#2 — Launching February Deep Dives
I’ve wanted to run an experiment like this for a while—creating space to tackle real-world challenges and rapidly iterate on my approach as I learn what works best for different people.
On Monday, I launched February’s low-cost, high-impact Deep Dives. Within days, 15 of the 22 slots were booked. (As of today, there are still 6 left if you’d like to try one.)
The first sessions happened on Thursday. And I loved running them. They feel like a cross between a great product review, an interview, and a coaching conversation—deep listening, structured facilitation, and then serving as a tour guide through the different paths each challenge presents. It’s been a long time since I left a workday feeling this energised. These sessions have been a strong reminder that I’m on the right path.
They’ve also been a great way to learn what people want to work through. 60 minutes is plenty of time when there’s a clear outcome in mind. And if there isn’t, shaping that together at the start increases the quality of takeaways and actions an individual is able to leave the session with.
Refining My Positioning
Through these Deep Dives and ongoing initial calls, I’ve been reflecting on who I’m best set up to serve and how I position myself to meet those needs. Previously, I thought of my work in a binary way—coaching for individuals OR advising for companies. But I’m realising that these lines are often blurry. In reality, both individuals and teams want elements of both.
I’m now exploring a more team-oriented positioning, focused on the outcomes I drive rather than strict role definitions. This means blending leadership coaching with strategic advisory work in a way that adapts as an organisation and its leaders evolve.
I’m also sharpening my view of the companies and leaders I’m the strongest fit for: growth-stage product companies that have found strong product-market fit and are now scaling product lines and teams. It’s not easy. But I’ve spent a lot of time at this inflection point and love the challenges it brings.
Three Learnings From the Process
• Granola is an excellent tool for writing strong follow-ups, but nothing replaces leading with my own synthesis and top 2–3 key takeaways.
• Two weeks’ notice seems to be the sweet spot for announcing and booking these sessions. Thursday, Feb 13th was the first to fully book, within 24 hours of opening on Feb 3rd.
• Good sleep, exercise, and nutrition are essential to sustaining a full day of deep conversations. A helpful reminder to pace myself to ensure the best outcomes for every session.
Emotional Themes From the Week
I asked ChatGPT to pull 10 emotional themes from my journals throughout the week: Excitement, Self-Doubt, Clarity, Gratitude, Tension, Validation, Frustration, Empowerment, Satisfaction, and Confidence. That pretty much sums it up.
Until next time ✌️