Todd Weinstein | Coffee House Coaching Episode Summary

1. Best coaching advice received

• “Trust the lull”—embrace quiet periods in business and coaching.
• Growth isn’t always linear; bursts of impact are normal.
• Patience and presence in sessions are essential.
• Advice originated as business wisdom, but now deeply influences coaching.
• Helpful perspective especially for new coaches dealing with self-doubt.

2. Did you ever doubt coaching was for you?

• Yes—especially early on and during COVID dry spells.
• Corporate stability was hard to leave.
• Doubt became fuel to innovate, rebuild, and refine.
• Trusted in community and personal growth to weather the uncertainty.
• Recommitted through reflective moments.

3. What are you still improving in coaching?

• Letting go of the urge to “teach” or share tools.
• Breaking old facilitation habits.
• Learning to replace models with powerful questions.
• Signposting when offering a resource to maintain coaching boundaries.
• Striving for discernment on when to share vs. stay silent.

4. Most outrageous thing you’ve done in a session

• Wrote and performed a song with guitar summarizing a coaching engagement (!).
• Client’s reaction = “somewhere between shock and awe.”
• Not his usual move—but led to follow-on work!
• Creative burst turned bold risk.
• Probably won’t do it again—but never say never.

5. What still makes you uncomfortable in coaching?

• Clients expecting transactional results (e.g., “I just want a promotion”).
• Major values misalignment between client and coach.
• Need to recontract and clarify coaching boundaries.
• Balancing empathy with maintaining professionalism.
• Managing disappointment when a session doesn’t go deeper.

6. Advice to new or aspiring coaches

• Turn down the volume of your inner critic.
• Be fully present—the answers are in the client, not your head.
• Trust your gut about fit and chemistry.
• Own your process and speak up if something feels off.
• Vulnerability + awareness = stronger connections.

7. How are you using AI in coaching?

• Personalizes tools and worksheets for clients.
• Uses AI for idea generation and synthesis (e.g., 360 themes).
• Co-creating in sessions to enhance creativity and speed.
• AI = assistant, not replacement.
• Encourages curiosity, exploration, and ethical boundaries.

8. What have you learned about yourself through coaching?

• Brings his full self to the work—analytical, creative, and vulnerable.
• Not everyone is the right fit, and that’s OK.
• Confidence without arrogance = magnetic to clients.
• Coaching is a growth journey for the coach too.
• “Who you are is how you coach” (shoutout to Pam McLean).

Bonus: Something most don’t know

• Obsessed with travel: 20+ countries, 5 continents.
• Northern Lights viewer, wallaby feeder, high-altitude hiker.
• Believes in maintaining a traveler’s mindset everywhere—even at home.
• Bucket list: Iceland & Scandinavia.