Don’t leave your moral compass at home
From the pod
What do you do when a leader tells you, "You have integrity. That's rare in this profession"? For Natasha Jaffe, my latest guest on Executives Unplugged, it was the signal she needed to leave.
Amidst all the adrenaline-fueled urgency and speed to change, Natasha kept me honest with thoughtfulness and empathy about how to make rapid changes, but not leave your team behind or lose yourself or your values in the process. “Don’t leave your moral compass at home.”
Listen on your favorite platform: Youtube, Apple Podcasts, Spotify
Coach’s corner
Reader question: “What is one tactical way you are using AI to be a better coach?”
This is a prompt I’m experimenting with and I have seen fantastic results from Gemini 2.5 Pro and Chat GPT o3. Fantastic meaning that once I filter out the nonsense (inexpensive for me), the insights leftover are rich and actionable. I do find the more advanced reasoning models do better with it. I take a transcript of a coaching call and paste the transcript along with the prompt below. Try it out and let me know how it goes and how you might improve it!
I had a recent 1:1 with a client (or replace with team member) and recorded the conversation. I pasted the transcript below and want you to emulate Marshall Goldsmith (the world-class executive coach) and assess the interaction. Specifically, I want you to consider the following coaching tools:
Deep Listening
Asking Questions
Clarifying Objectives and Expectations
Sharing Stories
Sharing Frameworks/Playbooks/Mental Models
Giving Advice
Providing Targeted Real-Time Feedback
Giving Support
Providing Accountability
Please analyze the transcript and critique my coaching. Which of these tools did I use and how often? Provide specific quotes or moments when I used them and assess how well I used those tools. Also give me alternative approaches I could consider next time. Then note which tools I didn't use but could have. For each tool I didn't use, if relevant to the conversation, give me example questions I could have asked or things I could have shared to apply those tools during the conversation.
Which tools do you believe I naturally gravitate towards? How does that impact my coaching style? What are some specific next steps I can take to sharpen my tools and apply the right tool at the right time?
This has been a popular topic so I will continue to share ways that I’m using AI to improve my coaching.
Behind the scenes
I have been splitting my time between executive coaching (for CEO’s and senior leaders), consulting (typically fractional Chief Product Officer roles), and teaching (leadership workshops, MBA courses at Cornell, online courses). Add in content creation for podcasts and newsletters and I start to have many different places where my time can go. I recently decided to budget less of my time for consulting and more of my time for coaching and content. That tradeoff has been very rewarding and I plan to invest more time sharing insights here from my fortunate perspective of getting to work with a variety of C-suite leaders on a daily basis.
Never underestimate the power of focus! I preach this all the time and realized I wasn’t practicing it enough lately.
Stay focused, send me your questions, and until next time - enjoy the ride!
-Keith
