Entrepreneurs and volunteers, please use this guide to discuss the following questions. Some questions are for both of you to answer, some questions are just for the entrepreneur or just for the advisor / mentor to consider.

Section 1: Get to know each other

Hopefully, you’ve already had an intro meeting or conversation before agreeing to work together, but in case you haven’t, be sure to take a few moments to introduce yourselves!

1. Both: Share a brief background. Where are you from? What is your favorite thing to do?

2. Entrepreneur: Why are you building this business?

3. Advisor / mentor: Why are you interested in volunteering with this program?

4. Entrepreneur: What does success look like for your business?

5. Advisor / mentor: What are your top three strengths?

Section 2: Review Community Guidelines

Make sure you discuss and agree on the following important ways of working together: 

• Do you agree to communicate and meet on a regular basis for a specified amount of time?

• Do you agree to be respectful of each others time and boundaries?

• Will you openly discuss feedback and agree to sometimes disagree?

• Will you share information and be transparent? 

• How will you foster a positive working relationship?

• How will you help facilitate a two-way learning relationship?

• Do you agree to ask for help in understanding when needed?

• Do you agree to maintain strict confidentiality?

• Will you regularly assess the value of the relationship and discuss how it might be improved?

Section 3: Figuring out what an entrepreneur needs

1. Entrepreneur: What was the request for support you made on skysthelimit.org?

2. Both: Is this a short-term advising relationship or a long-term mentoring relationship?

3. Both: What resource(s) are we using to work together? Here are some Skysthelimit.org resources you may want to consider:

   1. Launch4: This is recommended for entrepreneurs who have a business idea but haven’t launched it yet.

   2. Start Your Business Checklist: This is a good tool for mentors and entrepreneurs to work on the whole process of building a business.

   3. SMART Goal-setting Template: Excellent for helping set specific goals for yourself as well as a method for how to achieve them using SMART goals and the SPAR Goal-Attainment Process.

   4. Ecommerce4: Are you selling something online? Get started and get tips in this step-by-step guide.

   5. Service4: This one offers guidance to entrepreneurs offering a service like event planning, photography, design, or consulting.

Section 4: How you will work together

Making a Commitment - Meeting Duration & Frequency

1. Both: How long do you intend to keep meeting together? What date will be your last meeting? Or do you not know yet?

2. Both: How often are you meeting together? Once a week? Once a month?

   • Tip: When first committing to work together, Skysthelimit.org members typically commit to 2 - 4 meetings per month for at least 3 months.

3. Both: Do you want to set up a regular time to meet every week/two weeks/month? If so, what day and time?

4. Both: How long do you think each meeting will be? 

   1. Tip: Sometimes shorter meetings are more productive! Try setting your meetings to 45 minutes. If you find you need more or less time, you can always adjust the duration of the next one.

Meeting Communication Plan

1. Both: Where/how will you meet? Will you meet in person? On a phone call? Via Skype, Zoom, or Google Hangout?

2. Both: What if one of you needs to cancel or reschedule? How much time notice should be provided to reschedule? How should you let the other person know?

3. Both: Will you communicate outside of your meetings? If so, through what messaging platform and how quickly will you expect or be able to provide responses?

4. Both: How would you describe your communication and working style? Casual? Professional? Warm and Friendly? Straight to the point?

Section 5: Privacy and confidentiality

1. Both: What discussion topics, if any, will remain confidential?

Section 6: Providing Feedback

1. Both: Do you agree to provide each other with regular feedback on how the mentoring/advising relationship is going? If so, how will you provide this feedback?

2. Do you agree to use STL’s on-platform rating system to provide our program team with feedback about how your match is going so that we can make sure you are having a positive experience. Please note: This feedback will only be seen by STL’s program team.

Section 7: Next steps

After discussing all of the above, hopefully you are feeling more confident about working together and are ready to schedule your next meeting. Don’t forget to use the “Collaboration” tab to confirm your commitment and keep track of your meeting progress, and set an agenda for the next meeting.

• What will the entrepreneur do before the next meeting, if anything?

• What will the advisor / mentor do before the next meeting, if anything?

If your discussion raised any red flags about your compatibility and you no longer want to work together, don’t worry! Just log back in and Explore the Community to find someone new to match with. Or, email program@skysthelimit.org to set up a Match Consultation.