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 coaching

• Get 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 coach

• The 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 meal

• It’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 Highlights

1) Best coaching advice you’ve gotten

• Coaching is more about listening than talking
• Ask multiple layers of questions before offering insight
• Let clients uncover their own answers
• Resist the urge to jump in early

2) What are you still trying to improve about your coaching?

• Slowing down despite decades of experience
• Asking more follow-up questions
• Avoiding knee-jerk solutions
• Letting the real issue surface naturally

3) Most outrageous thing you’ve done in a coaching session

• Told a CEO he was the primary problem
• Ended a lucrative engagement on ethical grounds
• Refused to be an “ally” to blame-shifting
• Walked away when accountability was impossible

4) What still makes you uncomfortable?

• Leaders who blame everyone else
• Lack of self-awareness and humility
• Resistance to honest self-reflection
• Coaching people who won’t look in the mirror

5) Advice for new or aspiring coaches

• Learn how to truly listen
• Know what you don’t know
• Stay in your lane
• Don’t pretend to be the expert in everything

6) What have you had to conquer to be a great coach?

• The urge to “fix” too quickly
• The temptation to impress with answers
• Walking away when coaching won’t work
• Accepting that not everyone is coachable

7) How are you using AI in your coaching practice?

• Content creation and thought leadership
• Eliminating the blank-page problem
• Expanding solution options for clients
• Supporting judgment, not replacing it

8) What have you learned about yourself?

• Delivery matters as much as insight
• Experience must be paired with empathy
• Trust and relationships drive change
• Coaching is art, not just science

Fun Stuff Question

• Favorite movie: Patton
• Why: history, leadership, discipline, stoicism
• Belief: ancient wisdom still applies today
• Leadership lesson: study history or repeat it

Question-by-Question Highlights

1) Best coaching advice you’ve gotten

• Don’t be attached to the client’s outcome
• Presence improves when control is removed
• Client commitment matters more than coach frustration
• Missed actions are data, not failure

2) What are you still trying to improve about your coaching?

• Leaning more into somatic awareness
• Asking “where do you feel that?” more often
• Trusting body signals as much as intellect
• Slowing down instead of goal-chasing

3) Most outrageous thing you’ve done, tried, or said in a session

• Told clients they weren’t ready for coaching
• Paused engagements instead of pushing through
• Redirected clients to books instead of sessions
• Prioritized service over revenue (wild, I know)

4) What still makes you squirm or uncomfortable?

• Ignoring internal discomfort
• Not asking the question her gut is screaming
• Leaving insight “on the table”
• Playing it safe instead of pushing edges

5) Advice for someone new to coaching

• Learn multiple coaching models
• Don’t copy other coaches, synthesize them
• Stay a student of coaching forever
• Let formulas guide early, not define forever

6) What have you had to conquer to become a great coach?

• Attachment to doing it “right”
• Fear of losing clients by being honest
• The urge to rescue instead of reflect
• Trusting that readiness can’t be forced

7) How are you using AI in your coaching practice?

• AI note-taking with client opt-in
• Using transcripts to deepen recall
• Exploring tools and exercises with curiosity
• Letting tech support presence, not replace it

8) What have you learned about yourself through coaching?

• Imposter syndrome is universal
• One-on-one depth beats loud rooms
• Curiosity is her superpower
• Being heard changes everything

Fun Stuff Question

• Favorite 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 Gotten

• Ask 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 Session

• Deploying 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 Coaching

• Give 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 Conquer

• Ego. 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 Summary

1️⃣ Best Coaching Advice

• Come 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 Improving

• Deepening 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 Done

• Asked 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 Uncomfortable

• Taking 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 Coaches

• Focus 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 Conquer

• Shifting 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 AI

• Uses 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 Yourself

• Coaching 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 Movie

• Amélie — 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 Genius
• Memories of her wonderful son Benjamin
• Working with clients with a big legacy perspective
• Learning to say no and opening up space for her "perfect" client
• Tuning in to her clients
• There is no such thing as impossible
• Advice on working deeper with clients
• Can't take anyone deeper than you've gone on yourself
• The Activity Brain Dump
• "Hell Yes" / "No, not for now" / "Maybe"
• The energy audit
• Never too late to "go deep" with your client
• Create space for miracles
• Are 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 coach

Highlights from my conversation with Tory

Moving 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 know
• Corporate outsider
• Licensed Psychotherapist
• Finding his Niche early on
• www.blackexecutivemen.com
• Therapy vs coaching
• Jewels clients see themselves in him
• Passionate about growth and professional success
• Clarity and the puzzle pieces, getting them all on the table
• His Process = Clarity / Decisions / Actions
• Working with his own coach to get the confidence he needed
• Creating a Buddy System with his clients
• Coming from tissues, tears and trauma
• Daily 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 session

• Calling 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 Question

• Guilty 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.

. Best coaching advice you’ve gotten?

• “What would it take to let it go?” – helped her shed self-limiting beliefs.
• Learned during a Georgetown fishbowl coaching session.
• Empowered her to define herself and step into a bigger space.

2. What are you still trying to improve?

• Contracting with clients to avoid misalignment.
• Daily work on presence—removing the “static.”
• Asking, “Are we still in the right conversation?”

3. Most outrageous/courageous thing you’ve done in a session?

• Telling a client they might need more support beyond coaching.
• Delivering hard truths with subtlety and courage.
• Felt “the clench” but leaned into trust and honesty.

4. What still makes you squirm?

• Clients showing up with “I don’t know.”
• Managing the pressure to “perform.”
• Using honesty and redirection to stay in alignment.

5. Advice to new coaches?

• Get into supervision—it’s essential support.
• Coaching can be lonely without intentional community.
• Keeps coaches anchored, self-aware, and growing.

6. Something you’ve had to conquer?

• Transitioning from corporate to private practice.
• Proving to herself (and her husband) she could sustain independence.
• Leaning on referrals and relationships rather than sales.

7. Are you using AI in your practice?

• Not directly in sessions, but useful for writing and teaching.
• Encourages her daughter to use it for transactional challenges.
• Sees AI as a supportive tool, not a threat.

8. What have you learned about yourself?

• She can do hard things and thrive as a solopreneur.
• Built a sustainable practice without business development.
• Relationships and trust drive her long-term success.

Fun Stuff: Favorite Movie

• Rocky IV (music, energy, inspiration).
• Pitch Perfect 2 and The Greatest Showman.
• Loves movies with music and strong dialogue—even if “questionable.”