How to Coach an Entrepreneur

How to Coach an Entrepreneur

What are the most common characteristics of an entrepreneur?

Entrepreneurs are a completely different breed than your average client. They are visionaries and can see opportunities that others cannot. They are creative and strategic thinkers. They thrive in a world without constraints. They are risk-takers and impulsive. The risk is often more significant than the opportunity. They often leave a trail of chaos and ingenuity for others to clean up. They are great at having multiple ideas and projects going at once. They love to start things, and they can quickly get bored. They are often best at working alone. They are quick and can rush. If they are unable to keep up with their pace, they may feel frustrated.

What are the most common mistakes coaches make when working with entrepreneurs?

Do not try to slow them down or change them.

Successful coaches accept entrepreneurs for who they really are and don’t try to change them. Let them run, and let them get out of your way. Learn from them. They can move so fast that they forget to take into account risks and challenges. You can help them think more clearly, brainstorm, create scenarios, and identify blind spots.

Conserve balance and sustainability

Entrepreneurs may forget to take care of the basics of their daily lives in their rush to succeed. Be aware of prolonged periods of neglect. They are optimists but masters of illusion. You should lookout for signs of stress. Entrepreneurs have the ability to turn minor problems into significant opportunities. It’s called gearing. This is what a good coach will do: role-play any role that is appropriate. This is an art.

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Respect their creativity, and the risk tolerance

Entrepreneurs are very cautious about taking on risks. Accept it and collaborate with them. Sometimes, you may have to be flexible. Your tolerance for risk should be the foundation for your strategies and goals. Entrepreneurs love to think up new ideas. They love to communicate. Let them talk. Coaching is all about listening. Entrepreneurs need someone who listens and responds enthusiastically to their beliefs. They are looking for positive reinforcement.

What advice would your public servants give entrepreneurs who are dealing with entrepreneurs?

Many of the same principles apply to professional advisors. One distinction is essential. Actual coaches won’t give you advice. Proper coaches will help you to discover your own potential by asking questions. Professional advisors, such as accountants, are expected to offer professional advice. They are experts in their field and must be able to interpret and share their knowledge. Entrepreneurs are the decision-makers, so give them your opinion and let them make the final decision. Give them options.

Be proactive

Entrepreneurs move fast. Entrepreneurs are quick and take risks. They also make frequent decisions. They don’t know everything. They value professional advisors who are able to give them a thoughtful opinion and can foresee risks or scenarios they don’t know about.

Be available and responsive.

Entrepreneurs want the answer now. They are quick to make decisions and have short attention spans. They are not interested in the details: big picture, clear guidance, fast turnaround.


Listen to what your client needs. Learn about their personalities. Flexibility is key to accomodating your client’s needs. They speak fast, and you communicate fast. Give them succinct information. They want to see options. Run scenarios. They expect you will be there for them when they need you, not two days later.

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Answers are found in questions.

Learn to listen. Learn how to ask tough questions. A coach can teach you the same techniques that are useful for accountants and sales professionals. Ask open questions such as “what, where, when?” and “how.” Practice questioning techniques like clarifying, asking questions, paraphrasing, summarizing, and probing.

Reaffirm commitments

After you have reached an agreement with your client, you can repeat it to them to clarify: “So, I understand that you want me to submit your tax return no later than Monday 31 July. Is that correct?” Or “My expectation is you will sign the contract and return it to me by Wednesday. Is that reasonable?”

Real-time data

Old information is the worst thing for entrepreneurs. Time is money. They need both lead indicators (prospects and conversion rates, average sales, purchase frequency, purchase frequency, etc.) as well as lag indicators (customers, sales, and profits) in their management reporting. Sales pipelines are essential management information.

Structure and system

Entrepreneurs need structure and a system. They are often not the best people to do it. They hire a coach or personal assistant, a consultant, or an accountant.

It is a rewarding and exhilarating experience to coach entrepreneurs. It’s a rollercoaster ride, and there is never a dull moment. As a public practitioner, it can be equally rewarding to support them. Get ready to ride the ride of your lifetime.

Dennis Roberts assists small business owners/operators in starting, running, and growing their businesses from conception to exit. His services include strategic advice, mentoring, coaching, and advisory boards, as well as facilitation.

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