193: What Happens in Coaching?

193: What Happens in Coaching?


What the heck we talk about and do inside coaching sessions

This week's issue of Cultivating Resilience is brought to you by Discover Your Story with ChatGPT—an interactive workshop by Kristina Flynn and Jason Shen on March 21st

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)
What We Do in Coaching
Discussion topics and activities that come up in exec coaching sessions with Jason Shen


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

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