Seven Ideas for Employee-to-Entrepreneur Transition with a Mentor

Subhasis Ghosh
7 min readOct 11, 2023

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Have you ever wondered how interacting with a mentor can help you transition from an employee to an entrepreneur?

If so, you are not alone. While many people dream of becoming their boss, they often face various challenges along the way. A mentor can be a valuable ally in this journey, offering insights, advice, and support based on their experience.

As a business-oriented leader with over 30 years of experience, having built and managed a portfolio of businesses invested in and mentored several startups, I have curated ideas and strategies that can help you. In this article, I will share some of the benefits of having a mentor and how to find and work with one effectively.

A mentor is someone who succeeded in your sphere of interest and is willing to share their knowledge. Mentors are not teachers, coaches, or bosses but friends, role models, or guides. They can help you by:

- Identifying your strengths: A mentor can help you discover your strengths, passions, and values and how to use them in your entrepreneurial journey. They can also help you overcome your fears, doubts, and limiting beliefs that may hold you back from pursuing your goals.

- Exploring possibilities: A mentor can assist you in exploring different opportunities, markets, and niches that suit your skills and interests. They can also introduce you to their contacts, partners, and customer networks and help you build relationships that benefit your business.

- Learning from their experience: A mentor can share their success and failure stories with you and what they discovered from them. They can also provide feedback on your ideas, plans, and actions and suggest ways to improve them. Additionally, they can warn you of potential pitfalls and challenges that you may face and how to avoid or overcome them.

However, finding a good mentor takes work. There is a shortage of mentors because successful people are often busy becoming more successful, and those who are not proud of some aspects of their journey hide themselves. Furthermore, they may only be willing or able to mentor someone they know or trust. Therefore, you need to be proactive and strategic in your search for a mentor.

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Here are some ideas that can help you find the right mentor:

#1. Identify your goals: Before looking for a mentor, determine what you want to achieve and the help you need. This can sharpen your search and focus on the right people. Remember that you need both specialists and generalists, depending on your needs. For example, you may not want your brain surgeon to be a great squash player, singer, or mountaineer. Similarly, you don’t want your business mentor to be an academic professor who can only explain theories.

#2. Research potential mentors: Once you have identified your goals, find people who have already achieved them or something similar. You can use online platforms like LinkedIn, Twitter, or Medium to search for profiles, articles, or podcasts of successful entrepreneurs in your field. Attending events, workshops, or webinars where they may speak or participate can also help. You could also seek referrals from friends, family, or colleagues who may know someone suitable.

#3. Reach out: Contact potential mentors and express your interest in learning from them why you are interested in them as a mentor and what kind of help you seek. Show that you have done your homework on them and their work. Outline what you want to learn from them and how they can benefit from mentoring you.

#4. Follow up: If they respond positively, follow up with them and arrange a meeting or a call. Be flexible and accommodating to their schedule and preferences. Prepare by researching their background, achievements, and challenges. Have some questions ready to ask them about their experience and advice. Be prepared to share your story, goals, and challenges with them.

#5. Build rapport: During the meeting or call, be friendly, attentive, and curious. Listen actively to what the mentor says and show appreciation for their time and wisdom. Share your ideas and feedback honestly and respectfully. Avoid being too pushy or needy for their attention or approval, and avoid being too passive or timid for their input or guidance. Find a balance between being assertive and humble.

#6. Follow through: Follow up with them after the meeting or call by sending a thank-you note or message. Act on their suggestions and report back on your progress or results. Keep in touch regularly by updating them on your situation and asking for their input when needed. Respect their boundaries and expectations by not contacting them too frequently or asking for too much from them.

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If you’re an entrepreneur and have a mentor to guide you, here are some ideas to help you work with them on your entrepreneurial journey:

#1. It’s a two-way street: Having a mentor can be an excellent asset for your entrepreneurial journey. However, mentoring is not a one-way street. It’s a two-way relationship that requires mutual trust, respect, and commitment. It would be best if you were willing to learn from your mentor and contribute to their growth and success. It would be best to compensate them appropriately for their time and value delivered. Be open to their feedback and challenge them with your ideas and perspectives. And always show gratitude for their support.

#2. Mentoring is good for you and your mentor: By mentoring you, your mentor can overcome their biases. A mentor can learn from your different background, experience, and worldview. Your mentor can benefit from new insights and perspectives that challenge their assumptions and broaden their horizons.

#3. Sponsorship is better than mentoring: A sponsor advises and advocates for you in front of others. They can help you access resources, opportunities, and recognition that can boost your career. They can also protect you from potential threats or obstacles hindering your progress. A mentor can become a sponsor if they are impressed by your performance and potential and have the influence and credibility to vouch for you.

#4. Scaling requires trade-offs: To scale a startup and prioritize resources, you may need to sacrifice efficiency and tolerate bad management until you break orbit. Scaling a startup requires making trade-offs between speed, quality, and cost. It also requires dealing with uncertainty, complexity, and chaos. A mentor can help you navigate these challenges by sharing their relatable experiences and lessons learned from scaling their businesses. They can also help you avoid common mistakes and pitfalls derailing your growth.

#5. Coaching, mentoring, and collaboration: As an entrepreneur, you must constantly learn new skills, solve problems, and adapt to new situations. You must coach, mentor, and collaborate with others in your team or network. A mentor can help you develop these competencies by providing feedback, guidance, and support. They can also help you find other coaches, mentors, or collaborators who complement your strengths and weaknesses.

#6. Choose your mentors wisely: Not all successful people are good mentors. Some may have achieved success through unethical or illegal means. Some may have selfish or ulterior motives for mentoring you. Some may need to have updated or relevant knowledge or skills. You need to invest in mentors who have ethical success and can share their knowledge generously and honestly with you.

#7. Have a toolkit: To make the most of your mentoring relationship, you need a toolkit that helps you prepare for, conduct, and learn from your mentoring sessions. Here are four essential documents to include in your toolkit:

- Goal statement: This document outlines your goals as an entrepreneur and the specific kind of help you need from a mentor to achieve them.

- Progress report: This document tracks your actions, results, and what you’ve learned from each mentoring session.

- Feedback form: This document collects your thoughts and feedback on the quality and effectiveness of your mentoring sessions.

- Learning journal: This document is a place to record your reflections and insights from each mentoring session. It’s a great resource to look back on as you grow your business.

In conclusion, a mentor can be a powerful catalyst in your journey from an employee to an entrepreneur. By leveraging their experience, you can tap into hidden strengths within yourself, uncover new possibilities, and achieve success beyond what you thought possible. However, finding and working with a mentor requires your commitment, dedication, and a willingness to learn and grow. By embracing the process of identifying your goals, researching potential mentors, and building a solid relationship, you can unlock your abilities and contribute to your growth and success.

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I guide executives and business owners through transitions with mastermind sessions and insightful writing on leadership, geopolitics, technology, and startups.

Please feel free to check out more insights from Apex Group: http://apex-insights.com/.

You can also connect with me on LinkedIn here.

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Subhasis Ghosh

Business Leader | Board Advisor | Certified & Accredited Independent Director | Guiding Startups and Small Businesses, Crafting Insights, and Always Inquisitive