193: What Happens in Coaching?

We all field questions about our work. The other day, after a round of introductions, the person sitting next to me asked me to describe what kind of coaching I do.

It was a fair question. She had spoken to several coaches in the past and each one had a different style. She was trying to get a lay of the land.

The truth is, some people have worked with executive coaches in the past, others have worked with career or mindset or leadership coaches. Each experience has its own unique flavor. And similarly, the work I do in coaching varies based on the situation, relationship dynamic, and particular tendencies of the client.

That said, I decided to put together a page that describes some noteworthy conversations, interactions, and topics of discussion that came up in recent coaching sessions.

You'll notice a blend of reflection and inner work alongside more strategic questions and challenges, as well as more tactic questions related to personnel, growth, product, and communication.

All clients are anonymized and the topics are intentionally vague. But if you've ever wondered what a coaching session might be like with me, here are 10-ish examples (I'll try to add more when I can!)

Here's a few examples:

Male Founder (South Asian, Seed, pivot)

• Considered a major product / strategy decision that needed immediate action
• Examined which values founder wanted to prioritize when making the decision
• Brainstormed possible alternatives or backup plans if decision backfires

Male Executive (White, Series B)

• Discussed how to give feedback to senior manager currently on a performance improvement plan (PIP) and setting expectations on what "good looks like"
• Discussed how to create more space in schedule to prioritize strategic planning amidst a challenging and unexpected family emergency

Female Founder (woman, South Asian, in transition)

• Explored and reinforced significance of founder's identity shift over 2 years of entrepreneurial endeavors (sometimes a return to the same place on XY coordinates masks a shift in the Z dimension)
• Discussed how to act out of authentic desire rather than from place of scarcity as founder reenters the workforce in a new role (tough job market + possibility of moving for a role was creating stress)

—Jason

PS - If you are a client and think you recognize our conversation, would be curious if you have any reactions

How I Can Help You

🧢 Executive Coaching: 1:1 coaching for outlier founders & executives that unlock transformational growth over 4+ month engagements (schedule a call)

🛠️ Participatory Workshops: Interactive seminars designed to learn and practice crucial skills for navigating complex transitions—storytelling, emotional intelligence, experimentation and more.

🎤 Keynote Talks: High energy presentations that challenges audiences to dream bigger and act bolder in the pursuit of excellence.

Coming soon: Templates, exercises, and other low-cost ways to build resilience and develop your outlierness.

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