By Amy Gannon

Building a business is a messy, iterative process. Coaching an entrepreneur through that process can be equally messy — and often ineffective — if the coach does not bring the right approach.

Madison has a number of business coaching services, some free and some for a fee. Thanks to groups like the Small Business Development Center, Merlin Mentors, gBETA, the Social Good Accelerator, and Doyenne, Madison is fortunate to have dozens of experienced business people willing to share their time with aspiring founders.

Sometimes, that coaching is very valuable. It can help entrepreneurs work through obstacles and find breakthroughs. But, sometimes, attempts at coaching entrepreneurs can do more harm than good.

In this post, I want to build on my previous posts about coaching from a place of confidence and humility and the biases we learn from our culture. If you haven’t read those posts, please read them when you have a chance.

Today, I want to explore what it looks like to coach someone as they enter the unknown territory of entrepreneurship. And, to take a look at how our biases can play out in the coaching process.

Quality entrepreneurial coaching for start-up ventures embraces three key concepts:

  1. Entrepreneurship is a human endeavor
  2. Ideas are seeds that need tending
  3. Designing the process is the priority


Entrepreneurship is a Human Endeavor

At its core, entrepreneurship is about human beings making things happen. People bring their life experiences, personalities, and skills sets to the work. They also bring their hopes and fears and personal challenges. This is what makes each entrepreneur beautifully unique.

When people enter the entrepreneurial process, they are often quite vulnerable. They are challenging themselves to do something they have never done before—building a new business. But stepping outside your comfort zone is…well, uncomfortable.

Quality coaching looks at the entrepreneur holistically — teasing out both the vision AND the doubt. Our job as coaches is to engage the human first. To actually SEE the person in front of us in all her glory. We start by thoughtfully asking questions: Who is she, how does she experience the world, what are her big, audacious goals, and what are her ideas for achieving them? Begin with her, and the business will follow.

Coaching that makes people feel invisible and without voice will usually fail. If you can’t see me, you can’t coach me.

I frequently hear from women entrepreneurs about negative experiences they’ve had with coaching. Over and over I hear that the coach couldn’t, or wouldn’t, see or value them. She couldn’t be her full self or tell her full story to the coach.

Because women and people of color do not fit the stereotypical version of what entrepreneurs look like, they often spend a significant amount of time trying to demonstrate they are legitimate and worth the coach’s time. Coaches, driven by their cultural biases (conscious or unconscious), approach women and people of color very differently than they do White men. They engage with a higher level of skepticism and focus on what is lacking versus what is amazing. They focus on the problems rather than the potential. And, they may not even realize they are doing it.

Men get asked questions about potential for gain (promotion questions), while women get asked about potential for loss (prevention questions), according to a Harvard Business Review study. Research also shows that men delivering the exact same pitch as women are twice as likely to get funded. It isn’t about the idea as much as the person proposing it and the investors biases.

A coach who lacks self-awareness can derail an entrepreneur, sending her off in directions that are effective or comfortable for him, but not for the entrepreneur or her customers.

Ideas Are Seeds that Need Tending

People often ask me, “How do you tell an entrepreneur that her idea is bad?” My response is that it’s not our job as coaches to tell anyone their idea is bad. We do not serve as judge and jury.

An entrepreneur’s idea usually isn’t fully formed yet. Ideas are not like Campbell’s soup — pick the flavor you want and just add water. Ideas are seeds that need to be tended to; they need the right nourishment to grow into what they are meant to become.

Our job, as a coach, is to explore who the entrepreneur is and what she is trying to achieve. Then, we can work with her to evolve her idea — shape it into something that is aligned with her vision and with the needs of customers.

I certainly share my business knowledge and experience, offering feedback that might be difficult to hear. My goal is to help the entrepreneur explore what her options might be, understand some of the trade-offs, and creatively design a path forward. Sometimes that might mean completely shifting the original plan. But, to be clear, that is her decision to make. Not mine.

A problem I often observe is that people, including some business coaches, evaluate ideas as static (rather than dynamic) and evaluate from their personal life experience. They have difficulty recognizing when they are NOT the target market. If they don’t have the problem or wouldn’t pay for a service, they assume no one else would either.

Women and people of color are often seeing problems and solutions from a whole different perspective and may be focusing on a target audience that is very different from their coach.

We live in a world where men and White people can live in relative ignorance about the experiences of people from different social and economic groups. Their arrogance and/or fear can prevent them from educating themselves. This lack of understanding can be a limiting factor in their ability to effectively support entrepreneurs.

I am not suggesting coaches must have the same lived experience as the entrepreneur or the target audience in order to be helpful. On the contrary, coaching is actually a tremendous opportunity for growth. Quality coaches have the self-awareness and confidence to embrace the opportunity to learn from the entrepreneur and the community she is working to serve.

Coaches who honor the expertise of the entrepreneur, recognizing that she might know something they don’t, can be great allies in the entrepreneurial process.

Designing the Process Is the Priority

If we understand that ideas are dynamic, then helping entrepreneurs design experiments to explore options is the most valuable work of a coach. Entrepreneurs typically have a lot of different ideas swirling in their heads about how they could build their business. They are both excited about the ideas AND overwhelmed by them. They have trouble figuring out which of the ideas they should prioritize and how they should focus their time and energy. They have trouble structuring a path from Point A (where they are now) to Point D (where they think they want to be).

A good coach recognizes that it is almost impossible for an entrepreneur to plan out in advance an efficient and productive path from A to B to C to D. This is the nature of the entrepreneurial process, not a reflection of the intelligence, skill or potential of the individual.

Coaches listen, add their own ideas, and help build structure into what feels like a random and chaotic process. Coaches help entrepreneurs design experiments and ask questions that help the entrepreneur better understand themselves, their customers, and their product/service design. These smaller steps gather critical information that will inform decision-making and subsequent activities. Each step forward can build confidence, competence, and credibility.

Traditionally, our cultural perceptions of “mentor” and “protege” imply an automatic power differential. We often think of mentors or coaches as the ones with the information, connections, and wisdom, which they generously bestow upon the mentee. When we combine these outdated notions of mentors with the gender stereotypes we hold, it can lead to some troublesome dynamics.

The role of a coach is to help guide the process, not provide the answers. Coaches need to be comfortable with ambiguity and sharing power; they need to be good at design and discovery.

When coaches engage with entrepreneurs from a position of power and authority, they focus on giving the answers — telling entrepreneurs what they should do — rather than helping entrepreneurs design a process for discovering the answers themselves. Some coaches feel the need to prove they are the smartest one in the room, ultimately undermining their own value. Sometimes this comes from arrogance, but just as often from a lack of confidence.

Unfortunately, this approach doesn’t lead to the best outcomes for either party or for the business. If the entrepreneur challenges the coach, the coach can become upset and may discount her. The entrepreneur can’t be her full self in the interaction, which destroys trust and limits progress. Maintaining a coach’s ego cannot be the primary focus of the interaction. Again, many coaches may not realize what is happening.

For coaching to be effective, the coach and the entrepreneur must play on a level playing field. They need to feel like partners in the process, each with something to contribute and something to learn. At Doyenne, we recognize that the label “coach” is quite fluid. One day I may be the one giving coaching, another day I may be the one getting coached. We recognize that everyone has their own expertise.

In 2018, Doyenne will be launching the Doyenne Coaches Program. We are training a team of people who can support women entrepreneurs in their entrepreneurial journey. This new initiative will expand the number of women and businesses we can engage and amplify impact we can have on the economy.