Happy October! Below are a few updates from me that I’ve been sharing with friends and family of Jeff LLC, so I decided to also drop them here.
My coaching practice is growing steadily. I’m working mostly with senior product leaders although that is beginning to widen. Across almost 200 coffees, Zoom calls, and other convos I’ve had this year, a few common themes keep coming up, with AI-related changes running through many conversations. It’s been a hectic time in tech and it’s clear there is both opportunity and excitement as well as real stress and chaos – all wrapped up together.
I recently started coaching product leaders through Sidebar, a professional development platform and community. (I’m one of the coaches they route their members to.) I have a couple of other similar partnerships in flight.
Some travel, too. This has been a highlight for us. So far in 2026, Charlene and I have been able to work from – and explore – a few different places, including the California and Arizona desert, London, Amsterdam, Paris, Washington, DC, and Seattle. This is the most extended travel we’ve been able to do in a while, and we’ve loved being more flexible with location as a new experiment. As you’d expect, we have some favorite coffee spots in each place. Ping me if you’d like any recommendations. One real favorite: Back to Black in central Amsterdam.
Coach training milestone. I’ve finished my initial coaching coursework and am working toward certification. The training was long and challenging and helped me sharpen how I listen and structure coaching sessions and arcs. Most of all, I got more curious. I also got a chance to meet some really warm, interesting people too. I was surprised at how many companies have trained exec coaches as employees.
I’ve been playing with writing more regularly. Mostly here on Substack with some LinkedIn mixed in for now. I’m trying to make it a weekly and then ideally daily habit, even if only for myself in some cases. I’ve enjoyed writing at different points in life and it helps me clarify what I think, so I’m also playing with work topics vs. branching out more widely.
Some of my most-read essays so far this year:
Answer First: A Simple Framework for Executive Communication — The lesson I learned the hard way in a room full of leaders.
How to Onboard into a New Leadership Role: 7 Lessons from 25 Years — Gathering context is only the beginning. Here’s the playbook I’ve kept evolving.
September 11: My morning working at the world’s largest news website — Twenty-five years ago, I was an associate producer at Yahoo! News — the morning everything changed.
New Year’s Eve Lentils — A Tradition We Never Skip — A Roman rooftop, a bowl of lentils, and a ritual we’ve kept ever since.
I hope you are getting the chance to enjoy some of fall.
Know anyone I should be talking with? Most of my clients have come through people I know. If someone in your network has recently stepped into a bigger leadership role or is working through difficult change or what’s next, I’d welcome an introduction.
I have room for two, possibly three, new clients before the end of the year. Feel free to connect us directly by email or just ping me.