s never about the food alone.Conversation is the real main course.Care, intention, and presence matter more than the menu.A great meal is a shared experience, not a transaction.

Question-by-Question Highlights1) Best coaching advice you’ve gottenCoaching is more about listening than talkingAsk multiple layers of questions before offering insightLet clients uncover their own answersResist the urge to jump in early2) What are you still trying to improve about your coaching?Slowing down despite decades of experienceAsking more follow-up questionsAvoiding knee-jerk solutionsLetting the real issue surface naturally3) Most outrageous thing you’ve done in a coaching sessionTold a CEO he was the primary problemEnded a lucrative engagement on ethical groundsRefused to be an “ally” to blame-shiftingWalked away when accountability was impossible4) What still makes you uncomfortable?Leaders who blame everyone elseLack of self-awareness and humilityResistance to honest self-reflectionCoaching people who won’t look in the mirror5) Advice for new or aspiring coachesLearn how to truly listenKnow what you don’t knowStay in your laneDon’t pretend to be the expert in everything6) What have you had to conquer to be a great coach?The urge to “fix” too quicklyThe temptation to impress with answersWalking away when coaching won’t workAccepting that not everyone is coachable7) How are you using AI in your coaching practice?Content creation and thought leadershipEliminating the blank-page problemExpanding solution options for clientsSupporting judgment, not replacing it8) What have you learned about yourself?Delivery matters as much as insightExperience must be paired with empathyTrust and relationships drive changeCoaching is art, not just scienceFun Stuff QuestionFavorite movie: PattonWhy: history, leadership, discipline, stoicismBelief: ancient wisdom still applies todayLeadership lesson: study history or repeat it

Question-by-Question Highlights1) Best coaching advice you’ve gottenDon’t be attached to the client’s outcomePresence improves when control is removedClient commitment matters more than coach frustrationMissed actions are data, not failure2) What are you still trying to improve about your coaching?Leaning more into somatic awarenessAsking “where do you feel that?” more oftenTrusting body signals as much as intellectSlowing down instead of goal-chasing3) Most outrageous thing you’ve done, tried, or said in a sessionTold clients they weren’t ready for coachingPaused engagements instead of pushing throughRedirected clients to books instead of sessionsPrioritized service over revenue (wild, I know)4) What still makes you squirm or uncomfortable?Ignoring internal discomfortNot asking the question her gut is screamingLeaving insight “on the table”Playing it safe instead of pushing edges5) Advice for someone new to coachingLearn multiple coaching modelsDon’t copy other coaches, synthesize themStay a student of coaching foreverLet formulas guide early, not define forever6) What have you had to conquer to become a great coach?Attachment to doing it “right”Fear of losing clients by being honestThe urge to rescue instead of reflectTrusting that readiness can’t be forced7) How are you using AI in your coaching practice?AI note-taking with client opt-inUsing transcripts to deepen recallExploring tools and exercises with curiosityLetting tech support presence, not replace it8) What have you learned about yourself through coaching?Imposter syndrome is universalOne-on-one depth beats loud roomsCuriosity is her superpowerBeing heard changes everythingFun Stuff QuestionFavorite movies: The Princess Bride (classic), Love Actually (Hugh Grant wins)Celebrity look-alikes: Laura Linney, Kirsten Bell (15 pounds ago, allegedly)Strong opinions on names, silence, and Italian pronunciation

1. Best Coaching Advice You’ve GottenAsk more questions instead of charging in with solutions.Slow down the instinct to “fix”—curiosity beats expertise.Socialize ideas rather than bulldozing with brilliance.2. What Are You Still Trying to Improve?Reducing compound questions (her version of the coaching filibuster).Releasing the impulse to control the conversation.Allowing clients to answer imperfectly without “rescuing” them.3. Most Outrageous Thing You’ve Done in a SessionDeploying the wildcard question: “What am I not asking you that I should be?”Admitting out loud when a session feels stuck.Handing responsibility back to the client instead of forcing an insight.4. What Still Makes You Uncomfortable?Knowing when to interrupt clients who go on context marathons.Managing the tension between venting and progress.Timing the interruption like Double Dutch: jump too early and you break an ankle.5. Advice for Someone Considering CoachingGive yourself to the infinite, unpredictable paths a conversation can take.Let go of steering, engineering, and controlling outcomes.Trust the process even when it feels like you’re floating in space without gravity.6. Something You’ve Had to ConquerEgo. Full stop.The belief that being the smartest person in the room is the job (it isn’t).Breaking lifelong habits formed as a lawyer and high achiever.7. How Are You Using AI in Your Coaching Practice?Barely—AI helps run the business, not the coaching room.Protecting the human heart of coaching is a priority.Belief that if you show up like a robot, you’re easier to replace by one.8. What Have You Learned About Yourself Through Coaching?She’s a lifelong learner who never wants to stop honing her craft.Coaching opened an entire new intellectual landscape she wants to master.Minimalism and presence are more powerful than frameworks and prep.Fun Stuff Question(Bridget Jones, blue crabs, Severance, and a reality-TV confession.)Favorite movie: Bridget Jones’s Diary (and she knows you’re judging her).Favorite meal: backyard Maryland crab feasts—an entire family ritual, not a menu item.Favorite show: Severance, plus a guilty-pleasure detour into Love Is Blind. 

 8 Questions + 1 Fun Stuff Summary1️⃣ Best Coaching AdviceCome empty — show up without your agenda or rucksack of tools.Be nothing for your client; let their story lead.The less you bring, the more emerges.2️⃣ What You’re Still ImprovingDeepening the art of listening to understand, not respond.Using somatic awareness — grounding, feeling feet, breath, and body connection.Staying present instead of preparing a response.3️⃣ Most Outrageous Thing DoneAsked a founder, “What if this company isn’t yours to build?” and stayed silent.Invited a high-performing board to consider, “What if your ceiling is your floor?”Held everything neutral — courage through calm curiosity.4️⃣ What Still Makes You UncomfortableTaking notes during sessions — breaks connection and presence.Managing the tension between documentation and deep listening.Letting silence hold more value than written words.5️⃣ Advice for New CoachesFocus equally on your state of being and the business of coaching.Learn to consciously create your internal state before each session.Build awareness of how your presence shapes every client interaction.6️⃣ What You’ve Had to ConquerShifting from doing to being — from tools to trust.Letting go of performance mindset from engineering roots.Embracing neutrality and imperfection in the coaching journey.7️⃣ How You Use AIUses ChatGPT and Gemini daily for proposals, tone checks, and ideation.Exploring creating custom AI agents for repetitive business tasks.Sees AI as a creative partner, not a threat — a reflection tool, not a replacement.8️⃣ What You’ve Learned About YourselfCoaching meets him where he is in every season of life.Always keeps a coach — it’s a non-negotiable business expense.Strives to be “the best coach in the world” — not from ego, but from intention.🎬 Fun Stuff Question — Favorite MovieAmélie — a French film he saw three times in one week.Loves its color, music, and magic.Proof that beauty, like coaching, is found in the small details. 

Highlights:Operating from the Zone of Excellence to the Zone of GeniusMemories of her wonderful son BenjaminWorking with clients with a big legacy perspectiveLearning to say no and opening up space for her "perfect" clientTuning in to her clientsThere is no such thing as impossibleAdvice on working deeper with clientsCan't take anyone deeper than you've gone on yourselfThe Activity Brain Dump"Hell Yes" / "No, not for now" / "Maybe"The energy auditNever too late to "go deep" with your clientCreate space for miraclesAre you a match to what you are asking for?Coming from the goal NOT to the goal

https://www.victoriawobber.com/Tory Wobber brings so much energy to this podcast and she provides a perspective on her coaching niche and how she became a coachHighlights from my conversation with ToryMoving to and coaching in Mexico / Coaching PHd's looking for jobs in industry (this is what tory did) / Paying it forward, then formalizing / Consulting vs coaching / Grieve the loss of their academic identity / Having lived what she is coaching / Visualizing your future / Who am I if I'm not my job / Pint size insights / Helping clients get "unstuck" / Skills are there, helping with the mindset shift / Asking clients to stand and breathe / Finding the right coaching course / The dip and getting to mastery / PB&J conversation

Highlights:Started coaching at age 5, yea I knowCorporate outsiderLicensed PsychotherapistFinding his Niche early onwww.blackexecutivemen.comTherapy vs coachingJewels clients see themselves in himPassionate about growth and professional successClarity and the puzzle pieces, getting them all on the tableHis Process = Clarity / Decisions / ActionsWorking with his own coach to get the confidence he neededCreating a Buddy System with his clientsComing from tissues, tears and traumaDaily Newsletter

Question Summaries 1️⃣ Best coaching advice you’ve gotten“It doesn’t have to be about who — it can be about what.”Freed her from the pressure to niche by audience; she leaned into values.Shifted her entire perspective on what authentic coaching looks like.2️⃣ What are you still trying to improve about your coaching?Learning to embrace silence rather than fill it.Recognizing her own “know-it-all” tendencies and stepping back.Seeing pauses as productive — where the client’s best thinking happens.3️⃣ Most outrageous thing you’ve done, tried, or said in a sessionCalling BS when clients hide behind surface-level stories.Pushes hard — but only when deep trust exists.Trusts her instincts to dance between mentor, consultant, and coach.4️⃣ What still makes you squirm or uncomfortable?Talking about money and “selling” her value.Learning to see pricing as respect for her own worth.Embracing “Hell yes or Hell no” as her filter — no “Hell maybes.”5️⃣ Advice for someone new to coaching“You have to break yourself open to become a great coach.”True learning comes from going inward and unlearning old habits.Coaching is an inside-out profession — not a set of tools.6️⃣ What have you had to conquer on your path to being a great coach?Releasing the need to fix others (and her kids).Choosing curiosity over control, especially as a parent.Accepting that not everyone wants to grow — and that’s okay.7️⃣ Are you using AI in your coaching practice?Uses AI as a thought partner to spark creativity and expand thinking.Blends AI with tools like Enneagram and Positive Intelligence for depth.Encourages clients to ask AI, “How should I use a coach?”8️⃣ What have you learned about yourself through coaching?A lifelong fascination with human consciousness.Rediscovered her teenage love of psychology and helping people grow.Realized her impact comes from curiosity, connection, and consciousness.🎬 Fun Stuff QuestionGuilty pleasure: playing with the snarky “Monday” GPT for humor and insight.Loves how it’s both validating and thought-provoking.Proof that self-discovery can come with sarcasm.