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      top 10 questions Before coaching

      Further Exploration

      Coaching can be a powerful addition to a startup — but how do you know if Let's Make Great! is right for you? Well, here are the top 10 questions founders ask before they dive into our work together... from the practical to the philosophical!

       

      What Is Your Coaching Style?

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      My coaching style is collaborative, adaptive, and empathetic. I believe the answers lie within you, and my role is to help uncover and amplify those insights through thoughtful questioning, reflection, and strategic guidance. I combine objective observation, motivational coaching, and the occasional challenging question to push you forward. Additional resources: Testimonials | My Writing

       

      Will You Give Me Direct Advice?

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      My goal is to help you discover your own best path forward, rather than offering one-size-fits-all solutions. I may share insights or experiences that are relevant, but my focus is on empowering you to find answers that align with your unique circumstances. When it comes to practical matters—like tools or resources—I’m happy to share specific recommendations.

       

      Why Does Coaching Get So Personal?

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      Your startup is an extension of you—your values, beliefs, and vision are woven into its DNA. By exploring the personal side, we can uncover hidden obstacles, clarify your motivations, and leverage your strengths more effectively. This personal introspection is often the key to unlocking real business growth.

       

      How Long Is Each Session?

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      Each session typically lasts 75 minutes. This extended format allows us to dive deep, especially during the latter part of the session where most of the transformative insights emerge. We can adjust the timing if needed, but generally, the longer sessions create the most meaningful breakthroughs.

       

      Why Should I Think Out Loud?

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      Thinking out loud is a powerful tool during coaching sessions. It helps bring hidden thoughts and assumptions to the surface, making them easier to address. By verbalizing your ideas, you gain new perspectives, and I can help you identify patterns, ask deeper questions, and reflect more effectively. This process often leads to moments of clarity and breakthroughs that can propel your business forward.

       

      What Do You Offer in the Sessions?

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      In each session, I offer a mix of personalized coaching techniques tailored to your needs. This includes strategic frameworks, guided reflection, challenging questions, and a supportive space to explore ideas. The goal is to uncover insights, clarify your direction, and develop actionable steps. Whether you need accountability, a sounding board, or strategic planning, our sessions are designed to meet you where you are.

       
       

      What Happens After Each Session?

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      After each session, you’ll receive a summary of the key insights, action steps, and any notes that will help you stay on track. Many founders find it helpful to re-listen to session recordings, which are available upon request, to further solidify their learnings.

       

      Why do founders work with you?

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      I don't hold traditional coaching accreditations, and I understand that this may be a concern for some (it was on my mind too). Over time, I realized that my intense curiosity and preference to 'learn by doing' — generated insights across decades of real-world experience, peer learning, alongside extensive reflection, writing, and speaking.

      I often joke that I graduated, not only from the University of Maryland but also YouTube University! To be clear, I have taken formal courses in executive coaching, THNK methodology, and neuro-linguistic programming... amongst others. And I've found each offers it's own insight and spin on the same question: how do we grow?
       

      How Personal Is the Relationship?

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      Coaching is all about you and that's by design. Founders constantly must prioritize others, so this is the rare opportunity for you to be the sole focus. While I won’t be interrupting or sharing my own stories, I'll quietly guide, intensely observe and provoke deeply to push us towards greater growth, clarity and impact.

       

      How Should I Use Our Sessions?

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      That’s entirely up to you, and it depends on your needs. Some founders need extra accountability, while others want a space to explore ideas or gain clarity. You can use sessions for strategic planning, troubleshooting challenges, or simply as a sounding board. Whatever the focus, our work will always align with your ultimate goals. If you're still brainstorming, try our goal setting worksheet.

       

      Final Thoughts

      Coaching is a powerful tool that adapts to your needs, challenges, and aspirations. If you still have questions, don’t hesitate to reach out. The answers may already be within you—we’re just here to help uncover them and bring them to life.

      This doesn’t cover everything, of course, so if you’re still unsure email us or schedule a call and we will figure it out together. The goal is for you to feel confident and prepared to embark on this transformative journey.

      — Brian

      Thinking partner for thoughtful founders

       

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