s1e11: What Happens In a Coaching Session?

What actually happens inside a coaching session? In this episode of The Intentional Organization Podcast, Sara Hicks and Mathias Meyer look back at their own experiences as coaching clients. Sara sought help while navigating co-founder tension after raising a Series A. Mathias started when he became the sole CEO of his company and realized he wasn't sure what the role was supposed to look like. Both found a place to work through decisions, relationships, and the loneliness that can come with leadership.They share the practical details: introductory calls, preparation questions, homework, and the check-ins that turn a conversation into action. Mathias remembers sorting his work into what belonged above and below the waterline, and the discomfort of asking his team for two things he was doing well. Sara recalls a question on her intake form that opened up a deeply personal conversation about her parents' health.The conversation explores what it feels like to have someone hold up a mirror, notice recurring patterns, and ask the question you've been avoiding. Sara and Mathias discuss rehearsing difficult conversations, building confidence through practice, and recognizing growth that can be hard to see in yourself. They also reflect on how they approach coaching alongside mentoring and sharing their own experience, and on the distinction they draw between coaching and therapy.They close by considering what makes a coaching relationship work: trust built over time, a willingness to do uncomfortable work, and a coach whose approach fits what you need. Sometimes the value is a new perspective. Sometimes it's a question that helps you say out loud what you already know, and decide what to do next.**Keywords**executive coaching, leadership, startup founders, CEO, co-founder relationships, vulnerability, feedback, difficult conversations, confidence, accountability, personal growth, finding a coach**Takeaways*** Coaching can start with a crisis, a new role, or a desire to strengthen a working relationship before problems develop.* The CEO role changes as a company grows. Looking closely at how you spend your time can help you decide where your attention is most useful.* Preparation can go beyond business goals. Personal circumstances may shape how you show up at work and what support you need.* A coach can help you see patterns, explore options, and recognize your own contribution to a difficult situation.* Asking what you're doing well can feel just as uncomfortable as hearing what needs to change. Both can be part of learning.* Practicing a difficult conversation gives you a place to try the words, experience pushback, and prepare to act, even if the nerves remain.* Reflection becomes more useful when it leads to a concrete next step: what will you do, when will you do it, and what support will help?* Working with someone over time gives them a chance to notice progress you might overlook and remind you of challenges you've already handled.* A coach may sometimes offer perspective from their own experience. The decision about what to do with it remains yours.* Introductory conversations with a few coaches can help you explore fit, while trust in the relationship takes time to build.Full transcript and links to all resources mentioned can be found here: https://intentionalorganization.com/podcast/s1e11-inside-a-coaching-session