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Powerful Questions to Support Your Coaching Business

Posted by Janine Hopkinson | December 10, 2018 | Comments (3)

Many of us feel called to coaching because we love working with people and supporting them as they overcome obstacles, whether in fitness, career or other aspects of their lives. From there, many coaches decide to work independently as entrepreneurs or solopreneurs by launching a coaching business.

While you may indeed be an extraordinary coach, as any seasoned entrepreneur will tell you, when you’re running a business, you’ll be called upon to wear many, many hats (not just your favorite one).

This is why, when I coach entrepreneurs, I invite them to look beyond their service offering and business acumen to how they hold themselves in the roles of a business owner. The questions I ask reveal the deeper belly and belief systems—which, as coaches, we know are the places folks tend to get stuck.

I call this process an Entrepreneuship Audit, which is an honest look from the perspective of you-as-entrepreneur where you play best, where you tend to hang out, and what your beliefs are about the places you tend to avoid.

While working through an audit with the support of a business or career coach is ideal for helping you find solutions to optimize your business in service of your vision, you can use the following shortened version of the Audit as a self-guided reflection.

The Entrepreneurship Audit

Please set aside distraction-free time to feel into these questions. It can be helpful to write your answers on large, loose sheets of paper. In Part 2 of the exercise, you’ll be able to review them side by side.

Part 1

Start by reflecting on three of the key roles all entrepreneur-coaches play in a given period: The Dreamer, The Expert and The Operator.

Even before you read the descriptions, feel into each of these three roles.

Which one speaks to you most vividly? Why?

The Dreamer

The Dreamer brings vision, ambition and big picture capacities to the business. The Dreamer fuels projects with questions like “What else?” and “What if?” and sees and says yes to opportunities as they arise. The Dreamer is at home in the future and the potential of your business.

What is your relationship to your Dreamer? Explore these reflection questions:

  • How comfortable am I creating, imagining and envisioning my business?
  • In what ways am I receptive to new ways of envisioning my customer? Our relationship?
  • How might I benefit from growing my creative capacity to differentiate my business?
  • When my ideas don’t work or are slow to bring to life, what is my felt experience?

The Expert

Think of the Expert as you-the-coach. Without the expert, there is no business!

The Expert is concerned with what they like to do…and doesn’t appreciate the distractions that get in the way of their doing. The Expert has a narrow, focused lens, and is concerned with manifesting within these parameters.

Ask yourself:

  • How much energy can I realistically invest in coaching every day? Every week? What am I checking for to know if I am at capacity?
  • How loosely (or tightly) do I hold my niche and why?
  • In what ways might I explore expanding, reviewing and re-articulating what I know my niche to be?

The Operator

The Operator is responsible for the machine behind the Expert.

This can look like admin, accounting, information technology (IT), contract writing, website maintenance and much more. The Operator is focused on processes, getting things done, and tangible outcomes.

Consider the following:

  • Reading the description of the Operator, what is my gut reaction?
  • What systems of support do I have now in my business that I long to improve upon?
  • What are the tasks or areas I tend to avoid: financial, administrative, strategic, interpersonal, logistical?
  • What am I prepared to let go of to achieve growth in these areas?

Part 2

Return to your reflection answers after a break of a day or two. Place your sheets beside each other, or pin them up on a wall so you can step back and get a fresh read. What are the patterns you see emerging?

  • Where do you tend to want to hang out?
  • Where are you resistant to exploring?
  • Knowing that you only have limited working hours in any given day, what do you most need to shift in the service of your business?
  • What’s the one area you can shift your energy towards or away from today that will have a positive impact on your business?


Additional questions will most likely arise as you work through this Entrepreneurial Audit. I encourage you to regularly set aside time for a reflection process like this one to track your personal growth as an entrepreneur and identify where it’s time to shift, grow, develop or delegate.

Best of luck in your growth and business development.

janine hopkinson headshot

Janine Hopkinson

Janine Hopkinson is an independent coach, consultant and entrepreneur. After a 20-year career as a creative director in global advertising agencies, she founded Métier Coaching + Culture, a coaching and consulting business that accompanies creative professionals and organizations through transformations great and small. She is a certified Yoga instructor and Professional Integral Coach, weaving together the deep wisdoms of felt experience and empathic understanding in her coaching practice. Her mission is to help others move through life’s inevitable periods of change and uncertainty with a sense of grace and clarity that is uniquely their own. You can find her at

The views and opinions expressed in guest posts featured on this blog are those of the author and do not necessarily reflect the opinions and views of the International Coach Federation (ICF). The publication of a guest post on the ICF Blog does not equate to an ICF endorsement or guarantee of the products or services provided by the author.

Comments (3)

  1. Brooke says:

    This is an excellent post. Thank you so much- just what I want to dive into as I work on my vision of myself as a business owner this year. Truly- all my gratitude!

  2. Thank you, Janine!
    The article totally gives me a good picture of the reality of running a coaching business. I will do the exercise this month for sure!

  3. Thank you Janie says:

    Thank you Janine for this thought provoking exercise, as I am an experienced Corporate professional and a good Coach but I am a novice Entrepreneur and I am finding it a hard and scary slog as I work to reverse engineer myself and set up my own practice so every bit of support is welcomed. Thank you. Fiona

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