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.”

1. Best coaching advice you’ve gotten?

• Learn to be comfortable with silence—it creates space for clients to process.
• Silence isn’t emptiness, it’s presence that can be more powerful than words.
• Listening deeply reveals both verbal and non-verbal cues.

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

• Not jumping in too quickly when clients pause or hesitate.
• Allowing clients the time to fully process their own journey.
• Practicing “listen before you talk” as a lifelong discipline.

3. Most outrageous thing you’ve done, tried, or said in a coaching session?

• Being honest and naming observations clients may disagree with.
• Framing it as “putting something on the table” for exploration.
• Setting an agreement upfront that disagreement is not only okay, but welcome.

4. What still makes you squirm or uncomfortable in a coaching session?

• Few things do now, but violent or abusive disclosures would be a boundary.
• Acknowledges that’s not his skill set and wouldn’t want to “get past it.”
• Would always seek to refer a client to someone better suited.

5. If I were new to coaching, what advice would you have?

• Start with your why—if it’s about “me” instead of the client, rethink it.
• Focus less on tools/templates and more on presence and service.
• Keep personal stories in check so sessions stay client-centered.

6. What is something you’ve had to conquer on your path to being a great coach?

• Letting go of self-criticism and unrealistic standards.
• Learning to give himself the same grace he gives clients.
• Remaining humble when impressive people place their trust in him.

7. Are you using AI in your coaching practice?

• Uses AI primarily for note-taking, freeing him to be fully present.
• Leverages AI responsibly—clients give permission and feel comfortable with it.
• Sees AI as another data point, not a replacement for human presence.

8. What have you learned about yourself through being a coach?

• To be less hard on himself and walk his own talk.
• That humility and patience grow with every client relationship.
• The “95% rule”: most people genuinely want to do the right thing.

🎬 Fun Stuff Question – Favorite Movie? (Hoosiers)

• Loves the themes of second chances and underdogs overcoming odds.
• Connects personally to the underdog story in his own life and career.
• Believes the film reflects resilience, belief, and community support.

Highlights:

• 🎭 Pioneers in using improv for coaches—it’s transformative and energizing!
• 🙌 Believes that who you are is what makes your coaching truly impactful.
• 🎤 Betsy’s comedic roots bring improv and humor into the mix—because coaching can be FUN!
• 🗣️ Experimented with "3 Word Coaching"—small, impactful, and powerful.
• ⏱️ Tried the “Interrupting Experiment”—a fresh take on communication dynamics.
• 🚨 The only rule of improv coaching? PARTICIPATE—because that’s where the magic happens.
• 🗣️ “We’d rather DO than just listen”—action is always the answer.

• 🌟 Two mentor coaches who serendipitously found each other in 2018—and the magic began.
• 🛠️ Honing their coaching skills together and absolutely loving the journey.
• 💡 Gaining invaluable insights by immersing themselves in others’ learning processes.
• 🎁 Coaching at 40 became a beautiful gift for Amy’s kids—a ripple effect of growth.
• 😂 Adding levity to coaching sessions—proof that growth doesn’t have to be so serious.
• ⏳ Their 2-hour workshops fly by, leaving everyone engaged, energized, and asking for more.
• 🤝 Merging coaching ethics with the principles of improv for unique and innovative sessions.

1. Best coaching advice you’ve gotten?

• Burnout revealed his limits — realizing boundaries are essential.
• Reframing resilience: strength isn’t always pushing through.
• Knowing your edges can actually serve you as a coach.

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

• Building consistency in reflection practice.
• Shifting from second-guessing to learning and growth.
• Allowing grace and patience when reviewing sessions.

3. Most outrageous thing you’ve done, tried, or said in a coaching session?

• Jokingly told a client, “You care too much.”
• Boldly told another client, “I don’t believe you,” when evidence didn’t match her words.
• Used blunt honesty paired with trust and humor to spark insight.

4. What still makes you squirm or uncomfortable in a coaching session?

• Turning up the heat when clients blame others.
• Calling out patterns without overstepping into judgment.
• Finding balance between observation and blunt challenge.

5. If I were new to coaching or considering being a coach, what advice would you have?

• Always start with why someone wants to coach.
• Trust your intuition instead of over-orchestrating sessions.
• Relax and allow conversations to flow naturally.

6. What is something you’ve had to conquer on your path to being a great coach?

• Learning to set boundaries on workload and availability.
• Avoiding oversubscription that compromises client quality.
• Accepting courage is required to say “no” or pause.

7. Are you using AI in your coaching practice, if so how?

• AI helps with mock and case interviews for clients.
• Offers structure for problem-solving but math needs double-checking.
• Still more of a supplement than a core coaching tool.

8. What have you learned about yourself through being a coach?

• Struggles mirror clients’ challenges — self-awareness is key.
• Patience with self is harder than patience with others.
• Coaching continues to deepen listening and presence.

Fun Question: Do you have a bad haircut story?

• ’80s “big hair” that grew outward like a chia pet.
• A regrettable pencil-thin mustache in college.
• A short-lived goatee experiment at graduation.

1. Best coaching advice you’ve gotten?

• “People are not problems to be solved” – coaching isn’t fixing.
• Coaching is about creating space, not offering solutions.

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

• Letting go of the need to perform; embracing emergence.
• Staying longer in the not knowing, resisting the urge to advise.

3. Most outrageous (or courageous) thing you’ve done in a coaching session?

• Somatic work: having a client turn and face a wall to access deeper wisdom.
• Telling a client, “I don’t think I’m helping you”—which unlocked the engagement.

4. What still makes you squirm in coaching?

• Coaching clients stuck in the “doldrums” or victim mindset.
• Holding ambiguity without forcing action or clarity.

5. If I were new to coaching, what advice would you have?

• Who you are matters more than what you do—presence is everything.
• Avoid the trap of ‘getting it right’—ditch the powerful questions playbook.

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

• The need to always “get the A”; perfectionism.
• Becoming an experiential learner who’s willing to fail forward.

7. Are you using AI in your coaching practice?

• Uses ChatGPT for supervision prep, self-reflection, and content creation.
• Believes what’s easy today will be done by AI, so coaches must evolve.

8. What have you learned about yourself through coaching?

• That wisdom exists below the neckline—heart and gut matter.
• She’s more warm, creative, and intuitive than she ever imagined.

Fun Stuff: Guilty Pleasure?

• Journaling at the Pannikin Coffee Shop over breakfast—no Wi-Fi, just vibes.
• A self-date that invites introspection and people-watching bliss.