Bring your toughest question.
Leave with a real answer.
Office hours with Penny Tremblay. No slides, no script — just one open hour where you bring whatever leadership challenge is actually on your plate, and work through it live.
You don't need another webinar.
You need somewhere to think out loud about the conflict, the conversation, or the decision that's actually sitting on your desk this week — with someone who's spent decades helping leaders navigate exactly that.
Most professional development happens on a schedule that has nothing to do with when you actually need it. By the time a workshop rolls around, the moment has usually already passed.
I felt very fortunate to have the opportunity to participate in the Drop-In. Going in, I had planned to join as a "fly on the wall," simply listening and learning, as I didn't feel I had much to contribute or discuss. Within moments, Penny made me feel completely comfortable, and I found myself opening up about both professional and personal challenges.
Spending time with Penny in the Drop-In provided an opportunity to ask questions and have a discussion that reinforced and expanded on the course content. The conversation was engaging, supportive, and helped me reflect on how I can apply the concepts in both my professional and personal life. I came away with three pages of notes, practical ideas, and new perspectives that I can put into action. I would highly encourage future participants to take advantage of the Drop-In.
Ask Penny — Virtual Drop In Program
A 60-minute live drop-in call where participants bring their own real questions and challenges and get direct, real-time advice from Penny — no fixed agenda, no prepared slides.
Why join a Drop-In session
Come as you are
No agenda to follow and nothing to prepare — just bring your own question.
Direct access to Penny
Real-time advice from a Harvard-trained mediator and founder of the Sandbox System™.
Real airtime
Small enough that your question actually gets addressed — not lost in a webinar chat.
Learn from the room
Every question raised is a chance to see your own challenge from a new angle.
Who it's for
- ✓Managers and emerging leaders facing a live conflict, trust, or team challenge
- ✓HR and People leaders who want an outside perspective on a tricky situation
- ✓Alumni of The Sandbox System™ workshops who want ongoing access to Penny
- ✓Anyone curious about Penny's approach before a full workshop or cohort
Founder of The Sandbox System™, Penny is a 20+-year professional speaker, trainer, mediator, and coach who has delivered keynotes and breakout sessions at conferences internationally and is a hands-on trainer who designs every session from real stage experience — not theory. She is author of Sandbox Strategies for the New Workplace. Certified: Harvard’s PON – Advanced Mediation, WFI’s Workplace Fairness and Workplace Restoration, eSpeakers Virtual Speaker, Teacher of Adults, and HBDI Practitioner.
Upcoming sessions
60 minutes, 12:00–1:00 PM ET. Pick the one that fits your calendar — every session is open floor.
Frequently asked questions
No. Some people show up knowing exactly what they want to ask; others figure it out as the conversation goes. Both are welcome.
That's completely fine. Plenty of participants get value from the questions other people raise without ever speaking up themselves.
No — to keep the conversation candid, sessions are not recorded and are not shared afterward.
Pricing is listed at registration. Payment is processed securely online at the time you reserve your seat.
Reserve your seat using the registration link above — you'll receive a confirmation with the call details.
Reserve your seat
Space is limited to keep the conversation real. Bring your question — leave with a real answer.
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