What Happens in Session? Each session is unique, and that’s part of what makes coaching so powerful. It’s a co-creative experience that requires both of us to be in sync—finding connection, diving into exploration, and unlocking insights together.
While it often feels magical, there’s a logic underpinning our journey. Let’s demystify what happens during a founder coaching session.
The 4 Phases of a
Founder-Coaching Session
We follow a structured yet flexible approach to ensure every session is productive, meaningful, and focused on your growth. Our sessions are designed around four key phases: Check-In, Updates, Deep Dive, and Check-Out. This approach allows us to make the most of our time together, while also providing room for adapting based on your unique needs.
1. Check-In (1-5 minutes)
The first phase of every session is a brief check-in. This helps us transition out of the busy hustle of your day-to-day and into a space of introspection and focus. I may ask you how you’re feeling or what’s on your mind, giving us both an opportunity to gauge your current state and set a tone for our conversation.
Why it matters: The check-in helps to establish a connection to your inner thoughts and emotions. It allows us to acknowledge your current mindset, which is crucial for diving deeper into the work we need to do together.
2. Updates (5-10 minutes)
After checking in, we’ll move into the updates phase. This is where you’ll share any progress, setbacks, reflections, or anything notable that has happened since our last session. It’s a time to connect the dots between previous sessions and the present moment, ensuring continuity in our work.
Why it matters: Updates provide context for our discussion and help us track your progress over time. It’s a great opportunity to celebrate wins, reflect on challenges, and ensure we’re building on each session effectively.
3. Deep Dive (40-60 minutes)
The deep dive is the core of our session. During this phase, we’ll explore the most pressing topics, challenges, or opportunities that are on your mind. This could mean brainstorming solutions to a problem, reflecting on personal challenges, or developing new strategies for your business. Often, we may not know exactly what the main topic will be until we start talking, but this flexibility allows us to address what matters most in the moment.
Why it matters: The deep dive is where real transformation happens. By dedicating the majority of our time to exploring key topics in depth, we can identify patterns, uncover insights, and develop actionable steps that move you forward.
4. Check-Out (5-15 minutes)
Finally, we conclude each session with a check-out. This phase is all about solidifying the takeaways from our conversation. We’ll summarize key insights, decide on action steps for the upcoming weeks, and ensure you leave with a sense of clarity and direction. This is also a time to reflect on how you’re feeling compared to the beginning of the session.
Why it matters: The check-out helps anchor the insights and progress we’ve made during our session. It ensures that you leave each meeting with actionable steps and a clear understanding of what comes next, making it easier to continue building momentum between sessions.
Final Thoughts: Strategic Introspection
Every founder's journey is different, and that's why our sessions are never one-size-fits-all. These four phases—Check-In, Updates, Deep Dive, and Check-Out—provide a guiding structure that allows us to adapt to what you need most at any given moment. Whether it's focusing on a breakthrough idea or supporting you through a difficult challenge, our time together is about finding what truly drives your growth.
Coaching isn't about ticking boxes—it's about diving into what matters most for you, and ensuring that you leave each session inspired, clear, and ready to take action. If you're curious about how this looks in practice, check out the real-life case study linked below.
Our approach always aims to be flexible enough to meet you where you are, but structured enough to drive consistent growth and results. Whether we’re celebrating wins, tackling challenges, or exploring new ideas, every session is designed to propel you forward.
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Brian Tam
Thinking partner for thoughtful founders
