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Initial Conversation Guide

The first meeting between an entrepreneur and an advisor or mentor

Congratulations, you’ve been matched! In some cases, an entrepreneur may have a question that can be addressed in one session. However, in many cases, the entrepreneur’s request will require more than one working session.

Before your first meeting:

If you are an entrepreneur:

1. Please review our Entrepreneur Orientation!

2. Review the advisor/mentor’s Skysthelimit.org profile and LinkedIn profile in order to get a sense of their background.

3. Be ready to clearly describe where you are in your business and specifically what needs you are hoping to address with this advisor or mentor.

If you are an advisor or mentor:

1. Please review our Volunteer Orientation.

2. Review the Entrepreneur’s skysthelimit.org profile and Business Plan prior to the call.

During your first meeting:

1. Start by getting to know one another – ask each other a question or two about what you learned in their profile, about their business, or even about how their day is going!

2. Then focus on the business need. Take the time to talk about where the entrepreneur’s business is currently and what the overall vision is, for their business. Then discuss the request for help and make sure the advisor/mentor clearly understands what is being requested.

3. If appropriate, resolve the entrepreneur’s questions during the call.

4. If the request will take more than one conversation: Clarify specifically what the goal of the next call or meeting will be. Determine what (if anything) either the entrepreneur or the advisor/mentor needs to do in preparation for the next meeting. Agree on a meeting time and location for the next meeting.

After any meeting:

1. As a courtesy, we strongly suggest that you follow up from the meeting by text or email to confirm any follow-up meetings and acknowledge the time you spent together with “Thank you” or “Nice meeting you”!

2. Confirm any additional meetings 2-3 days beforehand to avoid potential confusion or frustration with canceled or missed meetings.

Let us know if we can support you further – just contact our program director, if you need help.



Guide to Advising & Mentoring

Connect and Build a Relationship

Giving you the tools you’ll need to foster a meaningful connection with your match.

Meet your advisee or mentee where they’re at in their journey

Making a meaningful impact as a business advisor or mentor on skysthelimit.org starts with understanding the individual who you’re working with. Our entrepreneurs’ dynamic needs often include:

Building self-confidence, combatting discrimination, learning soft and hard business skills, such as, responding to an email in a professional and timely manner, or managing a project deadline. Creating and following a roadmap for achieving their business goals, ability to remain financially stable, and networking with people in their industry.

Embody our core tenets to lay the groundwork for a lasting relationship

First, focus on building a relationship of trust. The first part of building a trusting relationship is showing the other person you’re excited to meet them and collaborate with them! Proactively reach out to each other. Be a good listener. Avoid jumping to conclusions or immediately administering advice.

Empower the entrepreneur to help themselves

We model and teach where possible, subscribing to the adage “if you catch a fish for someone they eat for a day, if you teach someone to fish, they can eat for a lifetime,” but where appropriate, we provide templates or initial frameworks such as, a contract template, logo, or QuickBooks setup, which they can re-use with little to no help.

Model businesslike behavior

We proactively communicate, come to scheduled meetings promptly and prepared, follow up on promises, and are responsive to emails and calls.  Maintain these high expectations for yourself and for your mentee – while also accepting that no one is perfect!

Subscribe to the lean startup model

We encourage entrepreneurs to start small, test often and generate revenue as soon as possible versus seeking loans and investments as a way to get started.

Check out our Guide to your first meeting for more guidance on how to engage with your Entrepreneur.

Teach, Guide, Counsel, Do

Provide the support that your entrepreneur needs

Advisors and mentors provide some combination of these four kinds of support based on what a young Entrepreneur needs.

TeachGuideCounselDoTeach entrepreneurs skills (both soft skills and Pathway-related skills), habits, and mindsets. Ask probing questions, instill focus, and hold problem-solving discussions with entrepreneurs supporting them through their journey. Provide specific advice on different areas of business, such as how to create a budget, a brand strategy, or develop a proposal. Helping entrepreneurs actually build parts of their business, making relevant introductions in your own network, etc.

An advisor or mentor is not responsible for:

  • Direct “sponsorship”

  • Focusing on the advisor’s or mentor’s business interests

  • Doing everything for the young entrepreneur

  • Too task-focused

  • A conflict of interest

  • Getting stuck in the details

Use available resources to provide the best support possible

Our entrepreneurs are often looking for detailed help in specific areas of their business. We have created numerous Entrepreneur Resources that you can leverage to structure your advising and mentoring sessions. As always, if you have any questions, concerns, or ideas for new resources, please reach out to program@skysthelimit.org!

Check out our resources for entrepreneurs!

Set ExpectationS

Being aware of potential challenges throughout your experience can help you proactively set expectations with your entrepreneur.

Relationships are complicated. Being aware of potential challenges can help you prevent or prepare for inevitable obstacles.

  • Inadequate definition of roles and expectations

  • Conflicting values or not a good personality fit

  • Meetings are repeatedly re-scheduled or missed

  • Relationship difficulties & lack of commitment

  • Wanting to give up

  • Unreasonable demands for help and support

Wrapping up a relationship with an entrepreneur is just as important as starting the relationship – setting expectations can help make this transition easier

If you and/or your entrepreneur feel ready to wrap up the work you’re doing together, here are a few steps we recommend:

1. Talk to each other about your readiness to wrap up the relationship. If you need any support on this, contact our Program Director! In that conversation, be sure to recap what went well, the progress made, and provide encouragement and support to the entrepreneur!

2. Discuss the most pressing needs of the entrepreneur now, and encourage them to request an advisor or mentor on skysthelimit.org to meet that need!‌‌

3. Be sure to rate your experience working with the entrepreneur – this will not be shared and will improve our ability to match you with the right future entrepreneurs.

4. If appropriate, feel free to leave the door open to the entrepreneur to contact you at some point in the future in areas where you’re comfortable supporting them.

5. If you feel inclined, offer your feedback to the skysthelimit.org team to help us continue to improve our work.

6. Match with another entrepreneur on skysthelimit.org!