Your First Conversation

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The "getting to know you" phase is the most critical stage of the business mentoring relationship, so don't rush it. Building a trusting relationship requires sufficient time and dedicated effort. Focus on getting to know each other, sharing your experiences and goals.

Be curious. If you're an entrepreneur, share why you have chosen entrepreneurship and how you are working to make your dream a reality. If you're a mentor, share your personal experiences with business and why you are volunteering your time.

While you build your relationship, also begin planning your meetings. Make them more frequent at first and ensure that both of you are actively involved in the mentoring process. Be predictable and consistent, and don't miss appointments.

Create a Road Map

Once you both have a solid understanding of the business problem, work with your match to establish goals and objectives toward solving this problem—i.e., a "road map" for your mentoring relationship. Develop small, manageable steps that are specific, measurable, realistic, and able to be accomplished within a reasonable amount of time. Clearly define the desired outcomes of the relationship. In each meeting, clarify and restate the goal to each other and identify the next steps related to the goal.

Lay Some Ground Rules

  • Express your expectations and commitments. Know the specific challenges you plan to address.

  • Establish a preferred feedback style (written, verbal, direct, etc.).

  • Establish clear communication channels and a timeline for interaction.

  • Be clear about the mentor's core competencies and how much weight the entrepreneur should give to advice within and outside of these competencies.

  • Establish confidentiality. Anything shared should remain confidential.

For Entrepreneurs: Tips on Receiving Feedback

  • Be respectful and responsive to feedback, whether or not you implement the advice. Be clear about your use of feedback.

  • Push back when appropriate. Express respectful reservations if you feel advice is inappropriate, or not feasible.

  • Take your mentor's advice seriously, even if it is difficult, and put this advice in your own context to determine its role for you.

For Mentors: Questions to Ask Entrepreneurs

  1. Why are you in this business? This question is about aspiration and purpose. What drives the entrepreneurs to do this work?

  2. What are you doing well that is helping you to get there? This question helps spotlight core strengths. What does the entrepreneur do better than the average business owner?

  3. What are you not doing well that is preventing you from getting there? This is about facilitating an honest and critical assessment of challenges or weaknesses in a person or company that is slowing their success.

  4. What will you do different tomorrow to meet those challenges? Progress cannot be measured by hard work alone. Someone might have a great work ethic but focus on the wrong priorities. People also have a tendency to practice and repeat what they are already good at doing. It is human nature to show off your best side and hide weaknesses.

  5. Where do you need the most help? The entrepreneur's answers to the first four questions, as well as your own strengths, relationships, and learning resources, can help you determine where to focus.


  • The Mentoring Group, "A Proven Process for Successful Mentoring" (2003).
  • A.K. Tjan, "Five Questions Every Mentor Must Ask," Harvard Business Review (2009).
  • Women's Technology Cluster, Social Fusion Program, "Relationship Tips for Mentors and Mentees" (2009).